Despite an A-list patronage—the Obamas are frequent visitors—Martha’s Vineyard is one of New England’s loveliest and most low-key islands. At its heart, the Vineyard is about the simple pleasures of summer.
Work with Indagare to design the perfect itinerary for an immersive journey. Our travel experts know the destination inside and out, and they can make recommendations based on your travel needs and preferences.
Indagare can craft a customized itinerary with special access to the Vineyard’s exclusive private beaches, fun classes for the whole family and guided touring of the sites that have attracted artisans, artists and writers since the 1960s. Here is just one example of what our destination experts can create for you.
Relax into your long weekend in Martha’s Vineyard with a lazy beach day at one of the exclusive private waterfronts, like Lucy Vincent or Lambert’s Cove. You can also participate in activities as fishing, paddle boarding and kayaking. Enjoy brunch at an Indagare-recommended restaurant and then have an early picnic dinner on the beach as the sun sets over the water.
Explore Down Island, which is made up of three of the most populated towns in Martha’s Vineyard. Down Island is perfect for shopping and enjoying New England specialties like lobster. You can visit such sites as the Gingerbread Houses in Oak Bluffs, and then make your way to Edgartown, the most glamorous of the three. After strolling the main street and snapping gorgeous photos, enjoy a wine tasting before dinner at one of the local restaurants.
Drive west towards Aquinnah against the backdrop of technicolor-blue ocean and green rolling hills that makes Up Island such a treat. Up Island, which resembles the Irish countryside, is where nature lovers will find the best hiking trails and a fantastic nature preserve, the Polly Hill Arboretum. Art lovers will also discover the outdoor sculpture garden at the Field Gallery. End the day with an indulgent private dinner in the greenhouse restaurant at Beetlebung Farm.
We only feature hotels that we can vouch for first-hand. At many of them, Indagare members receive special amenities, including upgrades, early check-in, breakfast, spa credits and more. Look for the Indagare Plus logo in the reviews.
The Charlotte Inn, which touts itself as being “behind the times on purpose,” finds the perfect middle ground between luxurious and charming.
The Harbor View is both close to town and right on the water, making it great for families who want to walk to dinner while still enjoying direct beach access.
Martha’s Vineyard’s most famous attraction, albeit kitschy, is a guaranteed home run with children. The country’s oldest carousel in use, Flying Horses is packed with tourists during the summer months. Snag the lauded brass ring and you’ll be allowed to...
Originally a Methodist meeting ground, this gathering of pastel-colored cottages could accurately be described as a real life Candyland. Built in the “Carpenter’s Gothic” style, the gingerbread cottages are painted in hues ranging the full color spectrum, and feature unique...
Martha’s Vineyard’s southern shore is among the longest uninterrupted stretch of beaches north of Florida. Not all of them are open to the public, since Massachusetts is the one of only two states that allow private beaches (the other is...
A great way to explore the islands and waters surrounding Martha’s Vineyard is to reserve a boat and captain for a day charter. Anything from a sunset cruise aboard a luxurious catamaran to a private party on a traditional schooner...
Everything we recommend is sourced first-hand by our well-traveled team and incredible network of insiders and resources around the world. Here are some the latest articles, interviews, and book and film recommendations not to be missed.
Lying off the Massachusetts coast, Martha's Vineyard is as well-known for its famous visitors—from the Obamas and Caroline Kennedy to Bill Murray and Amy Schumer—as for its delightfully mellow scene.
Summer weekends in the Northeast often see city dwellers flocking in droves to the waterfront retreats of the Hamptons or Cape Cod, making the low-key, less crowded Block Island feel like an even more tranquil escape. With its quintessentially New England grey-shingled houses and...
Cumberland Island, the southernmost of the Georgia barrier islands, is one of the world’s most secluded, pristine natural habitats. Occupying an area larger than Manhattan, the island boasts three ecosystems, including salt marshes, forest and miles of beach, where wild...
At Indagare, we believe in the transformative power of books, and that reading has the power to broaden the mind and inspire exploration. Here, the Indagare editors reveal the just-released titles filling their beach bags this summer, from nonfiction travelogues to...
A trip here can easily be combined with these amazing destinations and more. Contact our team to craft the perfect itinerary.
Despite continuously serving for more than 200 years as the political, economic and cultural hub of New England, Boston’s reputation as a staid municipality with rabid sports fans hadn’t changed much over the years. Now home to a bevy of...
Nantucket is to New England what the Hamptons are to New York; an elite, elegant and chic escape from the city. But with nary a traffic light in sight, Nantucket entrances visitors with its old whaling town charm, and surprisingly low-key glamour.
America’s First Resort,” Newport has set itself apart from New England’s other seaside enclaves for nearly four centuries. The town celebrates its colonial architecture and Gilded Age mansions with style, and its harbor is a yachting mecca. Just beyond the...
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