Schooner Woodwind

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

Cheers

Guest on schooner drinking out of bottle of wine

Wife celebrating our time together with a personal toast aboard the Woodwind Photo by Craig Wolf of Edgewater, MD

Family Love!!

Mother and three children smiling as they enjoy their sail

We had the best time this past August on our race night! Thank you for the family memories! Photo by Geraldine herlihy of holden, massachusetts

Autumn Splendor

Streaked orange dusk over Annapolis skyline

The most amazing sunset cruise we’ve ever experienced. Photo by Barb Miller of Quarryville, Pennsylvania

sunset cruise

Sail and rigging of schooner with big yellow sun shining through

a beautiful sunset cruise ending to a perfect day in Annapolis Photo by Jillian Denker of Newtown Square, PA

She’s Gaining Capt’n

One schooner gaining ground on the first schooner on a windy day

Helping to trim the main during the 1st Wednesday evening race of the season on our trip to Annapolis a couple years ago. Photo by Greg Tkal of Ballston Lake, New York

Happy!

Happy smiling couple sailing away into the evening waters

From our May 2017 Schooner Woodwind outing – Wed.night sailboat races; coming home Photo by Patricia Trujillo of Annapolis, MD

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