The Caribbean is a beautiful region that attracts visitors from all over the world. Massive coral reefs host vibrant fish life. Warm temperatures offer a break from winter’s cold. And, a location that is tantalizingly close to the United States makes it an easy to visit destination.
The Best Caribbean Islands to Visit in 2024
If you are asking which island is the best, people would be justified asking a question back: best for what?
What makes an island the best will come down to what you are looking for. With that in mind, I’ve gone over a few categories that people might have in mind if they are looking for a place that is the best out of all the Caribbean islands.
For Passport-free Travel
Of the United States’s five permanently inhabited territories, two are in the Caribbean: Puerto Rico and the U.S. Virgin Islands. If you don’t currently have a passport and want to go on a quick getaway, a trip to either could be just what you need.
Between the two, Puerto Rico is easily the more affordable. Flights are available from New York for under $300 per person round trip. You can easily find hotel rooms under $100 a night near the water.
A trip there is a chance to work on your Spanish, but you won’t be lost if you don’t speak the language. Around half of all Puerto Ricans speak English daily.
The U.S. Virgin Islands are considered among the most expensive places to visit in the Caribbean. The flight from New York will cost about twice what you’ll spend getting to Puerto Rico.
Most hotel rooms are in the $200 to $300 range per night. USVI is an English-speaking destination, which can reduce stress if you are monolingual and worried about being able to communicate.
In the end, though, it’s worth jumping through the hoops to get your passport. You’ll be able to see so many more places.
For Natural Beauty
Large areas of islands throughout the Caribbean were subject to slash and burn clearing to make room for colonial agricultural products. Other areas, however, were spared and still display natural beauty and are largely untouched.
The island of Tobago is a great place to go if you want to spend some time snorkeling and lazing on the beach. If you head to the leeward side of the island, you’ll wind up by Englishman’s Bay, a deep and calm body of water.
On the shores, you’ll find lush rainforest with trails that are great for hiking. Redditors particularly recommend the area around Guilpin Trail.
Dominica has been dubbed the Nature Island of the Caribbean. Morne Trois Pitons National Park is a tropical rainforest where you’ll find hot springs, prehistoric giant ferns, and colorful local flowers.
The trails head up into the hills, allowing you to hike through a magical cloud forest. In Jamaica, the mountainous region in the southeast was a refuge for first the Tainos and then later the Maroons fleeing their enslavers.
Today, the Blue and John Crow mountains are destinations for ecotourism. You can enjoy sustainable tourism here that includes green accommodations, bird watching tours, hiking, and camping.
For a Party
Carnival is not just one date in the Caribbean. Different Caribbean countries host carnival celebrations throughout the year. Trinidad’s Carnival is an annual last hurrah before Lent. Party goers take their costumes seriously and commission them months before the celebration.
Carnival starts before sunrise the Monday before Ash Wednesday. It’s celebrated with soca music, parades, and dancing in the streets.
In the Guadeloupe Islands, their pre-Lenten carnival starts heating up in January. The first day of the carnival is January 6, the Feast of the Epiphany. Major events continue all season, culminating on Fat Tuesday just before Lent.
Traveling in midwinter? Consider heading to the Bahamas for Junkaroo. This festival starts on Boxing Day (Dec 26) and runs straight through New Year’s Day. The biggest party is on Bay Street in Nassau, but there are celebrations on every island.
Carnivals are not just for the winter months, though. The Cayman Islands kicks off the warm weather carnival season with their Batabano festival in May. The festival coincides with the start of turtle nesting season.
The name comes from a Caymanian term referring to the tracks egg-laying turtles leave in the sand. In Barbados, they celebrate a three-month Crop Over Festival. This one begins in late July when the sugar cane is harvested and continues until early August.
The Caribbean has been inhabited by humans for at least 6,000 years. Native cultures persisted there until European contact. The Caribbean was the first area Spanish explorers landed, touching ground in modern Cuba, Bahamas, and the Dominican Republic.
In the centuries after, multiple European countries installed colonies, clearing forest for plantations and erecting buildings in their own countries’ architectural styles.
Much of that history can be explored through museums and preserved historic sites. If you’re the type who wants an educational angle when they travel, there are multiple islands that can give you the historic attractions you are looking for.
Barbados offers many opportunities to learn about the history of the island. The Blackwoods Screw Dock is the world’s oldest surviving ship-lift, and gives you an opportunity to explore the maritime technology that drove European exploration.
The Garrison historic Area in Bridgetown has many examples of English architecture from the 1890s. You can also unwind with a day at the horse races. Garrison Savannah has been hosting weekly races since its opening in 1845,
Caguana Indigenous Ceremonial Park in Puerto Rico is considered one of the most important Taíno-culture archeological sites.
Visitors can see limestone artifacts like tiles and petrographs, which were made during the 1300s and 1400s by indigenous people. There are courtyards and plazas where important ceremonial events were held.
There are 23 UNESCO Heritage sites in the Caribbean. Cuba tops the list in this respect, with nine sites within the country. You can walk the streets of Old Havana or explore the first coffee plantations in the southeastern part of the island.
Curaçao is an area where you can see Dutch, Spanish and Portuguese influence. In Willemstad, the city is broken into four distinct historic districts where many examples of the original architecture still exist.
The multicultural city is also the site of Mikvé Israel-Emanuel, which is the western hemisphere’s oldest, continually used synagogue.
You can also visit the Museum Kurá Hulanda, which documents the country’s historic ties with West Africa. The historic city of Santo Domingo in the Dominican Republic is still laid out in the grid system established in 1498.
The city was adopted as a World Heritage Site in 1990. History buffs will also enjoy touring Brimstone Hill Fortress National Park in Saint Kitts & Nevis.
Thisfort offers a well-preserved example of military architecture of the 17th and 18th centuries. Another destination for military history lovers is Martinique’s capital city Fort-de-France The 17th century Fort St Louis dominates the southeast corner of seafront park Place de la Savane.
Parts of the fort are open for tours. Others are still in use by the country’s navy. Guyana is a place to visit for more indigenous history.
In Georgetown, you can explore the country’s past at the National Museum and the Walter Roth Museum of Anthropology. The Botanical Gardens display over 200 bird species and a wealth of local plant life.
Best Caribbean Islands to Live In
When you get to the Caribbean, it’s not uncommon to feel like you never want to leave. Can’t you just live there forever?
One catch when it comes to expats eying the Caribbean: most countries there are pretty strict businesses about hiring noncitizens. In most countries, employers need to demonstrate that they are hiring you for a job that can’t be done by someone locally.
And, being unable to draw a paycheck can, unfortunately, be an impediment to making a place your full-time address. But, wide adoption of remote work has changed that. More and more people are working from home, and are able to move their working operation to anywhere there’s internet.
Many people do this moving place to place, just staying as long as they can without a visa. In most places, this can be anywhere from 90 to 120 days. If you want to spend longer in a single place, though, there are no visas that can help you set down (shallow) roots.
Several Caribbean countries are now wooing remote workers with working visas designed for digital workers. Most run around a year and require you to prove you are able to support yourself while you are in the country.
Depending on the country, the visa may be a one-off or may be renewable. The BEATS program in the Bahamas, for instance, allows you a one-year visa that can be renewed twice.
Dominica, for instance, offers a Work in Nature (WIN) visa good for 18 months. To qualify, you need an income of at least $50,000 a year. St. Lucia’s “Live It” visa program does not specify a minimum income to qualify.
You just need to prove “sufficient funds” when submitting your application. Columbia’s requirements are even more lax, with a minimum required income of $800 per month. (Not an island, I know. But, it’s worth mentioning, as it is a popular expat destination.)
Grenada’s minimum income for a digital nomad visa is lower than its neighbors. You’ll only need to prove an income of at least $37,000 to secure a one-year visa to live and work in the country.
The Bahamas has a program that is unusual in that it also allows students to gain visas to study remotely in the country. The visa, known as BEATS, is good for one year.
There’s no specific income requirement; you just need to prove you have enough income or savings to support yourself. If you have kids at home, they can attend virtual school while you work remote from your normal job.
The Caymans, unsurprisingly, goes way the other way when it comes to affordability. The minimum required income here is $100,000, which is in line with the country’s high cost of living.
Not up for a visa application? Consider Nevi and St. Kitts. They allow visa-free stays in the country of up to six months. No matter where your tropical lifestyle fantasies take you, be sure to do some real world research before you go.
Internet can be slow and unreliable in many destinations. And, in places where you can find it, you are likely to pay quite a lot for your service. It’s also worth investigating whether your employer is okay with you working outside the country.
Frequently Asked Questions
Still have questions? These are answers to some common ones:
What is the best overall Caribbean island to visit?
The best will depend on what you are looking for. Whether you want the lowest travel costs, the most beautiful scenery, or the most active nightlife, the answer will be different for everyone. Consider how you would spend your ideal vacation day and start from there.
What is the number 1 tourist island in the Caribbean?
The top tourist destination in the Caribbean is the Dominican Republic, which posted over 8.5 million visitors in 2022.
What is the most beautiful safe Caribbean island?
Most places in the Caribbean are safe to visit. Most are beautiful in their own way. Many votes go to St. Barts, which is a very low crime destination.
Where is the prettiest place in the Caribbean?
Ask 20 different people and you’ll get 20 different answers. We personally think that St. John is one of the most picturesque islands in the entire Caribbean.
Summing Up: The Best Caribbean Islands to Visit
There is no single answer to this question. The region can’t be summed up in a single visit, as each country and each island are unique.
Figure out what you want from your trip, then start researching to see which islands will offer that experience. Many people choose a different destination each time, others fall in love with a single spot and go back again and again.