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…

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…

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…

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…

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!

: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…

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…

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!

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…

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…

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…

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…

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…

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!

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…

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…

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…

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…

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…

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…

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…

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…

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

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…

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…

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…

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…

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…

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…

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.…

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…

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…

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…

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…

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.…

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…

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…

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

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…

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…