Active island living in Oak Bluffs, Edgartown, and beyond.
The 180-square-mile island conjures up images of beautiful sea captain’s houses, cobblestone streets, and lighthouses. It’s also got miles of pristine beaches, pretty farmland, and extensive nature trails—oh, and a famous merry-go-round and lots of ice-cream stands—making it ideal for a family escape. Come over by ferry and get around the old-fashioned way—on two feet or wheels. You just may spot the Kennedys, Clintons, or Obamas doing the same.
The Winnetu Inn & Resort
This family-owned hotel has one-to-four-bedroom suites, cottages, and home rentals, all fronting South Beach in Edgartown. The 54-suite Winnetu is as close as the Vineyard gets to a mega-resort, with a library, fitness center, and vast lawn outfitted with a nine-hole putting green and a turtle pond. Fire-truck rides, face painting, and a life-size chess board are all on hand to entertain kids.
The Steamship Authority
To get there, take the car ferry from Wood's Hole, MA, to Edgartown on Martha’s Vineyard. It’s a short, pretty trip through calm waters. $130 round-trip
Play in the gentle surf, perfect for children (with both lifeguards and nearby restrooms). You won’t witness a better sunset than here, a two-minute walk from the fishing village of the same name. Pack a picnic and a blanket—it gets cold at dusk.
Flying Horses Carousel
In the village of Oak Bluffs, check out the Flying Horses Carousel, and 1876 amusement that retains its original glass eyes and horsehair trimmings.
Long Point Wildlife Refuge
Walk these 600 acres of windswept dunes, hiking trails, and unspoiled coastline.
Among the Flowers Café
Comfort food (apple-cinnamon crêpes) is served outdoors near the dock in Edgartown (breakfasts are popular).