Schooner Woodwind

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

Mr. Jack

This is Jack’s 11th time sailing the Woodwind with his wife Julie. I met them last year when we were both on. We stay in touch on FB because of that sail and our love for sailing. So when they came this year they invited me to join them for a meet up 🙂 Photo … Read more

Perfect Sunset

Picture of the Woodwind 1 from the Woodwind 2 while racing on the last night of Wednesday night Races. Photo by Stacie Zarriello of Annapolis, MD

Sunset on the Schooner

My husband and I took a sunset cruise on the Schooner Woodwind on Aug 16th. The crew was absolutely amazing. I was excited and expected that it would be fun but our expectations were surpassed. Lovely boat, crew and beautiful bay. We look forward to returning and will most definitely be cruising with you all … Read more

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