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 Historic Inn, Hotel, Annapolis, LodgingFrom August 29 to October 2, 2016, the beautiful 74-foot schooners Woodwind and Woodwind II will sail the Chesapeake Bay 7 days a week and three times daily. The most romantic journey is the last of the day, a breathtaking Sunset Sail. Annapolis is known as “America’s Sailing Capital”, and there is no better way to see the historic maritime city than on a magnificent two-masted sailboat.

Family Business

Captain Ken and Ellen Kaye were public school teachers who retired after 25 years and founded the business in 1993. Their daughter Jennifer became a Captain in 1996. The Kayes take pride in making each passenger’s Annapolis sailing experience memorable with the help of their engaging and enthusiastic crews.

Woodwind and Woodwind II

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

Cruise Sights

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

Sunset Sail Theme Days

Sunset Sails offer the following events on weekdays. Click here for more information: Sunset Sails

History Mondays – Sponsored by the Historic Annapolis Foundation, the cruise will offer a speaker who will educate passengers regarding the history of Annapolis and the Chesapeake Bay.

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

Wednesday Night Races – Woodwind and Woodwind II will race against each other with passengers aboard until the end of the season. A total of 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 original work and playing acoustic instruments.

An 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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