Miles of beachfront, five bustling towns renowned for their history and coastal-inspired menus, and oozing with traditional New England charm, Martha’s Vineyard is an extension to the Massachusetts’ mainland, but also reflects a lifestyle of its own. Only a 45-minute ferry from the hook of Cape Cod, it’s a favored summer destination for both quick day trips and long weekends, but why rush? Stay awhile and explore with our destination guide for this enchanting island.
Where to Stay:
As one of four boutique hotels in The Edgartown Collection, The Christopher is a whimsical abode for the colorful traveler. Bright accents pop against the subtle, coastal hues tying the island’s quintessential past with a burgeoning modernity at the heart of Edgartown and within steps of the town yacht club.
Also in Edgartown, Harbor View Hotel positions travelers closer to the beach and popular photo opp near the town’s harborside lighthouse. The grand 117-room resort emulates “the Great American Summer,” portraying the island’s old world essence through a contemporary nautical theme. There’s also an onsite pool with a full bar, and is definitely an iconic spot to be, and be seen.
Where to Eat:
Chef Joe Monteiro delights diners with a casual patio and seafood-centric bistro in Edgartown, ideal for a sun-drenched afternoon of slurping back local oysters on the half shell and rosé.
For fine dining on the waterfront, reserve a table at this Vineyard Haven hotspot. The white linens set the tone for a memorable evening, with expertly crafted cocktails and elevated seafood dishes highlighting the freshest catch from throughout the island.
Where to Drink:
Nothing beats a local brew, and that’s exactly what you’ll find at this Edgartown brewery and taproom. Creating fresh beer daily, Bad Martha offers up to 10 different styles on draft at any given time, from summer ale to hard seltzer and a coffee porter. Settle into their verdant patio, surrounded by Donaroma’s Nursery and enjoy the change of scenery and a taste of the Vineyard.
Where to Visit:
Take a stroll against the towering cliffs of Gay Head Beach on the island’s westside.
Gingerbread houses, Oak Bluffs
Spend a day bopping in and out of the shops (and harborfront bars) of Oak Bluffs and finish up at the pastel houses, affectionately nicknamed “Gingerbread” homes. Refuel at the string of harborfront bars, like the sand-floored Sand Bar or the local hotspot, The Ritz.
This popular Vineyard beach is a go-to for sunset; we suggest picking up a lobster at The Net Result and bringing it down for a casual, island-style picnic while the sun melts into the sea.
Don’t forget the rest of the island’s towns
Vineyard Haven, Chilmark, and West Tisbury comprise the rest of the Vineyard’s main towns, and each offers a different feel. The best way to experience them all is by bike, pedaling at leisure to explore all they have to offer. Stop by Martha’s Vineyard Made to take home a trinket from the island; sip a cup of joe at Chilmark Coffee Company and cruise along the rolling hills of the residential West Tisbury.