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. 7/20 to 8/27/21 <------![Homestead Gardens](https://www.eyeonannapolis.net/wp-content/uploads/2021/06/CrapeMyrtle-2021.jpg")
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4/26 to 5/9 <----- ![Homestead Gardens Herb & Veggie Weekend](https://www.eyeonannapolis.net/wp-content/uploads/2021/04/HG-HERB-VEGGIE-APR21.jpg")
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SHamrock Feb 15 to mar 31 2021 
Tag: Sailing
12th Annual Classic Wooden Sailboat Race
Come out and see a spectacle of beautiful classic wooden sailboats as they race along the mouth of the Severn River! The race will take place on Sunday, September 12 […]
12th Annual Classic Wooden Sailboat Race
Come out and see a spectacle of beautiful classic wooden sailboats as they race along the mouth of the Severn River to showcase their history and elegant design! The race […]
CRAB Cup
Join Chesapeake Region Accessible Boating on August 21 for it’s 15th annual CRAB Cup at the Eastport Yacht Club and party, Race and Poker Pursuit 12-3pm & shore party 4-9pm […]
Singles on Sailboats Brunch
Singles on Sailboats is holding our final brunch of the winter with speaker Kristen Berry of Gale Force Sailing. His topic is Sailing with Purpose. Kristen is a full-time sailing […]
Singles on Sailboats Sailing Skills Seminars
Save the Date! Saturday, February 9, 2020, Singles on Sailboats (SOS) will hold a SASSY event OPEN TO ALL: Non-Members, novice to expert sailors. A day of Seminars, Awards, Skills, […]
Women’s Sailing Club of Annapolis
Please join us June 27th at 6:30 PM for a fun event to go over all the parts of the boat before you would set sail. (You have to sign […]
Women’s Sailing Club of Annapolis
Suddenly SIngle Handed. This vital workshop will teach you how to cope with an emergency situation, determining what needs to be done and the order to do it. Here you […]
Women’s Sailing Club of Annapolis
Please join us March 7th at 7pm for a Woman’s Sailing Workshop. All skill levels Welcome. Suddenly SIngle Handed. This vital workshop will teach you how to cope with an […]
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
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 […]
The Annual Great Chesapeake Bay Schooner Race Start Watch aboard the Schooner Woodwind II
: 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 […]
Brews in the Breeze Lunch Cruise aboard the 74-foot Schooner Woodwind
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 […]
Weems & Plath Tent Sale
Enjoy deep discounts on discontinued, overstock & sample nautical and weather instruments at our 27th Annual Tent Sale. A portion of sales from Saturday, Oct. 6th will be donated to […]
Sailing Cruise with live music aboard the 74-foot Schooner Woodwind
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. […]
Sailing Cruise with live music aboard the 74-foot Schooner Woodwind
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. […]
Sailing Cruise with live music aboard the 74-foot Schooner Woodwind
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. […]
“Sail Away” while learning the history of the Chesapeake Bay aboard the 74-foot Schooner Woodwind
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 […]
September Wine in the Wind
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 […]
Classic Wooden Boat Regatta
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 […]
Sailing Cruise with live music aboard the 74-foot Schooner Woodwind
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 […]
“Sail Away” while learning the history of the Chesapeake Bay aboard the 74-foot Schooner Woodwind
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 […]
Sail Away” while learning the history of the Chesapeake Bay aboard the 74-foot Schooner Woodwind
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 […]
Black Ankle Winery Dinner Cruise
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 […]
