The 10 most popular Caribbean islands to visit in 2026

Want to escape the winter blues? The Caribbean islands are a popular holiday destination in wintertime due to their consistent sunshine, warm temperatures and stunning beaches. 

While the islands are known for their white sands and turquoise waters, each offers its own unique highlights. Some islands are ideal for exploring waterfalls, rainforests and adventure activities, while others provide the perfect setting for beach relaxation, jet skiing and rum cocktails.

We have analysed Google search data to identify the top trending Caribbean islands heading into 2026. We focused on the percentage increase in searches for "holidays to…" each Caribbean island by comparing this year's autumn/winter search volume with that of last year. This research resulted in a list of the top 10 most popular islands.

Contents:

1. Jamaica
2. Dominican Republic
3. Cuba
4. Tobago
5. Barbados
6. Aruba
7. The Bahamas
8. Puerto Rico
9. Grenada
10. Turks and Caicos Islands

1. Jamaica

Average January temperature: 26°C

Jamaica experienced the highest increase in search data among the Caribbean islands from winter 2024 to winter 2025, showing an increase of 244.8%.

Jamaica is a vibrant Caribbean island famous for its music, culture and natural beauty. It is recognised as the birthplace of reggae, ska and dancehall music, with its capital, Kingston, a UNESCO City of Music. Key attractions include the Seven Mile Beach and Rick's Café in Negril, renowned for its stunning sunsets. Additionally, you can explore Dunn's River Falls in Ocho Rios, where you can climb the terraced cascades that rise 600 feet high.

Cruising to Jamaica

Jamaica has three main ports – Ocho Rios, Falmouth and Montego Bay. Ocho Rios is the most popular, known for Dunn's River Falls and Mystic Mountain's bobsled rides. Falmouth, the newest and largest port, features Georgian architecture and is close to Martha Brae River rafting. And finally, Montego Bay, the island's tourist capital, is home to famous beaches like Doctor's Cave Beach, the lively "Hip Strip," and historic sites such as Rose Hall Great House.

Check out our cruises to Jamaica here. 

2. Dominican Republic

Average January temperature: 25°C

The Dominican Republic experienced the second-largest increase in search data, with a rise of 144.1% between winter 2024 and winter 2025. 

The Dominican Republic is a Caribbean nation sharing the island of Hispaniola with Haiti. The island's capital, Santo Domingo, was founded in 1496 and features a UNESCO-recognised Colonial Zone. Visitors will also find luxury resorts and beautiful beaches, such as Bavaro Beach, located in Punta Cana. Notable attractions include the Samaná Peninsula, which is great for whale watching from January to March, Pico Duarte, the Caribbean's tallest peak, and Lake Enriquillo, the largest lake in the Caribbean.

Cruising to the Dominican Republic

The Dominican Republic has several major cruise ports. On the North Coast, Puerto Plata, Amber Cove, and Taíno Bay serve as hubs for adventures such as the 27 Waterfalls of Damajagua and historical sites in Puerto Plata. Further south, La Romana is the gateway to Catalina Island, while the port in Santo Domingo offers easy access to the historical Colonial Zone.

Explore our selection of cruises to the Dominican Republic here. 

3. Cuba

Average January temperature: 22°C

Cuba is an excellent winter destination, with searches for “holidays to Cuba” increasing by 79.4% compared to last winter. 

Cuba is the largest island in the Caribbean, with plenty of attractions to see. According to TripAdvisor, it is home to the best beach in the Caribbean, Playa Varadero, which features white sands, warm waters and stunning sunsets. A key location to visit includes the historic capital, Havana. There you can stroll through the cobbled streets of Old Havana, take a vintage car ride along the Malecón and enjoy a Cuban cocktail at a bar like El Floridita, a favourite of the famous writer Hemingway.

Cruising to Cuba

If you're considering a cruise to Cuba, there are three main cruise ports: Havana, which allows immediate access to Old Havana; Cienfuegos, known for its French colonial architecture and nearby attractions such as the Bay of Pigs and El Nicho waterfalls; and Santiago de Cuba, the island's second-largest city, renowned for its rich culture, music and revolutionary history.

Discover all available Cuba cruise itineraries.

4. Tobago

Average January temperature: 26°C

There has been a 51.5% increase in searches for "holidays to Tobago" from winter 2024 to winter 2025.

Tobago boasts the Main Ridge Forest Reserve, the oldest legally protected forest in the world, and the Nylon Pool, a natural wonder perfect for swimming and snorkelling. Must-visit destinations on the island include Pigeon Point, renowned for being one of the most beautiful beaches in the Caribbean with excellent reef tours, and Argyle Falls, the highest three-tiered waterfall in Tobago, where visitors can enjoy a swim after a jungle trek.

Cruising to Tobago

Cruises dock at the Scarborough Cruise Port, located in the capital city. This port is near the historic centre, providing easy access to historical sites such as Fort King George, which offers panoramic views of the harbour, as well as Scarborough Market, where you can find local crafts and spices. 

See our current deals on Tobago cruises here.

5. Barbados

Average January temperature: 26°C

Barbados has seen a 48.6% increase in Google searches compared to last winter. 

Known as the historical birthplace of rum, Barbados is home to the oldest commercial rum distillery, Mount Gay. The island is unique for its coral limestone formation, which contributes to its stunning 80 white-sand beaches. January is the perfect time for exploring UNESCO World Heritage sites such as its capital, Bridgetown, snorkelling over shipwrecks in Carlisle Bay, or enjoying the local Oistins Fish Market.

Cruising to Barbados

Bridgetown Cruise Terminal, which is located just outside the capital, offers access to the UNESCO-listed historic area of Bridgetown via a short taxi ride or a 15-20 minute walk. This port frequently serves as a homeport, allowing passengers to start and end their cruise itineraries here.

See our collection of Barbados cruises here. 

6. Aruba

Average January temperature:  26°C

The next Caribbean island on the list is Aruba, which has seen a 46.2% increase in search data. 

Known as "One Happy Island," Aruba is part of the ABC Islands located off the coast of Venezuela and is a constituent country of the Netherlands. The island is renowned for its consistently excellent weather and unique blend of cultures, featuring Dutch and the local Creole language, Papiamento. Visitors can enjoy calm, turquoise waters and stunning white-sand beaches like Eagle Beach, as well as the rugged, desert-like landscapes found within Arikok National Park.

Cruising to Aruba

For those cruising to Aruba, the main cruise port is located in the capital city, Oranjestad. Passengers can easily walk from the terminal directly into the downtown area, which is famous for its brightly coloured, Dutch-influenced colonial architecture, luxury shopping options and a complimentary downtown tram service.

Your Aruban adventure awaits. Find your cruise here.

7. The Bahamas

Average January temperature:  21°C

The Bahamas saw an increase in search data of 16.2% between this winter and last winter.

The Bahamas are renowned for their clear waters and a diverse archipelago of over 700 islands, with around just 30 being inhabited. The Bahamas are also an excellent destination for those who love wildlife. The famous swimming pigs can be seen in the Exuma Cays in the Bahamas, a bucket-list opportunity for many. You can also swim with nurse sharks at Compass Cay, a private island in the Exumas. Additionally, the Andros Barrier Reef is the world’s third-largest, and it attracts divers and marine life enthusiasts to the islands.

Cruising to The Bahamas

Nassau on New Providence Island serves as the main hub, offering access to the historic downtown, Straw Market and Paradise Island. Freeport on Grand Bahama Island provides a quieter experience near Lucayan National Park. Major cruise lines also have private islands, including Royal Caribbean's Perfect Day at CocoCay and Carnival's Half Moon Cay.

View and  book your unforgettable Bahamas cruise here.

8. Puerto Rico

Average January temperature:  25°C

“Holidays to Puerto Rico” searches have increased 16% from last year to this year. 

Puerto Rico, located in the northeast Caribbean Sea, is a vibrant blend of Spanish, American and Caribbean cultures. The island is famous for being the birthplace of the piña colada, which has been the official drink of the island since 1978. For those who love the outdoors, El Yunque National Forest can be found on the northeast corner of the island and is the only U.S. tropical rainforest. Key attractions include Old San Juan, a UNESCO World Heritage Site with colourful colonial architecture, and Culebra Island, famous for Flamenco Beach, often ranked among the world's most beautiful beaches.

Cruising to Puerto Rico

The main port for cruises is the San Juan Cruise Port, which offers easy access to the historic centre of San Juan. The Pan American Cruise Terminal, used for larger ships or homeporting cruises, is located across the bay and requires a short taxi ride to the historic area. Occasionally, the Ponce Port on the southern coast welcomes cruise ships, allowing guests to explore the colonial architecture of the "Pearl of the South."

Explore our latest voyages to Puerto Rico here.

9. Grenada

Average January temperature = 25°C

Grenada has seen a 15.9% increase in Google searches this winter compared to last winter.

Grenada, known as the "Island of Spice," is a beautiful Caribbean island that often has an aroma of spices like cinnamon and cloves in the air. Visitors can discover the world's first Underwater Sculpture Park in Molinere Bay with 75 sculptures, created to aid marine conservation. The site is even listed as one of National Geographic’s 25 Wonders of the World. There’s also the famous two-mile stretch of white sand at Grand Anse Beach, and the mountainous rainforest of Grand Etang National Park with its stunning crater lake and waterfalls.

Cruising to Grenada

Grenada has one primary cruise port situated in the capital city of St. George. This port is renowned for its picturesque horseshoe-shaped harbour, which provides immediate access to historic sites such as Fort George, where visitors can enjoy stunning views of the city. Additionally, the Market Square offers a great opportunity for visitors to shop for the island's famous spices.

Discover all available Grenada cruise itineraries here.

10. Turks and Caicos Islands

Average January temperature:  25°C

Searches for holidays in Turks and Caicos have increased by 6% from last winter to this winter.

The Turks and Caicos Islands are famous for their stunning beaches, turquoise waters and diving. The main tourist hub is Providenciales, home to Grace Bay Beach and its 12 miles of beautiful sand, protected by a barrier reef. Meanwhile, the historic capital of Cockburn Town, located on Grand Turk, is home to 18th-century architecture, a historic lighthouse and wall diving with a 7,000-foot drop. Tourists can enjoy both luxury relaxation and adventure in these beautiful islands.

Cruising to Turks and Caicos 

The Turks and Caicos Islands have one main cruise port at the southern tip of Grand Turk Island. It offers a large pool, the biggest Margaritaville in the region, shopping and a beachfront. Ships dock directly at the pier for easy access to the complex or a quick taxi ride to historical sites like Cockburn Town and Fort George.

Check out our Turks and Caicos cruise itineraries here.

Book your Caribbean getaway with Iglu Criuse today

Ready to escape the chill? Explore the warmth and stunning turquoise waters of the Caribbean with our collection of Caribbean Cruises. Browse our options, including luxury Caribbean cruises, all-inclusive cruises and more. Prefer a journey closer to home? View our cruises departing directly from the UK or Europe.