Schooner Woodwind Sailing Cruises

Woodwind Sailing Cruises is a family owned and operated business operating out of historic Fort Footlock Military base in Annapolis, MD. We offer 3 unique sailing cruises aboard the 74-foot wooden schooner Woodwind. Whether you are looking to be captivated by the beauty of your surroundings or experience a new adventure, we invite you to join us on our cruises! Gather your friends and family and visit this amazing destination at 80 Compromise St, Annapolis, MD 21401/

What are your sailing cruises?
The Woodwind Sailing Cruises include sailing on the Chesapeake Bay on the 74-foot wooden schooner Woodwind, cruising to historic locations, and enjoying a sunset dinner. These sailing cruises include sailing past the Maryland shoreline, the Washington D.C. shoreline, the Delaware shoreline, and the Southern Pennsylvania shoreline. During the sailing cruises, passengers also have access to the Woodwind’s outdoor deck, where they can relax and enjoy the sights. Our sailing cruises also feature educational presentations about the history of each location and the sailing vessel, and how the vessels work.

The sailing cruises are a unique way to experience the beauty of the Chesapeake Bay and to learn about the sailing vessel. You can choose from 3 sailing itineraries: the Low Country, the Southern Maryland Shoreline, or the Delaware Shoreline. Each sailing itinerary offers a different experience, with varying weather and light conditions. The sailing cruises are scheduled year-round, and are available on demand, as well as for special events.

Where can we sail from?
The Woodwind sails from the Chesapeake Bay in Maryland, near the Washington D.C. area, in Virginia, and the Delaware shoreline. We sail past the Maryland shoreline, the Washington D.C. shoreline, the Delaware shoreline, and the Southern Pennsylvania shoreline. The Woodwind can be chartered anywhere in the U.S. The Woodwind can also be chartered by special events, such as corporate team-building events and weddings.

When can we sail?
The sailing cruises can be scheduled year-round, but are most commonly scheduled during the summer months from late June to the end of August. The sailing trips are daily, and last between 1 and 3 hours. You can also choose to book a sailing cruise for a specific date, such as a wedding or corporate team-building day.

The Woodwind’s sailing season runs from the end of June to the end of August. The rest of the year is when you’ll see the Woodwind in port in Annapolis, Maryland. We offer sailing cruises year-round, but the availability of the vessel is slightly reduced during the winter months.

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