The 5 best Caribbean Islands to visit and when to go

Whether you want to relax on sandy beaches, snorkel, visit a volcano, or enjoy Caribbean food - there's a Caribbean Island experience for everyone. In this guide, I have selected the best Caribbean Islands to visit along with things to consider when booking. Which will you choose for your next vacation?

Factors to consider when picking a Caribbean Island to visit

A woman in a bright green bikini driving around a huge sunken boulder in a crystal-clear sea.

Two women in bikinis strolling down a white sand beach.

Boy hanging over a palm tree by a Caribbean beach smiling at the camera

With so many Caribbean islands to choose from, there are a few things to consider before deciding on a destination. Let's take a look:

The weather

The Caribbean experiences good weather throughout most of the year. However, it can be cooler in December and January, especially in the mornings. So, if you’re visiting the Caribbean for Christmas or Valentine’s Day, choose one of the hotter islands, such as Aruba. On the other hand, it can get very hot on the beach in the summer. Whenever you have the chance, reserve or rent a cabana. I traveled with my girlfriends to Aruba and we lounged on the beach for most of the day. Those of us who were under the cabana were protected, and the rest of us got sunburned. Many of the beaches and hotels offer cabanas and they are well worth the investment.

Activities and attractions

Looking for buzzy nightlife? If so, popular islands like Trinidad and the Bahamas, where celebrities often visit, might fit the bill. There you’ll find several beachside bars where you can grab a drink. More adventurous types should head to Jamaica, where you can spend time outdoors riding ATVs or ziplining through the forest. If you’re more interested in a quiet vacation, the Turks and Caicos might suit you best. There you can stay at a private beachside villa where you can sunbathe without being seen. The US Virgin Islands is a particularly good place to take children because of its many family-friendly resorts, which include fun activities for all ages.

Getting there

Where are you flying from? If you’re in Miami or Fort Lauderdale, you’re just a short flight from Nassau, Puerto Rico, and the Bahamas. In fact, depending on what island you’re visiting, you can be there in less than 2 hours. You can also find several flight deals from major cities like New York City to the Bahamas or the Dominican Republic, or from Los Angeles to Jamaica. Hailing a taxi on the Caribbean islands can be expensive, so renting a car is a good option for getting around. If you don’t want to hire a car, many of the islands, including Barbados and St. Lucia, have good public transportation. You can also stay in a walkable neighborhood like Sandy Point in the Virgin Islands, or a beach town like Eagle Beach in Aruba.

Accommodation options

Would you prefer to stay in a large resort or a boutique beachfront hotel with quick access to sandy beaches? There are several large hotels in San Juan, Puerto Rico, each with its own restaurant, spa, and convention center. There, you’ll be a short drive from the beach but close to various city amenities like shopping and dining in San Juan. If you want to be just steps from the beach, consider the island of Jamaica, where you’ll find many charming hotels within a short walk of Negril Beach.

Budget

Of course, your budget will be important when you’re making your Caribbean travel plans. The cost of hotels and food can fluctuate depending on the island you choose. For example, Trinidad and Tobago, along with Punta Cana in the Dominican Republic, have many budget-friendly hotels to choose from. You can also save money by visiting the islands outside of peak season, typically from September to November. Although staying at an all-inclusive resort might be more costly, it will make tracking your spending in the Caribbean easier, because pretty much everything is part of the package (including food and various activities).

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The best Caribbean Islands

1. The Bahamas, the best Caribbean Islands to visit for nightlife

A pig swims in crystal-clear waters of a beach.

Colourful and modern townhouses on the coastline with moored yachts on the turquoise sea.

Hands making a toast with glasses of cocktails.

The Bahamas is home to scores of bars, many of which open after hours. Some are on the beach, where you can dance in the sand, while the heart of the city is home to luxurious nightclubs with grand staircases and famous DJs playing the latest hits. Stay at one of the party resorts for a club-like atmosphere that lasts from morning to night. This is also a great way to meet people if you're traveling solo.

For partying, the best time to visit the Bahamas is around Spring Break (March/April) or later in the spring (May/June).
For the best nightlife, consider booking your stay in Nassau.

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2. Jamaica, the best Caribbean Island to visit for adventure

A male local paddles a bamboo raft on the forest lagoon.

Jamaica is one of the best Caribbean Islands to visit if you like outdoor adventures. For something a little different, there are several waterfalls where you can go climbing, soak in relaxing waters, or row through caverns. Jamaica also provides opportunities to surf, go ziplining over waterfalls, or horseback ride. Visit Mystic Mountain in Ocho Rios to enjoy rainforest bobsledding – no snow required.

The best time to visit Jamaica is in the winter months to avoid the really hot weather.
The best cities to visit are Negril, Montego Bay, and Kingston (the capital city).

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3. Barbados, the best Caribbean Islands for foodies

Rows of colourful houses gracefully perch on the soft white sand, while swaying palm trees dot the landscape.

A hearty meal consisting of lobster, two varieties of salad, and white rice.

An inviting beachscape with white sand and aquamarine waters under a sunny sky.

Foodies will love getting a taste of Barbados. On the island, there are numerous bars, rum shops, fine dining restaurants, and food trucks where you can sample an array of tropical dishes. Don’t leave without trying some of the island’s most popular dishes and drinks, such as fish cakes, guava cheese, chicken feet, and rum punch. Visit in mid-October for the Food & Rum Festival, which takes place on the southwest end of the island, to meet celebrity chefs and try lots of local cuisine. If you fancy brushing up your kitchen skills, why not learn to cook Creole and Caribbean dishes while you’re on vacation, several places on the island offer cooking classes.

The best time to visit Barbados is in the winter.
The best places to visit include Bridgetown (the capital city) and Saint James.

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4. Dominican Republic, the best Caribbean Island to visit for history lovers

A white church looming over a city street crowded with parked cars.

The Dominican Republic has a rich history, having become independent in 1844. There are several historical sights to discover around this island to help you learn more – these include the El Faro a Colón, a monument in La Isabela near Santo Domingo, and the UNESCO World Heritage Site in Santo Domingo, the capital of the Dominican Republic.

The best time to visit the Dominican Republic is early to late spring when the weather is at its finest.
Santo Domingo is the best city to visit in the Dominican Republic.

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5. Puerto Rico, the best Caribbean Island to visit for tropical rainforests

A man skillfully surfs on the wavy beach by the lush island.

The piercing rays of the sun cutting through the trees hovering above a path crammed with parked cars and buildings.

High angle view of person gazing at palm plants in tropical rainforest

See a variety of plants and wildlife on a tour of El Yunque National Forest in Puerto Rico. While visiting the park, you can also enjoy a swim, go for a hike on the trail, or hop on a horse to see even more of the forest. Just be sure to take your bathing suit and camera along – this is a photographer’s paradise.

The best time to visit Puerto Rico is winter or spring.
The best cities to visit in Puerto Rico are San Juan (the capital) and Ponce.

"One of the most popular events is the Trinidad Carnival, which takes place in February and is a colorful carnival similar to Mardi Gras. Carnival participants often throw mud, paint, and flour for added fun. If you’re into music, there are several Caribbean festivals that you might enjoy, such as the Crop Over Festival held in July in Barbados, which features calypso bands. If you prefer reggae music there’s Sumfest, which also takes place in July on the island of Jamaica."

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Plan your visit to the Caribbean islands

A building with light green exterior walls and white arched mouldings around its windows and doorway.

A visit to the Caribbean can be great for a family holiday, an adventure vacation, or a romantic getaway. No matter your reason for traveling to this exotic destination, there’s an island that will suit your travel style and budget. The Caribbean Islands are a beautiful place to make memories, so start planning your island vacation today. Find the best flight deals, hotels, and vacation packages for your preferred island.

Not sure when to travel? Check out KAYAK’s Best Time to Travel tool for personalized recommendations.

Caribbean Island FAQS

A man tossing a young boy in the air as a woman watches from behind them on the beach.

In most cases, US citizens will not need a visa to visit the Caribbean islands. However, typically you must present a passport with at least 6 months of validity beyond your departure date.

In addition to the Virgin Islands and the Bahamas, there are a couple of lesser-known islands that are great for families with younger children. One that stands out is Dominica. This is a great place for kids to experience nature, as you can walk one of its many nature trails to see the local wildlife or visit the botanical garden to see native plants. There are also pretty beaches on this island, most of which are less crowded, making them more comfortable and safer for parents traveling with young children.

The best Caribbean Islands to visit on your next vacation