Escape the Winter on These 3 Caribbean Islands

Published on December 1, 2020

Maybe it was Treasure Island, or perhaps Robinson Crusoe, that put a picture of the tropical island into our collective imagination. Or more probable still, Hawaii 5-0. Whichever it was, there’s something about a tropical island that calls to the soul. Coconut palms, soft acoustic music, cold cocktails on the sand. The idea of a Caribbean island home evokes a feeling of relaxed content. But is it affordable? It can be, yes.

We’re not suggesting that you look at the Bahamas, Antilles, or Virgin Islands as good-value retirement destinations. They’re not, particularly. A two-bedroom beachfront home on one of these islands typically costs more than $1 million. But on three islands we prefer, you can live your Caribbean dream for much, much less.

The truth is, the Caribbean is not reserved solely for billionaires and oligarchs—in fact, if you know exactly where to look, you can find islands where your living costs could be less than in a U.S. or Canadian suburb. Restaurant meals for less than $10, rents for under $500 a month, condos for $65,000…these are real prices, real places. A retirement on some of the Caribbean’s most beautiful islands is well within a reasonable budget. Here’s where to find it:

Option 1: Laidback Paradise on Roatán

Avoiding the Caribbean clichés of steel drum bands and flocks of hair braiders working crowded beaches, Roatán, in the Caribbean Sea just off the coast of Honduras, stands alone. Rising nearly 1,000 feet above the perpetually warm waters, this tiny tropical jewel is covered with lush jungle flowing up steep hillsides, across sheer ravines, and blanketing broad valleys. Sandy beaches are plentiful, and a steady trade wind from the east keeps the air moving. Roatán is spectacular.

The weather is tropical, with temperatures usually in the mid-80s F, up to 90s F on summer afternoons. It’s just south of the major hurricane highway, and compared to its northern neighbors, Roatán has mostly been spared from these monsters.

On a recent scouting trip, I stayed at the Turtle Beach Resort, on the west end of the island. Water taxis pass by frequently and can be hailed from the resort’s private dock, taking you to restaurants and shopping. Roatán’s west end is where you’ll find all the action. You’ll find dozens of small bars here, offering all the fruity umbrella drinks, as well as some good bar food. If you want to spend a night mixing with travelers and locals, this part of the island is where you want to be.

There’s also immediate access to the clearest water imaginable. Here I waded into a natural aquarium. I was only waist-deep into the gin-clear, warm water before I saw my first spray of fan coral and then noticed it was everywhere. I wasn’t prepared for the visual impact.

Finger-length fish in neon-bright yellows, reds, and violets darted about like oversized poker chips, and small schools of shimmering, slender needle fish cruised by, checking me out. Just beyond the end of the resort’s short pier, a large, green moray eel guarded the entrance to her home, sharp teeth clearly visible. And all this while I was wading in only a few feet of water.

If you’re on the hunt for your personal island retirement escape, Roatán offers a lot, for a price that would be unthinkable on islands such as Antigua or Grand Bahama. In either of the latter locations, $1 million may just get you into the game. Here, though, there are plenty of affordable opportunities to own a slice of Caribbean paradise.

While you can find homes in the $120,000 to $150,000 range, they are rare and may not fit your requirements. That said, there are always gems to be found. I came across a one-bedroom, one bathroom house with a nearly completed apartment of the same size. It’s in the desirable Sandy Bay area, and the owner is willing to complete it for a total price of only $119,000.

Move your budget closer to $200,000, or maybe up to $275,000, and the market expands. For only $189,500, you could have a trendy, water-access home in a safe, protected harbor. How cool is that? Located in Pitts Lagoon, this one-bedroom, one-bathroom home (perfect for sailors) includes a lower level rental unit of the same size. And you can tie your sailboat to the deep-water dock. Water, backup power, a private lagoon for swimming, and a boat launch all come as part of the low HOA monthly fees.

If you aren’t quite ready to purchase, you can find rentals on Roatán in the $950 to $1,500 range.

Roatan is the perfect place to learn to dive.

“It’s like getting a diamond for the cost of a pearl,” says Kendall Beymer, who has been living full time on Roatán for over four years. “I have lived throughout the Caribbean, and Roatán clearly provides the best overall value for my money.”

Kendall operates two large luxury catamarans that cater to upscale clients. He says Roatán’s cost of living is extremely reasonable. “I live a very nice life for around $3,200 a month, and that includes plenty of restaurant meals. It’s easy,” he says. “But like every other place, it all depends on your lifestyle.”

Longtime expat Carol Luber retired here early from a successful career in information technology.

“I love to swim. Ocean or pool, it doesn’t matter. Also, we have a wonderful music scene here, and sometimes I just hang out with my friends,” says Carol. “I also admit to some bar hopping, but frankly, those costs can add up, so I do some entertaining in my home. I can walk down my dock and visit with fish, watching the dive boats launch their divers on the reef. Honestly, life here is tough to beat.”

Except for electricity, the cost of living is reasonable and provides exceptional value for dollars spent. Medical care is improving, too. With the recent completion of the new, private Hospital Cemesa, residents can receive top-notch surgical and non-surgical care provided by a team of professionals. You’ll also find individual physicians, as well as the public hospital (although it can sometimes be short of needed supplies). Finally, a dedicated expat and registered nurse, Peggy Stranges, who came to Roatán in 2001, founded and now runs Hospital Esperanza, better known around the island as Miss Peggy’s Clinic.

This non-profit and highly organized endeavor operates to serve all people of the island. It uses a network of volunteer medical professionals, including students from the finest medical schools in the U.S. It also maintains a staff of physicians, nurses, technicians, and pharmacists. All patients pay a tiny fee, only a few dollars, for services.

The topography of Roatán is breathtaking. The valleys, gorges, and ridges, all covered in dense jungle, provide homes to large macaws, monkeys, coatimundis, and what seems like millions of hummingbirds. Reaching for your camera becomes a reflex.

On the south side of the island’s west end, three commercial zip-line operators offer canopy tours. This is a fun way to experience an overhead view of Roatan’s stunning topography. South Shore Zipline and Canopy Tours are close together and offer similar experiences. Dense jungle covers broad valleys and steep ravines, and zip lines are an exciting way to see it, if you look quickly. Prices start at about $60 per person.

There’s also an attitude on Roatán that I haven’t found on other islands. It promotes respect for the environment and seems to pull all residents together—locals, tourists, and expats alike. I believe it goes beyond the need to protect the reef for the good of the economy. It is inherent in the culture, and to come to Roatán mandates that you buy into that culture.

For those who are prepared for island life, take a hard look at Roatán—the most beautiful island I have ever seen, and the only one that has ever tempted me.

Learn to dive on Roatán

Roatán is the perfect place to learn to dive. The water is almost always calm and crystal clear, without dangerous currents to complicate things.

Off the sheltered coast of Roatán, the water is as clear as you’ll find anywhere on the planet. ©

Local resorts and dive centers normally offer introductory lessons, and the prices are hard to beat. For about $110, you’ll enjoy a four-hour session under the close, direct supervision of a PADI (Professional Association of Diving Instructors) certified instructor. You’ll start out on the dock with a briefing about the gear, safety rules, and underwater behavior. Then you’ll move into waist-deep water, kneel down, and experience your first underwater breaths. Next, you’ll head to a shallow, confined water area to practice skills and add confidence and control, followed by a short swim around the area. At this point, you’re ready to go diving.

You usually board a small boat for the ride to the nearby reef. There you’ll follow an anchored line up and down a few times, getting more comfortable. At the end of four hours, you’ll be swimming freely about the confined area.

If you want to continue and get your open water certification, that usually takes an additional two days and costs about $400. But you’ll almost always receive credit for the money you spent on your introductory dive. 

Option 2: Active and Cosmopolitan: The Dominican Republic

Reefs, jetties, palm fronds, and boats. The Caribbean dream is within grasp in Cabarete. ©

By Jason Holland

When I told friends and acquaintances that I was headed to the Dominican Republic, many broke into wide grins and mentioned they’d visited…and loved it.

Invariably, though, they’d been to beach resorts, mostly in the resort area of Punta Cana. I was more interested in seeing where you could live at the beach, long-term, comfortably. That brought me to the towns along the north coast, where small but thriving expat communities have sprung up in the past couple of decades.

Cabarete and Las Terrenas—the two towns lie along the northern coast, just a little less than a hundred miles apart—offer the best in laid back Caribbean living: Walkable beach towns with plenty of conveniences, beautiful scenery, great restaurants, active nightlife, and fun-loving communities of friendly locals and welcoming expats. The expat community includes a huge percentage of Canadians, a good number from the U.S., and plenty of Europeans.

Las Terrenas has a very European feel. First settled by French hippies in the 1970s, when there was no electricity or paved roads, this spot on the Samaná Peninsula has since grown into a sophisticated destination that retains a Gallic flair. Step into the French-run grocery store, Supermercado Lindo, and you find a huge selection of imported wine, cheese, and charcuterie, without a huge import markup. Shop hours and signs are often in French, and you hear the language spoken as you walk around town.

It’s a very multicultural scene in Las Terrenas.

It was fun to see older French men concentrate on their game of pétanque as they sipped pastis. A scene straight out of rural France, were it not for the tropical beach backdrop.

The sizable Italian population has brought their language, too, as well as espresso, pasta, and traditional wood-fired oven pizza. There are also plenty of North Americans, as well as locals and middle- and upper-class Dominicans visiting from the capital on weekends and holidays. It’s a very multicultural scene.

Cabarete is a little different. There’s plenty going on both on the sand and in town, whose heart is one long road that parallels the beach. The town is where you’ll find shops and such, with access roads to developments and inland neighborhoods branching off. Along the water, you have a long strip of beach bars and restaurants. But much of the action is in the water.

If you enjoy fishing, snorkeling, boating, or other watersports (Cabarete is the kiteboarding capital of the world), you’re in luck. And if you’d rather watch the water from a hammock strung up between two palms, there are plenty of spots. I was shocked at how affordable it was, from my $6 dinners to plentiful fresh produce and seafood, to rents at $400 or even less for a walk-to-the-beach condo.

It’s a rare thing on a Caribbean island. But you really can live well for much less in the Dominican Republic. It all depends on your lifestyle (and how many gourmet French dinners you enjoy). But all in, a retired couple could do well on $2,500 a month, with maid service and eating out a few times a week.

You can live on the beach (or close to it) very affordably on the north coast, with plenty of units in waterfront, resort-style condo communities under $100,000. Because these are small towns, you’re always pretty much within walking distance to the beach, restaurants, the market, banks, and anything else you may need.

For $130,000, you can pick up a one-bedroom, recently refurbished condo on Punta Popy beach in Las Terrenas. It has two community pools and 24-hour security; plus, you can walk to the heart of town on the sand. In the center of town is a loft-style condo for $99,500. A two-bedroom condo, walkable to the beach in Las Terrenas, is listed at $89,250. Nearby, but in a gated community on the water, is a duplex townhouse for $149,900, with three bedrooms and furniture included.

In Cabarete’s Kite Beach, east of the main part of town, is a two-bedroom condo with community pool and 24-hour security for $65,000. If you want to maximize your time kiteboarding, it’s perfect. Otherwise, you can check out properties near the town center, like a one-bedroom, fully furnished condo on the beach for $99,000. A two-bedroom condo, walkable to the beach, is listed at $125,000. It comes fully furnished and has a community pool.

If you want to try before you buy, you can find high-quality and affordable rentals in good locations, too, with furnished condos starting at $400 and up for a walk-to-the-beach, two-bedroom (although I found some folks paying even less). Sometimes utilities, internet, and/or maid service are included. A two-bedroom casita in Las Terrenas, with a small yard, is available for $500 a month.

You can secure a long-term rental through a real estate agent or property manager, but often you can get much cheaper options if you network in person or check local Facebook pages for Las Terrenas and Cabarete. These pages are great to join, as they are where expats and locals network, announce community events, buy/sell vehicles and household goods, and much more. Las Terrenas has turned into quite a bustling beach town, with low-slung development spread out along a series of gold- and white-sand beaches lined with palm trees. But you’ll still find glimpses of its previous life as a simple fishing village.

Early one morning, as I strolled past the camp where open boats are brought up on the beach, I spoke with a local fisherman who—as his companions mended nets and rigged tackle—was filleting a dorado (mahi-mahi). I could have had it for $3 a pound.

A furnished condo on the beach for $99,000.

In the heart of the Pueblo de Los Pescadores former fishermen’s shacks (spruced up and turned into restaurants and bars) is a must-visit: One Love Surfshack, a restaurant/bar run by a retired Canadian Mountie and his wife. Trivia night on Thursdays is a great time to meet local expats…and have a good time with new friends.

Cabarete, on the other hand, is all about watersports. Its beach draws sailboarders and kite surfers from around the world. You’ll see dozens crisscrossing the bay, taking advantage of steady easterly trade winds. The winds pick up in the afternoon, especially from June to August, just enough to cool you off from the heat of the day. When evening comes, there’s a relaxed party feel. Be sure to check out Los Gringos for the Sunday afternoon expat meet-up, as well as Voyvoy for open mic night on Sunday evenings. There I met Randy Jenne, a drummer and University professor from Edmonton, who spends summers in Cabarete.

“It’s a small town, and the expat community is a smaller town within it. Everybody is very friendly and ready to share their experiences with newcomers,” says Randy, who rents a two-bedroom condo within walking distance of the beach for $700 a month. “If you come in the morning for paddle boarding, it’s very quiet. In the afternoon, you have kiteboarding. And at night, it’s a party. There’s something for everybody.”

In either town, meals at nice restaurants (everything from Italian to American sports bar fare, tacos, and vegetarian and vegan options are available) can be had for $8 a plate. Be sure to try the conch or lobster dishes, whichever one is in season. Local meals of rice, beans, and a protein will run you a couple of bucks. But keep in mind the 18% sales tax, and that many places also automatically add a 10% service charge.

You won’t break the bank at the grocery store, either. Thanks to a very productive agricultural sector, fresh fruits and veggies are varied and cheap. Even produce not typically grown in the region, like apples and broccoli, is available, because of cool-weather highland farming areas. Tomatoes are 80 cents a pound (by the way, they use pounds in the Dominican Republic), and red apples are $1.25 a pound. Corn on the cob costs $2.35 for three ears. Of course, there is abundant tropical fruit, too: guava, mango, and more. The local variety of passionfruit, called chinola, makes a wonderful juice, and it’s available just about everywhere.

Other basic items are cheap, too. You can get a pound of ground beef for $2.25 and a whole chicken for $3.62. For bigger purchases, and for gathering the necessities for setting up house, there are options, as well. On the north coast is the country’s second-largest city, Santiago de Los Caballeros, which is about 90 minutes from Cabarete. Here you have an international airport, large hospitals and clinics, a PriceSmart warehouse shopping club, and more. And from Las Terrenas, it’s only two-and-a-half hours’ drive to Santo Domingo, the capital city of 3.6 million. If you need something, you can get it there. Santo Domingo even has IKEA. And its colonial centro, founded in 1496, is one of the oldest European-founded cities in the Western Hemisphere.

Cars and electronics are pricey, though, and expats typically bring these from home. And if the heat (highs are in the mid-to-high 80s F during the day, cooling off to the 70s F at night) and humidity (80%) gets to you, your electric bill can soar if you leave your air conditioning running day and night.

Nevertheless, for relatively small beach towns, Cabarete and Las Terrenas are well served for necessities. And both have high-quality healthcare options. Las Terrenas has a hospital with specialists and a 24-hour emergency room (Clínica Especializada Internacional), as well as a large medical clinic. Cabarete has a small clinic in town, as well as a hospital—Cabarete Medical Center—with an emergency room and specialist care on the road to the nearby town of Sosúa. These facilities can do minor surgeries.

About an hour-and-a-half drive from Cabarete, in the city of Santiago de Los Caballeros, is the region’s best and largest hospital, Hospital Metropolitano de Santiago. It has an MRI facility, cancer center, robotic surgery, and other services.

Costs are quite cheap, and local, international, and travel insurances are generally accepted. A Canadian couple I met pay just over $1,000 a year for full coverage medical and dental insurance. If you pay out of pocket, expect to pay $60 to $80 cash for a specialist visit; $250 for a root canal; a CAT scan for $100; and an MRI for a few hundred.

For serious health issues, especially from Las Terrenas, many expats head to Santo Domingo. It’s on the southern coast a two and a half hours’ drive south across the breadth of the island. There you can find the country’s top doctors.

It’s an impressive array of healthcare options, reflecting this small nation’s priorities. Bear in mind that the Dominican Republic, which shares the second-largest island in the Caribbean, Hispaniola, with Haiti, is still developing. Some of the roads can be pitted with potholes. And short power and water outages are common. As with any vacation destination, petty crime—such as break-ins while you’re away, or somebody walking off with your bag at the beach while you’re swimming—is an issue. For the most part, though, it’s safe.

Of all the beach destinations I’ve visited in Latin America over the years, the Dominican Republic’s north coast is now definitely one of my favorites.

Public Transport in the Dominican Republic

Getting around the Dominican Republic’s north coast beach towns is easy, once you get the hang of the island’s quirky public transportation. You can walk just about everywhere in Cabarete and Las Terrenas. But for trips to outlying areas or between towns, simply stand on the side of the main road and hail one of the large vans that pass every few minutes. These guaguas cost less than $1, so be sure to bring change or small bills. They can be quite packed. So get friendly with your seatmates.

If you’re more adventurous, you can jump on the back of a motoconcho—a motorcycle taxi (or, as one driver joked, the Dominican Uber). Very handy for quick rides around town. For longer rides (or if you don’t feel comfortable zooming around on a motorcycle in traffic without a helmet), there are also car taxis for hire.

Plenty of expats also have cars, as well as motor scooters and ATVs. But you have to be a defensive driver here—and that’s an understatement.

Option 3: Getting Away From It All on Isla Mujeres

By Don Murray

With tropical weather normally providing temps in the mid-80s F, habitually warm waters on all sides, and a perpetual sea breeze that delivers the thrills of soaring seabirds, Isla Mujeres, off Mexico’s Caribbean coast, maintains a loyal complement of full-time residents, seasonal snowbirds, and short-term vacationers. It is no longer a hidden gem. Rather, it has grown into a mature destination, where expats can enjoy an affordable island retirement in casual, Caribbean comfort.

After our first winter, we didn’t want to leave.

Isla Mujeres is a tiny island. Technically, it’s divided into the “downtown” zone on the northern tip, along with the “mid-island” and “south end” areas. But there’s not much difference to note among them. Just over four miles long and less than a half-mile wide, this diminutive tropical retreat offers just the right feel—and is just the right size—to constantly remind you that you’re on an island. And yet you’re close enough to the mainland and the city of Cancún to avoid claustrophobia.

Isla Mujeres’s north end has a very nice beach (appropriately called North Beach) bedded with soft, white sand. Beach bars offer ice-cold beer, tropical cocktails, and good, simple food. Small palapas set up on the sand accommodate skilled masseuses offering half-hour massages for 400 pesos (about $20). However, the island’s primary draw is not the beaches. It’s the casual island vibe, where high fashion means wearing shoes, and weddings are often conducted in swimwear.

Transportation to and from the island is provided by a fleet of modern, high-speed ferries that maintain a frequent daily schedule between several terminals in Cancún. Cost for a roundtrip ticket is about $20, and it’s a comfortable 30-minute ride.

Isla offers dozens of bars and restaurants, and most have at least two versions of margaritas. (The Soggy Peso bar is my personal favorite.) In typical island fashion, the relaxed pace of life almost demands that residents and visitors pay no attention to the time. The posted operating hours for many small shops and stores are understood to be approximate. Full-time residents number fewer than 20,000. The population swells when boatloads of snowbirds flock to Isla during the cold winter months up north.

On Roatán, Isla Mujeres, or the Dominican Republic, live a life as relaxed or busy as you choose. ©Jason Holland

Life on Isla Mujeres can be very affordable. Retired expat John Pasnau and his wife Valerie occupy an 800-square-foot home with two bedrooms, a modern bathroom, a small sitting area/living room, and a very functional kitchen. It comes furnished, air-conditioned, and has a small fenced yard. They pay $800 a month, including all utilities.

There is a wide variety of home types on Isla Mujeres. Within the same neighborhood, you can find traditional Maya structures with stone foundations, stick walls, and thatched roofs…next to modern, low-rise condos whose height is restricted to three levels. The latter can cost from around $145,000 to over $500,000.

I found a newly constructed one-bedroom, one-bathroom home in a nice neighborhood for $158,000. This would be a great home for a retired couple, or it could be put to work as an income property. There is even enough land to build another unit.

“We actually purchased our property on our second trip to the island,” says Rob Goff. “Julie and I thought it would be a good investment and we’d place it into the local rental pool. But once we got down here, we realized how much we enjoyed the slower pace of life,” says the former Missouri resident. “I decided to retire, and we’d winter on Isla. But after our first winter, we determined that we didn’t want to leave. We went back to the States for a few weeks and sold everything. That was over a year ago and we still love it every day.”

Grilled lobster tail and a fresh juice cost about $8.

Life on an island, any island, costs a bit more than life on the mainland. But Isla Mujeres offers an affordable Caribbean lifestyle and tremendous value for dollars spent. The freshest possible seafood is available in every restaurant, and a breakfast of eggs Benedict topped with grilled lobster tail and a fresh juice costs about $8.

I learned of one expat who lives on Isla entirely on a Social Security check of around $1,700 a month. His apartment is small, and he pays 6,000 pesos a month (about $325) in rent. He lives a very comfortable life and puts $300 in his bank account each month, so he can fly home to see his kids and grandkids a couple of times a year.

Just a 30-minute boat ride from the bright lights of Cancún, Isla Mujeres is much quieter by nature. ©

Isla Mujeres has dozens of small, family-owned convenience stores and two modern supermarkets. As you’d expect, prices are slightly higher than the mainland, due to the cost of transportation.

“A bottle of local beer, Indio, is only 20 pesos everywhere. That’s about $1. And I can buy a whole chicken for about $3.30. A large bottle of Coke is 12 pesos (65 cents) and a big loaf of bread is 14 pesos (75 cents),” says John Pasnau.

“A couple can live in grand style on Isla for $2,500 to $3,500 a month, which includes rent, utilities, frequent meals in restaurants, and a couple of trips to Cancún each month for major shopping,” says Robb Goff.

Residents tend to their minor-to-moderate medical needs in a recently constructed community hospital. With 13 beds, a modern lab and X-ray department, ultrasound capabilities, emergency services, and even a new decompression chamber for diving accidents, this facility is a great addition for those who need immediate treatment. It even has a labor-and-delivery department.

Several physicians offer traditional medical care through their local offices, too. And expats who participate in the national health plan, Seguro Popular, can be treated for little, if any, payment. While the local island hospital is gaining popularity among expats, many of the long-term residents still prefer to catch the short ferry ride to Cancún, with its four major hospitals and hundreds of doctors and clinics.

Many believe that the best thing about Isla Mujeres is the access to great boating and world-class fishing. The proximity to a bountiful reef, the world’s second largest, provides the required eco-system to generate tons of aquatic life. You can keep your own boat in one of several safe and inexpensive marinas for $300 to $500 a month. And, of course, dozens of charter boats, with professional captains and crews, are available for offshore excursions for trophy game fish. Half-day charters run about $500.

For those who make Isla Mujeres their full-time home, owning one or two motor scooters, or investing in an electric golf cart takes care of transportation needs. And plenty of taxis are around if you’ve had too many margaritas at the Soggy Peso.

If you are one of the many who dream of carving out a new life on a small Caribbean island, Isla Mujeres may be just what you had in mind. High-speed internet service is available and inexpensive. The power rarely fails, and fresh water isn’t a problem. The markets have all the necessities, the hospital provides good care, and the casual island vibe will probably add years to your life, anyway.

The article Escape the Winter on These 3 Caribbean Islands by Don Murray first appeared on International Living. 

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