Which is the best Caribbean island to go on holiday?

The best Caribbean island to go on holiday really depends on what kind of experience you’re looking for. Aruba is perfect if you want year-round sunshine and a destination that sits outside the hurricane belt. St Lucia offers breathtaking natural beauty with its dramatic Piton mountains, lush rainforests, and romantic resorts such as Sandals. For culture and lively festivals, Barbados is a standout choice with its mix of white-sand beaches, local rum distilleries, and vibrant nightlife. Those seeking tranquillity and perfect beaches will love Turks & Caicos, home to the famous Grace Bay, while the Bahamas offers fun for families and couples alike, especially at the Atlantis Resort, which can also be paired with a Florida twin-centre holiday. Jamaica is another popular option for music, adventure, and warm hospitality, with a new Beaches family resort adding even more appeal.

What is the best month to visit the Caribbean?

The best time to visit the Caribbean depends on your priorities. The dry season from December to April offers the best weather with warm days, low humidity, and little rain, making it the most popular (and expensive) time to go. For fewer crowds and better value, the shoulder months of May, June, and November strike a great balance between good weather and lower prices. Travellers on a budget might look at September and October, though these fall within the hurricane season and bring a higher chance of rain. If you want reliable sunshine in summer, Aruba, Curaçao, and Bonaire are ideal as they lie outside the main hurricane belt.

What is the nicest and safest Caribbean island?

When it comes to the nicest and safest Caribbean islands, several destinations consistently stand out. Anguilla, Cayman Islands, Aruba, Barbados, Turks & Caicos, and St Barts are often regarded as among the safest, thanks to low crime rates, friendly communities, and excellent tourist infrastructure. As with anywhere, visitors should still exercise basic travel precautions, but overall, these islands are known for their welcoming and secure environments.

What are the 13 Caribbean countries?

There are 13 sovereign Caribbean countries, each offering something unique: Antigua and Barbuda, The Bahamas, Barbados, Cuba, Dominica, Dominican Republic, Grenada, Haiti, Jamaica, Saint Kitts and Nevis, Saint Lucia, Saint Vincent and the Grenadines, and Trinidad and Tobago. Together, they represent the vibrant heart of the Caribbean, with a blend of cultures, languages, and landscapes.

What is considered the prettiest Caribbean island?

As for the prettiest Caribbean island, that’s a tough choice, as each island has its own special charm. Many travellers consider St Lucia the most beautiful, thanks to its soaring Pitons and lush tropical scenery. Antigua is loved for its 365 pristine beaches, while Turks & Caicos dazzles with its soft white sands and turquoise lagoons. The Exumas in the Bahamas are famed for their sandbars and crystal-clear waters, the British Virgin Islands for their sailing adventures, and Dominica for its waterfalls, hot springs, and untouched rainforests. No matter which island you choose, the Caribbean promises spectacular scenery, warm hospitality, and unforgettable memories.

Caribbean Holidays 2026/2027 | Caribbean Island Holidays

Discover more of the Caribbean

Falling into the world’s top ten beach destinations, Caribbean holidays 2026 / 2027 offer dreamy days spent on pristine white sands, long evenings sipping rum beneath starry skies, and stays at some of the most luxurious Caribbean all-inclusive resorts.

Caribbean holidays are perfect for families and couples alike, and the Caribbean is a fantastic holiday destination year-round but especially in the Christmas School Holidays / Summer School Holidays! Working with our partner airlines Virgin Atlantic, Aer Lingus, and British Airways, our Caribbean experts can secure your flights and holidays with a choice of Economy, Premium Economy, or the pure luxury of Business and First Class travel.

Whether you’re looking for romantic escapes, family getaways, or adventurous island hopping, our team will craft your perfect Caribbean all inclusive holiday experience from start to finish.

Barbados – The Perfect All-Inclusive Escape

Barbados is a timeless favourite for those seeking the best Caribbean all-inclusive holidays. Fly direct to Barbados from Manchester with Aer Lingus and Virgin Atlantic, and fly direct to Barbados from Heathrow on Virgin Atlantic and British Airways and arrive in paradise ready to unwind. From the golden sands of Carlisle Bay to the calm turquoise waters of Mullins Beach, Barbados combines tropical beauty with lively island culture. Sample world-famous Mount Gay rum, explore the UNESCO-listed capital Bridgetown, or simply relax at one of the island’s many luxury beachfront resorts. For honeymooners and couples, elegant boutique hotels offer romance and seclusion, while families can enjoy vibrant resorts with fantastic activities for all ages.

Bahamas – Atlantis & Florida Twin Centres

The Bahamas are home to stunning beaches, crystal-clear waters, and the world-famous Atlantis Paradise Island Resort – one of the Caribbean’s most iconic destinations. Perfect for families, couples, and groups, Atlantis offers incredible waterparks, marine life encounters, and luxury all-inclusive experiences. The Bahamas also make a wonderful Florida and Bahamas twin-centre holiday, combining the excitement of Orlando’s theme parks with the laid-back elegance of Caribbean island life. With excellent flight connections from the UK, you can easily enjoy the best of both worlds on your next Caribbean holiday.

Turks & Caicos – White Sands and Turtle Watching

For pure serenity and barefoot luxury, the Turks & Caicos Islands are hard to beat. These islands are famed for Grace Bay Beach, often voted one of the most beautiful in the world. The calm turquoise waters are ideal for snorkelling, paddleboarding, and watching the resident turtles drift gracefully through the shallows. Resorts here specialise in exclusive Caribbean all inclusive holidays like at Beaches Turks and Caicos, with personalised service and unspoiled natural beauty at every turn. Whether you’re a couple seeking peace and privacy or a family looking for gentle adventure, Turks & Caicos delivers unforgettable Caribbean charm.

Jamaica – New Family Beaches Resort Opening

Jamaica continues to be one of the Caribbean’s most loved islands, offering a perfect blend of tropical scenery, warm hospitality, and cultural energy. From the stunning beaches of Montego Bay to the waterfalls of Ocho Rios, Jamaica offers adventure, relaxation, and rhythm in equal measure. Excitingly, a new Beaches Resort is opening soon, providing a fantastic option for families looking for a world-class Caribbean all inclusive holiday with fun for every generation. Enjoy endless activities, beautiful beaches, and exceptional dining while discovering Jamaica’s unmistakable spirit. Jamaica also makes for a great honeymoon destination thanks to it's seven Sandals Resorts including Sandals Montego Bay Resort, Sandals Royal Plantation and Sandals Ochi Beach Resort.

Aruba – Year-Round Sunshine Outside the Hurricane Belt

For those seeking guaranteed sunshine, Aruba is the ideal Caribbean island. Fly direct with British Airways and enjoy a destination that sits safely outside the Caribbean hurricane belt, making it perfect for travel even in the summer months. With its year-round sunshine, soft white sands, and crystal-clear waters, Aruba is a haven for beach lovers. Dutch-Caribbean charm, friendly locals, and luxury resorts make this island ideal for couples, honeymooners, and families alike. Aruba’s calm climate and reliable weather make it one of the best destinations for a summer Caribbean holiday.

Cuba - History and Culture

Charter Travel can fly you direct with Virgin Airlines to the beautiful island of Cuba, seemingly forgotten about for over 40 years, isolated from many tourists it is a fascinating place to visit. Combine a stay in Havana and watch trademark cigars being made or relax and enjoy a Mojito made locally with traditional rum. We can arrange an all-inclusive holiday at one of the many beaches which stretch along the island's coastline.

St Lucia – Romance, Adventure, and Sandals Resorts

St Lucia is the epitome of Caribbean beauty, famous for its lush rainforests, volcanic beaches, and the iconic twin peaks of the Pitons rising majestically from the sea. This island is perfect for both romance and adventure – hike through tropical trails, bathe in natural hot springs, or enjoy a sunset cruise along the coast. For couples, Sandals Resorts in St Lucia provide the ultimate in luxury and exclusivity. With three magnificent resorts – Sandals Grande St Lucian, Sandals Halcyon Beach, and Sandals Regency La Toc – guests can enjoy a “Stay at 1, Play at 3” experience, accessing all restaurants, pools, and beaches across the island. It’s the ultimate Caribbean holiday on Virgin Atlantic or Aer Lingus, designed for couples seeking unforgettable romance, fine dining, and tropical bliss.

More Caribbean Island Adventures

The Caribbean offers so much more to explore. In Antigua, you’ll find 365 beaches – one for every day of the year – along with the historic Nelson’s Dockyard, once home to Admiral Horatio Nelson. St Lucia entices visitors with its majestic Pitons, lush rainforests, and romantic luxury resorts. In Grenada, explore spice plantations, visit waterfalls, or dive into the famous Underwater Sculpture Park, a world-first and a must-see for divers. For those who enjoy cultural heritage and beautiful beaches, Cuba remains a fascinating option – explore Havana’s vibrant streets before relaxing on a stunning Caribbean coastline.

Why Book Your Caribbean Holiday with Charter Travel

Charter Travel can arrange flights, accommodation, and tours to all of these incredible destinations. Fly with Virgin Atlantic, Aer Lingus, or British Airways and let our dedicated Caribbean specialists design your perfect holiday. Whether you’re seeking a Caribbean holiday on Virgin Atlantic, a Caribbean holiday with Aer Lingus, or an indulgent Caribbean all inclusive holiday, our experts will tailor every detail to your needs.

We can also organise Caribbean cruises with Royal Caribbean or an adult-only cruise experience on Virgin Voyages – the world’s largest fully-rigged sailing ship. Let Charter Travel be your first choice for luxury Caribbean holidays. Call us now on 01635 551011 and speak to one of our expert consultants to start planning your dream escape today.

Caribbean Special Offers

Popular Caribbean Destinations

Barbados Holidays

Barbados holidays offer beautiful blue skies, crystal waters and golden beaches. The island’s East coast boasts amazing wild surfs, and the West coast offers the perfect calming waters of the Caribbean Sea.

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Bahamas Holidays

Bahamas Holidays 2026 / 2027 offer beautiful sunshine, white sand beaches and amazing hotels. Visit Atlantis Resort, swim with the pigs in The Exumas, visit Grand Bahama and more!

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Jamaica Holidays

Jamaica Holidays are fabulous all year long! The coast is scattered with hotels of all shapes and sizes, but the most popular areas are Montego Bay, Ocho Rios and Negril. From all Inclusive resorts to boutique hotels, there is something for everyone!

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Aruba Holidays

Aruba Holidays 2026/ 2027 offers visitors amazing white sandy beaches, spectacular sunshine, stunning natural beauty, friendly culture, fabulous hotels and more!

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Turks and Caicos Holidays

Turks and Caicos Holidays 2025/2026. Stay in luxury resorts, relax on stunning golden sand beaches and fly with direct with Virgin Atlantic / British Airways. ABTA and ATOL Protected.

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Saint Lucia Holidays

Saint Lucia Holidays pristine beaches, activities galore, beautiful hotels, creole cuisine and unforgettable sunsets are just some of the memories you will take away with you after you have experienced the island of St Lucia

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Cuba Holidays

Book a holiday to Cuba, experience the real captivating side of Cuba speak with Cuban specialists, make your Cuba holiday a Cuba twin Centre ABTA and ATOL

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Sandals Holidays

All-inclusive Sandal holiday resorts with world famous volcanoes and spectacular scenery and vast number of beaches and many secluded coves you can discover. This is the ultimate exotic tropical paradise experience, perfect locations for a honeymoon or wedding.

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Beaches Holidays

The popular Beaches Resorts situated in Turks and Caicos, and Negril, and Ochos Rios are beautiful family orientated resorts

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