Caribbean Travel Guide for First-Time Visitors

Winter sun here we come! There’s more to the Caribbean than dreamy beaches though. Here’s a quick and easy guide to eight different Caribbean islands, all ideal for holidays between December and Easter.

Some are perfect for lazy days on the beach and a very leisurely holiday. Others are better for exploring and staying active. Why not combine two islands for a two-week Caribbean holiday?


Tranquil and low-key, Anguilla has long been one of our favourite winter sun destinations. It’s an upcoming destination focused on high-end luxury, which won’t stay untouched for long. Just fly to Saint Martin then hop across the water by light jet or private boat.

Beach lovers and seekers of barefoot luxury will be spoiled here. Anguilla lacks the buzz or glamour of other islands, rather, it’s a cosy haven for escapism.

Recommended resort: Belmond Cap Juluca is fresh from a $121 million renovation. It has the island’s best beachside location, finest rooms and Bellini Club benefits.


The beaches are gorgeous and they’re just for starters. Rich local culture, amazingly friendly people, spectacular nature and plenty of iconic sights all come together here.

Expect adventure in its most authentic form and bump Cuba to the top of your bucket list, before it draws big crowds.

Recommended resort: Luxury isn’t very high or extravagant on Cuba – incredible hotels are not why you travel here. Still, start your trip with the country’s best hotel, the Gran Hotel Manzana Kempinski La Habana.

Saint Barths

Super yachts, designer boutiques, swanky hangouts and Michelin dini​​ng, Saint Barths is a little like the Courchevel or Monte Carlo of the Caribbean – it’s French speaking as well. Travel here via Saint Martin and prepare for glitzy vibes.

Essentially a glamorous island playground for jet-setters, with picture-perfect beaches and boundless entertainment.

Recommended resort: Rosewood Le Guanahani is one of our favourite Caribbean resorts. It’s more laid-back and secluded than the Cheval Blanc. Hotel Guanahani was the 1990s celebrity hangout. Rosewood has revived it.

Saint Martin

A small and diverse island that’s very accessible, with easy connections to other nearby islands like Saint Barths and Anguilla. Cobblestone streets, turquoise waters, great gastronomy, sprawling resorts, remote beaches and lively bars: this island packs a lot into a small space.

Consider Saint Martin as your three-night Caribbean layover. Experience how its atmosphere, sights and multiculturalism is quite different to the rest of the region.

Recommended resort: La Samanna, A Belmond Hotel, is by far the best hotel on the island and the only true five-star property. Ideal for the start or end of a longer Caribbean holiday.

Holiday on the Beach This Winter?

Dominican Republic

The Dominican Republic is usually stereotyped as a destination for all-inclusive, overcrowded mass tourism. This beautiful mountainous island is more than large enough to hold secrets and hideaways for the discerning traveller as well.

Be alone on blissful white-sand beaches, explore the vibrant local culture, dive into Caribbean waters and go on adventures, because there’s much more to the Dominican Republic than your resort.

Recommended resort: Amanera is the most exclusive and secluded hotel in the Caribbean’s most visited country. It’s tucked into nature with stunning private residences.


The Bahamas was the quintessential beach getaway. It still can be, when you avoid the cruise ships and mass tourism crowds.

Popular and iconic, with many options for active days away from the sand, including golf and yacht charters. The Bahamas is busy and bustling, with so many options for all the family.

Recommended resort: Rosewood Baha Mar delivers smart elegance, outstanding service and undeniable calm, amid all the attractions of Baha Mar. Comfortably our favourite choice in the Bahamas.


Intrepid explorers will revel in Jamaica, a Caribbean island with incredible nature as well as the famous reggae and rum culture. Expect to come home with stories your friends will scarcely believe.

Jamaica serves tropical luxury galore. If you want authenticity with your white sands then jump into this island’s rich flavours.

Recommended resort: Half Moon Resort in Montego Bay is Jamaica’s best known luxury resort, though Round Hill is just as good, as well as being more understated and secluded.

Turks and Caicos

A gem for beach lovers and honeymooners, with over 100 islets and the finest white sand in the Caribbean. Divers are also spoiled here and it’s a dream destination for getting around in a private yacht.

Exotic and pristine in beauty as well as luxury, the Turks and Caicos archipelago invites you to unwind and explore the clearest of waters.

Recommended resort: Como Parrot Cay is the best private island resort in the region while Amanyara is an exceptional resort on one of the world’s best beaches. Grace Bay Club is great for families and Rock House is the country’s newest five-star beach resort.

Your Winter Caribbean Beach Holiday

Where will you go for your winter sun? This is our easy beginner’s guide to the Caribbean. You can enjoy personalised travel recommendations from one of our travel designers – one of them is just home from a trip in Jamaica!

We have other Caribbean ideas to share with you as well, like an invitation to stay on Richard Branson’s private island.

So when you look outside at the winter cold, you know there’s somewhere else you could be.

Holiday on the Beach This Winter?

Let’s plan your next holidays

View more destinations

Other articles you might like