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Martha's Vineyard

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 for
    Families | Romantics | Ultimate Indulgers
  • When to go
    March-May | June-August | September-November
  • Ideal length of stay
    3-5 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-LP

    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.

    • Day One:

      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.

    • Day Two:

      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.

    • Day Three:

      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.

Check availability at Indagare-recommended hotels.
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Indagare's Emma Pierce
“Martha’s Vineyard’s most famous attraction is the country’s oldest carousel in use, Flying Horses. Albeit kitschy, it is a guaranteed home run with children. Snag the lauded brass ring and you’ll be allowed to stay on for an additional ride.”
Ready to go and in need of expert trip planning? Contact us today.
Check availability at Indagare-recommended hotels.

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