st barts caribbean
Image: Shutterstock

On island time: Where to holiday in the Caribbean this winter

30 Nov 2023 | Updated on: 01 Dec 2023 |By Annie Lewis

Dreaming of sunnier climes? Us too. Here’s where we recommend you catch a flight to in the Caribbean, pronto

The land of breezy mountain peaks, glimmering shores, pillow-soft beaches and mood-busting beats is appealing all year round but, rather unsurprisingly, even more so once London’s winter chill sets in. Situated off the Gulf of Mexico, the Caribbean comprises more than 700 islands, islets, reefs, and cays boasting a plethora of wild attractions – think waterfalls, emerald rainforests and hot springs – and luxury in the form of some of the most impeccable five-star hotels south of America. Read on for our Caribbean destination guide and discover stays where you’re almost guaranteed to bask under golden sun and teal skies throughout December and beyond. 


One of the most famous island countries in the Caribbean, Barbados is situated in the east of the archipelago and is home to stars including singer Rihanna and cricket legend Sir Garfield Sobers. The capital is Bridgetown, famous for its British colonial architecture, 17th-century garrison, Jewish history and horse racing course. Go beyond the port city to discover more than 80 pristine white sand beaches – Mullins Beach, Pebbles Beach, Soup Bowl and Silver Sands are must-sees – where you can charter kayaks, fishing boats, luxury catamarans and jet skis, try your hand at spearfishing or help out local conservationists. As Barbados is the birthplace of rum, it would be rude not to sample some of the finest drams in the country – but we’ll leave it to the locals to recommend those… 

Where to stay: Coral Reef Club

Family-owned and run, the Coral Reef Club is one of the most prestigious hotels in Barbados – and for good reason. Set on a picturesque beachfront, the hotel boasts 88 cottage garden-style rooms, with some suites situated in the lush forest that fringes the shores. Recent refurbishment saw the addition of luxury cottages and Coral Terrace, as well as enhancements to the club’s five-star spa, gym and tennis courts. The hotel’s flagship restaurant overlooks Barbados’s west coast – and recently saw guest chefs such as renowned chef Ollie Dabbous from Hide showcase new menus – while the thoughtfully decorated bar hosts many local calypso, jazz, piano and reggae bands to entertain guests all night long. We’d recommend visiting Holetown too, which is just a 15-minute walk away and offers an array of authentic restaurants and boutiques. 

From £485 per night, visit


curacao Beaches-Playa-Forti Caribbean island

Dotting the northern tip of South America, Aruba has historically overshadowed other Dutch-Caribbean destinations of Bonaire and Curaçao – but no longer. Having now established itself as a must-visit thanks to its spectacular landscapes and vibrant culture, there’s plenty to appeal to the most discerning of island travellers. From Cas Abao’s waving palm trees and reefs to Klein Curaçao’s stranded shipwrecks, there are more than 38 beaches to choose from when it comes to finding the perfect sunbathing spot. Elsewhere, discover local delicacies at the food market in the capital Willemstad, a UNESCO World Heritage Site in its own right, or stop by Curaçao’s famous snack bars, or snèks. While you’re in the capital, take a moment to admire Willemstad’s famous street art and murals, and for art aficionados, join an art walk to discover the work of local artists. 

Where to stay: Laman

Laman curacao pelikan villa Caribbean island

Located in Jan Thiel on the southwestern coast of Curaçao, Laman is a spectacular resort nestled amidst rolling hills and beautiful beaches while boasting all of the luxurious amenities you’d expect from a five-star hotel – think stylish bars and restaurants with impeccable service. However, the resort-style residential development is, in fact, home to three distinct turn-key residences ideal for second-homers: Kiwa Luxury Apartments, Strea Luxury Hill Villas, and Pelikan Luxury Water Villas. The former offers an exquisite beachfront experience with elegant two-bedroom apartments and private balconies while the larger three-bedroom Strea Hill Villas provide a serene escape thanks to private infinity pools. Those after ocean living should invest in a Pelikan Water villa: a unique over-water bungalow designed to blend into the sea. Just imagine this being your Caribbean home-from-home year after year… 



jamaica caribbean
Montego, Jamaica. Image: Shutterstock

While it is famous for being the birthplace of reggae, there’s much more than Jamaica’s laidback beats to tempt travellers to the third-largest island in the Caribbean. Boasting a topography that ranges from high mountains and dense rainforests to turquoise reefs and white sandy beaches, Negril and its Seven Mile Beach is one of the best places on the island to take to the water, while Kingston is great for experiencing an authentic taste of the island. Don’t miss the Bob Marley Museum housed in the singer’s former home, the range of native flora and fauna at Hope Botanical Gardens and, north of the city, the Blue Mountains famous for their coffee, walking trails and waterfalls.

Where to stay: Jamaica Inn

North of Kingston, the five-star Jamaica Inn is situated at the heart of Ocho Rios and features its very own 700m private beach. Having celebrated its 65th anniversary this year, the family-owned hotel possesses laidback charm and warm, friendly service. The 55 rooms are bright and breezy, with some including huge verandas decked out with sofas to enjoy vistas of the great blue beyond. Feast on Jamaican favourites under an almond tree canopy moments from the shore at Teddy’s Beach Grill, and book a massage at the Ocean Spa. This Jamaican estate counts Ian Fleming, Marilyn Monroe, Arthur Miller and Noel Coward among its former clientele – and if it’s good enough for them, it’s good enough for us. 

From £368 per night, visit

St Barts

st barts caribbean
Gustavia, St Barts. Image: Shutterstock

Widely known as one of the most glamorous destinations in the world, and where New York and Paris’ social set holiday during the winter (we’re firm believers in if you can’t beat them, join them), this French-speaking Caribbean island is famous for its white sand beaches and designer boutiques, which set up shop in the capital of Gustavia. Encompassing a yacht-filled marina, wander the capital to discover high-end restaurants – fine dining foodies will love the Michelin-starred Restaurant St Barts – and historical attractions such as the Wall House, which harks back to the island’s Swedish colonial era. Go beyond the city to discover 22 public beaches, or head to Grand-cul-de-sac for water sports and Anse de Flamands, famous for its wide sandy plains and safety, if you have little ones in tow. 

Where to stay: Regent Seven Seas Cruises

Explore the island from the comfort of a five-star floating home thanks to Regent Seven Seas Cruises, which offers a round-trip tour of the Caribbean from Miami. Alongside pit stops at Dominica, Antigua and the Dominican Republic, the magnificent cruise liner will also anchor in the shimmering bay of Gustavia so explorers can discover all there is to offer at the centre of bustling St Barts. Hop back on board at the end of the day to enjoy the all-suite accommodation, impressive restaurants, spa, gym and shopping boutiques. 



grenada caribbean
St George's Town, Grenada. Image: Shutterstock

Otherwise known as the Spice Isle, Grenada’s hills are famously home to countless nutmeg plantations while its picturesque capital, St George’s, has become famous for the pastel-coloured houses fringing the waterfront. Foodies will enjoy tours of Grenada’s three award-winning rum distilleries and five organic chocolate factories, while adrenaline junkies can dive into the world’s first underwater sculpture park, and zipline through the lush rainforests. Grand Anse Beach is one of the island’s most famous tourist hotspots, and just a 30-minute drive away lies Grand Etang National Park, where you can chase waterfalls and admire the Grand Etang Lake: an extinct volcano crater now filled with water. Don’t miss the Mona monkeys swinging from the branches, too. 

Where to stay: Calabash Hotel

Calabash, which is the only Relais and Châteaux hotel on the island, is home to just 30 upscale suites which have just emerged from a renovation completed in October and feature modern luxuries, Elemis amenities and private balconies showcasing unparalleled panoramas of the Caribbean Sea. There are four dining options to choose from, including the fine dining, vine-covered Rhodes restaurant specialising in local flair, and the newly-launched Izakaya, serving Latin-Japanese sharing plates at the poolside bar. Discover Zero Mile treatments, using local ingredients, in the spa or while the days away on a sunbed by the sandy shore. If there’s one thing we can guarantee, it’s that you won’t want to come home… 

From £990 per night, visit

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