10 Best Islands to Live On for Easy Transitions

December 27, 2014

We chose these islands because they’re exotic in their own ways, yet they don’t require a life raft or a machete to survive.

Read more in our Ultimate Best Islands to Live On Guide.

Best Islands to Live on For Easy Transitions: USVI, Move to an Island


Moving here is like moving from New York to Florida. But if you want to be a resident (and get personal tax breaks), you have to prove that you live here for more than 183 days a year. Great for investors. Multiple tax benefits make the USVI perfect for the business savvy. And the Economic Development Authority is here to help.
Best Islands to Live on For Easy Transitions: Hawaii, Move to an Island

Big Island, Hawaii

No worries about foreign residency here, and even though Maui, Kauai and Oahu combined could all fit within the Big Island, its population is considerably less than the others’: 200,000 residents are spread across 4,806 square miles and surround the world’s tallest mountain (Mount Mauna Kea, much of which is under the ocean). Jon Whittle
Best Islands to Live on For Easy Transitions: Turks and Caicos, Move to an Island

Turks and Caicos

Fewer than 40,000 people call this their permanent home. Those who have made the move say the mellow vibe and open spaces make the permit fees worth it. English is the language and the U.S. dollar is the currency. Owning property isn’t so easy though. Zach Stovall
Best Islands to Live on For Easy Transitions: Dominican Republic, Move to an Island

Dominican Republic

It’s an easy flight to and from the U.S., and housing is affordable in every direction since the value of the peso dropped a few years ago. Jon Whittle
Best Islands to Live on For Easy Transitions: Penang, Move to an Island


The medical care gets high marks from expats, and the country has an expat office to help ease the move overseas.
Best Islands to Live on For Easy Transitions: Puerto Rico, Move to an Island

Puerto Rico, Northwest Coast

Small towns like family-friendly Aguadilla and Isabela, known as the “Garden of the Northwest,” make this region of Puerto Rico a calmer, safer bet than the hectic cities of San Juan or Ponce. And hiking, horseback-riding, kiting, scuba diving — those are no longer vacation activities or even weekend jaunts for residents here. They’re happy hour. Zach Stovall
Best Islands to Live on For Easy Transitions: Ireland, Move to an Island


Easy move? Across the Atlantic? It’s a long way to Ireland by boat, that’s true. What’s easy is the transition to the Irish way of life. People care about people here, and they speak lovely English. There’s also a consciousness growing island-wide about healthy eating and playing. Go down to the corner pub for a pint of Guinness at the proper temperature and an Irish music_ seisiún_ — not a performance but a shared local experience. The same goes for just being here. Living in Ireland isn’t a catered vacation. It’s the good life.;
Best Islands to Live on For Easy Transitions: Whidbey Island, Move to an Island

Whidbey Island, Washington

The easiest move, of course, depends where you’re moving from. But just a bridge crossing or short ferry ride off the upper-left coast of the US lies a pastoral paradise—organic farms, cafes and wineries, small towns, perhaps the world’s freshest seafood. Yes, it can rain here, but the tradeoff is the evergreen beauty of the Northwest, visible at jaw-dropping Deception Pass and also everywhere.;
Best Islands to Live on For Easy Transitions: Hawaii, Move to an Island

Oahu, Hawaii

With extraordinary mountains, great beaches, and indoor/outdoor cultural opportunities from ukulele playing to surfing the beginner-friendly waves of Waikiki, this is pure Hawaii. Plus Honolulu has the mall for whatever-you-need shopping. And moving here is as simple as selling your winter wardrobe and getting on a plane. OK, that’s an exaggeration, but for Americans there’s no bureaucratic hoop-jumping and no language barrier. You don’t even need a passport, though you’ll want one for trips to the rest of the Pacific and Asia.;
Best Islands to Live on For Easy Transitions: Florida Keys, Move to an Island

Florida Keys

A subtropical island attached by road to an American state, so you can drive your moving van right to the beach? That’s a change both easy and profound. Whether you stop in Key Largo still commuting distance from Miami, opt for the outback wildness of Big Pine Key, or go all the way to Key West where the sun sets every single day, you can’t go more than 113 miles wrong. The living is easy too, mostly barefoot. People speak English and spend US dollars in the so-called Conch Republic. Other than that, it’s a world apart—with a bridge.;

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