Annapolis
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Underway in America’s Sailing Capital

The relationship between the City of Annapolis and the ocean date back centuries. Located in the heart of the Chesapeake Bay, Annapolis is commonly referred to as “America’s Sailing Capital.” During your next trip to 134 Prince – Luxury Boutique Hotel in Annapolis, consider getting underway with Schooner Woodwind, offering Annapolis Sailing Cruises since 1993. Help raise the sails, steer the boat, or simply sit back and relax as Woodwind sails from the historic Annapolis waterfront, past the Naval Academy and cruises into the Chesapeake Bay. 

Schooner Woodwind offers daily cruises – public or private – on their two beautiful, wooden, 74-foot schooners, Woodwind and Woodwind II, for a true sailing experience in Annapolis, Maryland.

Sailing season starts in April each year, so if your travel itinerary allows, take part in the ancient seafaring tradition of sailing. As technology has changed nearly all aspects of humanity, the tradition of sailing remains fundamentally unchanged. 

The skill and knowledge of the crew is matched only by their humor and pure enjoyment of bringing first-time sailors underway in America’s Sailing Capital – Annapolis.

134 Prince – Luxury Boutique Hotel is a five-suite boutique hotel located in Downtown Annapolis. 134 Prince offers a luxury residential retreat for those looking to be in the heart of the action. Our spacious common areas, elegantly landscaped gardens, and luxurious guest rooms offer tranquility mere steps away from the U.S. Naval Academy, award-winning Annapolis restaurants, and charming boutiques that line the brick sidewalks of Historic Annapolis.