Martha’s Vineyard, Massachusetts
Sit back, sip wine (BYOB), and pretend you’re a Kennedy aboard this 60-foot twin-hull catamaran. The cruise glides past homes once owned by whaling ship captains in the 1800s. Wind direction determines the route—passing either Chappaquiddick Island or the town of Oak Bluffs.
The view: Edgartown Lighthouse, sailboats in Nantucket Sound, and yachts
When to go: Memorial Day weekend through September
Rate: $55; 508/627-7500 or madmaxmarina.com