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Travel

The winter sun destinations beloved by old-money elites

Francesca Syz
23/09/2026 05:15:00
Cobbler’s Cove on Barbados retains an atmosphere of low-key privacy - Nick Smith
Cobbler’s Cove on Barbados retains an atmosphere of low-key privacy - Nick Smith

With hot summers no longer a novelty in the UK, many of us are shifting our focus towards winter sun instead. As a nation, we’ve been trying to escape our bleak midwinters for centuries and some of the classic getaways are as lovely as ever. But where can you go for a winter-sun escape like the old-money elite?

Barbados

Great excitement ensued when British Airways (then BOAC) launched the first weekly flight from Heathrow to Barbados in October 1953. Wealthy foreigners had already been visiting for about 200 years to seek cures for respiratory illnesses – including a 19-year-old George Washington, who accompanied his tuberculosis-ridden brother Lawrence there in 1751, hoping the clean air and warm weather would cure him, which it did.

Celebrities such as Judi Dench and Sigourney Weaver have stayed at Cobbler’s Cove - Nick Smith
Celebrities such as Judi Dench and Sigourney Weaver have stayed at Cobbler’s Cove - Nick Smith

In the late 1800s, wealthy Europeans and North Americans began to arrive in Barbados on luxury ocean liners, but it was new flight that really put it on the map. Celebrities from Frank Sinatra to Agatha Christie began to arrive, many staying at the Coral Reef Club or in the private villas of friends. Then came glitzy Sandy Lane (later very loudly frequented by the late Michael Winner), and then in 1968, the lovely Cobbler’s Cove – a quiet, elegant boutique hotel popular with those who genuinely appreciate low-key privacy, like Judi Dench and Sigourney Weaver – an atmosphere it retains to this day.

How to do it

Turquoise Holidays offers seven nights at Cobbler’s Cove in Upper Circle Suite with breakfast from £3,685 per person based on two sharing (including economy flights and private airport transfers) based on travel in February. Book by October 31.

Mustique

British peer and socialite Colin Tennant bought the neglected island of Mustique in 1958 for £45,000 with a plan to turn it into an agricultural venture. A year later, he would gift a 10-acre plot to Princess Margaret as a wedding present, on which she built her house Les Jolies Eaux and invited every imaginable member of high society to visit her there. Later came Sir Paul McCartney, Sir Mick Jagger and David Bowie.

Today, the private island remains a firm favourite with the Prince and Princess of Wales, who have visited at many different times of year, but are big fans of decamping there in winter. Apart from it being spectacularly beautiful, it also has a zero tolerance for paparazzi so it’s a great place to holiday in luxury under the radar.

Sir Paul McCartney, Sir Mick Jagger and David Bowie are among the icons to have fallen in love with Mustique - Lucy Fleming
Sir Paul McCartney, Sir Mick Jagger and David Bowie are among the icons to have fallen in love with Mustique - Lucy Fleming

The island is home to the most extraordinary villas, including Le Jolies Eaux, which you can rent from $33,000 (£24,700) per week, but if you’re looking for something a little more affordable, consider booking a room at the island’s only hotel, The Cotton House, which has just launched a new spa. It’s also just a five-minute walk from Basil’s Bar, where the Wednesday night Jump Up is still the place to hang out.

How to do it

If you can squeeze in a trip before December 18, rooms at The Cotton House start from £690 per night, including breakfast. After that, the rate jumps to £1,120 per night until the end of April, but that’s still a lot cheaper than shelling out for a villa. Flights to St Lucia or Barbados with British Airways cost from £500 return, then it’s a twin otter hopper flight to the island for an additional £630 per person return. See www.mustique-island.com.

Tangier, Morocco

While it may not be warm enough for a traditional beach holiday during the winter months, glamorous, eccentric Tangier, on the northwest corner of Morocco and just nine miles across the Strait of Gibraltar from Spain, is perfect for a sunny break exploring the historic kasbah, medina and local cafés without the crowds. It’s also just a three-hour flight from the UK.

The first grand hotels were built in the second half of the 19th century to cater for an influx of diplomats and wealthy Grand Tourists – wealthy young upper-class men who took a long-distance trip to complete their education and social maturation. Tangier was designated an International Zone in 1923, which meant social freedom and no taxes. Consequently, over the years it attracted many writers and artists including Times correspondent, traveller and socialite Sir Walter Burton Harris and artists Henri Matisse and Edgar Degas.

Villa Mabrouka sits in a 1940s villa once owned by Yves Saint Laurent
Villa Mabrouka sits in a 1940s villa once owned by Yves Saint Laurent

Later, Francis Bacon discovered it, as did Beat Generation bohemians such as Jack Kerouac and Allen Ginsberg and, of course, the jet-set billionaires like Woolworth retail heiress (and Cary Grant’s ex) Barbara Hutton and publisher Malcolm Forbes.

Today, a whole new generation of creatives is calling Tangier home, and one of the loveliest places to stay is Jasper Conran’s Villa Mabrouka, a 12-room hotel housed in a modernist 1940s villa once owned by Yves Saint Laurent.

How to do it

Rooms at Villa Mabrouka cost from €400 (£340) in January; Ryanair flies from London Stansted to Tangier from €61. See villamabrouka.com. For a package, Abercrombie & Kent offers a four-night tailormade trip to Tangier in December, staying at Villa Mabrouka on a B&B basis, from £2,900, based on two sharing, including flights from the UK and private transfers. See abercrombiekent.com.

Palm Beach, Florida

Donald Trump may think he put Palm Beach on the map but it was American industrialist and oil tycoon Henry Flagler, who single handedly turned Florida’s Atlantic coast into a modern holiday destination in the 1880s and 1890s by extending the railway to reach it and building a series of grand hotels, including The Breakers, which is still going strong today (albeit in a different building as the original burnt down in 1903).

Palm Beach became the winter retreat of society families such as the Vanderbilts and the Pulitzers, who built grand estates. Architect Addison Mizner was responsible for the Mediterranean Revival Style that permeates everything, and the spectacular just re-opened Vineta Hotel is a brilliant revival of that revival.

Palm Beach has been a hideout for the rich and famous since the late 19th century - iStockphoto
Palm Beach has been a hideout for the rich and famous since the late 19th century - iStockphoto

If staying isn’t quite in the budget, why not book a table in the courtyard at the hotel’s Coco Restaurant and stay at The Brazilian Court, in the heart of Palm Beach’s historic district.

How to do it

Abercrombie & Kent offers a five-night tailormade trip to Palm Beach in February from £3,695 per person, based on two sharing, staying at The Brazilian Court on a B&B basis, including flights from the UK and private transfers. See abercrombiekent.com.

Madeira, Portugal

The first tourists to Madeira were wealthy Britons in the 19th century hoping to ease their respiratory illnesses. Madeira became a high-society health retreat. The opening of Reid’s Palace in 1891 (now a Belmond hotel) significantly widened its appeal, adding aristocratic European pleasure seekers into the mix. Winston Churchill famously stayed at Reid’s Palace and painted there, and it’s where Bernard Shaw learnt to tango.

Madeira became a high-society health retreat in the 19th century - getty
Madeira became a high-society health retreat in the 19th century - getty

If you’re on a bit more of a budget, check into the charming Castanheiro Boutique Hotel and pop to Reid’s Palace, 10 minutes away in a taxi, for afternoon tea or a drink at the bar.

Winter in Madeira is pleasantly warm rather than hot, with lots of sunny, dry days, particularly in the south of the island, where you’ll find the capital Funchal (and Reid’s Palace). While December to February is the wettest time of year, it is rare to get long periods of rain, and it means the island is lush and green. It’s the ideal mild winter-sun break – and best of all it’s less than four hours from the UK.

How to do it

Sunvil offers a seven-night stay in a standard room at Castanheiro Boutique Hotel in Funchal with breakfast from £1,430 per person, based on two sharing, including return economy flights from London Gatwick to Funchal, 23kg hold-luggage allowance and private transfers, based on a January 25 departure. See sunvil.co.uk.

José Ignacio, Uruguay

Punta del Este was originally the summer playground for wealthy South Americans, but by the 1970s it had been heavily developed and lost much of its original charm. Keen to escape all that, they migrated 30 miles east to José Ignacio, an unpretentious fishing village on a secluded peninsula, in search of rustic simplicity. It has become a wealthy bohemian enclave but somehow has remained unspoilt, sleepy and rustic.

Boho-chic hotel Bahia Vik exemplifies José Ignacio’s barefoot charm
Boho-chic hotel Bahia Vik exemplifies José Ignacio’s barefoot charm

Today the crowd includes Shakira, Ronnie Wood and Leonardo Di Caprio, plus scores of tech bros, but also Uruguayans, Argentines, Brazilians and Chileans. To be in the thick of things, head to Parador La Huella at Playa Brava for lunch, check out one of the local wineries and browse the straw hats and ponchos in Paula Martini’s atelier. Or just take a stroll on the vast sweep of sandy beach.

How to do it

Latin America specialist Humboldt Travel offers 10 nights in Uruguay from £4,700 per person based on travel in December, including a stay at boho-chic Bahia Vik in José Ignacio and stops in Carmelo and Montevideo, plus international flights, all private transfers, accommodation with daily breakfast, and some tours. Price based on two sharing.

by The Telegraph