Located just south of Cape Cod, the triangular-shaped island of Martha’s Vineyard is undeniably one of the most exclusive summer hideaways in the U.S. For such a jet-set destination, however, it also maintains a reputation for friendliness. (Case in point: Strangers tend to wave at each other on the expansive beaches, something not often seen in such upscale enclaves.)
These unique elements make the Vineyard an especially perfect destination for a summer such as this one. Good vibes and spacious outdoor landscapes abound, and the island boasts a soothing charm that feels a world away from the crowded bustle of the Northeast’s metropolitan cities.
Sunrise over Martha’s Vineyard. Photo courtesy Harbor View Hotel.
Just short of 100 square miles and encompassing a handful of welcoming towns, the Vineyard offers a variety of vastly different “scenes.” There’s the peerless allure of Edgartown, the quietude of the interior farmland, the gingerbread cottages of Oak Bluffs, and the remote, otherworldly coastal beauty of its western villages (chief among them is Aquinnah, aka Gay Head). Adding to its idyllic ambiance, iconic New England lighthouses dot many a spit of sand.
This peaceful summer paradise is easily accessible by Tradewind Aviation’s regularly scheduled shuttle flights, private shuttles, and charter flights. For those looking for a much-needed escape, here’s how to spend a weekend in Martha’s Vineyard. Each of the establishments we’ve highlighted is ready to safely welcome guests, ensuring your getaway is relaxing and stress-free — as any Vineyard weekend should be.
FRIDAY
Photo courtesy Harbor View Hotel on Martha’s Vineyard.
4 p.m. Check into Harbor View Hotel, which celebrates its 130th anniversary this year and recently underwent a top-down renovation of its coastal-contemporary décor. Located less than half a mile from the center of Edgartown (a three-minute bike ride), Harbor View is the quintessential Vineyard abode. Amenities include an outdoor, heated seawater pool, as well as a new fitness center. At the hotel, the main inn is the center of the action, but families should take note of the specialty accommodations, including the one- to three-bedroom Captain’s Cottages and the 2,270-square-foot Presidential Skyhouse (boasting four beds, five baths, and spectacular views).
6:30 p.m. An Edgartown institution courtesy of Eli Levy and Jamie Zambrana, the Atlantic Fish & Chophouse is beloved for its USDA Prime steaks, whole branzino, and numerous lobster dishes, from the lobster arugula salad to the lobster ravioli with beurre blanc — and especially the crowd-pleasing black truffle lobster mac & cheese. Don’t leave without trying the decadent five-layer Valrhona chocolate cake or the French-style Nutella cheesecake. If you’re opting for take-out, enjoy it at nearby Lighthouse Beach at dusk.
SATURDAY
Edgartown Books on Martha’s Vineyard. Photo courtesy Quadri Okunga.
9 a.m. Massachusetts is blueberry country, so rise and shine and head down to Bettini, the Harbor View’s all-day restaurant, for blueberry buttermilk pancakes. After breakfast, stroll into town along North Water Street to admire the waterside homes festooned with globes of blue hydrangeas. It takes just 10 minutes to hit the town center, where you can browse contemporary art at Eisenhauer Gallery, casual wear at the iconic Black Dog, and women’s apparel and jewelry at Nell. Don’t miss the excellent indie bookstore, Edgartown Books, and be sure to grab some chocolate pecan fudge for later at Murdick’s, which has been using the same recipes since 1887.
Photo courtesy of The Black Dog in Edgartown, Martha’s Vineyard.
12 p.m. Pick out a beach cruiser at Martha’s Vineyard Bike Rentals, then if you’re up for an easy, hour-long bike ride, hop on and pedal to South Beach. The Vineyard is known for its well-paved bike paths, and the ride is flat and rural. After seeing the narrow strands of sand around Edgartown, you’ll find South Beach to be a shock: Accessible over grassy dunes, the Hamptons-like beach is long and wide, with golden sands.
Grab a drink and cool off at the hotel pool at Harbor View Hotel.
5 p.m. Cool off with a refreshing dip at the hotel pool, and order up a cocktail from the Roxy pool bar. (We recommend the refreshing One in a Melon, made with vodka, watermelon, and basil.) For dinner, walk over to the casual Seafood Shanty: The local oysters from Katama Bay, the tuna roll, and the lobster quesadilla are standouts.
SUNDAY
The clay cliffs of Aquinnah on Martha’s Vineyard. Photo courtesy: Harbor View Hotel.
10 a.m. Explore more of the island by car (hint: you can borrow a Mercedes from the hotel, one of its many stylish amenities). One of the more unusual spots is the Oak Bluffs Campgrounds, where hundreds of Victorian-era cottages show off their candy colors. Then head out to far-flung parts west, to Chilmark and the clay cliffs of Aquinnah, and keep your eyes peeled for the Chilmark General Store, where you can load up on a picnic brunch of kale salads, baguette sandwiches, fresh-baked banana bread, and cinnamon rolls.
Victorian-era cottages show off their candy colors in Oak Bluffs, Martha’s Vineyard. Photo: MVCC.
Finally, drive to Tisbury at the northern tip of the Vineyard to admire the West Chop Lighthouse, which dates from 1891 and stands 45 feet tall. It’s a wonderfully fitting way to cap off a visit to one of the Northeast’s most classic communities.
To learn more about Tradewind’s scheduled shuttle flights, private shuttles, and private charter flights to Martha’s Vineyard and booking your vacation, please visit our website. To receive a private charter quote, please complete our charter request form or contact our specialists at charter@flytradewind.com or 1-800-376-7922. To learn more about Tradewind’s comprehensive safety plan, please visit our COVID-19 Response page. For the latest travel updates, please visit our Travel Advisory page.Edgartown Books