Schooner Woodwind

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

Girls Just Wanna Have Fun!

My daughter and I decided to visit Annapolis and booked this sunset sailing. This was one of the best decisions I’ve made in some time! Everything from the ship, the crew and the experience itself was amazing beyond words. It was a much-needed fun time out for us. We definitely plan to sail with you … Read more

Bliss

Alice and Captain Delaney! Photo by Alice Jager of Arnold, MARYLAND

Cruising on the Wind

Spotted sailing out of Annapolis as we flew back from the eastern shore. Taken from 2500 ft. Photo by Chelsea Dorman of Silver Spring, MD

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