Holidays to the Caribbean 2026 & 2027
Tropical paradise awaits! With pristine white sand beaches, waters so clear you won’t believe they’re real, forget real life and simply relax.
The culture of the Caribbean reflects the French, Spanish, Portuguese, Dutch and British explorers who settled in the region and, of course, the many African slaves who worked on the plantations. Wherever you travel in the Caribbean, you will find relaxed and friendly locals, proud of their history and traditions.
Where to Go in the Caribbean?
Each brimming with their own personalities and diverse experiences, these five fabulous destinations capture everything travellers dream of when they picture the Caribbean, with easy access from the UK and from major locations in the USA and Canada.
Enjoy them on their own or combine them with a longer North America holiday:
Barbados is the Caribbean’s most easterly island is also one of the most beautiful. Just 21 miles long, Barbados boasts soft, white-sand beaches around its shoreline.
Originally claimed by the British in 1625, Barbados is now an independent nation and a member of the Commonwealth. English is the official language and the island’s British certainly lingers, notably in the Barbadians’ love of cricket! The island’s culture has similarly been shaped by its West African heritage, resulting in a laid-back lifestyle, and an incredible cultural fusion across food, music and celebrations.
Lying around 200 miles off the coast of Florida, The Bahamas is actually a collection of over 700, mostly uninhabited, islands.
Its capital, Nassau, on New Providence Island, is a vibrant blend of British and Caribbean culture, with many historic building and attractions and a lively harbour area. There are many delightful beaches nearby, with others to discover just a ferry ride away.
Jamaica is one of the largest, and most stunning, islands in the Caribbean. Pulsating reggae music is what probably first comes to mind, but Jamaica also offers enthralling natural landscapes, like Dunn’s River Falls and the Blue Mountains, incredible coffee and celebrated cuisine.
Whether you’re seeking adventure or relaxation, Jamaica fits the bill. Enjoy a plethora of outdoor activities, get stuck into the buzzing nightlife explore fascinating museums, or simply relax on the beach.
Puerto Rico conjures up images of colour-drenched villages, fringed by historic forts and beautiful beaches. The capital of San Juan is a great place to start your adventure, with welcoming locals, incredible eateries and plenty of history in ‘Old San Juan’, with its military stronghold and the original city walls.
The natural environments of Puerto Rico are spectacular too. El Yunque National Forest offers breathtaking hiking, with glistening waterfalls and serene natural pools. The island also boasts three of the world’s five bioluminescent bays in the world. Only visible to the naked eye, the algae in the water illuminates to a fluorescent blue when touched, making for an incredible spectacle.
As a US territory, Puerto Rico benefits from frequent flights from many popular American destinations, which makes a perfect city and beach itinerary.
Mexico’s Caribbean Coast makes an incredible, sun-soaked getaway, and it pairs perfectly with destinations in the US. Your days here can be as relaxed or as adventurous as you choose, from snorkelling over colourful coral reefs to exploring ancient Mayan sites like Chichén Itzá.
You can simply unwind in your blissful, all-inclusive beach resort, or if you venture beyond the hotel zone you’ll find local markets, fascinating archaeological sites and natural cenotes, perfect for swimming.
When is the Best Time to Visit the Caribbean?
The Caribbean enjoys a warm, sunny climate year round. However, July to October is considered the hurricane season, with higher rainfall and the threat of storms at that time.
The most popular time to visit is probably January to April when the temperature is slightly cooler and humidity lowest, but May and June are great if you like the warmth.
Multi Centre Caribbean Holidays
Why stop at just one island? On a multi centre Caribbean holiday, you can explore two or more islands, or even pair a Caribbean beach getaway with a city break in the USA, for example. At FREEDOM, our Travel Consultants can create a bespoke itinerary just for you.
Can I Visit Other Caribbean Islands?
Yes, we offer top class resorts throughout the Caribbean, with flights between, or to and from the UK. Talk with a FREEDOM expert about the Caribbean holiday you are looking for.
Can I Visit the Caribbean with America?
Yes, Freedom Destinations is a tailor made travel company that specialise in multi centre and multi destination holidays. The excitement of a USA or Canadian adventure with the laid-back serenity of a Caribbean beach resort makes a perfect combination.
Plan your holiday
