Schooner Woodwind

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

In the wake

I took this photo from the back of my friend’s boat in the summer of 2021. They told me it was the boat from “Wedding Crashers” and I decided I wanted to take a sail on it some day. I came back 3 years later with my boyfriend and we thoroughly enjoyed our adventure. My … Read more

Sunset on the water

Captain Delaney is at the wheel ending a perfect night of sailing on the water while the sun sets! Photo by Faith Cost of Media, Pa

Part of the Crew

Baby’s first sail! We’ve been on many trips as a family and were inspired by the crew after our last sail 2 summers ago. So inspired we named our son Crew and he loved his first ride! Here’s 3 generations of boat lovers. Thanks again! Photo by Sam Harbage of Glen Burnie, Md

Girl Captain!

Captain Shea with her Poppy and Captain Andy to guide her. Thanks guys! Perfect winds for the day! Photo by Ashley Grimm of Frederick, Md

Sunset Over Annapolis

Picture from last night’s sunset cruise made it in the Washington Post today. https://www.washingtonpost.com/weather/2024/08/02/dc-area-forecast-weekend-weather/?utm_campaign=wp_weather&utm_source=twitter&utm_medium=social Photo by Ron Cohn of Washington, DC

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