Salty breezes. Fresh-caught seafood. Storybook villages.
Just off the southern coast of Cape Cod, Martha’s Vineyard is the ultimate New England summer escape.
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Lay of the Land: At just 100 square miles, the Vineyard is split between down-island and up-island towns.
Down Island
Edgartown: Stately homes of 18th-century whaling captains line the streets of this historic town.
Oak Bluffs: Known for its Victorian cottages and kitschy fudge shops, this is the island’s tourist hub.
Vineyard Haven: Come here for one-off boutiques and the main ferry terminal.
Up Island
Aquinnah: Make the trek to this western town for its colorful clay cliffs and Gay Head Lighthouse.
Chilmark: Islanders escape the summer crowds for the quiet fishing villages along Chilmark’s coastline.
West Tisbury: The most bucolic area has acres of rolling farmland.
Getting Around
Catch a ferry from Massachusetts, New York, or Rhode Island. If you don’t bring your car, rent a bicycle or a moped. Taxis are also plentiful.
Stay: The island has no shortage of charming seaside inns. Here, five that top our list.
Beach Plum Inn: There’s a lot to love about this seven-acre hilltop retreat overlooking Menemsha Harbor, from its clutch of country cottages, where interiors are artful studies in pastels, to the restaurant’s panoramic water views and alpaca pen. Bonus: free passes to the private Lucy Vincent and Squibnocket beaches. Chilmark. $
Charlotte Inn: Towering linden trees frame the clapboard façade of this 1864 merchant’s house. The lobby is full of 19th-century oil paintings and Edwardian objets d’art; upstairs you’ll find 19 intimate rooms done up with plush canopy beds, grandfather clocks, and vintage steamer trunks. $$$
Dockside Inn: At this seaside Victorian Revival, a stone’s throw from the Oak Bluffs ferry terminal, wide wraparound porches are ideal for watching boats sail in and out of the harbor. The backyard garage is stocked with beach necessities, from ice chests to sand toys and loungers, and a 1956 Rolls-Royce is on hand for a spin around the island. Oak Bluffs. $
Hob Knob: Playful elements—dog-shaped lamps; chintz wallpaper—make the Hob Knob ideal for travelers seeking a whimsical alternative to the island’s old-school inns. Take a fishing trip around Vineyard Sound on the hotel’s 27-foot Boston Whaler—and bring back your catch for dinner. Edgartown. $$$
Winnetu Oceanside Resort 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. The hotel is just a 250-yard walk from South Beach. $$
Hotel Pricing Key
$ Less than $200
$$ $200 to $350
$$$ $350 to $500
$$$$ $500 to $1,000
$$$$$ More than $1,000
Eat: Martha’s Vineyard is all about farm-fresh ingredients and, of course, plenty of seafood.
Black Dog Tavern: A visit to the Vineyard isn’t complete without a stop at this waterfront landmark, mere steps from the main ferry. The rough-hewn interior is decorated with boat tackle and other seafaring objects, but grab a seat at an outdoor picnic table—if one is free. What to order? A lump crab cake sandwich and a bowl of quahog chowder. Vineyard Haven. $$
Hooked: Opened last year, the sibling to popular island spot Atria quickly became the place for in-the-know locals. Its buck-a-shuck oyster happy hour (in July and August) is a perfect prelude to dinner. Look for seafood classics (grilled salmon; soft-shell crab) and offbeat items such as Asian-style baby back ribs. Oak Bluffs. $$
State Road: Many of the ingredients here are picked from the restaurant’s own gardens. Dig into lemon-ricotta pancakes or the locavore burger, with house-made garlic dill pickles, in a wood-beam dining room outfitted with American antiques. West Tisbury. $$$
Sweet Life Café: An alum of New York City’s Aureole, chef Carlos Montoya turns out Frenchified American classics at this romantic Victorian town house—a favorite of the Obamas. Start with a bottle of Chardonnay from the cellar (it’s one of the island’s largest), then try the grilled rib eye with Parmesan velouté followed by a strawberry terrine. $$$
Faith’s Seafood Shack: The sashimi and lobster rolls alone are worth the trek to this no-frills, cliffside haunt near the Gay Head Lighthouse, complete with knockout ocean views. Aquinnah. $$
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