More than being known as a favourite summer destination for influential politicians (the Obamas are reportedly buying a US$14.5 million vacation compound on the island), Martha’s Vineyard has long been one of Cape Cod’s most picturesque destinations. Flushed with wealth, the island offers urbanites a relaxing and restful getaway — the type of vacation where you can reconnect with nature, enjoy sensational eats, and maybe spot a celebrity or two while you’re at it.

Despite being a popular playground for the upper class, Martha’s Vineyard thankfully has retained its down-home charm all these years, favouring boutique shops over chains, and cosy bistros over high-end restaurants. While there are no real ‘vineyards’ (the island was named after the daughter of explorer Bartholomew Gosnold, who observed many vines covering the land), the island is rich in natural produce, from fresh seafood to ripe fruits and cheeses from the more than 40 farms dotting the island. If you’re ready to explore all of Martha Vineyard’s charms, check out our guide below for the best attractions on the island.

Harbor View Hotel

Following a US$15 million renovation this year, there’s no better place to soak in the beauty of Martha’s Vineyard than at the Harbor View Hotel in Edgartown, which boasts unequivocally one of the best views on the island. A short jaunt to the Edgartown Lighthouse, this historic hotel has been completely redesigned with modern amenities and expanded experiences, while retaining the Victorian-style soul of the island’s most iconic property.

Luxury manifests in a colour palette of soft cream hues juxtaposed with rich mahogany and bold blues, with guest rooms designed in a handsome array of textures and prints. If you can, grab yourself a harbour-facing suite, where a luxurious king-sized bed, curved French windows overlooking the glittering harbour and cushy armchairs tempt you to stay indoors all weekend. Feeling thirsty? Enjoy a well-made tipple or iced tea on the wide verandah, or head indoors to brand new Bettini Restaurant to feast on sensational farm-to-table fare. The hotel also makes it easy to explore your surrounds at leisure with complimentary bikes and a fleet of flashy Mercedes-Benz for cruising the island in style.

Vineyard Square Hotel & Suites

If you’re looking to stay right in the heart of Edgartown, Vineyard Square Hotel & Suites is your best bet for cosy accommodation just steps away from the main thoroughfare in town. Vineyard mirrors the maritime vibe of the historic waterfront district with rooms decked out in cosy sea blues with brass accents, complete with white-shuttered windows and balconies overlooking the street (prime for people-watching on a lazy afternoon).

A spacious front porch is an excellent place to while away the afternoon, while amenities include a daily homemade continental breakfast, free bikes, and beach chairs and umbrellas to take to the beach. At dinnertime, scoot to Chesca right off the hotel lobby to enjoy rustic Italian cuisine and fresh seafood. Friendly concierge are eager to dish out recommendations for the best sights and eats in Edgartown, whether it’s grabbing a pint at The Newes from America Pub just across the street, or enjoying a cup o’ joe at nearby Espresso Love.

The Right Fork Diner

A short drive out of Edgartown will take you to The Right Fork Diner, a charming spot where you can savour breakfast or lunch with a view over the Katama Airfield. Watch the classic biplanes lift off from the grassy runway as you tuck into fluffy chocolate-chip pancakes and brioche French toast for breakfast, or crispy fried fish sandwiches, chowder and juicy burgers for lunch. The homestyle diner also does salads exceptionally well — don’t miss the kale salad, a veritable bounty of fresh produce — think Brussel sprouts, radicchio, carrots, Vermont goat cheese — drizzled in a bright Meyer lemon vinaigrette. Guaranteed, it’ll be the best ‘airport food’ you’ve ever had.

The Covington

Since opening in 2016, The Covington has become a perennial favourite, serving artisanal farm-to-table fare courtesy of head chef Chris Fischer. Dishes are beautifully plated but retain their rustic nature, from the ‘Harvest Plate’ with curried carrots and Anson Mills farro, to the squid ink spaghetti with twirls of black pasta surrounding a wobbly yolk. The kitchen pays particular attention to championing local producers — you’ll want to start your meal with the whipped feta with local honey, marmalade and house crumpets courtesy of the island’s own Mermaid Farm.

Behind the Bookstore

This back-door coffee shop (literally, you’ll find it out back of Edgartown Books), is no longer a hidden secret, but that doesn’t mean it’s not still serving some of the best java in town. Locals love stopping by in the morning for some chit-chat and their morning caffeine fix, while visitors often find themselves lingering for hours on end with a good book and a steaming mint latte. In addition to strongly brewed coffees, Behind the Bookstore also offers an irresistible pastry selection, breakfast and lunch items — pair the smashed burger with an espresso martini and have yourself a relaxing afternoon in the shaded front yard.

Lookout Tavern

It’s not a trip to Martha’s Vineyard without sampling your way around the island’s best lobster walls. Whether buttery and warm or cold mayo-drenched with herbs, you’ll want to sample the best rolls on the island at Roxana Bar, Grace Church and The Seafood Shanty. For a sumptuous lobster roll with a view, head to Lookout Tavern in Oak Bluffs, where you can watch the ships and sailboats carving slowly through the harbour while tucking into a hearty-sized lobster roll drizzled in warm butter in a toasted brioche bun.


Soak in the prime coastal views from the large windows of Bettini while savouring thoughtful island-to-table cuisine courtesy of chef Patric Martineau. With the island serving as inspiration, Martineau presents a diverse range of dishes with sustainable produce sourced from local farms, fishing boats, foragers and markets on the island. Local ingredients are woven into internationally-influenced recipes, from steamed bao buns with crispy pork belly, to Atlantic salmon pea-cream risotto and magnificent braised short ribs in a luscious red wine jus.

7a Foods

If you’re heading to West Tisbury to stock up on the gluten-free goods at the renowned Scottish Bakehouse, you’ll also want to leave room in your itinerary for a stopover at 7A Foods, where you’ll find one of the best sandwiches on the island. Named the Liz Lemon after the 30 Rock star, the epic sandwich is stuffed with a kaleidoscope of ingredients: hot homemade pastrami, turkey, Swiss, tangy Russian dressing, crispy coleslaw and potato chips for crunch, all on toasty rye bread. Other highlights include the breakfast egg sandwich and the toasted Italian sub.

Catch the sunset at Menemsha

Catching the sunset on the small beach at Menemsha is a must-do for any first-time visitor to Martha’s Vineyard. The quaint fishing village is a bit of a drive from Edgartown, but worth seeking out for the picturesque harbour, and the excellent seafood. Most locals choose to grab a dozen oysters, fresh lobster and crabs, and a cup of clam chowder from either Menemsha or Larsen’s Fish Market next door, then claim a spot on the beach in time to watch the sun dip below the horizon across Vineyard Sound. Pro tip: This part of the island is ‘dry’ (meaning no booze sold), so make sure you pick up a bottle of chilled wine on the way to sip with your seafood.

Visit the multi-coloured Aquinnah Cliffs

Not too far from Menemsha you’ll find the Aquinnah Cliffs; formerly known as Gay Head, it’s one of the most popular tourist sights on the island. Part of the Wampanoag reservation, the special area boasts stunning multi-coloured cliffs cascading down to the ocean below, made of successive layers of brown, grey, blue, and red clay carved by glaciers millions of years ago. Take a leisurely walk along the trail overlooking the cliffs, snap a pic of Gay Head Lighthouse, then browse the handful of local shops touting Wampanoag handicrafts.

Shop the boutique stores in Edgartown

From the streets lined with old captain’s houses with their picture-perfect white-shingled facades, to the plethora of quaint pubs and coffee shops — you’ll want to spend at least a day or two just exploring Edgartown. The best way to do this is undoubtedly on bike (most of the island is connected with well-paved bike lanes), or simply stroll along the streets popping into the quaint storefronts.

Boutique shoppers will find plenty to catch the eye: Find statement jewellery and accessories at Mikel Hunter, add to your art collection at Eisenhauer Gallery, stock up on fragrant bath soaps at Vineyard Bath Co, and pick up stylish outerwear at Backwater Trading Company. One of the most popular boutique shops, Slate, is a must-visit to dress yourself in head-to-toe island attire: from wide-brimmed sun hats to cosy cashmere sweaters, this stylish boutique shop has it all.

Pay a visit to the Gingerbread Cottages

From Edgartown, it’s a 30-minute bike ride to Oak Bluffs (allow for a stop-off at Joseph Sylvia State Beach, famous for being the setting of the beach scene in Jaws), another colourful and historic town. One of the must-visit attractions is the Flying Horses Carousel, constructed in 1876 and known as the oldest platform carousel in the nation. When hunger strikes, grab pastries at the uber-popular Back Door Doughnuts, then take a 10-minute stroll to the ‘Gingerbread Cottages’, a series of brightly painted (and highly Instagrammable) fairytale-like cottages that made up the old Methodist Campgrounds during the mid-1800s.

Spend a day on Chappaquiddick Island

The 3-minute Chappy Ferry to the island of Chappaquiddick is an attraction in itself (the small barge holds just three cars at a time); once on the other side, expect to spend half a day or so exploring the island and cycling the tree-lined roads. Make sure you bring provisions with you, and plan for a picnic at the Cape Poge Wildlife Reserve, the Mytoi Japanese gardens, or on one of the pristine sand banks.

Leslie Yeh
Editor in Chief
Having worked as a lifestyle editor for almost 10 years, Leslie is thrilled to be writing about the topic she loves most: wining and dining. When she's not out pounding the pavement for the latest new restaurant opening or tracking food trends, Leslie can be found at home whipping up a plate of rigatoni vodka and binge-watching Netflix with a glass of Sauvignon Blanc in hand.