Schooner Woodwind

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

Girls Just Want To Have Fun

Three ladies smiling and steering the schooner together

Our friend Laura is getting married, so we decided to do something fun together! It was a complete surprise when she found out that we are taking her on a sailing cruise. She was thrilled! The thee of us had a wonderful time, we had a chance to take over the wheel (under supervision of … Read more

Nephew Express

Group of five guests in blue t-shirts sailing the schooner together

I live in Annapolis and have no kids of my own, but managed to get my four nephews (one the wife of one nephew) to come to Annapolis for Memorial Day Weekend. It was the first time in 19 years that they were all together in one place! I wanted to share an experience unique … Read more

Just Showin’ Off

Four Blue Angel jets soaring over the schooner and water

The Blue Angels celebrate their return to Annapolis with a flyby for the Woodwind crew and guests in their famous diamond formation. Photo by Tom Lawrence of Baltimore, Maryland

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