Top 10 Sunset Cruises

From America’s Cup-style sailing to a jazz band on a catamaran, there’s something for everyone on these early-evening jaunts at sea.


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Top 10 Sunset Cruises: Schooner Woodwind
Photo: Schooner Woodwind

Schooner Woodwind

Annapolis, Maryland

Choose your own adventure aboard the 74-foot Woodwind or Woodwind II with daily themed cruises that might include regional microbrew sampling or America’s Cup-style racing. (Weekend sails are not themed.)

The view: Monuments from the United States Naval Academy—including Triton Light and the Annapolis skyline

When to go: May through September, or private charter sunset sails during October

Rate: $37 (themed sails), call for private charter prices; 410/263-8994 or


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