Classic Harbor Line, New York, N.Y.

It’s easy to forget that the Big Apple is an island. Explore the city’s waterways on Classic’s 1890s-style schooners Adirondack and Imagine, aboard which travelers sip complimentary beer while viewing the Statue of Liberty. To cruise around the island, try the mahogany-adorned 80-foot yacht Manhattan. While drinking champagne within the glassed-in 360-degree observatory, you’ll cut a path beneath the breathtaking George Washington Bridge and peek at both Roosevelt and Governor’s Island; come weekends, there’s brunch and Bloody Marys.

For more information: Sail-NYC