Editor’s Note: Some of the information below may be out-of-date. The British Virgin Islands and the U.S. Virgin Islands were heavily impacted by Hurricane Irma and Hurricane Maria. Please visit caribbeantravelupdate.com or for the latest news.
Every year, our Best Islands to Live On article is our most popular, and it’s not surprising. The dream of #SurroundMeWithWater becoming an everyday reality is one we all share: According to our reader survey, 80 percent of you have thought about moving to an island someday, and 75 percent have considered purchasing an island home.
Nearly 60 percent of readers are contemplating a move to the Caribbean — so we offer five top picks. You told us you’re concerned with the cost of island living — so we rounded up affordable options (plus one that’s worth the splurge, just for fun). A beach bum wants a different vibe from a city slicker — so we broke down locations by the personality type they suit best. Same goes for stages of life: Recent grads and retirees have varied needs, so we addressed each one. Plus, we share on-the-ground tips from expats who made the leap. We’re confident these islands will inspire your next move.
And now, in no particular order, our list of the Top 20 Best Islands to Live On.
Best Caribbean: Grand Cayman
When Jennifer Smith visited Grand Cayman on a Caribbean cruise in 2008, she never imagined she’d be living there with her husband two years later. “We realized Grand Cayman was very different from the other islands,” says Smith, who works as a controller for a real-estate developer and writes a blog called Offshore CPA, which offers tips for relocating expats. “We immediately fell in love with it.” So on their return to New Jersey, the pair researched the local job market and landed positions at two accounting firms — Grand Cayman is home to one of the world’s largest banking jurisdictions, with plenty of opportunities for finance-minded expats.
But don’t go buying a one-way ticket just yet. Anyone who wants to move there must have a valid work permit before he or she arrives, so it’s important to solidify employment before taking the plunge. And while the length of their work permits governs most expats’ time — a minimum of two years in most cases — some Americans have the chance to stay permanently. Wisconsinite Kim Kadiyala met her Caymanian husband in Chicago, moved near his family in Grand Cayman and now spends weekends at places like Starfish Point, a quiet beach on the island’s northern shore. Says Kadiyala, “I don’t think I’ll ever live in another place as beautiful as this.” — David LaHuta
- Population: 60,413
- Language spoken: English
- Average rent for a one-bedroom apartment: $874
- Starting home price: $150,000
- Cost of a gallon of milk: $6.51
Most Affordable: Dominican Republic
Matt Bokor immediately fell in love with the Dominican Republic for its cozy corner bars, rustic inns, cook shacks and especially the outgoing locals. “Dominicans are gregarious, welcoming and friendly,” says Bokor, who moved to the island from Miami. “They’ll have you dancing the merengue in no time.” The affordability of the island was appealing too. “We have sticker shock every year returning to Florida for our family reunion,” he says. “A pound of green peppers at the supermarket in Miami is about $4, compared with $1.20 here. Per pound, tomatoes are about 30 cents, and carrots are 25 cents. At the fishermen’s market in Las Terrenas, we bought 7 pounds of seafood for $40.”
There are a few downsides: traffic, power outages and crime. (Bokor points out that there is a heavy police presence.) In the end, though, the advantages win out. Bokor’s favorite thing of all is that convenience stores deliver. “Need eggs and orange juice first thing in the morning?” he says. “Just call. Run out of beer midway through the big game? They’ll bring it right to your door.” — Sarah Sekula
- Population: 10.4 million
- Language spoken: Spanish
- Currency: Dominican peso
- Average year-round temp: 80˚F
- Average rent for a one-bedroom apartment: $500
- Starting home price: $155,000
- Cost of a gallon of milk: $4
Best for Retiring: Bocas del Toro, Panama
Basil Stetson retired in Bocas del Toro to become a surf bum. It didn’t hurt that the exchange rate was beyond favorable — but not because he couldn’t afford a tonier location. Along with his fabric-designer wife, April Cornell, Stetson already owns on Grand Cayman. Rather, the low costs entice young energy, courtesy of backpackers. “The place feels fresh,” says Stetson. “I don’t want to live among high-rises and lots of old people.”
He adds, “It’s a small community.” How small? On Sundays, everyone can be found at the airport, where locals aren’t catching planes but fly balls — the runway is the community baseball field. Stetson might be retired, but he still speaks in business parlance. “Those games pay dividends,” he says. “Because of them, everyone knows who I am — one of the few gringos in the stands.” — Brooke Morton
- Population: 7,366
- Language spoken: Spanish
- Currency: USD
- Average year-round temp: 78˚F
- Average rent for a one-bedroom apartment: $450
- Starting home price: $80,000
- Cost of a gallon of milk: $7.00
Thinking of moving to Bocas Del Toro? The Red Frog Beach Island Community offers upscale villas and condos for sale. This new resort draws success from owners investing in a second home wanting to capitalize on Panama’s booming economy. The resort offers a vacation exploration tour to visit and see the unique nature, wildlife and the marvelous beaches in this little-known Caribbean Archipelago. Owners can rent their homes for income through the resort’s property management program. See the video or visit the website redfrogbeach.com to learn more. [Sponsored]
Best for a Small-Town Vibe: Ambergris Caye, Belize
Life on Ambergris is quiet. Slow. Morning rush hour is a dozen bikes wheeling over the bridge to the main town of San Pedro. Kirsten Miglio relocated from Chicago with her husband in 1993. Back then, the one road cutting lengthwise across the island saw just three golf carts, the other main means of transport. Now, Miglio struggles to estimate how many carts rumble along the dirt roads.
Around town, everyone is familiar with the couple, who own owns Ak’bol Yoga Retreat and Eco Resort, 2 miles south of San Pedro. “People remember faces; names are less important,” Miglio says. “There are little pockets of communities, like the French community, the yoga community, the divers, the fly-fishermen, the sailors,” she says, adding that most of the smaller groups gather often for happy hour, dinner or whatever it is that brings them together. — BM
- Population: 13,381
- Language spoken: English
- Currency: Belize dollar
- Average year-round temp: 79˚F
- Average rent for a one-bedroom apartment: $900
- Starting home price: $200,000
- Cost of milk: $2.76 for a quart-size box
Best Caribbean: Martinique
Spend a few days in Martinique, and you’d think you were in a tropical version of Marseille. After all, the French island is home to one of the region’s largest Francophone populations, including a burgeoning expat community from mainland France who’ve relocated for the locale’s black-sand beaches, lush rainforests and Caribbean joie de vivre.
The “Paris of the Antilles” also attracts folks from the U.S. who come to teach English — expats like Hayley Hund, who moved from Leavenworth, Kansas, in 2014 to work as an English teaching assistant. “It’s important to live like the Martiniquais,” says Hund, who enjoys practicing her Creole and eating anything au gratin. “The lifestyle has taught me to leave my watch at home and let my day develop at its own pace. As the locals like to say, ‘Il n’y a pas d’heures précises,’ or ‘there are no fixed times.'” — DL
- Population: 386,486
- Language spoken: French, Creole and English
- Average rent for a one-bedroom apartment: $800
- Starting home price: $170,000
- Cost of milk: $1.12 per liter
Most Affordable: Phuket, Thailand
With jungle-topped mountains, high-end dining, championship golf courses and internationally famous beaches, Phuket is an ideal setting for many foreigners from around the globe. As the largest island in Thailand, it has just about everything you need.
Top-tier medical care is easy to find and, better yet, reasonably priced. You’ll be close to an international airport, which means you won’t have to fly out of Bangkok (a major plus). There are plenty of international schools, and grocery stores are stocked with imported goods. Whether you rent or buy, it’s still extremely affordable. Keep in mind, however, that foreigners cannot own land in their name, but they may purchase a condo or home and lease the land. — SS
- Population: 620,000
- Languages spoken: Thai, English
- Currency: Baht
- Average year-round temp: 84˚F
- Average rent for a one-bedroom apartment: $510
- Starting home price: $168,000
- Cost of a gallon of milk: $6
Best for Recent Grads: St. Croix, USVI
Spend the day with the 20-something set on St. Croix, the largest of the three U.S. Virgin Islands, and you might ask if you’ve stepped into an REI or Michelob Ultra commercial. Scenes cut quickly between sailing to Buck Island to swim with turtles, hiking the northwest coast to snorkel in tide pools, and dancing on a roped-off street for St. Patrick’s Day.
It’s the world of Matthew Weicker, a scuba instructor who chose to make the largely undeveloped island home in July 2015. “St. Thomas feels less like an island and more like a city with lots of vehicles, and it’s very built-up. St. Croix is quieter, with old-island charm.” Its smaller population makes it easier to join the party, er, community. For Weicker, finding that island-style welcome was simple. “Hang out in town, grab a beer and just start talking to people.” Regarding employment, Weicker adds,”The best way to land a job is to walk into the restaurants, bars and tour companies in town and talk to who’s hiring — it’s much easier in person than over the phone.” — BM
- Population: 53,000
- Language spoken: English
- Currency: USD
- Average year-round temp: 85˚F
- Average rent for a one-bedroom apartment: $875
- Starting home price: $130,000
- Cost of a gallon of milk: $4.99
Best for Urbanites: Hong Kong
“Hong Kong is the densest place I have ever experienced,” says Laurie Goldberg, a craft-beer importer who jets often to New York and Tokyo. With Hong Kong’s huge population comes perks. For one: cheap cabs. Thirty minutes and the equivalent of $20 U.S. buys transit to the white-sand beaches and lush hiking trails of Tai Long Wan, which reminds her of Thailand.
As for city life, Goldberg — who has called Los Angeles and Hawaii home — found the transition seamless, thanks in large part to an expat community numbering 1 million. “It was similar to moving to a city in the U.S. — everyone speaks English — but it’s much easier to meet new people,” she says. She adds that the transient nature of Hong Kong’s expat scene makes it much more welcoming. After arriving in 2011 with her husband, Adam, his law-school chum introduced them to everyone he knew. Instantly, they had community. Nights out progressed from listening to a Journey cover band at the bar Insomnia to midnight foot massages, a uniquely Hong Kong tradition — all fueled by a craft-beer selection as international as the crowd enjoying it. — BM
- Population: 7.19 million
- Languages spoken: Cantonese, English
- Currency: USD
- Average year-round temp: 72˚F
- Average rent for a one-bedroom apartment: $3,200
- Starting home price: $675,000
- Cost of a gallon of milk: $11.34
Best Caribbean: St. Kitts
A sunny home with a new passport to boot? In St. Kitts, it’s as easy as writing a check. The destination is one of a handful of countries that offer a citizenship-by-investment program, in which $250,000 plus the cost of a home buys you Kittitian citizenship.
Or simply join the workforce. At Ross University — an accredited veterinary school that draws students from the U.S. and Canada — faculty positions are often available. Opportunities can also be found in construction, engineering and real estate, plus hospitality jobs at new hotels. “Several resorts are scheduled to open in the next few years,” says Derek Wales, a Massachusetts native who followed his girlfriend to St. Kitts in 2014 when she decided to attend Ross University, “so now is a great time to send in your résumé.” — DL
- Population: 40,000
- Language spoken: English
- Average rent for a one-bedroom apartment: $1,025
- Starting home price: $350,000
- Cost of a gallon of milk: $11.50
Most Affordable: Roatan, Honduras
Roatan, off the east coast of Honduras, is a hodgepodge of small communities with a large expat population. Pristine plots of land, untouched and exactly the way nature intended them to be, are still available for purchase. Deb Crofutt, who moved to the island in 2013, can attest to that. “You can buy land or an already built home for less than in the U.S.,” she says. “We own a 2,100-square-foot home on a quarter-acre of land, and our property taxes are about $130 a year.”
“Roatan is large enough to have conveniences and luxuries, such as dentists, yoga studios and high-end restaurants,” says Rika Purdy, an expat from Vancouver. “But it’s still small enough that you get to know your entire community and enjoy a slower pace of life. And due to the low minimum wage, which is about $15 per day, you can find quality housekeeping, childcare, cooks or home security for an affordable price.” — SS
- Population: 80,000
- Languages spoken: Spanish, Bay Islands Creole, English
- Currency: Honduran Lempira, but USD is widely accepted
- Average year-round temp: 80˚F
- Average rent for a one-bedroom apartment: $500
- Starting home price: $100,000
- Cost of a gallon of milk: $2
Best for Starting a Business: Oahu, Hawaii
“I found it quite easy if you pick the right market,” says Mike Davis of launching Extract Juice Bar in downtown Honolulu with wife, Stacey, in 2013. “Just find a niche that isn’t already exploited locally,” says Davis. Before flying out, the couple scoured Yelp and Google to get a feel for the island’s neighborhoods. After they arrived, they spent half a day sitting outside their intended shop location, studying foot traffic. Their product skews toward an affluent clientele, so they targeted the business district, fueled by tourism and military dollars. Davis also figured it wise to open doors at 6 a.m., when the suits clock in to do business with the mainland.
More importantly, the venture brought added benefits to the couple’s lives. They’re stoked that riding waves is now part of their everyday. Says Davis, “Two weeks ago, my fridge went down over the weekend. I was closed for three days and lost all my produce. But when you’re in Hawaii, how can you ever be mad that you’re on an island?” — BM
- Population: 953,207
- Language spoken: English
- Currency: USD
- Average year-round temp: 77˚F
- Average rent for a one-bedroom apartment: $1,300
- Starting home price: $60,000
- Cost of a gallon of milk: $5.49
Best for Foodies: Sicily, Italy
“Sicily’s architecture is very baroque, and its desserts are too — in fact, there’s flair and exuberance to all the island’s food,” says Jann Huizenga. She and her husband, Kim Crowley, spend half the year in Santa Fe, New Mexico, and the rest in a Sicilian town called Ragusa Ibla, population 3,000. When asked to share a favorite food memory, Huizenga pauses. In spring, the thing to do is join friends on hillsides, foraging for wild asparagus, fennel, capers and borage, a spinachlike green. The resulting bounty is cooked with pasta.
If you don’t have friends to scrounge with, try the restaurant I Bianchi, which is managed by a two-star Michelin chef and is known for its pastries and gelatos. Caffe Sicilia in the village of Noto is another Huizenga must-try, namely for its almond granita and its take on a Sicilian summer breakfast: gelato tucked inside a brioche.”It’s a great big thing,” she says, and as she describes the textures and flavor, it seems some of the island’s exuberance has rubbed off. — BM
- Population: 5 million
- Language spoken: Italian
- Currency: Euro
- Average year-round temp: 60˚F
- Average rent for a one-bedroom apartment: $400
- Starting home price: $170,000
- Cost of milk: $1.37 per liter
Best Caribbean: Virgin Gorda, BVI
“I love watching visitors react to our version of reality,” says Cassie Mitchell, who moved to Virgin Gorda from Royal Oak, Michigan, in 2012 to pursue a career in guest services. “It reaffirms why I’m here in the first place.” Of course, the BVI reality takes many forms. For her friend Scott Allerton, a Florida native who opened Carib Kiteboarding in 2003, it’s teaching visitors the sport. “My office is the ocean,” says Allerton, who has taught more than 1,000 people on Virgin Gorda’s Eustatia Sound, ideally suited for kiteboarding thanks to its consistent side-shore breezes.
On tiny Virgin Gorda, it’s small-town living at its sunniest: Grocery runs require boats, clocks give way to island time, and virtually everyone knows your name. “All of us expats share three traits that allow us to survive here,” says Mitchell. “Kindness, patience and optimism.” — DL
- Population: 29,151
- Language spoken: English
- Average rent for a one-bedroom apartment: $1,200
- Starting home price: $275,000
- Cost of a gallon of milk: $10.55
Most Affordable: Boracay, Philippines
Though Boracay is tiny, it has nine beaches, 30-plus nightlife spots and 27 dive sites. About an hour flight from Manila, it attracts fun-loving expats like Paul Fournier, who moved there in 2012. “I pay $296 per month for a studio apartment, including cleaning service, in the center of Boracay,” he says. “White Beach and Bulabog Beach are just a five-minute walk. I eat out daily because the food is so cheap. Beer in the beachfront bars averages out to $1.30 — the cheapest is only 84 cents.”
But one major drawback is medical expenses. “The healthcare quality on Boracay is not great,” says Fournier. “To find proper medical care, you have to leave the island — usually hopping a one-hour flight to a major city.” — SS
- Population: 20,000
- Languages spoken: English, Visayan, Tagalog
- Currency: Philippine peso
- Average year-round temp: 84˚F
- Average rent for a one-bedroom apartment: $400
- Starting home price: $100,000
- Cost of a gallon of milk: $7
Best for Starting a Family: Key Largo, Florida
“I was raised on the water, surfing, diving, skiing and fishing — it’s what I wanted for my kids,” says Steve Powers, who, along with his wife, Cheryl, has been raising three daughters since 2008 in the Norman-Rockwell-meets-Jimmy-Buffett landscape that is Key Largo. The couple knew they wanted to relocate to a Florida coast, and the Keys offer double the shoreline. Powers had always wanted to run a business, so when the local Sea Tow franchise, a marine-rescue company, became available, he took the helm.
In many ways, it’s exactly what the Powers had hoped, and now their kids live in the water. “It’ll be midnight, and they still have their swimsuits on,” says Steve. “I bought an outdoor projector, and they’ll want to watch Jaws while swimming.” Factor in the ocean and Gulf, and the possibilities become endless — more than enough to fill any childhood. — BM
- Population: 11,000
- Language spoken: English
- Currency: USD
- Average year-round temp: 80˚F
- Average rent for a one-bedroom apartment: $1,000
- Starting home price: $250,000
- Cost of a gallon of milk: $3.35
Best for Beach Bums: Maui, Hawaii
Find your Maui tribe, and you’ll find your Maui beach. Mothers with little ones gather at, appropriately enough, Baby Beach near Lahaina on the island’s northwest tip. Retirees: Wailea. Windsurfers meet for sessions at Kanaha Beach Park, near the airport. Those preferring drum circles find each other on the North Shore’s Baldwin Beach Park. Find Sylvia Whelchel, an Ayurveda practitioner from Oregon, with her people — women who shred — every morning at 6:30 at Ho’okipa Beach. “Even if the waves aren’t good, we still paddle out,” she says. “It’s our version of hitting the gym.”
Surfing is just one way Whelchel lets Maui shape her lifestyle. Surrendering to the island’s way of life is your best chance to find happiness. “It’s really common to see people move here, thinking their lives will be better,” she says. “But if they don’t change themselves, they’ll be in the same rut as they were before, working too much and whatnot.” Whelchel calls it letting go of the “mainland vibe.” She says, “Here, you’re admired for surfing big waves or for owning a truck that can carry all your sports equipment.” The island lifestyle isn’t about buying or owning possessions. It’s about something else entirely — a sense of community. — BM
- Population: 160,000
- Language spoken: English
- Currency: USD
- Average year-round temp: 75˚F
- Average rent for a one-bedroom apartment: $1,400
- Starting home price: $450,000
- Cost of a gallon of milk: $9.59
Best Caribbean: The Abacos, Bahamas
“The Abacos used to be the Wild West of the Caribbean,” says Austin Smith, who moved from Florida in 1989 to a 300-acre cay dubbed Lubbers Quarters. “It was like being a pioneer, but instead of arriving in covered wagons, we sailed in boats.” At the time, the island had no power or running water, which is a big difference from the Abacos of today. Chiefly because of its proximity to the U.S. — a mere one-hour flight from West Palm Beach, Florida — **the islands are now a haven for Americans looking for a second home or a full relocation from the States. **
And thanks to Smith’s latest project, owning a slice of paradise just got easier. In May 2016, he launched Lubbers’ Quarters, 12 two- and three- bedroom fractional-ownership cottages available to buyers for 13 weeks each year. For $165,000, cottages include 25 percent home ownership and a 23-foot boat to explore the archipelago. “It’s carefree home ownership at its best,” says Smith, who also developed a mobile app called Island Compass, which lets boaters identify points of interest on a smartphone without incurring costly roaming charges. “We’re building our resort by giving people a great deal on a house,” says Smith. “It’s a win-win.” — DL
- Population: 13,170
- Language spoken: English
- Average rent for a one-bedroom apartment: $925
- Starting home price: $150,000
- Cost of a gallon of milk: $12
Worth the Splurge: Moorea, Tahiti
Imagine living in Yosemite Valley without the crowds. “That pretty much sums up Moorea,” says Michael Poole, who relocated in 1987. He also lauds the affable community, interesting mix of cultures and incredibly good food, plus plenty of holidays and celebrations. “Life here is certainly enjoyed,” Poole says. “However, it’s not very easy to move here. It’s expensive, and there isn’t a rich expat culture. People want to live here because it reflects and fulfills their vision of a tropical paradise.“
“It’s true that things like food and cars are very costly,” says Laurel Samuela, an expat from California. “But we don’t have property taxes, and healthcare is very inexpensive. Plus, our lagoon is full of fish, and our garden is packed with mangoes, avocados and passion fruit.” — SS
- Population: 16,191
- Languages spoken: French, Tahitian, English
- Currency: French Polynesian franc
- Average year-round temp: 79˚F
- Average rent for a one-bedroom apartment: $723
- Starting home price: $350,000
- Cost of a gallon of milk: $4.51
Best for Health Fiends: Coolum Beach, Australia
A variety of factors draw health-minded individuals to the Sunshine Coast. For some, it’s the benefits of living near the ocean. This relaxed lifestyle was what Jamie Schwear had always dreamed of, especially in landlocked Arizona. In 2015, she arrived in the town of Coolum Beach, 90 minutes north of Brisbane. “I never found a place like this in the U.S. that I could afford,” says Schwear, who now lives across the street from the Coral Sea.
It’s a popular spot for the active set and a haven for surfers. Weekends are spent outdoors: strolling the Coolum boardwalk, where whales can be spotted June through November, and hiking in Mount Coolum National Park, named for its 680-foot peak. Perhaps the best part is how uncrowded paradise is. “The whole population of Australia is less than the state of Texas,” she says. For guaranteed solitude, she heads north to Noosa National Park. “We have miles and miles of coastline where you can walk the beach and be the only one, which is amazing. You become a part of wild, unspoiled nature.” — BM
- Population: 8,000
- Language spoken: English
- Currency: Australian dollar
- Average year-round temp: 80˚F
- Average rent for a one-bedroom apartment: $900
- Starting home price: $215,000
- Cost of a gallon of milk: $4.24
Read more about moving to an island:
10 Real Estate Tips for Moving to an Island | How to Move to St. John, USVI | Living in the Cayman Islands
Best for Starting Over: Cozumel, Mexico
Don’t be surprised at weight loss or lower blood pressure when starting a new life in Cozumel. Cruise-ship anchors aweigh, this 250-square-mile island settles back into slow rhythms, packaging the folksiness of a small Midwestern town with prime Caribbean beachfront. As for health benefits, new arrivals Joni and Karan Thadani said adios to Kansas in January, and they already need smaller shorts. Credit might be due to swapping their law practice for selling island real estate. Or to the mom-and-pop eateries dishing up their nightly dinners.
“It’s amazing that the restaurants all serve fresh, handmade food,” says Joni. Their diet is now mostly seafood, meat and produce, yet it’s cost-effective. Barbecue chicken with rice and beans fetches less than $5. For Karan, the answer is much simpler: “Nothing is better for your health than seeing the ocean every day.” — BM
- Population: 100,000
- Language spoken: Spanish
- Currency: Peso
- Average year-round temp: 80˚F
- Average rent for a one-bedroom apartment: $750
- Starting home price: $104,000
- Cost of a gallon of milk: $1.52
