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,

Delightful evenings
I had the opportunity to partake in two sailings with two groups of visiting friends. One was the Wednesday night race where not only did you participate in the two attraction schooners racing but... Read Full Review
Harbor Cruise
Lovely Cruise! We were looking for a way to get out on the water while visiting Annapolis for the first time as a USNA family. This was perfect for us! The younger boys loved getting to steer the... Read Full Review
Beautiful afternoon on the Bay
We took the 1230-230 cruise on a sunny autumn day. Captain and crew were friendly, experienced and knowledgeable. About 40 guests onboard---all ages. Beverages and snacks provided. Read Full Review

© TripAdvisor 2015