Schooner Woodwind

Enjoy Our Annapolis Sailing Cruises

Seeing as it's considered the “Sailing Capital of the U.S.,” no trip to Annapolis would be complete without getting out on the waters of the Chesapeake Bay. Lucky for you, we offer two 74-foot wooden schooners right here at the hotel dock. Hop aboard the Woodwind or the Woodwind II and let our expert sailing crews take you along the historic Annapolis waterfront, past the Naval Academy, and into the Chesapeake Bay. Depending on the strength of the wind, the schooners may make it all the way to the Chesapeake Bay Bridge. You may even be asked to be part of the crew during the excursion and help raise the sails or steer the boat!

Sailing cruises we offer:

  • Two-hour public sailing cruises
  • Private cruises
  • Schooner races
  • Boat & Breakfast overnight experience
  • Team-building events
  • Student groups
  • Wine and beer events
  • Foodie events
  • Multi-day cruises
The schooners sail in all types of weather except lightning. Excursions are available April through October. For more information and to book tickets, please visit or call 410-263-7837.