Last updated: August 6, 2025
Place
Annapolis Sailing Cruise: Schooner Woodwind
Annapolis Sailing Cruise: Schooner Woodwind
Quick Facts
Location:
80 Compromise St, Annapolis, MD 21401
Significance:
Annapolis Sailing Cruises: Schooner Woodwind offers hands-on sailing experiences that connect visitors to the Chesapeake Bay’s maritime heritage, ecology, and evolving environmental story.
Designation:
Chesapeake Gateways Network Site
MANAGED BY:
Amenities
2 listed
Dock/Pier, Water - Drinking/Potable
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 Lighthouse, and marine and wildlife. This Chesapeake Gateways Network Site, 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 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 Site, 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.
Each 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 Site, 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.