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,

An amazing July 4th!
Captain Jen and her crew were fantastic! Very knowledgeable, fun and engaging. We lucked out with the cover but no rain and enough wind for all the sails to be raised. A lovely time... Read Full Review
Spectacular sunset
We took the sunset cruise on the schooner woodwind out of downtown Annapolis on a warm Saturday evening. Thankfully there were good winds and the sails went up as soon as we cleared the harbor. It... Read Full Review
My husband and I celebrated our 33rd wedding anniversary by taking a sunset cruise. The crew made it known to everyone it was our anniversary. It was very special and we had a lot of fun. Highly... Read Full Review

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