Tickets On Sale Now

Adult Senior
 $43.00  $41.00 $29.00
Sunset & Weekends  $46.00  $44.00 $29.00


2017 will start on April 15

Tickets go on sale 6 days prior to the date you want to sail. 
If you can gather a group of 18 guests or more, then you can purchase your tickets much further in advance. Please visit our Group Sailing Page for more information.


General Information to Know Before You Buy…

Schooner Woodwind sails rain or shineOnce tickets are purchased, there are no refunds or exchanges.

We sail rain or shine unless the captain cancels the cruise due to unsafe conditions. We offer complimentary rain ponchos in case of rain.

  • There are no refunds or exchanges unless the captain cancels the cruise due to unsafe conditions.
  • The boat leaves on time, you will not be refunded if you miss the boat.
  • We have a cash bar filled with local microbrews, wine and bubbly. You cannot bring your own alcohol.
  • All policies listed in link below including parking, smoking, check in, footwear and more.

Please Remember:

  • Only soft soled shoes are allowed aboard.
  • All departures are from Pusser’s Caribbean Grille at the Annapolis Waterfront Hotel across from the City Dock (unless otherwise noted). Rates and schedule are subject to change without notice. Our schedule may vary due to weather, special events and group charters.
  • Tickets go on sale six days prior to the date you want to sail. Advanced ticket sales are available if you have a group of 18 or more people as a “Group Sail”.  Please call our business office at 410-263-1981.
  • Up-to-date schedule information is available on this page or calling (410)263-7837.

Please visit our frequently asked questions page.

© Copyright 2017. Running Free, Inc. DBA Annapolis Sailing Cruises: Schooner Woodwind. Annapolis MD. All right reserved. Privacy Policy.

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