Annapolis Restaurant Week
--> <-----
--> Wes Adams For Anne Arundel Conty Circuit Court Judge <-----
“Herrmann
“Herrmann
Insert future code here--> 1-1 to 1-31 Anne Arundel County Stop Smoking <-----
STANDARD HERMAN AD--> Anne Arundel County Stop Smoking <-----
Herrmann 40--> “Herrmann <-----
MD Higher Education Commission Near Completer
Insert future code here
Orioles Bud april 2020 to Sept 2020
“Nationals October 2019

Loading Events

← Back to Events

Schooner Woodwind: Annapolis Sailing Cruises

+ Google Map
80 Compromise St
Annapolis, MD 21401 United States

August 2017

Weds. Night Sailboat Racing Cruise aboard the Schooner Woodwind

August 2, 2017 @ 6:25 pm - 8:30 pm
Schooner Woodwind: Annapolis Sailing Cruises, 80 Compromise St
Annapolis, MD 21401 United States

Be part of the action every Wednesday night as the two wooden schooners, Woodwind & Woodwind II, compete in Annapolis’ summer racing series. Help the crew or sit back and watch 130 racing sailboats!

Find out more »

Sailing Cruise with live music aboard the Schooner Woodwind

August 3, 2017 @ 6:30 pm - 8:30 pm
Schooner Woodwind: Annapolis Sailing Cruises, 80 Compromise St
Annapolis, MD 21401 United States

Enjoy music performed by The Eastport Oyster Boys during a two hour sunset cruise aboard the 74-foot Schooner Woodwind. Recognized as the City of Annapolis and the Chesapeake Bay’s Musical Goodwill Ambassadors The Eastport Oyster Boys love to share their musical celebration of life on the shores of the Chesapeake and its scenic rivers with audiences of all ages. For two decades they have educated, amused and delighted thousands with their wit, wisdom and special message of stewardship and appreciation…

Find out more »

SOLD OUT: Acoustic Brunch with Ernie Halter

August 6, 2017 @ 10:00 am - 1:00 pm
Schooner Woodwind: Annapolis Sailing Cruises, 80 Compromise St
Annapolis, MD 21401 United States

An Intimate, All Ages Acoustic Show with ERNIE HALTER aboard the Schooner Woodwind for a concert on a beautiful sailing boat, including a light delicious brunch. Ernie Halter will play acoustically while at anchor in a secluded cove. He will play for over an hour and after the performance we will set sail on the 74-foot, classic wooden schooner, Woodwind. Raise the sails, steer the boat, sit back, relax and meet Ernie while sailing the Bay. In 2011 Justin Bieber…

Find out more »

“Sail Away” while learning the history of the Chesapeake Bay

August 7, 2017 @ 6:30 pm - 8:30 pm
Schooner Woodwind: Annapolis Sailing Cruises, 80 Compromise St
Annapolis, MD 21401 United States

Oyster Wars by Sherri Marsh. The Oyster Wars were a nearly century-long series of violent disputes between oyster pirates, the Maryland Oyster Navy and legal watermen from Maryland and Virginia. It is a tale of kidnapping, murder, machine guns, and honest folks just trying to make a living. Sherri Marsh Johns is a Smith Island native and the daughter of a waterman who “fought” in the Oyster Wars. Ms. Johns earned her Bachelor of Science degree at the University of…

Find out more »

Beer Tasting Sailing Cruise aboard the 74-foot Schooner Woodwind

August 8, 2017 @ 6:30 pm - 8:30 pm
Schooner Woodwind: Annapolis Sailing Cruises, 80 Compromise St
Annapolis, MD 21401 United States

Sample beer from DC Brau Brewery while enjoying the beautiful sunset under full sail. A brewery representative will be aboard and ticket price includes 3 samples of beer. When co-founders Brandon Skall and Jeff Hancock opened the doors to their brewery in 2011 on Bladensburg Road in NE Washington, DC Brau Brewing Company became the first packaging brewery inside the District of Columbia since 1956. DC Brau’s signature brews include: The Public (Pale Ale), The Corruption (IPA), The Citizen (Belgian-style…

Find out more »

Weds. Night Sailboat Racing Cruise aboard the Schooner Woodwind

August 9, 2017 @ 6:25 pm - 8:30 pm
Schooner Woodwind: Annapolis Sailing Cruises, 80 Compromise St
Annapolis, MD 21401 United States

Be part of the action every Wednesday night as the two wooden schooners, Woodwind & Woodwind II, compete in Annapolis’ summer racing series. Help the crew or sit back and watch 130 racing sailboats!

Find out more »

Sailing Cruise with live music aboard the Schooner Woodwind

August 10, 2017 @ 6:30 pm - 8:30 pm
Schooner Woodwind: Annapolis Sailing Cruises, 80 Compromise St
Annapolis, MD 21401 United States

:Enjoy music performed by Ken Wenzel during a two hour sunset cruise aboard the 74-foot Schooner Woodwind. With the release of “…Beneath Potomac Skies” – a 12-song, full-band collection of moments and memories culled from time spent in Washington DC, and many other locales – singer/songwriter/saxophonist Ken Francis Wenzel is eager to introduce his own roots-rock, country jazz-tinged take on love, learning, and life in contemporary America. Featuring several guest appearances from some of the DC area’s finest musicians, “…Beneath…

Find out more »

“Sail Away” while learning the history of the Annapolis area

August 14, 2017 @ 6:30 pm - 8:30 pm
Schooner Woodwind: Annapolis Sailing Cruises, 80 Compromise St
Annapolis, MD 21401 United States

The Key to Annapolis History, by Jeff Holland. The Key to Annapolis history lies right there in the harbor. It can’t be found by looking port; and it can’t by looking starboard. It’s only when you drop the hook that the secret can be found when you anchor, you’ll discover that the bottom of the harbor is only 12 feet down! Cruises depart from the Annapolis Marriott Waterfront Hotel at 6:30pm and returns at 8:30pm Tickets are $46/adult, $29/child under…

Find out more »

Weds. Night Sailboat Racing Cruise aboard the Schooner Woodwind

August 16, 2017 @ 6:25 pm - 8:30 pm
Schooner Woodwind: Annapolis Sailing Cruises, 80 Compromise St
Annapolis, MD 21401 United States

Be part of the action every Wednesday night as the two wooden schooners, Woodwind & Woodwind II, compete in Annapolis’ summer racing series. Help the crew or sit back and watch 130 racing sailboats!

Find out more »

Dodon Vineyard Sunset Sail Wine Dinner

August 20, 2017 @ 6:30 pm - 9:00 pm
Schooner Woodwind: Annapolis Sailing Cruises, 80 Compromise St
Annapolis, MD 21401 United States

Schooner Woodwind and The Vineyards at Dodon have partnered up for a very special evening sailing on the Chesapeake Bay while enjoying a 4 course, picnic styled wine dinner. The Vineyards at Dodonmakes amazing estate-grown wines from Anne Arundel County, you will be very impressed. About the Cruise: Schooner Woodwind’s Dinner Cruises are a very casual affair. Courses are served picnic-style and food is presented chilled or at room temperature. You will thoroughly enjoy the event aboard. We really do…

Find out more »

Solar Eclipse Viewing Cruise

August 21, 2017 @ 1:30 pm - 3:30 pm
Schooner Woodwind: Annapolis Sailing Cruises, 80 Compromise St
Annapolis, MD 21401 United States
$12 – $54

Sail away and watch the event being called the “Great American Eclipse”. While we are not in the area that will see the total eclipse, Annapolis is in the 79% coverage area, and it should be really cool to view from the water, while sailing. The previous time a total solar eclipse was visible across the entire contiguous United States was during the June 8, 1918 eclipse. Depart Annapolis at 1:30pm, return at 3:30pm. Each guest aboard will receive special…

Find out more »

Beer Tasting Sailing Cruise aboard the 74-foot Schooner Woodwind

August 22, 2017 @ 6:25 pm - 8:30 pm
Schooner Woodwind: Annapolis Sailing Cruises, 80 Compromise St
Annapolis, MD 21401 United States

Sample beer from DC Brau Brewery while enjoying the beautiful sunset under full sail. A brewery representative will be aboard and ticket price includes 3 samples of beer. When co-founders Brandon Skall and Jeff Hancock opened the doors to their brewery in 2011 on Bladensburg Road in NE Washington, DC Brau Brewing Company became the first packaging brewery inside the District of Columbia since 1956. DC Brau’s signature brews include: The Public (Pale Ale), The Corruption (IPA), The Citizen (Belgian-style…

Find out more »

SOLD OUT – Wine in the Wind Cruise aboard the Schooner Woodwind

August 27, 2017 @ 4:00 pm - 6:00 pm
Schooner Woodwind: Annapolis Sailing Cruises, 80 Compromise St
Annapolis, MD 21401 United States

Join us for a two hour sail around the Chesapeake Bay while sampling wonderful wines from Spain. The representative from the winery will introduce you to four special wines while we are under sail. The cruise will be a relaxing sail including 3-oz samples of each of the four wines featured. Along with each wine is a delicious, perfectly paired bite (we call them magnificent morsels) to go with each wine. Includes a take-home, boat friendly, wine glass by Go…

Find out more »

“Sail Away” while learning the history of the Annapolis area

August 28, 2017 @ 6:30 pm - 8:30 pm
Schooner Woodwind: Annapolis Sailing Cruises, 80 Compromise St
Annapolis, MD 21401 United States

The Key to Annapolis History, by Jeff Holland. The Key to Annapolis history lies right there in the harbor. It can’t be found by looking port; and it can’t by looking starboard. It’s only when you drop the hook that the secret can be found when you anchor, you’ll discover that the bottom of the harbor is only 12 feet down! Cruises depart from the Annapolis Waterfront Hotel at 6:30pm and returns at 8:30pm Tickets are $46/adult, $29/child under 12…

Find out more »

Beer Tasting Sailing Cruise aboard the 74-foot Schooner Woodwind

August 29, 2017 @ 6:25 pm - 8:30 pm
Schooner Woodwind: Annapolis Sailing Cruises, 80 Compromise St
Annapolis, MD 21401 United States

Sample beer from DC Brau Brewery while enjoying the beautiful sunset under full sail. A brewery representative will be aboard and ticket price includes 3 samples of beer. When co-founders Brandon Skall and Jeff Hancock opened the doors to their brewery in 2011 on Bladensburg Road in NE Washington, DC Brau Brewing Company became the first packaging brewery inside the District of Columbia since 1956. DC Brau’s signature brews include: The Public (Pale Ale), The Corruption (IPA), The Citizen (Belgian-style…

Find out more »

Weds. Night Sailboat Racing Cruise aboard the Schooner Woodwind

August 30, 2017 @ 5:30 pm - 7:30 pm
Schooner Woodwind: Annapolis Sailing Cruises, 80 Compromise St
Annapolis, MD 21401 United States

Be part of the action every Wednesday night as the two wooden schooners, Woodwind & Woodwind II, compete in Annapolis’ summer racing series. Help the crew or sit back and watch 130 racing sailboats!

Find out more »

Sailing Cruise with live music aboard the Schooner Woodwind

August 31, 2017 @ 6:30 pm - 8:30 pm
Schooner Woodwind: Annapolis Sailing Cruises, 80 Compromise St
Annapolis, MD 21401 United States

Enjoy music performed by Brandon Hardesty during a two hour sunset cruise aboard the 74-foot Schooner Woodwind. Brandon Hardesty is a singer/songwriter based out of Annapolis, MD. He has been touring the world for the last 10 years with his band Bumpin Uglies. Cruises depart from the Annapolis Waterfront Hotel at 5:30pm and return at 7:30pm. Tickets are $46 adults, $29 children under 12 yrs. and include a soft drink and snack. Beer and wine are available for purchase. http://www.schoonerwoodwind.com…

Find out more »

September 2017

Beer Tasting Sailing Cruise aboard the 74-foot Schooner Woodwind

September 5, 2017 @ 5:30 pm - 7:30 pm
Schooner Woodwind: Annapolis Sailing Cruises, 80 Compromise St
Annapolis, MD 21401 United States
$12 – $46

Sample beer from Union Craft Brewery while enjoying the beautiful sunset under full sail. A brewery representative will be aboard and ticket price includes 3 samples of beer. Beer is the union of water, barley, hops and yeast. A brewery is the union of beer, its brewers and the community it serves. Beer Unites! is not just a tagline, its the underlying philosophy of everything we believe in as a business. Good beer brings good people together for good times—and…

Find out more »

Beer Tasting Sailing Cruise aboard the 74-foot Schooner Woodwind

September 5, 2017 @ 5:30 pm - 7:30 pm
Schooner Woodwind: Annapolis Sailing Cruises, 80 Compromise St
Annapolis, MD 21401 United States

Sample beer from Union Craft Brewery while enjoying the beautiful sunset under full sail. A brewery representative will be aboard and ticket price includes 3 samples of beer. Beer is the union of water, barley, hops and yeast. A brewery is the union of beer, its brewers and the community it serves. Beer Unites! is not just a tagline, its the underlying philosophy of everything we believe in as a business. Good beer brings good people together for good times—and…

Find out more »

ailing Cruise with live music aboard the 74-foot Schooner Woodwind

September 7, 2017 @ 5:30 pm - 7:30 pm
Schooner Woodwind: Annapolis Sailing Cruises, 80 Compromise St
Annapolis, MD 21401 United States
$12 – $46

Enjoy music performed by The Shatners Unplugged during a two hour sunset cruise aboard the 74-foot Schooner Woodwind. We’ll be stripping down many of the dance tunes played in The Shatners band while adding songs from artists like Boston, Amy Winehouse, and the Bodeans for an eclectic variety of music to share. We’ll even throw in an original or 2 if those aboard are feelin’ it! We are thrilled to be part of the Woodwind’s lineup! Cruises depart from the…

Find out more »

Sailing Cruise with live music aboard the Schooner Woodwind

September 7, 2017 @ 5:30 pm - 7:30 pm
Schooner Woodwind: Annapolis Sailing Cruises, 80 Compromise St
Annapolis, MD 21401 United States

Enjoy music performed by The Shatners Unplugged during a two hour sunset cruise aboard the 74-foot Schooner Woodwind. We’ll be stripping down many of the dance tunes played in The Shatners band while adding songs from artists like Boston, Amy Winehouse, and the Bodeans for an eclectic variety of music to share. We’ll even throw in an original or 2 if those aboard are feelin’ it! We are thrilled to be part of the Woodwind’s lineup! Cruises depart from the…

Find out more »

Sail Away” while learning the history of the Chesapeake Bay aboard the 74-foot Schooner Woodwind:

September 11, 2017 @ 5:30 pm - 7:30 pm
Schooner Woodwind: Annapolis Sailing Cruises, 80 Compromise St
Annapolis, MD 21401 United States
$12 – $46

History Cruise: Eating, Drinking and Making Merry in Colonial Annapolis with Diane Rey. Set sail with Anne Catharine Green, Annapolis’ 18th century Printer to the Province, a woman far ahead of her time; to discover the kinds of activities that helped make Annapolis the “Athens of America” during its golden age. Learn about early tavern life, sought-after imports, the “clubbical behavior” of the celebrated Tuesday Club, and the whirlwind that was Annapolis’ social season, as drawn from the pages of…

Find out more »

Sail Away” while learning the history of the Chesapeake Bay aboard the 74-foot Schooner Woodwind:

September 11, 2017 @ 5:30 pm - 7:30 pm
Schooner Woodwind: Annapolis Sailing Cruises, 80 Compromise St
Annapolis, MD 21401 United States
$12 – $46

History Cruise: Eating, Drinking and Making Merry in Colonial Annapolis with Diane Rey. Set sail with Anne Catharine Green, Annapolis’ 18th century Printer to the Province, a woman far ahead of her time; to discover the kinds of activities that helped make Annapolis the “Athens of America” during its golden age. Learn about early tavern life, sought-after imports, the “clubbical behavior” of the celebrated Tuesday Club, and the whirlwind that was Annapolis’ social season, as drawn from the pages of…

Find out more »

“Sail Away” while learning the history of the Annapolis area

September 11, 2017 @ 5:30 pm - 7:30 pm
Schooner Woodwind: Annapolis Sailing Cruises, 80 Compromise St
Annapolis, MD 21401 United States

History Cruise: Eating, Drinking and Making Merry in Colonial Annapolis with Diane Rey. Set sail with Anne Catharine Green, Annapolis’ 18th century Printer to the Province, a woman far ahead of her time; to discover the kinds of activities that helped make Annapolis the “Athens of America” during its golden age. Learn about early tavern life, sought-after imports, the “clubbical behavior” of the celebrated Tuesday Club, and the whirlwind that was Annapolis’ social season, as drawn from the pages of…

Find out more »

Beer Tasting Sailing Cruise aboard the 74-foot Schooner Woodwind

September 12, 2017 @ 5:30 pm - 7:30 pm
|Recurring Event (See all)

An event every week that begins at 5:30 pm on Tuesday, repeating until September 26, 2017

Schooner Woodwind: Annapolis Sailing Cruises, 80 Compromise St
Annapolis, MD 21401 United States
http://www.schoonerwoodwind.com/buy-tickets/

Sample beer from Union Craft Brewery while enjoying the beautiful sunset under full sail. A brewery representative will be aboard and ticket price includes 3 samples of beer. Beer is the union of water, barley, hops and yeast. A brewery is the union of beer, its brewers and the community it serves. Beer Unites! is not just a tagline, its the underlying philosophy of everything we believe in as a business. Good beer brings good people together for good times—and…

Find out more »

Beer Tasting Sailing Cruise aboard the 74-foot Schooner Woodwind

September 12, 2017 @ 5:30 pm - 7:30 pm
Schooner Woodwind: Annapolis Sailing Cruises, 80 Compromise St
Annapolis, MD 21401 United States

Sample beer from Union Craft Brewery while enjoying the beautiful sunset under full sail. A brewery representative will be aboard and ticket price includes 3 samples of beer. Beer is the union of water, barley, hops and yeast. A brewery is the union of beer, its brewers and the community it serves. Beer Unites! is not just a tagline, its the underlying philosophy of everything we believe in as a business. Good beer brings good people together for good times—and…

Find out more »

Sailing Cruise with live music aboard the 74-foot Schooner Woodwind

September 14, 2017 @ 8:00 am - 5:00 pm
Schooner Woodwind: Annapolis Sailing Cruises, 80 Compromise St
Annapolis, MD 21401 United States
$12 – $46

Enjoy music performed by Dirty Screts during a two hour sunset cruise aboard the 74-foot Schooner Woodwind. Dirty ‘Little’ Secret is the lively acoustic side of local area favorite, Dirty Secret. With a variety of old school classic rock, blues, and a little country – there’s something for every music lover! Cruises depart from the Annapolis Waterfront Hotel. 5:30pm and return at 7:30pm. Tickets are $46/adult, $29/child under 12 yrs. and include a soft drink and snack. Beer and wine…

Find out more »

Classic Wooden Boat Regatta

September 17, 2017 @ 11:00 am - 2:30 pm
Schooner Woodwind: Annapolis Sailing Cruises, 80 Compromise St
Annapolis, MD 21401 United States
$12 – $46

Participate in the National Sailing Hall of Fame Classic Wooden Boat Regatta. They have invited the Woodwinds’ to participate in the race in the “Spirit of Tradition Class”. The course is approximately 5.4 NM and takes place in the Severn River. It is a 3 lap race with pursuit style race. Each boat has a rating, and by the rating they will get a start time. The pursuit style race challenges the competitors to sail through the other race boats…

Find out more »

Classic Wooden Boat Regatta

September 17, 2017 @ 11:00 am - 2:30 pm
Schooner Woodwind: Annapolis Sailing Cruises, 80 Compromise St
Annapolis, MD 21401 United States

Participate in the National Sailing Hall of Fame Classic Wooden Boat Regatta. They have invited the Woodwinds’ to participate in the race in the “Spirit of Tradition Class”. The course is approximately 5.4 NM and takes place in the Severn River. It is a 3 lap race with pursuit style race. Each boat has a rating, and by the rating they will get a start time. The pursuit style race challenges the competitors to sail through the other race boats…

Find out more »

“Sail Away” while learning the history of the Chesapeake Bay aboard the 74-foot Schooner Woodwind

September 18, 2017 @ 5:30 pm - 7:30 pm
Schooner Woodwind: Annapolis Sailing Cruises, 80 Compromise St
Annapolis, MD 21401 United States
http://www.schoonerwoodwind.com/buy-tickets/

Pirates of the Chesapeake with Heather Ersts. Pirates have plied the waters of the Chesapeake Bay for hundreds of years, and still do today. Hear tales of Black Beard, the town dubbed the “Nest of Pirates,” and today’s modern pirates as you sail along the same waterways they have sailed. Cruises depart from the Annapolis Waterfront Hotel at 5:30pm and return at 7:30pm. Tickets are $46/adult, $29/child under 12 yrs. and include a soft drink and snack. www.schoonerwoodwind.com 410-263-7837

Find out more »

“Sail Away” while learning the history of the Annapolis area

September 18, 2017 @ 5:30 pm - 7:30 pm
Schooner Woodwind: Annapolis Sailing Cruises, 80 Compromise St
Annapolis, MD 21401 United States

Pirates of the Chesapeake with Heather Ersts. Pirates have plied the waters of the Chesapeake Bay for hundreds of years, and still do today. Hear tales of Black Beard, the town dubbed the “Nest of Pirates,” and today’s modern pirates as you sail along the same waterways they have sailed. Cruises depart from the Annapolis Waterfront Hotel at 5:30pm and return at 7:30pm. Tickets are $46/adult, $29/child under 12 yrs. and include a soft drink and snack. http://www.schoonerwoodwind.com 410-263-7837

Find out more »

Beer Tasting Sailing Cruise aboard the 74-foot Schooner Woodwind

September 19, 2017 @ 5:30 pm - 7:30 pm
Schooner Woodwind: Annapolis Sailing Cruises, 80 Compromise St
Annapolis, MD 21401 United States

Sample beer from Union Craft Brewery while enjoying the beautiful sunset under full sail. A brewery representative will be aboard and ticket price includes 3 samples of beer. Beer is the union of water, barley, hops and yeast. A brewery is the union of beer, its brewers and the community it serves. Beer Unites! is not just a tagline, its the underlying philosophy of everything we believe in as a business. Good beer brings good people together for good times—and…

Find out more »

Sailing Cruise with live music aboard the 74-foot Schooner Woodwind

September 21, 2017 @ 5:30 pm - 7:30 pm
Schooner Woodwind: Annapolis Sailing Cruises, 80 Compromise St
Annapolis, MD 21401 United States
$12 – $46

Enjoy music performed by Deanna Dove during a two hour sunset cruise aboard the 74-foot Schooner Woodwind. Deanna Dove is best known as the “Island Girl” in her hometown for her compositional writing style about her lifelong experiences on the Chesapeake Bay. She has earned a loyal audience for her ability to craft songs that include elements of rock, pop, blues, alt-country and gospel into a distinctly individual style with a universal appeal. The “Island Girl” has established her reputation…

Find out more »

Sailing Cruise with live music aboard the Schooner Woodwind

September 21, 2017 @ 5:30 pm - 7:30 pm
Schooner Woodwind: Annapolis Sailing Cruises, 80 Compromise St
Annapolis, MD 21401 United States

Enjoy music performed by Deanna Dove during a two hour sunset cruise aboard the 74-foot Schooner Woodwind. Deanna Dove is best known as the “Island Girl” in her hometown for her compositional writing style about her lifelong experiences on the Chesapeake Bay. She has earned a loyal audience for her ability to craft songs that include elements of rock, pop, blues, alt-country and gospel into a distinctly individual style with a universal appeal. The “Island Girl” has established her reputation…

Find out more »

Sail Away” while learning the history of the Chesapeake Bay aboard the 74-foot Schooner Woodwind

September 25, 2017 @ 5:30 pm - 7:30 pm
Schooner Woodwind: Annapolis Sailing Cruises, 80 Compromise St
Annapolis, MD 21401 United States
$12 – $46

The Maritime Republic of Eastport…Still Revolting After All These Years with Kevin Brooks Join Eastport Oyster Boy and Local Revolutionary Kevin “Brother Shucker” Brooks for an entertaining look at the upstart “Maritime Republic of Eastport”‘s interesting and down right fun history through the past four centuries. Historic forts, world class boat building centers, proud diversity, resilient waterman and becoming the ever fun and ever mighty Maritime Republic of Eastport!… Join Kevin for this fun, irreverent and music filled journey through…

Find out more »

“Sail Away” while learning the history of the Annapolis area

September 25, 2017 @ 5:30 pm - 7:30 pm
Schooner Woodwind: Annapolis Sailing Cruises, 80 Compromise St
Annapolis, MD 21401 United States

The Maritime Republic of Eastport…Still Revolting After All These Years with Kevin Brooks Join Eastport Oyster Boy and Local Revolutionary Kevin “Brother Shucker” Brooks for an entertaining look at the upstart “Maritime Republic of Eastport”‘s interesting and down right fun history through the past four centuries. Historic forts, world class boat building centers, proud diversity, resilient waterman and becoming the ever fun and ever mighty Maritime Republic of Eastport!… Join Kevin for this fun, irreverent and music filled journey through…

Find out more »

Beer Tasting Sailing Cruise aboard the 74-foot Schooner Woodwind

September 26, 2017 @ 5:30 pm - 7:30 pm
Schooner Woodwind: Annapolis Sailing Cruises, 80 Compromise St
Annapolis, MD 21401 United States

Sample beer from Union Craft Brewery while enjoying the beautiful sunset under full sail. A brewery representative will be aboard and ticket price includes 3 samples of beer. Beer is the union of water, barley, hops and yeast. A brewery is the union of beer, its brewers and the community it serves. Beer Unites! is not just a tagline, its the underlying philosophy of everything we believe in as a business. Good beer brings good people together for good times—and…

Find out more »

Sailing Cruise with live music aboard the 74-foot Schooner Woodwind

September 28, 2017 @ 5:30 pm - 7:30 pm
Schooner Woodwind: Annapolis Sailing Cruises, 80 Compromise St
Annapolis, MD 21401 United States
$12 – $46

Enjoy music performed by Don Shappell &Don Sennett during a two hour sunset cruise aboard the 74-foot Schooner Woodwind. Don Shappelle is a singer/songwriter and guitarist who grew up on the banks of the mighty Susquehanna River and sings about the people, history and boats of the Chesapeake bay and it’s many beautiful rivers. Sailing songs and sing-alongs are part of Don’s repertoire and always get an audience involved. Performing with Don Shappelle is bassist and vocalist Don Sennett. Together…

Find out more »

Sailing Cruise with live music aboard the Schooner Woodwind

September 28, 2017 @ 5:30 pm - 7:30 pm
Schooner Woodwind: Annapolis Sailing Cruises, 80 Compromise St
Annapolis, MD 21401 United States

Enjoy music performed by Don Shappell & Don Sennett during a two hour sunset cruise aboard the 74-foot Schooner Woodwind. Don Shappelle is a singer/songwriter and guitarist who grew up on the banks of the mighty Susquehanna River and sings about the people, history and boats of the Chesapeake bay and it’s many beautiful rivers. Sailing songs and sing-alongs are part of Don’s repertoire and always get an audience involved. Performing with Don Shappelle is bassist and vocalist Don Sennett.…

Find out more »

October 2017

Brunch Cruise with Jay Nash with special guest Natalia Zukerman

October 1, 2017 @ 11:30 am - 2:30 pm
Schooner Woodwind: Annapolis Sailing Cruises, 80 Compromise St
Annapolis, MD 21401 United States

An Intimate, All Ages Acoustic Show with JAY NASH and special guest, NATALIA ZUKERMAN aboard the Schooner Woodwind for a concert on a beautiful sailing boat, including a light delicious brunch. Jay Nash will play acoustically while at anchor in a secluded cove. He will play for about an hour and after the performance we will set sail on the 74-foot, classic wooden schooner, Woodwind. Raise the sails, steer the boat, sit back, relax and meet Jay while sailing the…

Find out more »

SOLD OUT – Brews in the Breeze Lunch Cruise

October 8, 2017 @ 11:00 am - 1:30 pm
Schooner Woodwind: Annapolis Sailing Cruises, 80 Compromise St
Annapolis, MD 21401 United States

Join the Woodwind crew for an afternoon of beer tasting along with a delicious lunch. After we raise all our sails, we will start the tasting with the lightest of the four beers Tickets are $78 per adult and include lunch, four 6 oz. beers, and unlimited soda and water. Additional beer will be available for purchase. Maximum 35 guests Due to the Sail Boat Show ~ Cruise departs from the Annapolis City Marina in Eastport at 11:00am and returns…

Find out more »

Chesapeake Bay Schooner Race Start Watch aboard the Woodwinds

October 12, 2017 @ 12:00 pm - 3:00 pm
Schooner Woodwind: Annapolis Sailing Cruises, 80 Compromise St
Annapolis, MD 21401 United States

The Annual Great Chesapeake Bay Schooner Race Start Watch aboard the Schooner Woodwind II: Join in the excitement and watch the start of the race. There will be up to 25 plus schooners at the starting line. Seven of them are at least near 100+ feet. This is going to be incredible. Join the fun! They will be racing to the Norfolk area, we will cheer them on till it's time to go in. We will be under sail with…

Find out more »

Lighthouses of the Bay Sailing Cruise aboard the Woodwinds

October 14, 2017 @ 10:30 am - 2:30 pm
Schooner Woodwind: Annapolis Sailing Cruises, 80 Compromise St
Annapolis, MD 21401 United States

Sail by as many as 3 different lighthouses while learning about their history, importance, and present day condition from a guest lecturer from the Chesapeake Chapter of the US Lighthouse Society. The cruise includes a box lunch, soft drinks and snacks. Beer and wine are available for purchase. Due to the Power Boat Show ~ Cruise departs from the Annapolis City Marina in Eastport at 10:30am, returning at 2:30pm Tickets are $93/adult and $56/child under 12 yrs. with a children’s…

Find out more »

Dogfish Head: Brews in the Breeze Brunch Cruise

October 15, 2017 @ 11:00 am - 1:30 pm
Schooner Woodwind: Annapolis Sailing Cruises, 80 Compromise St
Annapolis, MD 21401 United States

Sail on a brunch-time cruise featuring Dogfish Head Brews on the Chesapeake Bay. After we raise all our sails, a fun, Dogfish Head brewery representative will let you know the beer line up for the day which will pair well with our delicious buffet brunch. Tickets are $84 per adult and include brunch, two drink vouchers for beers (or non-Dogfish Head wine), and unlimited soda and water. Departs Annapolis at 11:00 am and returns at 1:30 pm. Maximum 35 guests.…

Find out more »

April 2018

Opening Weekend for the 74-foot, Schooner Woodwind Sailing Cruises

April 14, 2018 @ 12:00 pm - 2:30 pm
Schooner Woodwind: Annapolis Sailing Cruises, 80 Compromise St
Annapolis, MD 21401 United States
+ Google Map
$12 – $46

Help raise the sails, steer the boat or just sit back and relax aboard the Schooner Woodwind. Nancy Hammond's "Woodwind" print will be raffled off on each cruise of opening weekend! For the month of April, weekday cruises require a 12 person minimum and one days notice, but no minimums on weekend cruises. Sail times are 12:30-2:30 & 3:00-5:00 and all cruises depart from the Annapolis Waterfront Hotel. Tickets are $46 for adults and $29 for children under 12 years…

Find out more »

Opening Weekend for Schooner Woodwind

April 14, 2018 @ 12:30 pm - April 15, 2018 @ 5:30 pm
Schooner Woodwind: Annapolis Sailing Cruises, 80 Compromise St
Annapolis, MD 21401 United States

Help raise the sails, steer the boat or just sit back and relax aboard the Schooner Woodwind. Nancy Hammond's "Woodwind" print will be raffled off on each cruise of opening weekend! For the month of April, weekday cruises require a 12 person minimum and one days notice, but no minimums on weekend cruises. Sail times are 12:30-2:30 & 3:00-5:00 and all cruises depart from the Annapolis Waterfront Hotel. Tickets are $46 for adults and $29 for children under 12 years…

Find out more »

Sailor’s Delight” Friday Night Cocktail Sailing Cruise aboard the 74-foot Schooner Woodwind

April 20, 2018 @ 5:30 pm - 7:30 pm
|Recurring Event (See all)

One event on April 21, 2018 at 5:30 pm

Schooner Woodwind: Annapolis Sailing Cruises, 80 Compromise St
Annapolis, MD 21401 United States
+ Google Map
$76.00

Sail away on one of our first sunset sails of the season. Enjoy great appetizers, cocktails, wine and beer as we enjoy the scenery of the Chesapeake Bay. Cruise includes delicious appetizers, two drink vouchers and a sunset sail from 5:30pm-7:30pm. Menu will be announced soon. Cruise departs from the Annapolis Waterfront Hotel and tickets are $76/adult with a maximum of 35 guests. www.schoonerwoodwind.com 410-263-7837

Find out more »

Sailor’s Delight” Friday Night Cocktail Sailing on the Woodwind

April 20, 2018 @ 5:30 pm - 7:30 pm
Schooner Woodwind: Annapolis Sailing Cruises, 80 Compromise St
Annapolis, MD 21401 United States

Sail away on one of our first sunset sails of the season. Enjoy great appetizers, cocktails, wine and beer as you enjoy the scenery of the Chesapeake Bay. Cruise includes appetizers, two drink vouchers and a sunset sail. Depart Annapolis at 5:30 pm, return at 7:30 pm. Tickets are $76 per adult with a maximum of 35 guests. Cocktail Cruise Menu: Assortment of Savory Dips served with Crostini and Crackers Pimento Cheese Olivada (Black Olive Spread) Hummus Sun Dried Tomato…

Find out more »

An Intimate, Acoustic Show with JESSE RUBEN aboard the Schooner Woodwind

April 29, 2018 @ 11:30 am - 2:30 pm
Schooner Woodwind: Annapolis Sailing Cruises, 80 Compromise St
Annapolis, MD 21401 United States
+ Google Map
$86

An Intimate, Acoustic Show with JESSE RUBEN aboard the Schooner Woodwind for a concert on a beautiful sailing boat, including a light delicious brunch and a relaxing sail. Jesse Ruben is a Philly born singer/songwriter currently living in Brooklyn. His songs have been heard on TV shows such as One Tree Hill, Degrassi, Switched at Birth, and Teen Mom. His most recent single, “This Is Why I Need You”, reached the top 10 in 12 different countries, and has been…

Find out more »

May 2018

Beer Tasting Sailing Cruise aboard the 74-foot Schooner Woodwind

May 1, 2018 @ 5:30 pm - 7:30 pm
|Recurring Event (See all)

An event every week that begins at 5:30 pm on Tuesday, repeating until May 29, 2018

Schooner Woodwind: Annapolis Sailing Cruises, 80 Compromise St
Annapolis, MD 21401 United States
+ Google Map
$12 – $46

Sample beer from DC Brau Brewery while enjoying the beautiful sunset under full sail. A brewery representative will be aboard and ticket price includes 3 samples of beer. When co-founders Brandon Skall and Jeff Hancock opened the doors to their brewery in 2011 on Bladensburg Road in NE Washington, DC Brau Brewing Company became the first packaging brewery inside the District of Columbia since 1956. DC Brau’s signature brews include: The Public (Pale Ale), The Corruption (IPA), The Citizen (Belgian-style…

Find out more »

Wednesday Night Sailboat Racing Cruise aboard the 74-foot Schooners Woodwind & Woodwind II

May 2, 2018 @ 5:30 pm - 7:30 pm
|Recurring Event (See all)

An event every week that begins at 5:30 pm on Wednesday, repeating until May 30, 2018

Schooner Woodwind: Annapolis Sailing Cruises, 80 Compromise St
Annapolis, MD 21401 United States
+ Google Map
$12 – $46

Be part of the action every Wednesday night as the two wooden schooners, Woodwind & Woodwind II, compete in Annapolis’ summer racing series. Help the crew or sit back and watch 130 racing sailboats! Cruises depart from the Annapolis Waterfront Hotel. 5:30pm-7:30pm. Tickets are $46/adult, $29/child under 12 yrs. and include a soft drink and snack. Beer and wine are available for purchase. www.schoonerwoodwind.com 410-263-7837

Find out more »

Sailing Cruise with live music aboard the 74-foot Schooner Woodwind

May 3, 2018 @ 5:30 pm - 7:30 pm
Schooner Woodwind: Annapolis Sailing Cruises, 80 Compromise St
Annapolis, MD 21401 United States
+ Google Map
$12 – $46

Enjoy music performed by Stick Mob during a two hour sunset cruise aboard the 74-foot Schooner Woodwind. Matt and Katie play with the Stick Mob, a folk-ameri-something-grass-n-stuff quintet from the hillbilly wilds of the nation’s capital. They love to play and sing beautiful old melancholy tunes as well foot-stomping originals. Cruise departs from the Annapolis Waterfront Hotel at 5:30pm and returns at 7:30pm. Tickets are $46/adult, $29/child under 12 yrs. and include a soft drink and snack. Beer and wine…

Find out more »

: Sailing Cruise with live music aboard the 74-foot Schooner Woodwind

May 10, 2018 @ 5:30 pm - 7:30 pm
Schooner Woodwind: Annapolis Sailing Cruises, 80 Compromise St
Annapolis, MD 21401 United States
+ Google Map
$12 – $46

Enjoy music performed by Stefan Heur during a two hour sunset cruise aboard the 74-foot Schooner Woodwind. Stefan Heuer is an award-winning singer songwriter residing in Washington, DC. His original music has reached ears all over the world. Heuer's newly released EP entitled "Jungle Dreams" is a sonic portrayal of his journey through losing a loved one. Stefan frequently performs at venues in DC and NOVA. Stefan mirrors elements of soul and blues, but his original music holds a strong…

Find out more »

Mother’s Day Brunch Sailing Cruise aboard the 74-foot, Schooner Woodwind

May 13, 2018 @ 10:00 am - 1:00 pm
Schooner Woodwind: Annapolis Sailing Cruises, 80 Compromise St
Annapolis, MD 21401 United States
+ Google Map
$12 – $92

This wonderful three-hour brunch cruise includes one free Bloody Mary or Mimosa and delicious food: homemade scones, quiche Lorraine squares, baked smoky salmon with hearty bread, grilled flank steak, fresh fruit salad, orange juice and homemade biscotti. Cruise departs from the Annapolis Waterfront Hotel at 10:00am, returning at 1:00pm. Tickets are $92/adult and $52/child under 12 yrs., maximum 40 guests. www.schoonerwoodwind.com 410-263-7837 Buy Tickets: https://schoonerwoodwind.zaui.net/modules/webBooking/index.php?action=Details&activityDate=1526184000&id=55

Find out more »

May Wine in the Wind

May 13, 2018 @ 4:00 pm - 6:00 pm
Schooner Woodwind: Annapolis Sailing Cruises, 80 Compromise St
Annapolis, MD 21401 United States
+ Google Map
$81

Join us for a two hour sail around the Chesapeake Bay while sampling wonderful wines. A representative from a winery will introduce you to four special wines while we are under sail. The cruise will be a relaxing sail including 3-oz samples of each of the four wines featured. Along with each wine is a delicious, perfectly paired bite (we call them magnificent morsels) to go with each wine. Includes a take-home, boat friendly, wine glass by Go Vino with…

Find out more »

“Sail Away” while learning the history of the Chesapeake Bay aboard the 74-foot Schooner Woodwind:

May 14, 2018 @ 6:30 pm - 8:30 pm
|Recurring Event (See all)

An event every week that begins at 6:30 pm on Monday, repeating until May 28, 2018

Schooner Woodwind: Annapolis Sailing Cruises, 80 Compromise St
Annapolis, MD 21401 United States
+ Google Map
$12 – $46

Enjoy a historically guided 2 hour sunset sailing cruise with one of our local historians. Cruises depart from the Annapolis Waterfront Hotel at 6:30pm and return at 8:30pm. Tickets are $46/adult, $29/child under 12 yrs. and include a soft drink and snack. Beer and wine are available for purchase. www.schoonerwoodwind.com 410-263-7837

Find out more »

Sailing Cruise with live music aboard the 74-foot Schooner Woodwind

May 17, 2018 @ 6:30 pm - 8:30 pm
Schooner Woodwind: Annapolis Sailing Cruises, 80 Compromise St
Annapolis, MD 21401 United States
+ Google Map
$12 – $46

Enjoy music performed by a local artist during a two hour sunset cruise aboard the 74-foot Schooner Woodwind. Cruises depart from the Annapolis Waterfront Hotel at 6:30pm and return at 8:30pm. Tickets are $46 adults, $29 children under 12 yrs. and include a soft drink and snack. Beer and wine are available for purchase. www.schoonerwoodwind.com 410-263-7837

Find out more »

Sailing Cruise with live music aboard the 74-foot Schooner Woodwind

May 24, 2018 @ 8:00 am - 5:00 pm
Schooner Woodwind: Annapolis Sailing Cruises, 80 Compromise St
Annapolis, MD 21401 United States
+ Google Map
https://www.schoonerwoodwind.com/events/category/music/

Enjoy music performed by Don Shappelle during a two hour sunset cruise aboard the 74-foot Schooner Woodwind. Don Shappelle sings and writes many songs about the Chesapeake Bay, it’s people, it’s boats and the many rivers that flow into the bay. Don grew up on the banks of the mighty Susquehanna River so many of his songs are influenced by that great river. Don also performs sailing and water oriented songs by other artists. Don Shappelle accompanies his songs on…

Find out more »

Sailing Cruise with live music aboard the 74-foot Schooner Woodwind:

May 31, 2018 @ 6:30 pm - 8:30 pm
Schooner Woodwind: Annapolis Sailing Cruises, 80 Compromise St
Annapolis, MD 21401 United States
+ Google Map
$12 – $46

Enjoy music performed by The Eastport Oyster Boys during a two hour sunset cruise aboard the 74-foot Schooner Woodwind. Recognized as the City of Annapolis and the Chesapeake Bay’s Musical Goodwill Ambassadors The Eastport Oyster Boys love to share their musical celebration of life on the shores of the Chesapeake and its scenic rivers with audiences of all ages. For two decades they have educated, amused and delighted thousands with their wit, wisdom and special message of stewardship and appreciation…

Find out more »

June 2018

“Sail Away” while learning the history of the Schooner Woodwind aboard the 74-foot Schooner Woodwind

June 4, 2018 @ 6:30 pm - 8:30 pm
Schooner Woodwind: Annapolis Sailing Cruises, 80 Compromise St
Annapolis, MD 21401 United States
+ Google Map
$29 – $46

During our 25th Anniversary Celebration Week, we invite you to join us for a special sunset sail with John Scarano and Ken Kaye as they discus the History of the Schooner Woodwind~ From Dream to Reality. 25 years ago, Ken, Ellen, and Jennifer Kaye had a dream realized with the building of the Schooner Woodwind at the Scarano Boat Yard, the second schooner that Scarano built. Listen to the Naval Architect and Designer of the boats talk with Ken Kaye…

Find out more »

Beer Tasting Sailing Cruise aboard the 74-foot Schooner Woodwind: 25 Years of Suds and Sails

June 5, 2018 @ 6:30 pm - 8:30 pm
Schooner Woodwind: Annapolis Sailing Cruises, 80 Compromise St
Annapolis, MD 21401 United States
+ Google Map
$12 – $46

During our 25th Anniversary Celebration Week, we invite you to join us for a special sunset sail with Hugh Sisson from Heavy Seas Brewery as he talks about how the craft beer industry has changed in Maryland in the past 25 years. Come reminisce with us and sample 3 beers from Heavy Seas Brewery while enjoying the beautiful sunset under full sail on our 74-foot schooner. Cruises depart from the Annapolis Waterfront Hotel at 6:30pm and return at 8:30pm Tickets…

Find out more »

Wednesday Night Sailboat Racing Cruise aboard the 74-foot Schooners Woodwind & Woodwind II

June 6, 2018 @ 6:30 pm - 8:30 pm
Schooner Woodwind: Annapolis Sailing Cruises, 80 Compromise St
Annapolis, MD 21401 United States
+ Google Map
$12 – $46

During our 25th Anniversary Celebration Week, we invite you to join us for a special sunset sail with Captain Jen and Captain Ken as they once again bring on the competition of Father vs. Daughter. Who’s boat will be on? Be part of the action as the Woodwind & Woodwind II, compete in Annapolis’ summer racing series. Help the crew or sit back and watch 130 racing sailboats! Cruises depart from the Annapolis Waterfront Hotel at 6:25pm and returns 8:30pm.…

Find out more »

Sailing Cruise with live music aboard the 74-foot Schooner Woodwind:

June 7, 2018 @ 8:00 am - 5:00 pm
Schooner Woodwind: Annapolis Sailing Cruises, 80 Compromise St
Annapolis, MD 21401 United States
+ Google Map
$12 – $46

During our 25th Anniversary Celebration Week, we invite you to join us for a special sunset sail to enjoy music performed by Crab Alley Lite during a two hour sunset cruise aboard the 74-foot Schooner Woodwind. They were one of the first bands to play on the Woodwind 25 years ago. Crab Alley founders Jeff Holland and Janie Meneely will join up for a Woodwind cruise and regale the crew with their original songs of the Bay and beyond. Serious…

Find out more »

June Wine in the Wind (Italy): Two hour sail on the Chesapeake Bay, sampling wines

June 10, 2018 @ 4:00 pm - 6:00 pm
Schooner Woodwind: Annapolis Sailing Cruises, 80 Compromise St
Annapolis, MD 21401 United States
+ Google Map
$12 – $46

A representative from the Tommasi Family Estates will introduce you to four special wines while we are under sail. The cruise will be a relaxing sail including 3-oz samples of each of the four wines featured. Along with each wine is a delicious, perfectly paired bite (we call them magnificent morsels) to go with each wine. Includes a take-home, boat friendly, wine glass by Go Vino with the Woodwind’s logo on it. You will be able to raise the sails,…

Find out more »

“Sail Away” while learning the history of the Chesapeake Bay aboard the 74-foot Schooner Woodwind

June 11, 2018 @ 6:30 pm - 8:30 pm
Schooner Woodwind: Annapolis Sailing Cruises, 80 Compromise St
Annapolis, MD 21401 United States
+ Google Map
$12 – $46

The Life of Frederick Douglas with William Ridgley. Frederick Douglass was described as a living counter-example that blacks we’re ignorant and unable to learn to read or write. Come learn how his everyday life was as a slave and how he was able to escape slavery. Born in Baltimore, raised in Annapolis, William grew up in Downtown Annapolis. He graduated Annapolis Senior High in 1989 and joined the Marine Corps. He served during Operation Desert Storm (92) and Operation Groundhog…

Find out more »

: Beer Tasting Sailing Cruise aboard the 74-foot Schooner Woodwind

June 12, 2018 @ 6:30 pm - 8:30 pm
|Recurring Event (See all)

An event every week that begins at 6:30 pm on Tuesday, repeating until June 26, 2018

Schooner Woodwind: Annapolis Sailing Cruises, 80 Compromise St
Annapolis, MD 21401 United States
+ Google Map
$12 – $46

Sample beer from Heavy Seas Brewery while enjoying the beautiful sunset under full sail. A brewery representative will be aboard and ticket price includes 3 samples of beer. Beer takes us on adventures. It allows us to discover new flavors and exotic cultures. Our quest for great beer can lead anywhere, from corner pubs to faraway breweries. For Heavy Seas founder, Hugh Sisson, beer altered the trajectory of his life. In 1980, intending to become a stage actor and director,…

Find out more »

Wednesday Night Sailboat Racing Cruise aboard the 74-foot Schooners Woodwind & Woodwind II

June 13, 2018 @ 6:30 pm - 8:30 pm
|Recurring Event (See all)

An event every week that begins at 6:30 pm on Wednesday, repeating until June 27, 2018

Schooner Woodwind: Annapolis Sailing Cruises, 80 Compromise St
Annapolis, MD 21401 United States
+ Google Map
$12 – $46

Be part of the action every Wednesday night as the two wooden schooners, Woodwind & Woodwind II, compete in Annapolis’ summer racing series. Help the crew or sit back and watch 130 racing sailboats! Cruises depart from the Annapolis Waterfront Hotel. 6:25pm and returns at 8:30pm. Tickets are $46/adult, $29/child under 12 yrs. and include a soft drink and snack. Beer and wine are available for purchase. www.schoonerwoodwind.com 410-263-7837

Find out more »

Sailing Cruise with live music aboard the 74-foot Schooner Woodwind

June 14, 2018 @ 6:30 pm - 8:30 pm
Schooner Woodwind: Annapolis Sailing Cruises, 80 Compromise St
Annapolis, MD 21401 United States
+ Google Map
$12 – $46

Enjoy music performed by Mike & Kelly Lange during a two hour sunset cruise aboard the 74-foot Schooner Woodwind. Mike and Kelly Lange are a husband and wife ukulele duo. Lifelong boaters, Mike & Kelly sing original and classic material, some with a maritime theme and some with a broader reach. Mike has played thousands of gigs in the mid-Atlantic and a handful overseas during the past several decades. Over the years he has performed with many popular bands in…

Find out more »

Father’s Day Brunch Sailing Cruise aboard the 74-foot Schooner Woodwind:

June 17, 2018 @ 10:00 am - 1:00 pm
Schooner Woodwind: Annapolis Sailing Cruises, 80 Compromise St
Annapolis, MD 21401 United States
+ Google Map
$12 – $92

Our Father’s Day Brunch Sail departs Annapolis for a three-hour Brunch cruise at 10:00 am and returns at 1:00 pm. Sailing cruise includes one free Bloody Mary or Mimosa and delicious food: homemade scones, quiche lorraine squares, blackened salmon with cusabi sauce served with hearty bread, grilled flank steak, fresh fruit salad, orange juice and homemade biscotti. $92 per adult, $52 per child. Maximum 35 guests. Cruise depart from the Annapolis Waterfront Hotel. 10:00am, returning at 1:00pm. www.schoonerwoodwind.com 410-263-7837

Find out more »

Sail Away while learning the history of the Chesapeake Bay aboard the 74-foot Schooner Woodwind

June 18, 2018 @ 6:30 pm - 8:30 pm
Schooner Woodwind: Annapolis Sailing Cruises, 80 Compromise St
Annapolis, MD 21401 United States
+ Google Map
$12 – $46

Legends and Lore of the Annapolis Waterfront by Dave Gendell Dave brings aboard and entertaining and compelling set of stories and insights around Annapolis history, the Naval Academy, the sailing scene, and the personalities that make Annapolis one of the world’s most unique waterfront communities. Cruise departs from the Annapolis Waterfront Hotel at 6:30pm and returns at 8:30pm. Tickets are $46/adult, $29/child under 12 yrs. and include a soft drink and snack. www.schoonerwoodwind.com 410-263-7837

Find out more »

Sailing Cruise with live music aboard the 74-foot Schooner Woodwind

June 21, 2018 @ 6:30 pm - 8:30 pm
Schooner Woodwind: Annapolis Sailing Cruises, 80 Compromise St
Annapolis, MD 21401 United States
+ Google Map
$12 – $46

Enjoy music performed by Kyle Offidani during a two hour sunset cruise aboard the 74-foot Schooner Woodwind. Born and raised in the bay area of Delaware- Kyle Offidani is a musician and songcatcher . Musically- Kyle draws inspiration from World music, Instrumental guitar, Roots, Blues, Soul, and Americana music. When listening to the sounds of Kyle, you will hear echoes of these genres Woven into the tapestry of his songs. Kyle writes with a strong notion of genuinity and vulnerability…

Find out more »

Sail Away” while learning the history of the Chesapeake Bay aboard the 74-foot Schooner Woodwind

June 25, 2018 @ 6:30 pm - 8:30 pm
Schooner Woodwind: Annapolis Sailing Cruises, 80 Compromise St
Annapolis, MD 21401 United States
+ Google Map
$12 – $46

The Key to Annapolis History, by Jeff Holland. The Key to Annapolis history lies right there in the harbor. It can’t be found by looking port; and it can’t by looking starboard. It’s only when you drop the hook that the secret can be found when you anchor, you’ll discover that the bottom of the harbor is only 12 feet down! Cruises depart from the Annapolis Waterfront Hotel at 6:30pm and return at 8:30pm. Tickets are $46/adult, $29/child under 12…

Find out more »

Sailing Cruise with live music aboard the 74-foot Schooner Woodwind

June 28, 2018 @ 6:30 pm - 8:30 pm
Schooner Woodwind: Annapolis Sailing Cruises, 80 Compromise St
Annapolis, MD 21401 United States
+ Google Map
$12 – $46

Enjoy music performed by Deanna Dove during a two hour sunset cruise aboard the 74-foot Schooner Woodwind. Deanna Dove is best known as the “Island Girl” in her hometown for her compositional writing style about her lifelong experiences on the Chesapeake Bay. She has earned a loyal audience for her ability to craft songs that include elements of rock, pop, blues, alt-country and gospel into a distinctly individual style with a universal appeal. The “Island Girl” has established her reputation…

Find out more »

July 2018

Sail Away” while learning the history of the Chesapeake Bay aboard the 74-foot Schooner Woodwind

July 2, 2018 @ 6:30 pm - 8:30 pm
Schooner Woodwind: Annapolis Sailing Cruises, 80 Compromise St
Annapolis, MD 21401 United States
+ Google Map
$12 – $46

Before the Bay Bridge, History of the Chesapeake Bay Beach Resorts by Stephanie Sperling. From the mid-1800s through the 1950s, countless resorts and summer communities sprung up along the shores of the Chesapeake Bay. People from Washington D.C. and Baltimore flocked here using new transportation networks, like steamships, trains, and paved roads. Most resorts featured rustic cabins for rent, swimming piers, and sandy beaches, and some even had animal shows, amusement rides, and gambling halls. Nearly all of these places…

Find out more »

Beer Tasting Sailing Cruise aboard the 74-foot Schooner Woodwind

July 3, 2018 @ 6:30 pm - 8:30 pm
|Recurring Event (See all)

An event every week that begins at 6:30 pm on Tuesday, repeating until July 31, 2018

Schooner Woodwind: Annapolis Sailing Cruises, 80 Compromise St
Annapolis, MD 21401 United States
+ Google Map
$12 – $46

Sample beer from Union Craft Brewery while enjoying the beautiful sunset under full sail. A brewery representative will be aboard and ticket price includes 3 samples of beer. Beer is the union of water, barley, hops and yeast. A brewery is the union of beer, its brewers and the community it serves. Beer Unites! is not just a tagline, its the underlying philosophy of everything we believe in as a business. Good beer brings good people together for good times—and…

Find out more »

Sailing Cruise with live music aboard the 74-foot Schooner Woodwind

July 5, 2018 @ 6:30 pm - 8:30 pm
Schooner Woodwind: Annapolis Sailing Cruises, 80 Compromise St
Annapolis, MD 21401 United States
+ Google Map
$12 – $46

Enjoy music performed by Doug & Tami during a two hour sunset cruise aboard the 74-foot Schooner Woodwind. Tami plays in the Annapolis music scene in a variety of projects (Timmie & Tami, Homegrown, formerly in The Shatners, etc), and is bringing in longtime friend Doug to play sunset sing-alongs with some original tunes sprinkled in as well! Everything from pop to country, we’ll set sail with something for everyone to enjoy! Band’s Facebook: https://www.facebook.com/TamboMusic/ Cruise departs from the Annapolis…

Find out more »

: “Sail Away” while learning the history of the Chesapeake Bay aboard the 74-foot Schooner Woodwind

July 9, 2018 @ 6:30 pm - 8:30 pm
Schooner Woodwind: Annapolis Sailing Cruises, 80 Compromise St
Annapolis, MD 21401 United States
+ Google Map
$12 – $46

Tunes and Tales of the Golden Age of Annapolis by Tom Guay Tom’s fiddle playing takes you on a trip back in time to The Golden Age of Annapolis (1750-1783). Tom plays brings the life and times of Annapolis to life with stories of the social and musical events that enriched the lives of this charming city. He also has a few stories about the fiery events in town that helped turn British America into the fledgling new nation. Tom…

Find out more »

Wednesday Night Sailboat Racing Cruise aboard the 74-foot Schooners Woodwind & Woodwind II:

July 11, 2018 @ 6:30 pm - 8:30 pm
|Recurring Event (See all)

An event every week that begins at 6:30 pm on Wednesday, repeating until July 25, 2018

Schooner Woodwind: Annapolis Sailing Cruises, 80 Compromise St
Annapolis, MD 21401 United States
+ Google Map
$12 – $46

Be part of the action every Wednesday night as the two wooden schooners, Woodwind & Woodwind II, compete in Annapolis’ summer racing series. Help the crew or sit back and watch 130 racing sailboats! Cruises depart from the Annapolis Waterfront Hotel at 6:25pm and return at 8:30pm. Tickets are $46/adult, $29/child under 12 yrs. and include a soft drink and snack. Beer and wine are available for purchase. 410-263-7837

Find out more »

Sailing Cruise with live music aboard the 74-foot Schooner Woodwind:

July 12, 2018 @ 6:30 pm - 8:30 pm
Schooner Woodwind: Annapolis Sailing Cruises, 80 Compromise St
Annapolis, MD 21401 United States
+ Google Map
$29 – $46

Enjoy music performed by Stefan Heuer. Stefan Heuer is a singer songwriter residing in Annapolis, Maryland. His original music as a solo performer has reached ears all over the world. Stefan performs at venues in Annapolis and around the DMV area. Stefan mirrors elements of folk, but his original music holds a strong foundation of blues and soul. Take a look at the band’s website https://www.stefanheuermusic.com and Facebook Page https://www.facebook.com/stefanheuermusic/ Cruise departs from the Annapolis Waterfront Hotel at 6:30pm and…

Find out more »

“Sail Away” while learning the history of the Chesapeake Bay aboard the 74-foot Schooner Woodwind

July 16, 2018 @ 6:30 pm - 8:30 pm
Schooner Woodwind: Annapolis Sailing Cruises, 80 Compromise St
Annapolis, MD 21401 United States
+ Google Map
$29 – $46

Pirates of the Chesapeake Bay by Heather Ersts. Pirates have plied the waters of the Chesapeake Bay for hundreds of years and still do today. Hear tales of Black Beard, the town dubbed the “Nest of Pirates,” and today’s modern pirates as you sail along the same waterways they have sailed. Heather Ersts is a public historian who specializes in heritage education, interpretation, and programming. She most enjoys connecting the public with historic sites and organizations through engaging programs that…

Find out more »

Sailing Cruise with live music aboard the 74-foot Schooner Woodwind

July 19, 2018 @ 8:00 am - 5:00 pm
Schooner Woodwind: Annapolis Sailing Cruises, 80 Compromise St
Annapolis, MD 21401 United States
+ Google Map
$29 – $46

Enjoy music performed by Mike & Kelly Lange during a two hour sunset cruise aboard the 74-foot Schooner Woodwind. Mike and Kelly Lange are a husband and wife ukulele duo. Lifelong boaters, Mike & Kelly sing original and classic material, some with a maritime theme and some with a broader reach. Mike has played thousands of gigs in the mid-Atlantic and a handful overseas during the past several decades. Over the years he has performed with many popular bands in…

Find out more »

“Sail Away” while learning the history of the Chesapeake Bay aboard the 74-foot Schooner Woodwind

July 23, 2018 @ 6:30 pm - 8:30 pm
Schooner Woodwind: Annapolis Sailing Cruises, 80 Compromise St
Annapolis, MD 21401 United States
+ Google Map
$29 – $46

The Oyster Wars by William Ridgely The oyster wars were series of sometimes violent disputes between oyster Pirates and authorities and legal Waterman from Maryland and Virginia in the waters of the Chesapeake Bay and the Potomac River from 1865 until around 1959. Born in Baltimore, raised in Annapolis, William grew up in Downtown Annapolis. He graduated Annapolis Senior High in 1989 and joined the Marine Corps. He served during Operation Desert Storm (92) and Operation Groundhog (Mogadishu, Somalia; 93-94)…

Find out more »

Sailing Cruise with live music aboard the 74-foot Schooner Woodwind

July 26, 2018 @ 6:30 pm - 8:30 pm
Schooner Woodwind: Annapolis Sailing Cruises, 80 Compromise St
Annapolis, MD 21401 United States
+ Google Map
$12 – $46

Enjoy music performed by Ken Wenzel during a two hour sunset cruise aboard the 74-foot Schooner Woodwind. With the release of “…Beneath Potomac Skies” – a 12-song, full-band collection of moments and memories culled from time spent in Washington DC, and many other locales – singer/songwriter/saxophonist Ken Francis Wenzel is eager to introduce his own roots-rock, country jazz-tinged take on love, learning, and life in contemporary America. Featuring several guest appearances from some of the DC area’s finest musicians, “…Beneath…

Find out more »

Everything Local Dinner Cruise aboard the Schooner Woodwind:

July 29, 2018 @ 6:30 pm - 9:00 pm
Schooner Woodwind: Annapolis Sailing Cruises, 80 Compromise St
Annapolis, MD 21401 United States
+ Google Map
$111

Enjoy our “Everything Local” themed dinner and drinks while under full sail on the Chesapeake Bay. This cruise will focus on food that you can grow yourself or purchase locally. Our caterer, Palate Pleasers, prides themselves on getting produce, meats, and many other ingredients from the local area. For our wonderful selection of alcoholic beverages we choose independent breweries and distilleries within a 70-mile radius. Menu To Be Determined. Tickets are $111 per adult and include three course dinner, 3…

Find out more »

September 2018

Sail Away” while learning the history of the Chesapeake Bay aboard the 74-foot Schooner Woodwind

September 3, 2018 @ 5:30 pm - 7:30 pm
Schooner Woodwind: Annapolis Sailing Cruises, 80 Compromise St
Annapolis, MD 21401 United States
+ Google Map
$12 – $46

History Cruise: Tale of 2 Cities: by Janet Williman Since 1845, America’s sailing capital and our Navy intertwined to engage with interesting characters from all of over the world. Delight in nautical skyline views; while discovering amazing, amusing and sometimes surprising stories. For example, a connection with the movie, King Kong is revealed during our sail. Janet Williman is a native of the Chesapeake Region. Her lifelong passions for history and Bay ecology were pursued at Johns Hopkins University; and…

Find out more »

Beer Tasting Sailing Cruise aboard the 74-foot Schooner Woodwind

September 4, 2018 @ 5:30 pm - 7:30 pm
|Recurring Event (See all)

An event every week that begins at 5:30 pm on Tuesday, repeating until September 25, 2018

Schooner Woodwind: Annapolis Sailing Cruises, 80 Compromise St
Annapolis, MD 21401 United States
+ Google Map
$12 – $46

Sample beer from DC Brau Brewery while enjoying the beautiful sunset under full sail. A brewery representative will be aboard and ticket price includes 3 samples of beer. When co-founders Brandon Skall and Jeff Hancock opened the doors to their brewery in 2011 on Bladensburg Road in NE Washington, DC Brau Brewing Company became the first packaging brewery inside the District of Columbia since 1956. DC Brau’s signature brews include: The Public (Pale Ale), The Corruption (IPA), The Citizen (Belgian-style…

Find out more »

Sailing Cruise with live music aboard the 74-foot Schooner Woodwind

September 6, 2018 @ 8:00 am - 5:00 pm
Schooner Woodwind: Annapolis Sailing Cruises, 80 Compromise St
Annapolis, MD 21401 United States
+ Google Map
$12 – $46

Enjoy music performed by The Eastport Oyster Boys during a two hour sunset cruise aboard the 74-foot Schooner Woodwind. Recognized as the City of Annapolis and the Chesapeake Bay’s Musical Goodwill Ambassadors The Eastport Oyster Boys love to share their musical celebration of life on the shores of the Chesapeake and its scenic rivers with audiences of all ages. For two decades they have educated, amused and delighted thousands with their wit, wisdom and special message of stewardship and appreciation…

Find out more »

Black Ankle Winery Dinner Cruise

September 9, 2018 @ 5:30 pm - 8:00 pm
Schooner Woodwind: Annapolis Sailing Cruises, 80 Compromise St
Annapolis, MD 21401 United States
+ Google Map
$111.00

Captain Jen fell in love with this winery’s location, wine and people that work at Black Ankle Winery. Black Ankle Vineyards is the culmination of a long-time dream of founders Ed Boyce and Sarah O’Herron (that’s us). They believe that the central Maryland Piedmont, sitting at the foothills of the Appalachian Mountains, has the right mix of rolling hills, rocky, low-fertility soils, regular breezes, sunshine and rain to be the home of some truly delicious wines — wines that express…

Find out more »

Sail Away” while learning the history of the Chesapeake Bay aboard the 74-foot Schooner Woodwind

September 10, 2018 @ 5:30 pm - 7:30 pm
Schooner Woodwind: Annapolis Sailing Cruises, 80 Compromise St
Annapolis, MD 21401 United States
+ Google Map
$12 – $46

History Cruise: Environmental History of the Bay by Alice Christman How is the Bay? It’s a popular question to ask when you are cruising. But how has the Bay changed is also a good question. We’ll talk about the environmental history of the Bay, starting with what John Smith saw leading up to today. Hosted by the Chesapeake Bay Foundation. Cruises depart from the Annapolis Waterfront Hotel at 5:30pm and return at 7:30pm. Tickets are $46/adult, $29/child under 12 yrs.…

Find out more »

“Sail Away” while learning the history of the Chesapeake Bay aboard the 74-foot Schooner Woodwind

September 17, 2018 @ 5:30 pm - 7:30 pm
Schooner Woodwind: Annapolis Sailing Cruises, 80 Compromise St
Annapolis, MD 21401 United States
+ Google Map
$12 – $46

History Cruise: Steamboats and Ferries of the Bay, by Mechelle Kerns Steamboats and Ferries were once common on the Severn River. They transported people, agricultural produce, and the seafood bounty that made the Chesapeake famous. They also were part of the leisure travel industry that has brought tourist to our beautiful capital city on the water for 100s of years. Dr. Mechelle Kerns is a Historical Archaeologist and History Professor (USNA and UMUC). She specializes in topics related to Colonial…

Find out more »

Sailing Cruise with live music aboard the 74-foot Schooner Woodwind

September 20, 2018 @ 5:30 pm - 7:30 pm
Schooner Woodwind: Annapolis Sailing Cruises, 80 Compromise St
Annapolis, MD 21401 United States
+ Google Map
$12 – $46

Enjoy music performed by Jason Ager during a two hour sunset cruise aboard the 74-foot Schooner Woodwind. Jason Ager is a dedicated father, a passionate college professor, and a hyper-literate original songwriter. Balancing a PhD in German Literature with a few days a week as a stay-at-home dad, Jason still plays more than 100 shows a year in the Mid-Atlantic region and beyond. On his third album, Porchlight, Ager’s talent as a storyteller shines as he weaves together the academic…

Find out more »

Classic Wooden Boat Regatta

September 23, 2018 @ 11:00 am - 2:30 pm
Schooner Woodwind: Annapolis Sailing Cruises, 80 Compromise St
Annapolis, MD 21401 United States
+ Google Map
$86

Participate in the National Sailing Hall of Fame Classic Wooden Boat Regatta. They have invited the Woodwinds’ to participate in the race in the “Spirit of Tradition Class”. The course is approximately 5.4 NM and takes place in the Severn River. It is a 3 lap race with pursuit style race. Each boat has a rating, and by the rating they will get a start time. The pursuit style race challenges the competitors to sail through the other race boats…

Find out more »

September Wine in the Wind

September 23, 2018 @ 3:00 pm - 5:00 pm
Schooner Woodwind: Annapolis Sailing Cruises, 80 Compromise St
Annapolis, MD 21401 United States
+ Google Map
$81

New Zealand to California. Join us for a two hour sail around the Chesapeake Bay while sampling wonderful wines from the Goldschmidt Winery, Alexander Valley & Beyond. The representative from the winery will introduce you to four special wines while we are under sail. The cruise will be a relaxing sail including 3-oz samples of each of the four wines featured. Along with each wine is a delicious, perfectly paired bite (we call them magnificent morsels) to go with each…

Find out more »

“Sail Away” while learning the history of the Chesapeake Bay aboard the 74-foot Schooner Woodwind

September 24, 2018 @ 5:30 pm - 7:30 pm
Schooner Woodwind: Annapolis Sailing Cruises, 80 Compromise St
Annapolis, MD 21401 United States
+ Google Map
$12 – $46

The Maritime Republic of Eastport…Still Revolting After All These Years with Kevin Brooks Join Eastport Oyster Boy and Local Revolutionary Kevin “Brother Shucker” Brooks for an entertaining look at the upstart “Maritime Republic of Eastport”‘s interesting and down right fun history through the past four centuries. Historic forts, world class boat building centers, proud diversity, resilient waterman and becoming the ever fun and ever mighty Maritime Republic of Eastport!… Join Kevin for this fun, irreverent and music filled journey through…

Find out more »

Sailing Cruise with live music aboard the 74-foot Schooner Woodwind

September 27, 2018 @ 5:30 pm - 7:30 pm
Schooner Woodwind: Annapolis Sailing Cruises, 80 Compromise St
Annapolis, MD 21401 United States
+ Google Map
$12 – $46

Enjoy music performed by Stefan Heuer. Stefan Heuer is a singer songwriter residing in Annapolis, Maryland. His original music as a solo performer has reached ears all over the world. Stefan performs at venues in Annapolis and around the DMV area. Stefan mirrors elements of folk, but his original music holds a strong foundation of blues and soul. Take a look at the band’s website https://www.stefanheuermusic.com and Facebook Page https://www.facebook.com/stefanheuermusic/. Cruises depart from the Annapolis Waterfront Hotel at 5:30pm and…

Find out more »

Sailing Cruise with live music aboard the 74-foot Schooner Woodwind

September 27, 2018 @ 5:30 pm - 7:30 pm
Schooner Woodwind: Annapolis Sailing Cruises, 80 Compromise St
Annapolis, MD 21401 United States
+ Google Map
$12 – $46

Enjoy music performed by Stefan Heuer. Stefan Heuer is a singer songwriter residing in Annapolis, Maryland. His original music as a solo performer has reached ears all over the world. Stefan performs at venues in Annapolis and around the DMV area. Stefan mirrors elements of folk, but his original music holds a strong foundation of blues and soul. Take a look at the band’s website https://www.stefanheuermusic.com and Facebook Page https://www.facebook.com/stefanheuermusic/. Cruises depart from the Annapolis Waterfront Hotel at 5:30pm and…

Find out more »

Sailing Cruise with live music aboard the 74-foot Schooner Woodwind

September 27, 2018 @ 5:30 pm - 7:30 pm
Schooner Woodwind: Annapolis Sailing Cruises, 80 Compromise St
Annapolis, MD 21401 United States
+ Google Map
$12 – $46

Enjoy music performed by Stefan Heuer. Stefan Heuer is a singer songwriter residing in Annapolis, Maryland. His original music as a solo performer has reached ears all over the world. Stefan performs at venues in Annapolis and around the DMV area. Stefan mirrors elements of folk, but his original music holds a strong foundation of blues and soul. Take a look at the band’s website https://www.stefanheuermusic.com and Facebook Page https://www.facebook.com/stefanheuermusic/. Cruises depart from the Annapolis Waterfront Hotel at 5:30pm and…

Find out more »

October 2018

Brews in the Breeze Lunch Cruise aboard the 74-foot Schooner Woodwind

October 7, 2018 @ 11:00 am - 1:30 pm
Schooner Woodwind: Annapolis Sailing Cruises, 80 Compromise St
Annapolis, MD 21401 United States
+ Google Map
$84

Join the Woodwind crew for an afternoon of beer tasting along with a delicious lunch. After we raise all our sails, we will start the tasting with the lightest of the four beers Tickets are $86 per adult and include lunch, four 6 oz. beers, and unlimited soda and water. Additional beer will be available for purchase. Maximum 35 guests Due to the Sail Boat Show ~ Cruise departs from the Annapolis City Marina in Eastport at 11:00am and returns…

Find out more »

The Annual Great Chesapeake Bay Schooner Race Start Watch aboard the Schooner Woodwind II

October 11, 2018 @ 12:00 pm - 3:00 pm
Schooner Woodwind: Annapolis Sailing Cruises, 80 Compromise St
Annapolis, MD 21401 United States
+ Google Map
$50 – $89

: The Annual Great Chesapeake Bay Schooner Race Start Watch aboard the Schooner Woodwind II: Join in the excitement and watch the start of the race. Tickets* are $89 per adult and $50 per child and include bagged lunch bottled water, soft drinks, and snacks. Beer and wine are available for purchase. *$10 of each ticket purchased will be donated to the Great Chesapeake Bay Schooner Race, a non-profit organization that races to save the Bay in conjunction with the…

Find out more »

Lighthouses of the Chesapeake Bay Sailing Cruise aboard the 74-foot Schooner WoodwindLighthouses of the Chesapeake Bay Sailing Cruise aboard the 74-foot Schooner Woodwind

October 14, 2018 @ 10:30 am - 2:30 pm
Schooner Woodwind: Annapolis Sailing Cruises, 80 Compromise St
Annapolis, MD 21401 United States
+ Google Map
$58 – $96

Sail by as many as 3 different lighthouses while learning about their history, importance, and present day condition from a guest lecturer from the Chesapeake Chapter of the US Lighthouse Society. The cruise includes a box lunch, soft drinks and snacks. Beer and wine are available for purchase. Due to the Power Boat Show ~ Cruise departs from the Annapolis City Marina in Eastport at 10:30am, returning at 2:30pm Tickets are $96/adult and $58/child under 12 yrs. with a children’s…

Find out more »
+ Export Events