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

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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

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
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
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
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
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
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
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
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
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 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
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
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
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
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
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
Spice Island Beach Resort

Spice Island Beach Resort

Grenada

With eight acres comprising lush gardens of lemon, almond and sea-grape trees on one side and golden sands the other, the Spice Island Beach Resort is a picturesque exotic paradise – with a touch of sugar and spice and all things nice.

Where to stay

Spice Island Beach Resort
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
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

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

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