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 destination.

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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Where to go in Caribbean

Anguilla

Anguilla

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

Anguilla
Antigua

Antigua

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

Antigua
St Vincent & The Grenadines

St Vincent & The Grenadines

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

St Vincent & The Grenadines
Barbados

Barbados

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

Barbados
St Lucia

St Lucia

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.

St Lucia
St Kitts & Nevis

St Kitts & Nevis

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

St Kitts & Nevis
St Barts

St Barts

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

St Barts
Jamaica

Jamaica

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

Jamaica
The British Virgin Islands

The British Virgin Islands

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

The British Virgin Islands
Turks & Caicos

Turks & Caicos

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

Turks & Caicos
Bermuda

Bermuda

Famous for its rose tinted beaches, shorts and year-round good climate, Bermuda is a good alternative to European summer sun.

Bermuda

What to do in Caribbean

Lunch at Scilly Cay

Lunch at Scilly Cay

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.

Lunch at Scilly Cay
Dive Peter Island

Dive Peter Island

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.

Dive Peter Island

Where to stay in Caribbean

Viceroy Anguilla, luxury hotel in Mexico

Viceroy 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.

Viceroy Anguilla
View at Cap Juluca, luxury hotel in Anguilla

Cap Juluca

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.

Cap Juluca
The Inn at English Harbour

The Inn at English Harbour

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.

The Inn at English Harbour
Carlisle Bay

Carlisle Bay

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

Carlisle Bay
Nonsuch Bay

Nonsuch Bay

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.

Nonsuch Bay
Jumby Bay

Jumby Bay

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

Jumby Bay
Cotton House

Cotton House

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.

Cotton House
Bequia Beach Hotel

Bequia Beach Hotel

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.

Bequia Beach Hotel
Petit St Vincent

Petit St Vincent

Just 50 years ago Petit St Vincent was a scruffy and run-down, uninhabited island. Cue Haze Richardson, a legendary Caribbean sailor, and the island was transformed into one of the most exciting of the Caribbean islands. Since his death in 2008, it has enjoyed further restoration, putting it on the map as one of the most illustrious and exclusive Caribbean hideaways.

Petit St Vincent
Sugar Reef

Sugar Reef

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.

Sugar Reef
The Frangipani

The Frangipani

The Frangipani started life as the home of a 19th century sea-captain, and overlooks the island’s historic harbour, Admiralty Bay.

The Frangipani
Little Good Harbour

Little Good Harbour

Located in the tranquil little fishing community of Shermans, Little Good Harbour’s charm is all down to it being one of the last family-run ocean front hotels on the fashionable west coast of Barbados.

Little Good Harbour
Cobbler's Cove

Cobbler's Cove

Set amidst three acres of lush tropical gardens on one of Barbados’s most picturesque and quietest beaches, this charming hotel blends the elegance of an English country manor with the beauty of Barbados.

Cobbler's Cove
The Atlantis

The Atlantis

Completely restored in 2009, the delightful Atlantis was the first hotel to open on the Island’s east coast back in 1883. Today, the property has the same great views over the rugged Atlantic coastline and is the ideal place to relax away from the more popular west coast.

The Atlantis
Hotel Chocolat

Hotel Chocolat

As the name suggests, chocolate is the primary theme of Hotel Chocolat, and situated on a working cocoa plantation, this is a hotel for those with a sweet tooth.

Hotel Chocolat
Cap Maison

Cap Maison

Perched above Smugglers Cove beach, the hotel occupies an elevated position in the north of the island, with unrivalled views across to Martinique and Pigeon Island.

Cap Maison
Jade Mountain

Jade Mountain

Set into a mountain with spectacular views over the Pitons and Caribbean Sea, Jade Mountain is made even more special by the fact that the entire fourth wall is missing from all of the rooms.

Jade Mountain
Sugar Beach, A Viceroy Resort

Sugar Beach, A Viceroy Resort

Located on a UNESCO world heritage site, Sugar Beach, A Viceroy Resort, is ideally placed in between the breathtaking Pitons on the pristine white sand Sugar Beach.

Sugar Beach, A Viceroy Resort
The BodyHoliday Le Sport

The BodyHoliday Le Sport

The BodyHoliday Le Sport is an all-inclusive luxury hotel with extensive facilities and the perfect place to unwind and rejuvenate, surrounded by stunning scenery on the St Lucia coastline.

The BodyHoliday Le Sport
Montpelier Plantation

Montpelier Plantation

An immaculate Relais & Chateaux property, Montpelier Plantation is set in a 60 acre sugar estate and has been meticulously restored in keeping with its heritage.

Montpelier Plantation
Nisbet Plantation

Nisbet Plantation

The charming Nisbet Plantation is a luxury hotel on Nevis, tucked away along the north coast on what was once, as the name suggests, a former sugar plantation.

Nisbet Plantation
Eden Rock

Eden Rock

Once Greta Garbo’s Caribbean hideaway, today Eden Rock is one of the finest boutique hotels in the Caribbean. Located within walking distance of the superb shops and restaurants of St Jean, the hotel is perched on top of a rocky promontory, with panoramic views of two beautiful beaches, the sea and a world beyond.

Eden Rock
Isle de France

Isle de France

Situated on one of the island’s most breathtaking beaches is this luxurious intimate property, which combines tropical beachfront luxury with French sophistication.

Isle de France
Round Hill

Round Hill

Round Hill is set on a peninsula on the northwest coast of the island near Montego Bay.

Round Hill
Jamaica Inn

Jamaica Inn

Ideally located on the edge of Ocho Rios, Jamaica Inn is an elegant and low-key hotel that has been associated with famous names such as Ian Fleming and Katharine Hepburn.

Jamaica Inn
GoldenEye

GoldenEye

Anyone with even a passing interest in James Bond (ie: 90% of the male population and a good proportion of the female one, too) should stay at GoldenEye. Sweeping statement for sure, but this was where author Ian Fleming created and wrote 13 of the 007 novels that spawned an international phenomenon.

GoldenEye
Strawberry Hill

Strawberry Hill

There’s more to Jamaica than sandy beaches, nice as they are. The island’s fertile internal slopes are a haven from the heat with spectacular views of the coastline and sparkling Caribbean Sea beyond, and also home to the Strawberry Hill, a seriously elegant plantation house hotel.

Strawberry Hill
Geejam

Geejam

Geejam is an achingly hip hide out on the coast near Port Antonio, drawing in all the cool kids to its tropical ambience and private recording studios, No Doubt it even attracts some celebrities.

Geejam
The Trident

The Trident

The Trident hotel in Port Antonio is a refreshing blend of old and new, with its 1960s original location and its ultra sleek 21st century facelift.

The Trident
Peter Island

Peter Island

The perfect Caribbean diving destination is privately owned and almost impossibly large, comprising 1800 pristine acres fringed with endless white-sand beaches.

Peter Island

Details for Caribbean

A little more info

LUXURY CARIBBEAN HOLIDAYS

The region is also 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.

BEACH HOLIDAYS AND MORE

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

Flight from London

8:00 hrs

Time Difference

GMT -4 hrs

Eleanor and Stephanie are our Caribbean experts and as seasoned travellers they have the inside track on the most memorable adventures.

Call us on +44 (0)20 7978 7333

Or enquire online

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