Schooner Woodwind

Now Sailing for the 2026 Season — Book Your Cruise Today!

Point of Sail

All Sails up on the Woodwind and a beautiful, breezy, late June day on the Bay! We were sailing fast and made it just north of the Bay Bridge that day. A Great Woodwind Sail! Photo by Eric Pritchett of Staunton, Virginia

Sailing under the Bay Bridge

Schooner heading under the Bay Bridge

Sailing on the Schooner Woodwind is an amazing experience anytime, but on this day the wind was strong enough to take us under the Bay Bridge…what a thrill!! Photo by Kim Gregory of Annapolis, MD

Baby”bump” on Board

Women silhouetted in the sunset on a sail

My husband took this in 2009, I was about 5 months pregnant, so it was my daughter’s first boat ride 🙂 We were celebrating my husband’s birthday on board the Woodwind. Beautiful, breathtaking sunset as well! Photo by Joy Almendarez of Linthicum Heights, Maryland

Helm Watch

Women in pink with dark cap on sailing the schooner

Seaman Sandy standing the helm watch. Photo by John Davidowski of Vacaville, California

Having fun on the Schooner Woodwind

Couple enjoying beverages and a sail on a sunny blue sky day

One of the great memories of Annapolis sailing on the Woodwind. My lovely shipmate surprised me the morning of sailing. As a retired Coastie, I was taken back to the good old days of being out at sea. Thank you for a wonderful experience. Photo by John Davidowski of Vacaville, California

Great Day on the Bay

Beautiful shot of both sides of the Bay Bridge as the schooner sails under

Strong winds on our 5th voyage aboard the Woodwind in 10 years took us beyond the impressive Bay Bridge. Many thanks to the crew for making our weekend in Annapolis most memorable. -Lew Morris and Kay Rupert Photo by Lew Morris of Alexandria, Virginia

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