2024 Sailing Season is coming! See you April 13, 2024!
2-hour Public Cruises
Spectacular Sunset Cruises
Daily 2-Hour Sailing Cruises
Specialty Cruise Calendar
Plan your Annapolis adventure now! Explore our incredible cruise offerings.
Schooner Woodwind sails up to 4 times daily from the Annapolis Waterfront Hotel
“Woodwind” sails up to four times daily throughout our summer season from the Annapolis Waterfront Hotel. Each trip is unique. Let our captains and crew make your trip most enjoyable and memorable. Help hoist the sails (all 4 of them) or take a turn at the wheel.
Throughout the sailing season, we offer special events that make any day exceptional. Embark on an unforgettable tour with a carefully crafted menu of food and drink. From special Mother’s & Father’s Day cruises to lighthouse cruises, seeing the Blue Angels overhead, and many other special occasions.
Sunset is a favorite time for a sail on the Woodwinds. The sunset over the Annapolis skyline is breathtaking. The golden glow reflecting off the sails as the sun descends near the horizon is an unforgettable sight.
Group Sails can purchase tickets further in advance. Public Tickets can only be purchased six days prior to the date you want to sail. All Service Fees are included on Group Sails. Guarantee the sail will not be booked for a private event.