Courtesy of Erica Cipollina
As compact as Martha’s Vineyard is — or simply the Vineyard, as locals affectionately abbreviate it — this New England island can feel much larger because of its three main towns: Oak Bluffs, Vineyard Haven, and Edgartown, all of which offer something different. There’s also Aquinnah, renowned for its towering seaside cliffs, the sleepier fishing village of Chilmark, and the less touristy, often labeled ‘residents-only’, West Tisbury.
A visit to the island isn’t complete without visiting them all, however, repeat visitors will surely play favorites, flocking back to their preferred destination. Don’t be intimidated, there’s something for everyone on Massachusetts’ largest island, and though it may not be the easiest to access, that only adds to its charm — because once you arrive, you’ll never want to leave.
Courtesy of Erica Cipollina
The Best Time to Visit Martha’s Vineyard
A New England island situated 80 nautical miles offshore in the Atlantic Ocean, the Vineyard is very much a seasonal destination. Summer is by far the best time to visit with balmy averages hovering in the 80s and a plethora of activities on offer; the winter can bring nasty, coastal storms and the majority of businesses will shutter during these months. If you’re planning a trip to Martha’s Vineyard in high season, you should book accommodations early (whether you’re looking for a luxe hotel or an Airbnb), as space is limited on the 100-square-mile island.
Repeat visitors may find that the shoulder-season months — April and September — are the best time to experience all of the island’s charm, without the chaos of high-season crowds. And if you’re lucky and willing to plan last minute, warm autumns may prompt the Vineyard to extend the season, so don’t completely write off October. With that said, if you have plans to visit a specific restaurant or shop during shoulder season, just make sure to check their website for off-season hours.
What to Do in Martha’s Vineyard
Hit the beach
With more than 20 beaches, the most obvious thing to do on the Vineyard is check out the beaches. Gay Head Public Beach shows off the towering Aquinnah cliffs, Menemsha is known for gorgeous sunsets, and Lighthouse Beach is walking distance from Edgartown. Elevate your beach day with a lobster roll or whole steamed crustacean with a side of seaweed salad from The Net Result.
Courtesy of Erica Cipollina
Rent a bike and pedal past the historical Gingerbread cottages of Oak Bluffs. Climb the West Chop Lighthouse or Edgartown Lighthouse for impressive views of the Vineyard. Visit the Flying Horses Carousel, which dates back to 1876.
Spend Time in and on the Water
Courtesy of Erica Cipollina
Whether you’re wading, paddleboarding, or surfing, playing in the surf is a crucial part of island life. You should also head out on the water for an afternoon, taking a traditional sailing lesson (try private lessons with Sail MV) or chartering a boat for the day (try Island Girl Excursions).
Pop into one of the harborside bars with airy decks and tiki cocktails, where you may just stay for the rest of the evening. Visit The Ritz MV for a taste of the island’s late-night, local scene — open year-round.
Where to Stay on Martha’s Vineyard
The Kelley House
Nestled in the former whaling port of Edgartown, The Kelley House Hotel still stands from the days when sea captain wealth developed the island. Don’t let 275 years of history fool you, though — Kelley House’s 54 rooms have been renovated to keep up with the times, emanating contemporary, nautical charm. The guests-only pool is a rarity on the island and a welcome respite from the hustle and bustle of the beaches during peak-season.
The Edgartown Collection
Courtesy of The Edgartown Collection
The Christopher, The Sydney, The Richard, and The Edgartown Inn are the four luxury boutiques in this hotel collection, totaling 69 rooms across Edgartown. Each property is tastefully renovated and reflects their own personality, from the island-inspired blue hues at The Christopher to the garden-reminiscent touches at The Edgartown Inn, you simply can’t go wrong.
Harbor View Hotel
Dan Cutrona/Courtesy of Harborview Hotel
Timeless but contemporary, this 117-room resort is at the center of it all, and somewhat of a landmark in its own right, thanks to its ocean-to-plate restaurant, Bettini. The hotel’s latest renovation lightened the interiors across a neutral palette of rosy hues and sandstone, accented by pops of seaside blues.
Rare Brick/Courtesy of Lark Hotel
Summercamp’s Oak Bluffs locale offers a change of pace with its retro-whimsical design elements and mission encouraging guests to “come be a kid again.” Amenities like Camp Canteen, with fun, nostalgic snacks (Dreamsicles, anyone?), and a vintage game room with a ping pong table, make this property the ultimate adult summer camp.
How to Get to Martha’s Vineyard
Accessible only by boat or plane, Martha’s Vineyard isn’t the easiest island to get to, but the journey is well worth it. Both The Steamship Authority and Hy-Line Cruises run year-round ferries, operating on limited schedules in the off-season (October through March) and increased service during high-season (May through September). The Steamship Authority leaves from Woods Hole, Massachusetts (on Cape Cod) and arrives at Oak Bluffs (seasonally) or Vineyard Haven (year-round) in 45 minutes. The ferry can accommodate cars, however, vehicle reservations are limited and pricey, so many vacationers choose to leave their cars in one of the long-term lots in Woods Hole. Hy-Line Cruises is a passenger-only ferry that also takes about 45 minutes, departing from Hyannis and arriving in Oak Bluffs. Reservations are strongly recommended for both ferry operators, particularly in the summer.
The Best Martha’s Vineyard Restaurants
19 Raw Oyster Bar
Courtesy of 19 Raw
Indulging in seafood is a rite of passage on the Vineyard, particularly seafood towers at 19 Raw Oyster Bar. Aim to arrive early and snag a seat on the patio tucked behind one of Edgartown’s main drags; slurping local oysters in the sunshine and dipping Jonah crab into cocktail sauce really welcomes you to island life.
Only open for dinner, this swanky restaurant specializes in new American fare and inventive craft cocktails. Overlooking Lagoon Pond, the dark-timber bar makes for a lovely sunset perch before moving to your candlelit table. The menu is particularly inspired by the sea, sourcing from regional fishermen and showcasing New England’s bounty.
Courtesy of Garde East
Sitting beachside on Vineyard Haven Marina, the sense of place at Garde East is palpable. Whether you secure a seat on the terrace or a window table, you won’t have any mistake as to your whereabouts, nor access to waterfront views. Open for lunch, dinner and Sunday brunch, don’t miss out on the house bread, with truffle butter and grilled oysters, regardless of when you visit. The rest of the menu is just as terrific as the grilled oysters; with incredibly fresh seafood, there are no wrong choices here.
The island’s newest Italian restaurant now ranks as one of the island’s best, with Naples-born chef Salvatore della Torre helming a menu flexing the flavors of his home country. From arancini and insalata to carbonara and ragu, Salvatores presents the best of Italy’s southern and northern regions to Union Street in Vineyard Haven.
A husband-and-wife duo opened this European-inspired restaurant as a place to relax, even naming it after the French word for “relaxation” or “relaxing.” You’ll find odes to the couple’s past travels throughout Spain, Italy, and France on the menu, along with the freshest ingredients from garden to ocean.
Courtesy of Massachusetts Office of Travel and Tourism
One of Edgartown’s liveliest bars, Alchemy, is also a must-visit for dinner. Chef Christopher Stam celebrates, and has been celebrating for more than two decades, island cuisine with classic New England flavors. Appetizers comprise a sort of global tapas, while mains offer fine-dining dishes for every palate, with surf and turf as a longstanding tradition.
The Black Dog
Even first-time Vineyard visitors will recognize the swinging black lab logo as a symbol of the island, which is why you simply can’t miss this classic tavern along Vineyard Haven Harbor. Founded in 1971, this eatery is always overflowing, especially as it’s one of the few restaurants open year-round. Don’t miss out on the legacy, and while you’re there, you may even want to pick up a souvenir shirt, the true proof of a Vineyard visit.