Luxury 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.

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Saskia, Will and Alexandra are here to help give you the inside track.

Why we think you’ll love it

  • Original Travel knows the region well, and can recommend the highlights from the best bars in Havana to the best dive sites in the British Virgin Islands, and everything in between.

Luxury Caribbean Holidays: The Detail

The Caribbean is surprisingly diverse, with British, Spanish, French, American and African influences making for a fascinating and mixed bag - for example, Cuba and Jamaica, two of the largest countries in the Caribbean, feel hugely different from each other.

Add a seductive combination of turquoise waters and dramatic (often volcanic) landscapes to the rich cultural heritage and a selection of activities from diving to sailing and its no wonder the Caribbean continues to capture the imagination of the luxury traveller.


Top picks for Caribbean

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

Lobby of Mount Cinnamon

Mount Cinnamon

Grenada

Set in tropical gardens with the white sands of Grand Anse Beach spread out before it, Mount Cinnamon Resort and Beach Club is a haven of laid-back luxury. Located at the Southern tip of Grenada, this boutique resort boasts uninterrupted views of the Caribbean Ocean.

Where to stay

Royal terns on poles

St Kitts & Nevis

Caribbean

Saint Kitts and Nevis were amongst the first islands in the Caribbean to be settled by Europeans.

Where to go

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

Dominican Republic

Dominican Republic

Caribbean

Occupying the eastern side of the island of Hispaniola (sharing the landmass with Haiti in the west), the Dominican Republic has long been the domain of the all-inclusive holiday package, but thanks to a handful of luxury hotels opening on some of the islands quieter coastlines, changes are afoot…

Where to go

Calabash Hotel

Calabash Hotel

Grenada

Five star service? Check - Calabash Hotel allows you to savour breakfast on your private balcony, attended by your personal maid. Gourmet dining? Check - one of the hotel’s restaurants is headed up by celebrity chef Gary Rhodes. Swathes of white sandy beaches? Check - this is Grenada.

Where to stay

Jamaican jerk chicken

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

Viceroy Anguilla, luxury hotel in Mexico

Four Seasons Anguilla

Anguilla

The Four Seasons Anguilla is among the best of the Caribbean luxury hotels, and on one of our favourite islands, too.

Where to stay

Peaceful lagoon

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

Amanera

Amanera

Dominican Republic

The much anticipated second Caribbean offering from Aman has found its home on the stunning shore of Playa Grande in the Dominican Republic.

Where to stay

The Grenadines Islands Caribbean Islands

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

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

St Lucia sea turtle

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

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

Boat on the beach 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

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

Grenada Beach

Grenada

Caribbean

Known as the "Isle of Spice", Grenada consists of three islands: Grenada, Carriacou, and Petit Martinique. They are located in the Eastern Caribbean at the southern end of the Windward Islands, only 100 miles north of Venezuela. Bordered by stunning beaches and dotted with picturesque towns, this verdant island has long been a major source of nutmeg, cloves, ginger, cinnamon, and cocoa.

Where to go

Lone tree at beach

Anguilla

Caribbean

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

Where to go

Once again thank you for your attentive & professional assistance with our last 2 holidays.

David

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