Welcome Aboard!

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!

  • October Sailing Schedule
    October Sailing Schedule
  • Specialty Cruise Calendar
    Specialty Cruise Calendar
  • Enjoy the beautiful views as part of your corporate teambuilding event.
    Private Sailing Cruises
    Private Sailing Cruises
  • Team Building
    Team Building
  • We educate girl scouts about the "Wonders of Water" and sailing using an interactive approach while cruising the Chesapeake Bay.
    Student Cruises
    Student Cruises
  • Schooner Racing
    Schooner Racing

Make your sailing experience a memorable one! Sail away with us!

Sailing Season starts April 13, 2019.

© Copyright 2019. Running Free, Inc. DBA Annapolis Sailing Cruises: Schooner Woodwind. Annapolis MD. All right reserved. Privacy Policy.

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

Be the FIRST to know!

Sign up to get the latest info on Specialty Cruises, Events, and Opening.

Thank you for signing up for Schooner Woodwind News. 

Schooner Woodwind