Caribbean holidays: Your guide to the best islands and hotels

The Caribbean comeback: Mesmerising views, swish hotels and guaranteed sun. No wonder Britons are flocking once more to the paradise isles!

  • We reveal how the Caribbean islands are getting ready to welcome back eager tourists 
  • There are some new resorts to enjoy that couldn’t open during the heights of the pandemic  
  • Resorts in St Barts and the British Virgin Islands have reopened after the devastating hurricanes of 2017 

The Caribbean has long been a favourite of British holidaymakers drawn to the islands’ sheer beauty, laidback vibe and fabulous weather. Here, in the first part of a new series, James Henderson reveals how bookings are soaring – and how the islands are getting ready to welcome back eager tourists after the pandemic.

Yearning for a winter break has an easy fix: the Caribbean. And with the islands open for business once again, holidaymakers are wasting no time in booking those long-missed places in the sun.

‘People are just so keen to get away,’ says James Bell of Turquoise Holiday Company, which has been sending sunseekers to the Caribbean for more than a decade. ‘Bookings are 20 per cent up on pre-pandemic levels.’

Elegant Resorts, a Caribbean luxury specialist, has revealed that the hottest ticket this year is for St Barts (pictured)

Tour operators and agents have been rushed off their feet, as bookings delayed by the global lockdown are reactivated and new ones fly in.

Seats can be hard to come by (though ever-fluid as airlines rejig schedules each month); in some places the only solution is to buy an upgrade. The best plan is to use a tour operator and employ tactical thinking.

If you are not restricted to school holidays, then demand is lighter but the weather just as good.

The best bet is the first fortnight of December, before the festive price hike, then during the lull after the New Year, from January 5 until the 20th.

And what of the hotels? With no certainty of when travellers would return, only a few have undergone major overhauls. However, there are some new resorts to enjoy that couldn’t open during the heights of the pandemic, while others, in St Barts and the British Virgin Islands, have reopened after the devastating hurricanes of 2017.

Elegant Resorts, a Caribbean luxury specialist, has seen the region develop over the past 30 years, and revealed that the hottest ticket this year is for St Barts. While it has the usual superb beaches, thanks to its French chic and sophistication it is unlike anywhere else in the Caribbean.

Guanahani, the island’s largest resort – although it has fewer than 70 rooms – reopens next month after a major rebuild. Its suites and cottages jangle in pastel colours on a 16-acre hillside, each with a terrace and sea view amid the greenery.

Book: Seven nights in an Ocean View Room at Rosewood Le Guanahani, B&B with flights, UK lounge access and private transfers from £8,395pp (

Anguilla has utterly magnificent beaches and, like St Barts, has excellent restaurants, villas and beach bars

Nearby Anguilla has long been on the radar of luxury travellers. It doesn’t have the physical drama or lushness of Jamaica or St Lucia – it is dry and flat – but it has utterly magnificent beaches and, like St Barts, has excellent restaurants, villas and beach bars. Aurora Anguilla is the revamped resort formerly known as Cuisinart. Under new management, it has lost the whitewashed walls and blue flashes of its Mediterranean inspiration, and now feels more metropolitan.

It was always well known for its spa, which remains, as well as its Greg Norman 18-hole golf course, and there are plans eventually to build a further nine holes.

Book: Suites start at £730 per night (; return flights on Virgin Atlantic cost from £605 with inter-island flights at £395.

The Morrow family has owned Jamaica Inn since 1950 and the 55-room hotel is the epitome of the island’s traditional hospitality. Bond author Ian Fleming played bridge with the owners here, sipped its martinis and then slipped it into Dr No.

The Morrow family has owned Jamaica Inn since 1950 and the 55-room hotel is the epitome of the island’s traditional hospitality. Pictured is the deck area in Cottage 3

It’s a glamorous, grown-up retreat in its own cove so offers fabulous privacy, plus no children under ten, no TVs, a cocktail party each evening and dress code for dinner. ‘All our space is outside,’ says owner Eric Morrow, ‘so guests can relax. Even when we’re at near full capacity, it doesn’t feel crowded.’

New for Christmas breaks will be a beachside pizzeria where guests can watch the stars come out and listen to the waves.

Book: From £378 per room per night, including breakfast (

When the pandemic struck, the British Virgin Islands had just about recovered from the 2017 hurricanes Irma and Maria, so previous visitors will see a lot of changes.

Little Dix Bay has had a complete rebuild. The resort is situated on a perfect bay, one of four locations selected by Caribbean pioneer Laurance Rockefeller to site his hotels – the scion of the wealthy American Rockefeller family had the pick of the islands when he sailed through in the 1950s.

Rebuilt: The smart Pavilion bar at Little Dix Bay resort in the British Virgin Island

The new Little Dix Bay retains the lovely rough-stone walls and shingle roofs of Rockefeller’s original, but gone are the terracotta tiles and in come a range of woods with light-coloured walls and fabrics, and a seam of deep blue. It also has an excellent spa and a good children’s club.

Book: Seven nights in an Ocean View Cottage at Little Dix Bay in February, including international and inter-island flights to Tortola and boat transfers, costs £4,540pp (

Elsewhere in the British Virgin Islands, Long Bay Beach Resort, set on a superb beach in Tortola, was new when the pandemic hit, so had to close its doors almost immediately after opening. Now running at full steam, it has 20 suites in three villas with a mix of bright walls, whitewashed and natural woodwork and black-and-white photographs.

Long Bay Beach Resort is located in Tortola, pictured above, and has 20 suites in three villas 

The air of seaside somnolence is perfected by a waterfront restaurant, beach bar and coffee shop (

The Aerial hotel sets itself a more conscious brief, using its fantastic setting on a clifftop on a private island, with a stupendous view over Sir Francis Drake Channel, to inspire guests with its focus on personal wellbeing. Or you could just hire the whole island and chill out (

And raffish old Saba Rock, a sail-up bar on a stone blip in the North Sound, has smartened up – now it has a funky, brightly coloured surfer vibe (

Sugar Beach Hotel, set between the twin Piton mountains on St Lucia, reopens next month after extensive work.

New look: The Sugar Beach Hotel in St Lucia has a new beach restaurant and high-tech fitness centre


The best of Caribbean life is outdoors, so it’s not difficult to keep your distance from other tourists. 

Most islands require visitors to be double vaccinated, and most of the top hotels require the same of their drivers and staff, so in theory you will be in an environment with a low likelihood of Covid transmission. However, vaccine take-up among the general population is fairly low in the Caribbean despite efforts to remedy that situation. And the Dominican Republic remains on the Government’s red list. 

There is a new beach restaurant and high-tech fitness centre, and cabanas around the central pool (with butler service), all surveyed from above by the Great Room restaurant which itself has been given a contemporary refresh to accompany the resort’s modern sculptures and artwork.

The beachfront bungalows have been restyled, the vanguard of a change to come in all the rooms.

Book: Seven nights in a Luxury Sugar Mill room, including flights, private transfers and UK airport lounges, from £3,299pp, room-only. Based on a December 12 departure (

If you prefer a breeze with your cocktail, head into the mountains to Hotel Chocolat’s Rabot Hotel. The high street chocolatier, which sources cocoa from plantations on St Lucia, is opening a further ten suites to take advantage of the view of the Petit Piton. There’s a cool new deck where you can create chocolate bars in a Bean To Bar experience.

Book: Rooms from £472 B&B per night (

Barbados will be fully back up to speed for the winter, but the island is also a transit for the smaller islands of the Grenadines, whose hotels are ideal if you wish to avoid the crowds. James Bell at Turquoise Holidays says: ‘We have seen a desire for a shorter stay on Barbados, with the buzz of Holetown and its restaurants, but then an escape to a barefoot island, like Petit St Vincent in the Grenadines, where guests can totally relax and enjoy a low-key vibe.’

The tiny island of Petit St Vincent, devoted to a single hotel, normally closes in September to clean up after the summer season. This year, however, its 20 or so cottages have been overhauled and are ready for winter sun-seekers. Internet access at the main Pavilion has also been upgraded, but of course the point of going there is to forget about the outside world entirely.

Petit St Vincent resort is comprised of 20 or so cottages that offer total privacy. Pictured is one of the rooms

Book: Seven nights in a one-bedroom cottage, including all meals, non-alcoholic drinks, international and inter-island flights to Union Island and boat transfers, costs from £6,759pp (

Despite the caveats of meeting Covid regulations, the Caribbean islands are essentially fully back up to speed for the winter. Confident hotel managers have even booked Santa to arrive on the beach on a jet-ski on Christmas Day and local bands are tuning up to play carols on steel drums.

Definitely something to satisfy that yearning for a winter break.

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