Nightlife Music Venue

Annapolis Sailing Cruises: Schooner Woodwind

80 Compromise St., Annapolis, MD 21401
(410) 263-7837

About Annapolis Sailing Cruises: Schooner Woodwind

Sail away on a 74-foot wooden, schooner with terrific local musicians performing while under full sail on the Chesapeake Bay. Schooner Woodwind specializes in 2-hour public cruises, as well as longer specialty cruises. On our Thursday night Sunset Sail, we have Local Music Thursdays. We get great performers that sing and perform aboard the boat as we are sailing in the Bay. We have a special listing of the different performers on our website. Raise the sails, steer the boat, or sit back and relax with a cold beverage while listening to wonderful, acoustic music aboard the “Woodwind”. We have a cash bar filled with local craft beer and wine. Certified for 48 passengers on each schooner. Departs from the downtown Annapolis Waterfront Hotel.



- Family Friendly

- Maximum Group:


- Reservation Recommended


- Alcohol Served

- Box Lunch Available

- Group Tours Available

- Private Tours Available

- Restrooms Onsite



- Payment Methods Accepted

American Express, Discover, Master Card, Visa,