Schooner Woodwind

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

Anniversary Sunset Cruise

Amazing sunset with rays reflecting up from clouds viewed over the helm of schooner

This stunning picture was taken at the very end of our sunset sailing cruise, the weather was gorgeous although slightly overcast the sun setting towards the end was the perfect ending to a wonderful cruise. Photo by Jay Majors of Washington, DC

Woodwind Take 2

Young girl holding a picture of herself when she was a toddler steering the schooner again

My daughter Madison, age 11, at the helm of the Woodwind, holding a picture of herself at the helm of the Woodwind II at age 5. Photo by Elizabeth Heuvelman of Leonardtown, Maryland

Helping Hand

Captain Mickey giving a young man sailing at the helm a high five

My wife Shannon entered a picture of our son Dane behind the wheel of the Woodwind. We wanted to enter a second photo of our son with the Captain. The Captain was so patient and friendly with our son and we thought the picture epitomized the great lengths the crew goes to to make sure … Read more

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