Schooner Woodwind

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

Student drivers

Maddy, Ellie, and Coraline setting sail for their first Woodwind cruise! A great time was had by all! Photo by Patricia Lopresti of Plympton, Massachusetts

Thomas Point lighthouse

This is Thomas Point Lighthouse as we approached from Annapolis. I like it because you can see how high the winds were by looking at the waves. Photo by Rachel Kimboko of Washington, DC

Sunset Race

Enjoying a view of Woodwind II during our sunset cruise race! (we won!) Photo by Caitlin Brutger of St. Joseph, Mn

Navy Veteran at Helm

Korean War Navy Vet. My dad. We were married in Annapolis in 2011 and took everyone on board for a reception. My favorite pic of my dad who has since passed. Photo by Kristen Hildreth of Medina, Oh

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