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.

Eleanor, Saskia and Isabel 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.
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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.


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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

More helpful tips
Flight from London

8:00 hrs

Time Difference

GMT -4 hrs


Top picks for Caribbean

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

Calabash Hotel
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
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
Grenada

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

Grenada
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
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
The Inn at English Harbour

The Inn at English Harbour

Antigua

The Inn at English Harbour enjoys a delightful location on a wooded headland at the entrance of the historic English Harbour, one of the most picturesque parts of Antigua.

Where to stay

The Inn at English Harbour
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
Hermitage Bay

Hermitage Bay

Antigua

With a distinctly Asian aesthetic, the all-inclusive Hermitage Bay sits handsomely in 140 acres of pristine vegetation on a blissfully remote bay just ten minutes from Antigua’s Jolly Harbour.

Where to stay

Hermitage Bay
St Kitts & Nevis

St Kitts & Nevis

Caribbean

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

Where to go

St Kitts & Nevis
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
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
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
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
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
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
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

The detailed knowledge of the team, attention to detail and personalised service is second to none and goes way beyond my expectations. Considerable effort is put into understanding my requirements, creating bespoke itineraries, ensuring the trip runs smoothly and also seeking feedback upon return. I always feel that the team care about ensuring we have the best possible trip with no glitches and for a competitive price.

Joe

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