Things to Do Tours

Annapolis Sailing Cruises: Schooner Woodwind

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

About Annapolis Sailing Cruises: Schooner Woodwind

Sail the Chesapeake on one of two, 74-foot wooden, schooners that offer a real Chesapeake Bay sailing experience for 2-hour public cruises, as well as longer specialty cruises. Sail past the US Naval Academy, gorgeous homes, and the historic city skyline. Raise the sails, steer the boat, or simply sit back and relax with a cold beverage. During the weeknights, we have History Mondays, Beer Tasting Tuesdays, Wednesday Night Match Racing, and Thursday Local Music Cruises. 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:


- Minimum 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,

Not a golliwobbler!
The skipper on our cruise started sailing when she was four years old. Her confidence, knowledge, and respect from the three-person crew show it. The paying guests get to help raise the sails, but... Read Full Review
Beautiful sunset and an incredible crew
My fiancé and I travelled to Annapolis for a few days just to enjoy the food, scenery, and bars. We had planned the trip prior to our engagement but there could not have been a better way to... Read Full Review
A must do, while visiting Annapolis!
Planned an afternoon sail/tour, the boat conveniently leaves from the center of town located next to dinning, pubs. All within walking distance of the academy. Captain and crew do a great job making... Read Full Review

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