Annapolis Sailing Cruises: Schooner Woodwind
Chesapeake Bay
Step aboard the schooners Woodwind or Woodwind II for a two-hour sailing adventure on the Chesapeake Bay. Departing from Annapolis, these classic 74-foot wooden vessels invite you to help raise the sails, take the helm, or simply relax while soaking in stunning views of the Bay Bridge, Thomas Point Shoal Lighthouse, and the marine life and wildlife of the Bay. This Chesapeake Gateways Network Experience, managed by Annapolis Sailing Cruises: Schooner Woodwind, offers an immersive connection to the Bay’s culture, history, and environment through an unforgettable sailing experience. Each public sail is shaped by the wind, weather, and guest curiosity. Watch ospreys dive for fish, watermen haul in their catch, or clouds hint at changing conditions. As you sail, the crew shares stories about the Chesapeake’s maritime heritage and wildlife. For visitors of all ages, this is more than a boat ride: it’s a chance to see the Bay from a new perspective. Special themed cruises, like the Monday night History Sail, explore topics from regional geology to historic landmarks. Youth groups and school trips are welcomed with hands-on programs that connect sailing to lessons in ecology, teamwork, and navigation. As a Chesapeake Gateways Network Experience, Annapolis Sailing Cruises: Schooner Woodwind fosters discovery, stewardship, and a lasting appreciation for the Bay. Visit their website to learn more and plan your trip.
