Welcome Aboard!

Public and Private Sailing Cruises on the Chesapeake Bay on the Schooner Woodwind

Join us on our two beautiful, wooden, 74-foot schooners, Woodwind and Woodwind II, for a true sailing experience in Annapolis, Maryland.


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!

Our Sailing Season for 2015 is over. We will return sailing in mid-April 2016.


Contract of Carriage

© Copyright 2015. Running Free, Inc. DBA Annapolis Sailing Cruises: Schooner Woodwind. Annapolis MD. All right reserved. Privacy Policy.

Site Designed by: Green Mountain Marketing & Advertising, Inc.