Sailing Season is Here. Join Us for a Sail!

Tickets On Sale Now

Public Sailing

Tickets go on sale 6 days prior to the date you want to sail. See “Group Sailing” or “Private Cruise” for booking further in advance.

Special Events

Our specialty sailing cruises are on sale now for this season. Embark on an unforgettable tour with a carefully crafted menu of food & drink.

Groups up to 16 guests

Groups can reserve space more than six days in advance so you can start planning your event now and know you have that date reserved.

Private Cruise

The captains and crew of the Schooner Woodwind look forward to welcoming your guests aboard for your exclusive private and future event!

General Information to Know Before You Buy…

Schooner Woodwind sails rain or shine

Once 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.

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 up to 16 people as a “Group Sail”.  Please call our business office at 410-263-1981.
  • Up-to-date schedule information is available by clicking here or calling (410)263-7837.
Schooner Woodwind