Caribbean Holidays: An Overview

The islands and hotels of the Indian Ocean might be vying for the affections of those in need of luxurious winter sun, but the competition means the Caribbean has had to pull its socks up, and this remains a very special holiday destination.

Eleanor, Saskia and Isabel are here to help give you the inside track.

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Original Highlight

Picture of beautiful seas in the Caribbean

With one of the longest travel seasons and within easy reach of Europe, a Caribbean diving holiday remains a favourite. Home to a variety of world class hotels, the diving in the Caribbean can be hit and miss, but choose your island wisely (that’s where we come in) and you are in for a treat both above and below the waves.

Louisa, Original Traveller

Top picks for Caribbean

Antigua

Antigua

Caribbean

With 365 beaches to choose from, you'll need expert advice to seek out Antigua's best spots on your luxury holiday.

Where to go

Antigua
Anguilla

Anguilla

Caribbean

Possibly Original Travel’s favourite hangout in the whole Caribbean, Anguilla oozes laidback charm.

Where to go

Anguilla
Dive Peter Island

Dive Peter Island

The British Virgin Islands

The Caribbean’s reputation for diving is actually somewhat patchy and this is certainly one part of the world that great hotels and great diving would appear to be mutually exclusive.

What to do

Dive Peter Island
St Lucia

St Lucia

Caribbean

The Grand Pitons, long stretches of white beaches, a huge range of water sports, and a drive-in volcano set St Lucia apart from its Caribbean neighbours.

Where to go

St Lucia
St Barths

St Barths

Caribbean

A tiny eight square mile corner of France in the Caribbean, St Barths is pretty idyllic and a firm Original Travel favourite.

Where to go

St Barths
Carlisle Bay

Carlisle Bay

Antigua

Opened in 2003, the immaculate Carlisle Bay resort is set on the unspoilt south coast of Antigua and offers chic, five-star accommodation.

Where to stay

Carlisle Bay
Jamaica

Jamaica

Caribbean

The most distinctive Caribbean island, in terms of landscapes and cultural influences, Jamaica works equally for romantic breaks and family holidays.

Where to go

Jamaica
View at Cap Juluca, luxury hotel in Anguilla

Cap Juluca

Anguilla

Insulated from the outside world, the hotel is a private, self-contained enclave set along two miles of pristine white-sand beaches on the southwest coast of Anguilla, looking out across the sea to the mountains of St Maarten.

Where to stay

Cap Juluca
Nonsuch Bay

Nonsuch Bay

Antigua

A new arrival to the luxury end of the Caribbean market, Nonsuch sits in its own small bay on the East coast of Antigua, and has an excellent winter sailing set up.

Where to stay

Nonsuch Bay
Barbados

Barbados

Caribbean

Barbados. The name alone summons up images of palm-fringed beaches, cricket, polo and rum punches. Not a bad little combo.

Where to go

Barbados
Viceroy Anguilla, luxury hotel in Mexico

Viceroy Anguilla

Anguilla

The Viceroy Anguilla is arguably the best new hotel to open in the Caribbean for a while, and on one of our favourite islands, too.

Where to stay

Viceroy Anguilla
Turks & Caicos

Turks & Caicos

Caribbean

Superb diving on more than 1,000 square miles of coral reef, and luxurious hotels.

Where to go

Turks & Caicos
Bequia Beach Hotel

Bequia Beach Hotel

St Vincent & The Grenadines

This boutique hotel is inspired by Oliver Messel’s stylish villas in Mustique - just nine miles west of Bequia - and surrounded by beautiful tropical gardens, it combines luxury, elegance and lashings of Caribbean charm.

Where to stay

Bequia Beach Hotel
The British Virgin Islands

The British Virgin Islands

Caribbean

The seas around the BVI’s are remarkably calm, and therefore a sailor’s paradise - making the BVI’s the ideal island hopping archipelago.

Where to go

The British Virgin Islands
Lunch at Scilly Cay

Lunch at Scilly Cay

Anguilla

The island of Anguilla in the Caribbean is little more than a glorified sandbank, albeit a sandbank with some of the best beaches and finest hotels in the Windward Islands, but what really makes this island stand out is the food. The quality of the eateries is exceptional, and the cherry on top of this delectable cake is the small island restaurant of Scilly Cay.

What to do

Lunch at Scilly Cay
Petit St Vincent

Petit St Vincent

St Vincent & The Grenadines

Seclusion thy name is Petit St Vincent. This private island in the Caribbean is the ultimate luxury antidote to the chaos of modern day life. Formerly discovered by US airman Haze Richardson whilst sailing in the Grenadines in 1963, the island has since been bought by business moguls Phil Paterson and Robin Paterson, who have reincarnated the property to a rather sublime state for its guests.

Where to stay

Petit St Vincent
St Vincent & The Grenadines

St Vincent & The Grenadines

Caribbean

Relax and unwind in style on St Vincent & The Grenadines, sampling a slice of the Caribbean high life.

Where to go

St Vincent & The Grenadines
Malliouhana

Malliouhana

Anguilla

In the 90s Malliouhana was, alongside Cap Juluca, one of Anguilla’s shining lights but of late – and with love – the place had been getting a little tired of late. That is until the cavalry, in the dashing form of the excellent Auberge Hotel Group, came riding to the rescue in 2014 and breathed new life into a Caribbean classic.

Where to stay

Malliouhana

Our enthusiastic experts are seasoned travellers with the inside track on the most memorable adventures.

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