In 1946, Errol Flynn washed ashore (well, he was never going to arrive in a conventional manner) on the Caribbean island of Jamaica after his sailing boat developed mechanical problems. He subsequently set up home on a tiny dot of land off Port Antonio — and in his wake trailed Grace Kelly, Marlon Brando (who stayed at Frenchman’s Cove Resort, the Caribbean’s first all-inclusive hotel), the late Queen Elizabeth and Winston Churchill.
A year before she married Prince Rainier of Monaco, Kelly posed for American photographer Howell Conant while on holiday in Jamaica. The image of her cross-legged on the beach is regularly mistaken for a Slim Aarons — Aarons also documented the rich and famous frolicking on sun-drenched shores, on yacht decks and poolside. These blue- and pastel-hued photographs coincided with, or perhaps helped contribute to, a boom in winter sun tourism that began in earnest in the 1950s. Back then, package holidays to Corsica and the Costa Brava cost around £30, or £1,000 adjusted for inflation. A decade later, the introduction of regular, non-stop commercial flights to the Caribbean meant that travellers from Europe could reach the archipelago in a single day, as opposed to three weeks by ship.
Though the travel time has barely improved in half a century, the enduring appeal of a winter sun holiday — the best antidote to the British gloom that descends each winter — is still going strong. Rampant tourism, of course, means that were Flynn and his Hollywood compatriots to reappear, they might fail to recognise their much-loved hideaways. So here’s where to wash ashore in the Caribbean and Central America today, in order to escape the crowds.
Best for beaches: Anguilla, the Caribbean
Holiday icons:
Harry Styles, who was photographed holidaying with Adele on the eastern Caribbean island in early 2020 (he reportedly left staff at one restaurant a $2,020 tip).
Why:
Anguilla does not look like much from the air — a slim and very flat squiggle of land (coral and limestone) with nothing bar ocean to the north, and Saint Martin and ample St Barths to the south. On the ground, though, is where Anguilla comes into its own; it’s the undisputed king of Caribbean beaches.
There are 33 in total, each one contrasting bands of unsullied, fine white sand and bright blue bleach-coloured water. The kind of colours that children use in their fantastical crayon drawings of beaches; the kind you assume don’t exist in real life. And there are upsides to the island’s flat topography: it rarely feels crowded, even during peak season, because there’s no infrastructure for large cruise ships and superyacht moorings, and the lack of hills and mountains means that any rain-weary clouds are more than likely to pass over unobstructed.
How:
Stay at Cap Juluca, A Belmond Hotel, a blistering white-walled hotel with North African flair that occupies a space on the fringes of Maundays Bay. Activities include snorkeling, scuba diving and sailing, as well as tennis and golf; the infinity pool is a given, as is an excellent spa. Ground-floor rooms come with easy beach access; first-floor ones with sea-facing roof terraces.
Best for adventure: Costa Rica
Holiday icons:
Brad Pitt; Michael Douglas
Why:
Costa Rica, sandwiched between the Caribbean and the Pacific, spans dense lowland rainforest, rain-fed volcanic craters and every kind of beach imaginable (sandy; volcanic; rugged), all of which beg to be explored.
Traverse the Corcovado National Park, snorkel through the Golfo Dulce, heli-surf the world-famous surf break around Roca Bruja, and dive alongside hammerhead sharks, manta rays, tuna and schools of snapper.
How:
Pelorus can put together once-in-a-lifetime adventures. Or hold out for the opening of Nihi Santo Tomás.
Best for yacht charter: Canouan, the Caribbean
Holiday icons:
The Duke of Sussex; George Clooney
Why:
Despite its proximity to Mustique and ‘where billionaires go to escape millionaires’ tagline, Canouan had managed to fly under the radar until earlier in 2023, when the Duke and Duchess of Sussex were photographed there. There’s a Mandarin Oriental, a Soho Beach House, a superyacht marina and a runway for private jets, but the fact that it’s largely sheltered from the Caribbean’s more volatile weather and has world-class snorkeling means it’s best experienced aboard a boat.
Michael Reyburn of Roccabella Yachts says that “yacht chartering ensures a seclusion that exclusive resorts can’t achieve.”
How:
Antelope IV (12 guests) is a clean canvas for creating your own bespoke luxury-yacht holiday. Enquire about her Caribbean availability through Roccabella.
Best for arts and culture: Mexico City, Mexico
Holiday icons:
Errol Flynn; Lewis Hamilton
Why:
The country’s frenetic capital, home to a burgeoning arts scene, is basking in a second cinematic coming of age. The first covered a 20-year period from 1936, the second is spearheaded by Alejandro González Iñárritu and Guillermo del Toro. Harry Hastings, founder of Plan South America, notes that “Cuba is best for people who want to bolster their private collections” but is pipped to the post by Mexico City when it comes to contemporary art festivals (Zsonamaco), open houses (Frida Kahlo; Luis Barragán) and museums (Jumex; Soumaya). “The soon-to-reopen Casa Orgánica by Javier Senosiain is mind-blowing,” he adds.
How:
Ask Plan South America to put together an entirely bespoke itinerary for you.
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