Join us on our two beautiful, wooden, 74-foot schooners, Woodwind and Woodwind II, for a true sailing experience in Annapolis, Maryland.
- 2-hour public sailing cruises
- Private Cruises
- Schooner Races
- Boat & Breakfast
- Team Building Events
- Student Groups
- Wine and Beer Events
- Foodie Events
- Multi-Day Cruises
Located in the heart of the Chesapeake Bay, Annapolis is “America’s Sailing Capital.” Help raise the sails, steer the boat, or simply sit back and relax as Woodwind sails from the historic Annapolis waterfront, past the Naval Academy and cruises into the Chesapeake Bay.
As a family business, we take great pride in making your sailing experience a memorable one. Our captains and crew are engaging and enthusiastic. Sail away with us!