Discover America's most exclusive islands
Martha’s Vineyard and Nantucket are two of the most exclusive destinations in the USA. Both are islands off Cape Cod in Massachusetts. Some of the most high-profile figures in the country have holiday homes on the islands. Martha’s Vineyard and Nantucket have become bywords exclusivity.
If you’ve done Provincetown and you fancy a change, these New England islands should be on your bucket list. Both Martha’s Vineyard and Nantucket are perfect for a relaxing, luxury staycation in the USA. Each island has different charms. It’s a case of deciding which one is best for you. So, time to pick, Martha’s Vineyard or Nantucket?
About Out Of Office
Out Of Office is a luxury tailor-made travel company with a focus on delivering exclusivity and inclusivity. Our passion for global adventure is matched only by our deep commitment to delivering exceptional five-star service.
Everything we do is customised and designed especially for you – our valued customer – based on your exact personal requirements. Each member of our team is widely travelled. This means you get access to first-rate travel insights and the best possible advice from our team of luxury travel experts.
Martha’s Vineyard has a more arty, bohemian vibe than Nantucket. Back in the 70s, Carly Simon and James Taylor bought their home on Martha’s Vineyard. They were the biggest power couple in the pop world. The bohemian but upwardly mobile style they embodied exemplifies Martha’s Vineyard in many ways. Simon still lives on the island in the same house.
The landscapes of Martha’s Vineyard may seem oddly familiar. Steven Spielberg filmed Jaws on the island – “Amity Island” is in fact Martha’s Vineyard. You can go on a Jaws tour and see the key locations he used. You’re very unlikely to be eaten by a shark in the process!
Martha’s Vineyard has long been a magnet for artists and writers – it’s the ultimate writer’s retreat. You’ll find some excellent galleries and art studios to explore. Film festivals are held in March and September. Nantucket and Martha’s Vineyard join forces in October during Fall for the Arts, a month-long arts festival.
Nantucket is smaller and more compact. You’ll find most cultural attractions in the Nantucket Cultural District. Take a trip to the Whaling Museum and get a feel for New England’s past. Spielberg filmed Jaws in this part of America for a reason: it was the heart of the whaling industry. The whaling ship in Moby Dick was from Nantucket.
Nantucket is only 15 miles west of Martha’s Vineyard, and the island itself is 15 miles long. You can “do” Nantucket pretty quickly. Martha’s Vineyard is bigger and there’s more to see, so if you’re going to do both islands in one trip it’s worth visiting for longer.
In Martha’s Vineyard, you’ll want to visit the Gingerbread Houses in Oak Bluff. The candy-colored houses look like something out of a fairytale. You’ll definitely want a picture of you standing in front of them and spend some time fantasizing about living in one. For a perfect New England experience, have lobster and clam chowder, preferably on Menemsha Beach on Martha’s Vineyard – advance booking recommended. It’s a very popular pastime.
There are three famous lighthouses to visit on Nantucket. As it’s small you can cycle around the island quite easily. Don’t miss the Sconset Bluff Walk along a path made of seashells. You’ll see many charming cottages.
Gay scene in Martha’s Vineyard & Nantucket
There’s no gay scene on Martha’s Vineyard or Nantucket – that’s all going down in Provincetown and Boston! Both islands are very gay-friendly though. In Martha’s Vineyard, you can explore Gay Head Cliffs and Gayhead Lighthouse (no sniggering at the back). Take in the upper trails along the cliff or take the pathways closer to the beach. You’ll be able to say you went to Gayhead Lighthouse!
Both islands boast some excellent luxury, boutique hotels. The Charlotte Inn is great for old-world charm in Martha’s Vineyard. It’s like a Victorian inn for gentlemen, but it’s not remotely stuffy. For classic New England chic, Hob Nob is a great choice. One of the best hotels in Nantucket is White Elephant. It’s a great luxury retreat comprised of the main hotel, two lofts and eleven cottages.
Martha’s Vineyard or Nantucket?
Nantucket is the native home of the preppy American aesthetic. You’ll see many well-heeled Americans enjoying their New England staycation in Nantucket. Peppy style is all about looking rich but effortless. You know the style as soon as you see it. Supposing you were writing a thesis about what it means to be preppy, you might begin in Nantucket. It’s a pretty great spot for people watching. In 2019, the median sale price on Nantucket property was $1.6 million. Most homebuyers will be looking for a second – or maybe third! – home when they buy in Nantucket.
Martha’s Vineyard is equally exclusive. It was recently hailed as the priciest summer vacation spot for families in America by Tripadvisor. Martha’s Vineyard has six towns and Nantucket has just one. There’s more happening in Martha’s Vineyard. It’s hard to pick one island over the other. So, if you’re looking for something upmarket with a more preppy vibe, Nantucket may win, and if you’re looking for upmarket with a boho vibe, Martha’s Vineyard wins. Our ideal itinerary would combine both Martha’s Vineyard and Nantucket.