Enjoying my 50th birthday aboard ship.
Photo by Aaron Deppen of Manheim, Pennsylvania
50 years of sunsets
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- 410-263-7837
- Buy Tickets
Public Sailing
Tickets go on sale 6 days prior to the date you want to sail. Advanced ticket sales are available if you have a group of 18 or more.
Specialty Cruises
Our specialty sailing cruises are on sale now for this season. Embark on an unforgettable tour with a carefully crafted menu of food & drink.
18 people or more?
Groups can purchase tickets 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 event!
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Schooner Woodwind
Annapolis Sailing Cruises
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“Love the good humor, kids' chance to skipper, and the historical parts were terrific.” – Kristen H. -
“Entertaining crew. Delightful sail, beautiful views. Thanks for a great experience.”
- Aime -
“Great crew, great captain, beautiful ship. A great experience for the whole group.”
– Hal -
Monday: Learn about the History of the Region Tuesday: Local Craft Beer Tastings Wednesday: Sailing Race Night— Join our Teams! Thursday: Acoustic Music NightsWeekday Sunset Sails -
“Amazing experience! I got to sail too! Thank you.” – Raya
Schooner Woodwind Sails up to 4 times daily from the Annapolis Waterfront Hotel
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