The Top 10 Caribbean Islands For a Holiday

With all those amazing Caribbean islands to choose from, it can be difficult to know where to begin planning your holiday in one of our fabulous luxury holiday rentals. However, you can take our expert advice when we say that there’s an island for every kind of holiday, whether you’re looking for a full-on, adrenaline-fuelled adventure, a romantic break with that special someone or an unforgettable family getaway. Simply browse our list of the top 10 Caribbean islands for your holiday, pick which one suits you best and then get booking!

1. St. Lucia

St Lucia means one thing – luxury! Whether you’re looking for a honeymoon that pulls out all the stops or the kind of holiday where your every whim is catered for, St Lucia has the facilities – not to mention the achingly beautiful villas – to make it happen. If you’re looking for adventure, try climbing the iconic Pitons, heading into the Chassin rainforest or enjoying some of the world’s best diving. The island’s musical pedigree also means there’s loads to choose from if you fancy a night on the tiles…

Best for: Adventure holidays, romantic honeymoons, spas and pampering.

2. Barbados

If you like your holidays full of adrenaline and adventure, this is the one for you. The huge swathes of beautiful natural parks on Barbados are ideal for exploration, while the lively waters are perfect for surfing. Better yet, there’s some varied and spectacular food on offer – everything from tasty street food to high-end dining. The capital of Bridgetown and the island’s many towns love to party, so if you’re after a fun-filled holiday in the Caribbean sun or a honeymoon that’s all about the nightlife, you can’t pick a better spot.

Best for: Shopping, non-stop holidays, and nightlife.

3. Jamaica

Big on food and big on flavour, Jamaica’s full of music, life and rhythm. Great if you’re looking for a resort-style holiday and want to spend your time in the thick of the action, living life to the fullest. As the home of reggae and jerk seasoning, you know everything in Jamaica is going to be big and bold, from the beautiful beaches to the Blue Mountain national park, where you’ll find waterfalls and walking trails straight out of some tropical dream. It’s also your ideal island pick if golf is your holiday recreation of choice, with plenty of courses to keep golfers of all abilities happy.

Best for: Food and drink, music and nightlife, and exciting honeymoons.

4. Grenada

Grenada’s got pretty much everything the Caribbean has to offer. Make the most of the romantic scenery by hiking in the rainforest, swimming in waterfalls or just driving around taking in the amazing views and wildlife. With such wonderful ingredients the food is superb and hanging out with the locals is a clear highlight. Grenada’s beaches are idyllic, scattered with bars and restaurants and launches for some unforgettable sailing and diving. It’s also the gateway to sleepy sister islands Carriacou and Petite Martinique which become pretty lively during festivals.

Best for: Scuba diving, food, and history.

5. Dominican Republic

The Dominican Republic offers a landscape of huge contrasts from golden white sand beaches and clear blue seas to inland rainforests and waterfalls – not to mention the deserts, lakes and mountains. The list of things to do is exhaustive. Get your culture fix by learning the merengue, explore colonial streets and buildings or sample the amazing local food and art. Out of town you can play on one of many championship golf courses, scuba dive, go whale-watching, windsurfing, fishing or sailing.  For the eco-conscious, there are some stunning areas of natural beauty and nature parks too!

Best for: Nature, watersports, and golf.

6. St. Barts

If you like to be seen in the right place (or want to catch those that are) then this is the island for you. St Bart’s is known for its chic islanders, French sophistication and exclusivity. There’s a burgeoning art scene for culture vultures, high-end restaurants for foodies as well as incredible beaches and superb spas for unwinding. For the more active, there’s bird-watching or you can explore neighbouring islands by boat. There is an abundance of high-end options in just about everything – from haute couture to beach-side villas – meaning that it’s great for a honeymoon if you really want to show your other half how much you care.

Best for: Glamour and über luxury, high-end food and drink, and perfect white beaches.

7. Antigua

One of the undeniable highlights of Antigua is its abundance of stunning beaches. Whether you’re wanting cocktails for newlyweds on the shore, paddling with the kids in shallow, turquoise coves or diving down into the depths with your trusty scuba gear, Antigua’s gorgeous coastline has you covered. The island also has a fascinating and turbulent history to explore, so be sure to take time out of your sun-worshipping to stroll around and learn a thing or two about the intertwining histories of Europe and the Caribbean.

Best for: Architecture, history, and hidden coves.

8. St Martin

Urbane and unpretentious, St Martin’s laid-back vibe means you’re more likely to find yourself chilling in with a beer in a beach hut than sipping overpriced cocktails in a neon-lit bar. It’s not all board shorts and breeziness thanks to half of the island being run by the French government (the other is a Dutch territory). The French food here is probably the best in the Caribbean, so honeymooners can enjoy some super-romantic evenings out! There’s also a great mix of stuff to do, and it’s well worth splitting your time between lounging on sandy, sun-kissed southern beaches and taking off for an adventure in the mountains of the north.

Best for: Food and dining, intriguing culture, and mountain adventures.

9. Tobago

A true tropical paradise, Tobago is neatly split into a bevvy of beautiful beaches on its western side with a dense, expansive rainforest (the oldest protected one in the world!) on the east. This means you’re sorted for trekking through miles of unspoilt foliage and maybe even a dip beneath a tropical waterfall. Tobago is also particularly famed for its diving thanks to some stunning coral reefs and sunken wrecks, and there’s an abundance of fun things to do including traditional Easter goat racing and an eclectic mix of festivals, including the annual Jazz festival in April.

Best for: Exploring luscious rainforest, scuba diving, boat trips and fishing.

10. Anguilla

It’s got less mass tourism than some of the other islands and thanks to the beautiful coastline it’s perfect if you’re into watersports – diving and sailing ahoy! The Anguillan locals are as warm and welcoming as the weather, and the sumptuous holiday villas on offer mean you’ll be able to enjoy the palm-fronted and pristine white beaches in the lap of luxury. Seeing as cruise ships aren’t allowed to dock, there are markedly fewer crowds – great for a fantastic honeymoon or romantic break where you can feel that the island is all yours.

Best for: Food and fine dining, romantic breaks, and snorkelling.

Yearning for a Caribbean getaway? Check out our full portfolio of villa holidays on Oliver’s Travels, or if you just want to know more, have a read of our 23 Destinations for 2023. Contact our concierge team for any questions! 

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