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.
More information

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.


Expand

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

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
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
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
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
Anguilla

Anguilla

Caribbean

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

Where to go

Anguilla
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
Jumby Bay, A Rosewood Resort

Jumby Bay, A Rosewood Resort

Antigua

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

Where to stay

Jumby Bay, A Rosewood Resort
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
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
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
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
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
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 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
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

Malliouhana
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 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
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

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

Call us on +44 (0)20 7978 7333

Or enquire online

Newsletter Sign-Up

Get the latest travel advice, information and inspiration in our weekly newsletter.

Brochure Sign-Up

Our beautiful, free brochure is packed with insider information and incredible travel ideas from every corner of the planet.
Get the brochure

About Us

We are a creative luxury travel company who take a thoughtful approach to creating tailor-made holidays that perfectly fulfil your needs. Read our story

Why Us

Our meticulous planning, in-depth knowledge, honest advice, award-winning service and financial protection all ensure that you will enjoy the most memorable holiday experience. Why us

Contact Us

Talk to our team of thoughtful experts about your travel needs:
Call:  +44 (0)20 7978 7333 Email: ask@originaltravel.co.uk Contact us online

Press

For all press enquiries, please contact our marketing team:
Call: +44 (0)20 3733 7939 Email: press@originaltravel.co.uk Contact us online

Close