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.
Perfect forFamilies | Romantics | Ultimate Indulgers
When to goMarch-May | June-August | September-November
Ideal length of stay3-5 Nights
Designing Your Journey
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.
3 Days: Essential Martha’s Vineyard
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.
Where To Stay
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.
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The Charlotte Inn
The Charlotte Inn, which touts itself as being “behind the times on purpose,” finds the perfect middle ground between luxurious and charming.
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Harbor View Hotel
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.
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