Nantucket or Martha's Vineyard: How to Choose
By Cassie Shortsleeve. Photos: Getty, Courtesy Nautilus.
In New England, travelers often choose sides for summer vacations: Martha’s Vineyard or Nantucket. For me, it was always the Vineyard. Every summer, my family would rent a home in outermost Aquinnah, where wild beaches and towering red-orange clay cliffs provide refuge from crowded ferry towns to the east. But then Nantucket came along: I met my fiancé on the sands of Surfside Beach and celebrate anniversaries dockside at Cru. Since then, travels have been split—summer bike rides on Chappy in the Vineyard, sunsets in Nantucket's Madaket.
For the few who frequent both islands, that’s often how it goes. “Nantucket and Martha’s Vineyard are a family,” says Mark Snider, owner of The Nantucket Hotel & Resort and Winnetu Oceanside Resort on Martha’s Vineyard. “The islands are different and they can be loved for what makes them special but ultimately, you love them equally.”
After all, since the whaling era that was their prime, Massachusetts’ favorite islands have shared a symbiotic relationship. Here, what makes them who they are.
Martha’s Vineyard
Travelers to the Vineyard may be dismayed to find that there are no vineyards—but a casual, ever-relaxed environment (that certainly lends itself to sipping wine seaside) makes the 26-by-9 mile island (a 30- to 45-minute ferry ride from Cape Cod) a true escape. “You can go almost anywhere on the island in shorts, a tee shirt, and flip flops,” says Rob Blood, CEO of Lark Hotels, which has two properties on Nantucket and three on Martha’s Vineyard.
Start in Oak Bluffs, a port town decorated with colorful, Victorian gingerbread homes. “I love the porch culture. With so many Victorian cottages and great summer homes, there is a laid back afternoon rocking chair, cocktail culture that oozes summer,” says Blood.
Foodies don’t have to switch islands either, as Martha's Vineyard has its own emerging scene. Head to lower Kennebec Avenue in Oak Bluffs, says Blood. “There’s one of the best whiskey-bourbon bars that I’ve ever been to, 20byNine; an amazing chef-driven bistro called Red Cat Kitchen; and an island-to-table fine dining restaurant called Down Island, all just steps from one another.”
Must-dos:
Bike the nine miles from Katama to Oak Bluffs. “This morning ritual is one of my happy moments,” says Snider. Six of the miles are along the ocean.
Take the bike ferry in Aquinnah to the old fishing village of Menemsha for takeout at the Galley. “The Vineyard’s great experiment is to visit the different parts of it so you have a sense of its history, diversity, and beauty,” says Snider.
Listen to live music at the Ritz in Oak Bluffs, says Blood: “Thursday nights there are particularly amazing.”
Nantucket
While travelers will find the Vineyard to be diverse and colorful, the Quaker roots of Nantucket forbid that, says Snider. “It was monolithically singular and gray.” Today, those historic gray-shingled homes are what make Nantucket authentic. “The island is very mindful of its culture,” says Snider.
After a two-hour plus ride on the slow ferry, the well-heeled spend days barefoot at the beach and evenings eating locally sourced meals in a no-stoplight downtown. “I have had some of the best meals of my life on that 14 by 3.5 mile island,” says Blood.
Beach bums and surfers also favor Nantucket for its 80 miles of beaches.
Must-dos:
Eat ice cream at the pharmacy on Main Street. “It’s not hip and cool," says Snider. "But it’s a wonderful throwback. How many pharmacies still have the old fashioned soda foundation?”
Rent a jeep, pick up a growler of beer at Cisco Brewery, stop at Bartlett’s Farm for lunch provisions, then hit Lady’s Beach. “To me, that is the perfect Nantucket day,” says Blood.
Appetizer-hop through town. “Start at Proprietors, then head to Dune, Nautilus, and Straight Wharf," Blood says. The next day, if you aren't still full, roll out of bed and head to Black Eyed Susan’s for brunch.
By the Numbers:
Lodging Martha’s Vineyard: 80+, not including rental properties Nantucket: 5 hotels, 38 inns (approximately 900 guest rooms)
Restaurants Martha’s Vineyard: ~80 Nantucket: 61 restaurants, 21 gourmet to-go outlets
Beaches Martha’s Vineyard: 124 miles of shoreline, 19 named beaches Nantucket: 80 miles of shoreline, 23 named beaches
Golf Courses Martha’s Vineyard: 4 Nantucket: 3
Cycling Trails Martha’s Vineyard: 44 miles Nantucket: 32 miles
This story originally appeared on Conde Nast Traveler.
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