Schooner Woodwind

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

Woodwind II July Sunset Cruise

Sunset over Annapolis viewed from the bow of schooner under sail

On July 18th, the Woodwind II set sail on a stormy evening. As the passengers persevered, ponchos and all, the sun came out and it was the most beautiful sunset any of us have ever seen. Photo by Elizabeth Pallante of Churchville, Pennsylvania

Captain Mickey

Black and white of captaining boat with a red white and blue flag

Photo taken on the Woodwind June 26, 2016 on the 4pm cruise. Captain Mickey at the helm navigating and narrating as we sail the Chesapeake Bay. Photo by Larry Breland of Aldie, VA

A Perfect Sail

Front of Schooner looking at the other schooner sailing sun slanting down

Wednesday evening boat races from June 22, 2016 aboard the Woodwind. Photo by Debbie Korb of Stevensville, MD

love my life

Both schooners sailing one following the other on a cloudy day

Photo from Wednesday Night.  Just checking to make sure the photo contest works this year. 🙂 Photo by jen kaye of Annapolis, Maryland

410-263-7837