In New England, there’s a sort of unspoken rivalry between Nantucket– and Martha’s Vineyard-goers. Both reasonably intimate islands, and both off the coast of Massachusetts’ other prime summer hotspot (Cape Cod), one may wonder how different these two places could truly be. That answer is really only discoverable upon a firsthand visit yourself, but let us help set the scene.
Martha’s Vineyard is about 45 minutes away from Woods Hole in Falmouth, via the Steamship Authority ferry. It’s the same port call for Nantucket, but the latter takes a little over an hour. The island of Martha’s Vineyard is only 100 square miles, but is relatively unconcentrated; its six towns (Edgartown, Oak Bluffs, Vineyard Haven, West Tisbury, Chilmark and Aquinnah) are spread throughout the island in populated pockets between uninhabited verdant land and sandy shores.
Each of the towns offers its own distinct personality, and what visitors seek from a vacation typically determines where they’ll stay. The beach crowd tends toward Aquinnah and West Tisbury (if they’re lucky enough to find an Airbnb up for grabs), while those looking for the island party vibe will want to stay around Oak Bluffs, and those who desire the best of both worlds stay at the center of it all: Edgartown. This is where the best hotels are, with quality bars and restaurants to match, and the beach only a mile away. That said, every corner of the Vineyard is as charming as the next, so pick a town and explore it all with our inside guide of the island, below.
Where to stay
One of the newest hotels on the island pays tribute to one of Martha’s Vineyard’s most historic buildings and former accommodations, the Kelley House, which dates back to 1742. Renovated and reimagined by Boston-based real estate firm Blue Flag Partners (they’re also behind Faraway Nantucket, which opened in 2021), the heritage property still offers Edgartown charm across its 58 rooms, but with a modern facelift for the savvy traveler. Like its sister property, the contemporary coastal interiors were designed to follow a fantastical narrative—here, of a local Vineyard woman from the 1960s who loved all facets of entertainment, including music, cocktails, statement antiques and plant and floral arrangements. The whimsical storyline presents an ethereal personality and cohesive flow throughout the sprawling property, from the suites overlooking the old whaling town, to the new pool, outdoor bar and gathering spaces, as well as the on-site boutique and restaurants.
Approaching this 117-room property evokes a feeling of visiting a wealthy relative’s summer mansion; the wraparound veranda and harbor views offer a sense of enticing comfort, all with the elegant touches of a seaside New England resort. The historic Harbor View Hotel was renovated in 2020, and all the rooms are now equipped with smart technology, sleek furnishings and a minimalist color palette accented by a swath of island blues, from indigo to turquoise. In addition to guest rooms, the resort features one- to three-bedroom Captain’s Cottages for larger parties and longer stays, as well as a swoon-worthy Presidential Skyhouse; a fourth-floor, one-bedroom penthouse with sweeping views of some of the island’s main attractions. These quarters can also be connected to the Sky Family Suite and Sky Guest Room for a complete takeover of the fourth-floor wing. Elsewhere on the property, there’s a heated swimming pool with cabanas, and two restaurants that were completely refurbished during the 2020 renovation.
Where to eat
A splurge-worthy vacation warrants a reason to get dressed up for a fancy culinary experience, so go ahead and reserve a table at Bettini. Start with a cocktail on the wraparound porch and take in the ocean views, before moving inside and making yourself comfortable in one of the scarlet, leather-clad chairs at this fine-dining restaurant. Serving refined American favorites with a coastal emphasis (think Clams Casino, grilled octopus and gulf of Maine swordfish, to name a few highlights on the seasonally-updated menu), Bettini’s also offers an impressive wine list. Indeed, the restaurant won Wine Spectator’s Award of Excellence in 2022, so don’t be afraid to dive into their vino book to discover something new, or splurge on one of the classic greats.
This Edgartown hotspot is open seven days a week for brunch, lunch and dinner, and with oyster in the name, you know what the highlights are here. The impressive raw bar is updated daily with some ten varieties of regional oysters, from the famed Katama of Martha’s Vineyard to favorites sourced from Maine and Rhode Island. Fresh seafood reigns supreme with their crudo and ceviche list, plus cooked entrees like lobster tacos and oyster po’boys.
For a more casual lunch or dinner option, head to this dockside haunt on Menemsha Harbor. Renowned for their lobster roll, Larsen’s also offers fish market favorites like steamers smothered in butter, stuffed quahogs and fish cakes. The outdoor tables are limited, but there’s plenty of seating along the docks—just watch out for the seagulls that may come and try to snag a bite. If you arrive before noon, you might be lucky enough to see the fishermen unloading that morning’s bounty.
This nautical dining room overlooks Vineyard Haven harbor, and serves up exceptional fare that’s inspired by the surrounding landscape. The chef’s preparation of the local catch is always a treat, as are staples like green curry mussels, olive oil poached halibut and pan seared striped bass.
When the Italian cravings hit, Salvatore’s authentic and homemade pastas are ready to satiate. Owned and operated by Naples-born chef Salvatore della Torre, this restaurant is a recent addition to Vineyard Haven’s culinary scene, and has already been met with praise. Expect traditional Italian cuisine with an island twist, like the lobster ravioli special.
Where to drink
Since opening in 2014, the Bad Martha Farmer’s Brewery in Edgartown has attracted a crowd eager to try its premium craft beer, and maintained a loyal set of patrons thanks to its laid-back atmosphere, set in a timbered facade surrounded by lush foliage on the Donaroma’s Nursery property. The onsite seven-barrel brewing system ensures fresh beer is served daily, with a constant rotation of 10 different Bad Martha beers. In addition to thirst-quenching brews, you’ll also find yard games, live music and beer-complementary grub.
Slip off your sandals and feel the sand beneath your toes at this Oak Bluffs venue, overlooking the harborwalk. The unique locale is an ideal spot to indulge in your first Dirty Banana, a popular frozen cocktail on this strip composed of a mix of dark rum, Kahlua, coffee liqueur, cream, chocolate syrup and fresh banana.
For more views, head to Aquinnah. This seasonal restaurant is perched on the celebrated Gay Head clay cliffs, which embody more of a Hawaii scene than that of a Massachusetts island. Whether you’re there for a refreshing midday sip after a walk on this renowned beach, or early evening when the fog might hover before sunset, the views here are the perfect place to while away time with your favorite cocktail.
The outdoor oasis, decorated with twinkling fairy lights and patterned umbrellas, is a picturesque downtown spot to start your evening. The menu features herbaceous libations, made using fresh, locally-sourced fresh ingredients.
Ask locals where they’re spending the evening, and they’ll likely lead you to The Ritz. A no-frills, Oak Bluffs dive that’s known for music and strong pours, it’s the place to be when the sun sets and the beloved waterfront bars lose the charm of harbor views.
What to do
Explore the Gingerbread Cottages of Oak Bluffs
What were once part of a 19th century Methodist campground are now historic fixtures in Oak Bluffs. Three hundred of the original structures remain, boasting pastel facades and ornamental accents like draped windows that reflect the architectural style of the period, called “Carpenter’s Gothic.”
Tour Signature Oyster Farm at Katama Bay
Like many of the best offerings on Martha’s Vineyard, this tour is seasonal (running from July through August); however, it’s the best way to learn about the salty bivalves that are served on the half shell throughout the island. All tours educate guests on oyster farming, include a boat ride in Katama Bay and end with freshly harvested oysters from that day (BYOB including beer and wine). If you’re really keen, you can learn how to shuck an oyster, too.
Sometimes vacations call for breaking a sweat, and on such a picturesque island, this doesn’t have to be *too* laborious. Rent a bike and explore one of the most popular bike routes at leisure. There’s also lighthouses to climb; the Edgartown Lighthouse and Gay Head Lighthouse are two popular ascents for views worth the quad burn.
Go to the beach
No Martha’s Vineyard trip would be complete without a visit to the beach. Whether spending a full day at Katama Beach, looking for nature along Lighthouse Beach or walking along Gay Head Beach, Martha’s Vineyard has some 20 sandy spots just waiting to be enjoyed.
Where to shop
Edgartown & Vineyard Haven
Specialty boutiques, vintage shopping and art galleries abound throughout Martha’s Vineyard. While you’ll find some familiar brands like Lululemon, Lilly Pulitzer and J.McLaughlin scattered along Edgartown’s Main Street, the majority of clothing and home accessories shops are locally-owned, like Salte, a travel-inspired lifestyle boutique, Tesori, a store with fine jewelry from local designers, and Chappaquiddick Wood Company, which offers bowls and hardwood products crafted on the island. In Vineyard Haven, ateliers like Magnetic North, The Trust Shop, The Seven Sisters and Lennox and Harvey offer high-end clothing to ensure you’re dressed in island style. There’s also a cluster of antique and secondhand stores around Menemsha, where treasures are buried but plentiful.
The Grey Barn & Farm
Located in Chilmark, this 100-acre property features a year-round Farmstand that sells cheese produced at their on-site, certified-organic creamery, in addition to fresh eggs, sourdough bread and pastries. The Farmstand also sells specialty items from local Island and Massachusetts purveyors, including photography and books. For those looking for a more immersive shopping experience, reserve a cheese tasting in advance; the experience includes a short, guided tour around the farm, before a tasting of five signature cheeses in the garden, accompanied by The Grey Barn’s charcuterie and fresh bread, along with essential accouterments from the Farmstand.