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,

beautiful evening sail
Although it was cloudy and we didn't actually see a sunset, the ride was great, crew was informative of the area, and kept our glasses full Read Full Review
Fun on the water
Great way to beat the heat! Crew was friendly and encouraged guests to assist and steer. We only had 8 guests on the vessel. Very reasonably priced. You receive a soft drink and a snack included! Read Full Review
Great Sailboat Ride with the Kids
The crew of the Woodwind were welcoming, engaging and hospitable. They made the voyage a great deal of fun, allowing our younger sons to steer the boat and had our older daughter help pull down the... Read Full Review

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