Schooner Woodwind

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

Ray Trimming the Stay

Woodwind taken from Woodwind II during a fiery sunset on June 22. Looks like a ray of the sun is reaching down to trim the staysail sheets to head up into the Woodwindy imagery. The Naval Academy Chapel dome is peeking out behind Woodwind’s stern. Photo by Randy Williams of Annapolis, MD

Mother’s Day Sail with Wind

We took the Mother’s Day sail in the afternoon when winds became more windy than expected. I joked that it was more of a Father’s Day present! Hey, it’s hard to drink bubbly when the boat is roaring! Photo by Tammi DeVan of Fairfax, VA

Captain Matthew

It was smooth sailing on our anniversary with Captain Matthew at the helm. Photo by Gary Sanderson of Hyattsville, MD

O Captain, my Captain….

The #1 member of Terry Ann’s “Go To Dudes” on this year’s thank you brew tour which took place on the Woodwind. June 4th, 2021 Photo by Randy Reynolds of Lewes, DE

Twin Spans

As we cruised beneath the Chesapeake Bay bridge, the spans converged at the horizon! Photo by Mare Glenn of Catonsville, MD

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