I’ve had the good fortune to visit almost every island in the Caribbean and I’m often asked where is the best place to go in this wonderful, charismatic region.
While we all share a vision of waving palms and a warm, turquoise sea, there is much more to these 30 islands and territories than we realise.
The range of landscapes stretches from idyllic coral cays to majestic, rainforest-cloaked mountains, while the cultural flavours include French, Spanish, Dutch, Irish and Creole.
Deciding where to put your toes in the sand this winter is a lot of fun, but to make things easier here’s my ultimate guide to my ten favourites – and which to book depending on your preferences.
BEST FOR FAMILIES: ANTIGUA
For beaches, sunshine and excellent family hotel facilities, pick Antigua. Flights are just over eight hours (much less than to some other islands) and soon after arriving you’ll be drinking a welcome rum by the pool. Antigua has a wide choice of all-inclusive beach hotels, including the well-run Blue Waters Resort with a complimentary kids club where children are welcomed with baby tortoises.
Other activities include trying out tie-dye techniques, fishing and ‘croquet madness’.
It’s a good idea to check a map before booking a hotel if you don’t want to be on an isolated stretch of coastline, as some are.
However, nowhere on Antigua is too far away and you can drive to most places in 45 minutes or so (visitantiguabarbuda.com).
MY TIP: Visit English Harbour to explore the World Heritage-listed Nelson’s Dockyard and a coastal park with trails (nationalparksantigua.com).
BOOK IT: Seven nights at Blue Waters Resort from £5,096pp for adults and £1,594pp for children, all-inclusive based on four sharing, including British Airways flights from Gatwick on February 15 and transfers (tropicbreeze.co.uk).
BEACHES: ANGUILLA
Waves crash against Shoal Bay Beach on the island of Anguilla
This British Overseas Territory, the most northerly of the Leeward Islands in the Lesser Antilles, enjoys clean, white sands and turquoise waters.
There are 33 beaches dotted around its main island – 16 miles long by three miles wide, with a highest point of just 240ft.
Expect great restaurants but no big ‘tourist attractions’ as such, aside from the sands.
Relaxation is what it’s all about with first-class hotels ranging from the stylish clifftop Malliouhana to Aurora Anguilla Resort, which has a water park and golf course (ivisitanguilla.com).
MY TIP: Book a trip to Prickly Pear Cays for a lobster lunch sailing aboard Tradition, a 45-year-old hand-crafted sailing boat (tradition-sailing.com).
BOOK IT: Seven nights at Zemi Beach House from £3,499pp, room only, including British Airways flights from Gatwick to Antigua on November 12, inter-island flights and transfers (turquoiseholidays.co.uk).
FOODIES: GRENADA
The Spice Island has a mountainous interior where you can take tours to see how Grenadians cultivate nutmeg, fruits and the cacao beans used for its award-winning organic chocolate.
It’s also a good choice if you’re not drawn to all-inclusives, as there are bars, shops and restaurants close to the resorts that border the two miles of well-maintained sands at Grand Anse Beach. You can also take a bus into St George’s, one of the prettiest capitals in the Caribbean (puregrenada.com).
MY TIP: Don’t miss River Antoine rum distillery, founded in 1785, which has a water-powered wheel shipped in from Derby.
BOOK IT: Seven nights at Coyaba Beach Resort from £1,720pp, B&B, including Virgin Atlantic flights from Heathrow on November 4 and transfers (justgrenada.co.uk).
NATURE-LOVERS: ST LUCIA
St Lucia is home to the Pitons twin peaks, which you can admire from the sea or by climbing to the top of Gros Piton
St Lucia is a scenic stunner and home to the World Heritage-listed Pitons, twin peaks you can admire from the sea or by climbing to the top of Gros Piton, which takes around four hours return.
Small luxury resorts are sprinkled around the neighbouring hills, including Hotel Chocolat’s Rabot Estate, which is adults only with a cacao-inspired restaurant, or Anse Chastanet is set on a 600-acre estate with two beaches bordering a marine reserve (stlucia.org).
MY TIP: While birdwatching is a big draw, there are also expert-led tours to discover the island’s reptiles, butterflies and flora (stluciawildlife.com).
BOOK IT: Seven nights at Anse Chastanet from £2,819pp, room only, including British Airways flights from Gatwick on November 24 and transfers (inspiringtravel.co.uk).
HISTORY: BARBADOS
THIS year marks the 400th anniversary of the arrival of the first English ship in Barbados and our ties with the easternmost island in the Caribbean remain strong. History lovers can explore a wealth of heritage attractions including parish churches, stately St Nicholas Abbey, Codrington College (founded in 1745) and the World Heritage-listed Garrison area of the capital, Bridgetown (visitbarbados.org).
MY TIP: Time your visit to catch the horse races at the Garrison Savannah track, which dates to 1845 (barbadosturfclub.org).
BOOK IT: Seven nights at Coral Reef Club from £4,545pp, B&B, including Virgin Atlantic flights from Heathrow on February 9 and transfers (elegantresorts.co.uk).
HIKING: DOMINICA
REACHED via Barbados or Antigua, Dominica is a vividly green and mountainous isle suiting travellers who prefer rainforest walks and birdwatching to beaches and nightlife. Tackle a section of the 115-mile Waitukubuli National Trail, which runs the length of the island, or take a hike to the silvery waters of Middleham Falls (discoverdominica.com).
MY TIP: Opening early next year, a new Austrian-built cable car will whisk visitors to 2,600ft to see the steaming volcanic waters of Boiling Lake (dominicacablecar.com).
BOOK IT: Seven nights at Jungle Bay from £2,640pp, B&B, including British Airways flights from Heathrow to Barbados on January 12, inter-island flights, arrival transfer and car hire (sunvil.co.uk).
ROMANCE: BRITISH VIRGIN ISLANDS
An hour’s flight west of Antigua, this picturesque British Overseas Territory is perfect for some loved-up beach time at a luxurious resort.
A standout example is Rosewood Little Dix Bay on Virgin Gorda which opened in 1964 and has serene rooms with mid-century interiors that rest beside a half-mile crescent of white sand. Rates include daily snorkelling trips and drop-offs on a castaway beach (rosewoodhotels.com).
MY TIP: To see more of the islands book a cabin on a shared catamaran cruise which comes with a skipper and chef (bvitourism.com).
BOOK IT: Seven nights at Rosewood Little Dix Bay from £6,100pp, B&B, including British Airways flights from Gatwick to Antigua on November 5, inter-island flights and transfers (bviholidays.com).
MUSIC FANS: JAMAICA
This dynamic, 146-mile-long island has given the world legendary figures as varied as Bob Marley, Usain Bolt and, via author Ian Fleming who lived there, James Bond.
Reggae fans can visit the Bob Marley Museum and Tuff Gong recording studio in Kingston, while the rural village of Nine Mile, where the iconic
singer was born and buried, offers an insight into his humble roots (visitjamaica.com).
MY TIP: Stay in two or three places, including the Blue Mountains, to make the most of exploring Jamaica, or book guided tours through your resort (islandroutes.com).
BOOK IT: A nine-night, small-group tour costs from £2,089pp, departing Kingston on January 21 and includes accommodation, transport, activities and breakfast; flights extra (explore.co.uk).
OLD SCHOOL CHARM: NEVIS
To reach Nevis, fly to St Kitts, then take the short boat transfer across to its quieter sister isle.
You’ll feel a long way away from mega cruise ships and the sprawling resorts of some other parts of the Caribbean. It’s home to characterful, family-run hotels lost in the hills, such as Montpelier Nevis, 60 years old in 2026, and the contemporary art-filled Golden Rock Inn (nevisisland.com).
MY TIP: Run by the island Water Department, the Friday night roadside barbecue on the outskirts of the capital, Charlestown, is a good place to meet locals, visitors and expats over some tangy jerk ribs.
BOOK IT: Four nights at Montpelier Nevis plus three at Golden Rock Inn from £1,799pp, B&B, including British Airways flights from Gatwick on November 1 and transfers (juststkittsnevis.co.uk).
PURE ESCAPE: CAYMAN ISLANDS
Most visitors to this affluent British Overseas Territory get no further than the gateway of Grand Cayman with its high-rise hotels and trendy restaurants.
Take a 35-minute flight on to Little Cayman and you’ll find a tiny, super-tranquil isle with just 170 residents, plus a 20,000-strong colony of red-footed boobies. Diving Bloody Bay Wall, which drops 6,000ft, is a star attraction (visitcaymanislands.com).
MY TIP: Neighbouring Cayman Brac is also worth a visit for its hiking, climbing and stargazing.
BOOK IT: One night at Sunset House, Grand Cayman, B&B, plus six at Southern Cross Club, Little Cayman, full board, from £7,200pp including British Airways flights from Heathrow on December 1, inter-island flights and transfers (originaltravel.co.uk).
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