There’s a lot to love about this seven-acre hilltop retreat overlooking Menemsha Harbor, from its clutch of country cottages to the restaurant’s panoramic water views.
The lobby of this 1864 merchant’s house is full of 19th-century oil paintings and Edwardian objets d’art; upstairs, 19 intimate rooms are done up with plush canopy beds and vintage steamer trunks.
At this seaside Victorian Revival, wide wraparound porches are ideal for watching boats sail in and out of the harbor. We love their 1956 Rolls-Royce, which is on hand for a spin around the island.
Playful elements—dog-shaped lamps; chintz wallpaper—make the Hob Knob a whimsical alternative to the island’s old-school inns. Take a fishing trip around the Sound on the hotel’s 27-ft. Boston Whaler.
The 54-suite Winnetu, steps from South Beach, is as close as the Vineyard gets to a mega-resort, with a library, fitness center, and vast lawn outfitted with a nine-hole putting green.
A visit to the Vineyard isn’t complete without a stop at this waterfront landmark. Grab a seat at an outdoor picnic table and order a lump crab cake sandwich and a bowl of quahog chowder.
The sibling to popular island spot Atria is now a place for in-the-know locals. Look for seafood classics (grilled salmon; soft-shell crab) and offbeat items such as Asian-style baby back ribs.
Dig into lemon-ricotta pancakes or the locavore burger, with house-made garlic dill pickles picked from the restaurant’s own gardens, in a wood-beam dining room outfitted with American antiques.
Chef Carlos Montoya turns out Frenchified American classics (grilled rib eye with Parmesan velouté; strawberry terrine) at this romantic Victorian town house—a favorite of the Obamas.
The sashimi and lobster rolls alone are worth the trek to this no-frills, cliffside haunt near the Gay Head Lighthouse in Aquinnah, complete with knockout ocean views.
At this bi-level restaurant and bar, the steak frites and fried risotto balls don’t distract from the tropical drinks such as tangy mojitos and gin-and-juices.
Peanut shells blanket the floor at the laid-back neighborhood pub, which stays packed until the wee hours. Try the Offshore Amber Ale—it’s brewed on site.
This railroad-style lounge draws crowds with innovative cocktails like the Brown Chicken, Brown Cow, made with Domaine de Canton ginger liqueur, Wild Turkey American Honey liqueur, and ginger ale.
This is a browser’s paradise of funky furniture and unique finds—quilts from India, jars of homemade mango-lime salsa, and kitchen chairs with denim covers.
Interior designer Liz Stiving-Nichols hand-selects each piece, from driftwood picture frames to porthole mirrors. Our favorite: her Townie Pillows, stamped with Vineyard town names and zip codes.
Opened in 1858, this general store is a throwback to an era when every neighborhood had a one-stop shop. Come here for picnic fixings, comic books, and, of course, your morning coffee.
At the light-filled glassworks studio, artisans create colorful vases and tableware. Best bet: the multihued pitchers.
This popular brand pays homage to the island’s preppy heritage with whimsical ties and polo shirts in various pastel shades.
Hundreds of Victorian gingerbread cottages fill this landmark district, built by Methodists who established camp meeting sites here in the 1800’s.
At this seven-year-old breeder’s farm, guests can feed the animals and take them for walks around the 19-acre grounds. Swing by the gift shop for alpaca hats sweaters made on the island.
The iconic 1881 lighthouse, originally built for Crane Beach, in Ipswich, was dismantled and brought by barge to the Vineyard. Climb the spiral staircase for views of the harbor and Chappaquiddick.
This converted barn houses an impressive and eclectic collection of paintings, sculptures, and photographs by over 75 artists. A highlight: black-and-white landscape photography by Alfred Eisenstaedt.
Hop a ferry to this island, 300 yards off the Vineyard’s eastern coast, for miles of empty sand and great bird-watching (spot blue herons and sandpipers).
Head to this 600-acre refuge in West Tisbury for windswept dunes, hiking trails, and unspoiled coastline.
You won’t witness a better sunset than at this beach, a two-minute walk from the fishing village of the same name. Pack a picnic and a blanket—it gets cold at dusk.
A great spot in Menemsha for clams on the half shell and watching the sunset.
At this fresh produce market, the fruits and vegetables come straight from the fields.
A lively café in Edgartown, loved by the locals for its steaming brews and iced coffee.
