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Annapolis, Historic Inn, LodgingFrom May 13 to October 1, 2017, the magnificent 74-foot schooners Woodwind and Woodwind II will sail the Chesapeake Bay seven days a week up to three or four times daily. The most romantic journey closes the day, the captivating Sunset Sail. Annapolis is world-renowned as “America’s Sailing Capital”, and there are no better views of the historic maritime city than on a magnificent two-masted sailboat.

Woodwind and Woodwind II

Designed to sail the Chesapeake Bay, Woodwind and Woodwind II were custom built for these waters. Both sailboats feature beautiful mahogany brightwork, shining chrome, and spacious cockpits. The Woodwinds are replicas of the classic, swift schooners used as “yachts” in the early 1900s.

Public Sailing Cruise Sights

The 2-hour Public Sailing Cruise provides passengers breathtaking views of the United States Naval Academy, Annapolis Harbor, Chesapeake Bay, the Annapolis skyline, and the Severn River. Wind direction and speed permitting, the cruise will also offer sightseeing of the Chesapeake Bay Bridge, Thomas Point Shoal Lighthouse, and Kent Island Regattas.

Sunset Sail Theme Days

The Sunset Sails on weekdays offer the following events Monday to Thursday.

History Mondays – Sponsored by the Historic Annapolis Foundation, the cruise will feature a speaker who will give passengers fascinating insights regarding the history of Annapolis and the Chesapeake Bay.

Beer Tasting Tuesdays – Passengers can sample great beers while sailing. A different brewery will be featured from the Mid-Atlantic Region monthly, and its representative will promote the qualities of their beer. Three samples are included with each cruise.

Wednesday Night Races – The crews of the Woodwind and Woodwind II will race against each other with passengers aboard until the end of the season. 130 other sailboats compete every Wednesday in Annapolis’s most famous summer sailing competition.

Thursday Local Music Series – Local musicians will entertain while the Woodwinds sail Chesapeake Bay. Singer-songwriters will be highlighted, singing their original work and playing acoustic instruments.

Friday, Saturday, and Sunday will not offer specific entertainment. Passengers will see the spectacular sights of Annapolis, along with gorgeous sunsets.

For More Information: Sunset Sails

Your Inn Near the Woodwinds

The Annapolis Waterfront Hotel, where you will come aboard, is less than half a mile away from Gibson’s Lodgings, a historic inn located in downtown Annapolis. Call us to reserve your room at our toll free number (877) 330-0057. We’ll be very happy to serve you and your family throughout the year.

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