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 luxury holiday destination.

Olga and Saskia are here to help give you the inside track.

Why we think you’ll love it

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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
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
Anguilla

Anguilla

Caribbean

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

Where to go

Anguilla
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
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
Jumby Bay

Jumby Bay

Antigua

Located two miles off the northern coast of Antigua, Jumby Bay is on a private and secluded island and is only accessible by boat.

Where to stay

Jumby Bay
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
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
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
Sugar Reef

Sugar Reef

St Vincent & The Grenadines

Sugar Reef is a boutique guesthouse in East Bequia, set in the heart of a 65-acre coconut plantation. The plantation looks onto a private, reef-protected bay giving uninterrupted coastal views of the Grenadines. It is also just ten minutes from the buzzing Port Elizabeth Harbour.

Where to stay

Sugar Reef
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
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
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
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
Cotton House

Cotton House

St Vincent & The Grenadines

Divide your day between the two bays, play a gentle game of tennis, indulge in a spa treatment, or sip a sundowner on the verandah.

Where to stay

Cotton House
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
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
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

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

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