Smart Guide to the Caribbean Islands

Tips for finding the right island for you and planning your vacation

Bill Fink,

AARP

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Published March 06, 2025

suitcases sit in front of colorful signs that point to saint barts, aruba and jamaica

AARP (Shutterstock)

Sunshine and warm weather, combined with full-service resorts, relaxing sandy beaches, calm waters and a laid-back lifestyle, have made the Caribbean a go-to vacation destination for generations.

The Caribbean is one of the literal hot spots for the 55-and-over traveler, with most islands reporting this age group to be their top visitor demographic. In the Dominican Republic, more than half of all visitors are 55 and over, with at least three other islands at nearly 50 percent of travelers.

But which island is right for you? With 28 unique island countries and territories in the Caribbean (and many additional islands within these territories), deciding which one to pick to visit can be a challenge.

Over the past 30 years, I’ve visited more than 15 Caribbean territories and many more islands within them, spending my time hiking, biking and driving across them and swimming, diving, fishing and sailing between them. I’ve sampled more than my fair share of local rums, snacked on conch fritters and johnnycakes, dined on fine bouillabaisse in colonial chateaus and jerk chicken fresh from streetside grills. Experiencing islands from the perspective of a budget backpacker, as well as splurging for five-star resorts, has given me a good feel for the “vibe” of various islands. It’s also given me a sense of what I like about each of them, and can recommend to others. Most importantly, it makes me realize how much I still have to explore and discover in this fascinating region, inspiring me and hopefully you for further adventures.

To help with your Caribbean vacation planning, AARP has put together a guide to choosing between many attractive destinations — whether you’re just visiting a single island or picking among cruise itineraries with multiple stops.

Based on criteria of safety, luxury, affordability, island culture, ecotourism and two-for-one experiences, AARP has selected islands that might best fit travelers targeting each of those qualities.

While opinions on which destination is “best” can be as numerous as grains of sand on an island beach, we hope this guide (with prices in U.S. dollars) gives you a good starting point to help make your dream Caribbean vacation come true.

Sun, sand and safety: Best islands where you’ll feel secure

The Caribbean is overall a very safe region to visit, with many islands rated the safest level of “1” on the U.S. Department of State Travel Advisory Map.

But don’t necessarily skip visiting an island, even if it temporarily has an elevated advisory level of “2” or “3,” like the Bahamas or Jamaica. These advisories usually come with the caveat that “tourist areas generally see lower rates of violent crime than other parts of the country, ” according to the State Department. In fact, the Jamaican Constabulary Force has reported only a 0.01 percent crime rate against tourists, a 10 in 100,000 occurrence. Still, on islands with an elevated caution level, take particular care about where you travel. Within the bubble of an all-inclusive resort or well-monitored tourist locations, you’ll probably be fine. But travel to certain neighborhoods or outlying areas should be skipped or done only with expert advice.

Even for those islands with the highest safety level, visitors should take State Department advice to “exercise normal precautions” while on vacation. This includes being aware of your surroundings, carrying valid international health and travel insurance, and heeding local tips about where to go at night — nowhere has a zero-crime rate.

A carnival celebration kicks off in Aruba, which consistently ranks as one of the safest destinations in the Caribbean.

Wings Global Media/Courtesy Aruba Tourism

Aruba

Walking along Aruba’s Eagle Beach and Palm Beach under the shade of palm trees, with calm blue Caribbean waters on one side and a lineup of luxury hotels like the Ritz-Carlton and St. Regis on the other, it’s easy to feel secure. Even at night, walking inland a block or two to a long, well-lit strip of both upscale and affordable shops, restaurants and bars, the vibe is lively and welcoming. At the capital and cruise ship port of Oranjestad further down the west coast, tourists stroll past knickknack shops without a care in the world — for good reason: Aruba is consistently ranked as one of the safest destinations in the Caribbean.

Aruba’s dependence on the tourism sector (composing more than 70 percent of its economy — the second highest in the world, according to the World Travel and Tourism Council) means the island has focused significant resources on the safety and well-being of its visitors. The island’s small size of only 70 square miles (about the size of Washington, D.C.) and limited population of about 108,000 makes safety management easier than on larger islands.

The Radisson Blu Aruba, an oasis of calm two blocks from the lively Palm Beach scene, ranks safety along with scenery as a choice point for the island and the hotel. “Our guests regularly tell us how safe they feel wherever they go around Aruba. There’s a reason why they call it ‘One Happy Island.’ It has long been a very safe and welcoming place for travelers, with low crime rates,” says Luigi Wix, general manager of the Radisson.

In fact, on a recent trip to Aruba, I accidentally left my backpack (with my wallet inside!) on the ground by the parking lot at a popular tourist spot. When I returned in a panic 30 minutes later, the backpack still sat there, undisturbed. While it’s not recommended to leave your valuables sitting out in any destination, this incident serves as an unintentional proof point about Aruba’s safety and consideration by both visitors and locals.

Aruba’s health and hygiene are also rated highly, with quality medical care available and water that’s safe to drink out of the tap, among the cleanest in the world.

Aruba’s bonus safety factor is that the island is far enough south in the Caribbean that it lies outside the hurricane belt, so you’re considerably safer during the peak hurricane season of June through November.

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While the Cayman Islands is famous as a safe place to put your money as a tax haven, the island is safe for visitors as well, with extremely low crime rates. The biggest hazard on the island is probably remembering to drive on the left side of the road (and watching for traffic in that direction).

Anguilla is ranked No. 1 as the safest Caribbean island on The Travel’s statistical list, and this British Overseas Territory is even proper enough to remind visitors to cover up that swimwear and “please shop with your clothes on. ”

Fabulous islands for luxury-seekers

Visitors to St. Barts often arrive in private jets or yachts.

Courtesy St. Barts Tourism

St. Barts

St. Barts (the English name for the French territorial island of Saint-Barthélemy) has long been the playground for jet-setters to visit, arriving in private planes or mega yachts. They stay in luxury suites and villas like those at Le Sereno resort, with its cool elegance and secluded beach cove, or the stylish, over-the-top luxury of Eden Rock. The resort’s six-bedroom, 17,000-square-foot Villa Rockstar is described as a “$200 million yacht on land” and rents for upward of $200,000 per week.

Relax by day and party all night in St. Barts beach clubs such as the famed Nikki Beach Saint Barth on Saint-Jean Beach or La Case at the Cheval Blanc on Flamands Beach. Shop the high-end stores in Gustavia such as Louis Vuitton and Cartier, as well as many local high-end boutiques.

As a French territory, St. Barts cuisine is delectable. Dine on French-Caribbean fusion at the restored colonial home of Le Tamarin, or sample fresh Caribbean fish prepared Japanese style in the island outpost of Parisian restaurant Kinugawa in Gustavia. The island’s culinary experiences are celebrated (and tasted) at its annual St. Barts Gourmet Festival each November.

Prices match the luxury setting on St. Barts. For the 12 months through December 2023, the island reported the Caribbean’s highest average daily rate for lodging, by far, with a wallet-busting figure of $2,696 per night. This is dramatically above the Caribbean average daily rate of $323 for the region (computed by CoStar, a real estate data and analytics provider). Note that this number is likely skewed higher due to limited reporting, but a quick check online shows hotels on St. Barts starting at more than $800 per night in March, although certain apartment rentals can be found with more affordable rates.

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The Turks and Caicos have become a go-to destination for luxury travel, with premium-class travel increasing by 73 percent in 2024, according to a ForwardKeys market analysis report. Accommodations there have one of the highest average daily rates in the Caribbean at $1,202 per night.

An island focusing on the high-end travel market, Anguilla is home to luxury resorts and private villas catering to exclusive experiences. Five-star resorts include Belmond Cap Juluca, Four Seasons and Malliouhana.

Islands to get your money’s worth: Affordability

Exploring outlying islands, such as Exuma, makes the trip to the Bahamas even more affordable.

Getty Images

Bahamas

With frequent and affordable flight connections with the U.S., including recently introduced winter-season direct flights from the West Coast, as well as plentiful cruise excursions, getting to the Bahamas is easy and affordable. The Bahamas’ huge supply of lodging choices, especially around Nassau, and an array of package tours (with deals available from warehouse clubs) make the island chain a great choice for budget-minded travelers. There are plenty of luxury options as well, including the lavish Ocean Club, a Four Seasons Resort featured in the James Bond movie Casino Royale.

Sandals Royal Bahamian is a great choice for couples looking for an affordable but still upscale, all-inclusive resort. And the strip of high-rise hotels and rental properties along Cable Beach provides enough options to fit most vacation budgets. Deal-hunters should look at lodging such as the Comfort Suites on Paradise Island, an affordable hotel that also provides full access to the upscale amenities at the neighboring Atlantis Resort.

Getting around the Nassau-Paradise Island area is cheap and easy. Options including local jitney public transit at $1.50 per ride (in U.S. or Bahamian dollars as they are fixed at equal value) and water taxis to Paradise Island for $6 can save you money on a rental car. For dining, while hotel and resort food (and especially cocktails) are usually very pricey, you can save plenty by self-catering via the appropriately named Super Value supermarkets around town.

A tip to find even more affordable options in the Bahamas is to explore outlying islands. “The Bahamas’ diverse islands feature affordable options beyond Nassau, with budget-friendly stays on Andros, Abaco and Cat Island, especially during the off-season from August to November,” says Natalia Lopez, a spokesperson for the Caribbean Tourism Organization.

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The Dominican Republic is notable for its many affordable packages, for all-inclusive resorts — particularly in the Punta Cana area — and the island’s frequent flight connections with the U.S. make getting there easy on the budget as well, according to the Caribbean Tourist Organization.

Puerto Rico benefits from multiple discount carriers with service to the island, dropping airfare prices so low you’ll be tempted to pop down there for lunch. Plentiful vacation rental properties in San Juan and in beach areas bring down lodging costs for weekend escapes and longer trips.

Jamming, java & jumbies: Islands best for cultural trips

Jamaica stands out with its deep history, music scene, renowned local cuisine and natural beauty, such as the rivers of Ocho Rios.

Courtesy Jamaica Tourist Board

Jamaica

While every Caribbean island is rightfully proud of its local culture, history, cuisine and festivals, a few islands provide more depth, variety and accessibility for visitors to experience it, be it via museums, tourist-friendly festivals or cultural-themed tours.

Jamaica is “considered by many to be the cultural capital of the Caribbean,” according to Donovan White, the island’s director of tourism. The island stands out with its deep history, many festivals, music scene, renowned local cuisine, and local rums and coffee.

Music is an omnipresent part of Jamaican culture you’ll experience in any visit. The birthplace of Bob Marley and reggae, Jamaica continues the beat with live nightly music at a dozen different venues, major music festivals like Reggae Sumfest and Rebel Salute, and your friendly neighborhood DJs at beach resorts throughout the island. The Bob Marley and Peter Tosh museums are must-visits for reggae fans.

Jamaica’s Indigenous and colonial history, including a legacy of slavery and independence, can be seen at many cultural attractions. More history can be seen with a visit to Fort Charles at Port Royal and Jamaica’s historic and active houses of worship, including the Ethiopian Orthodox Church in Bull Bay, the Sha’are Shalom Synagogue and Kingston Parish Church.

Jamaican food culture makes every trip a tasty one. It is a blend of African, Spanish, Indian and British influences, including iconic dishes like jerk chicken, curry goat and the ubiquitous ackee and saltfish plates. Jamaica’s Blue Mountain region grows some of the finest coffee in the region. It’s well worth a visit to taste the product and learn from the growers. The Blue Mountain Coffee Festival each March is a fun way to immerse yourself in Jamaican coffee culture.

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Trinidad and Tobago is deservedly famous for its world-renowned Carnival, taking place annually in February or March, full of parades, music, dance and costumed performers dancing as Moko Jumbie spirits. Group travel surged more than 50 percent for the event in 2023. Plus, Trinidad and Tobago’s eclectic mix of Indian, Caribbean and African cuisines make the island a sweet and savory adventure.

With a history entwined with the U.S. and a lengthy Spanish-governing heritage, Puerto Rico has a mélange of history, culture, food and music. Museums, old forts and churches mix with the modern cityscape of San Juan to produce a vibrant culinary base and an even livelier music scene.

Hues of green and blue: Destinations for ecotourism

The Vicissitudes sculpture is part of Grenada’s underwater sculpture parks.

Courtesy Pure Grenada

Grenada

Caribbean trips to laze at the beach or pool are great, but if you’re looking to explore further, Grenada and its neighbor islands of Carriacou and Petite Martinique boast a wealth of ecotourism adventures.

Inland from its pristine beaches, Grenada is dotted with about a dozen true mountains, most of which are covered in rainforests and sprinkled with 14 waterfalls, providing more than enough eco-adventures of hiking, swimming and exploring for a single visit. As an island that’s only 12 miles wide, after a short drive from the coast, you can find yourself immersed in a jungled landscape a world away from the manicured resorts.

Eco-adventure by sea is also one of Grenada’s features. The island’s signature ecotourist attractions are its two underwater sculpture parks, including “the world’s first,” according to the tourism bureau. This combination of concrete art gallery and artificial reef, introduced in 2006, features dozens of statues of human figures and abstract designs, all installed about 15 feet underwater. On calm, clear days, you can see many of the figures, including those in full masquerade carnival, just by snorkeling or via a glass bottom boat. However, for the best experience, go on a scuba dive tour to fully appreciate them. Sea life clings to the statues, changing them over time, and giving the whole installation a haunting effect. Grenada launched a second underwater sculpture park in late 2024 off the coast of Carriacou.

You can feel good staying at the many Grenada hotels that are committed to sustainability. The True Blue Bay Boutique Resort has dozens of eco-friendly initiatives, including its own electric bus and composting programs. It also leads beach cleanup campaigns and ecotours. The Petite Anse hotel grows much of its own produce, uses solar power and has partnered with a sea turtle conservation program.

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St. John, U.S. Virgin Islands, is notable for its national park that makes up two-thirds of the island. With undeveloped beaches, 22 hiking trails, rustic lodging and even some friendly wild donkeys, the park is well worth a visit. Visitors can also explore an underwater snorkel trail in the park’s protected waters in Trunk Bay.

Dominica’s “focus on nature and sustainability continues to be the driving force of our growth,” said Marva Williams, CEO of Discover Dominica, in a news release. In 2025, she said, Dominica will be “building out more experiences and opportunities for visitors to have easier access to some of our more sought-after attractions,” including the “world’s first whale reserve.”

Best two-for-one island experiences

Planes arriving at Sint Maarten’s airport fly over Maho Beach.

Ron Buskirk/UCG/Universal Images Group/Getty Images

St. Martin/Sint Maarten

The “Friendly Island” has been peacefully divided between the French side of St. Martin and the Dutch side of Sint Maarten since the two colonial powers signed a partition agreement in the 17th century. Since then, each side of the island has maintained its own language, culture and spirit, creating a great opportunity for visitors to enjoy the contrasts of dual histories packed within approximately 35 square miles.

In my experience, the French side of St. Martin has a more relaxed, peaceful, slow-paced feeling, while the Dutch side of Sint Maarten, particularly in its main city of Philipsburg, is a horn-honking, neon-sign-flashing, slot-machine-dinging embrace of the Type A active lifestyle.

The island’s contrasts can be seen via its most famous beaches. On St. Martin, the peaceful Grand Case Beach features a stretch of white sand bordered by gentle waters, chill resorts and cafes serving French cuisine. But on Sint Maarten’s Maho Beach bordering the airport, thrill seekers cling to a fence next to the runway as blasts of jet exhaust whip up a sandy whirlwind. Note the runway area is NOT recommended for safety; visitors can enjoy a more traditional beach day on Maho further down the shore. While Grand Case Beach does have its share of motorboats, parasailers and jet skis, the general contrast is between action and relaxation.

Away from the beaches, St. Martin is notable for its French-inspired cuisine. It is highlighted by Grand Case restaurants serving everything from fresh pastries to foie gras, wine and cheese tastings, and plenty of fresh fish served in French restaurants with a Caribbean twist. Stop by the stalls at St. Martin’s outdoor Marigot Market for a colorful display of the ingredients used in these meals.

Further inland on St. Martin, the peaceful feeling extends to the hiking trails around Pic Paradis, the island’s highest mountain, and the plantation ruins of the surrounding Loterie Farm area.

The Dutch side of Sint Maarten also has a good collection of beaches, resorts and quiet plantation walks, but Philipsburg’s collection of high-rise casino hotels, the busy shopping experience along Front Street and the throbbing nightlife scene add to the entertainment experience.

My personal choice is to base myself at a quiet resort on the French side of St. Martin and enjoy active excursions to the Dutch side to spice up my trip.

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Despite being the smallest independent country in the Americas at just over 100 square miles, St. Kitts and Nevis can still provide visitors with different experiences between its two islands separated by a 30-minute ferry ride. Both St. Kitts and Nevis feature fine white sand beaches, escapes into wild nature, and a fascinating history (Nevis is famously the birthplace of Alexander Hamilton). St. Kitts is better known as the more developed, adventure-focused destination with lively beach bars and zip-lining excursions. Nevis is a quieter, peaceful retreat, “a haven of intimacy and seclusion, where life moves at a gentler pace … an escape for those seeking peace and privacy,” says Marsha Henderson, the country’s minister of tourism.

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Bill Fink is an award-winning travel writer covering global adventures for BBC, Lonely Planet, Thrillist and many other outlets. Follow him @finktravels.