Jennifer Aniston’s annual New Year celebrations are the stuff of tabloid legend. With a selection of her famous friends in tow, she routinely decamps to the Mexican resort of Cabo San Lucas for a spot of winter sun, prompting a flurry of paparazzi airport shots and a handful of enviable Instagram stories.
The actress isn’t the only A-lister to return to a favourite destination for some seasonal stress-busting. With the money and the clout to go anywhere on earth, famous people still tend to cluster in the same spots (perhaps because their prices prevent the rest of us from getting in).
“They go to the same places every year,” says Jaclyn Sienna India, who has arranged trips for Mariah Carey, amongst others, and charges a £60,000 annual membership fee for her services (with holidays costing more on top). “They go to St Barths at Christmas and they go to Mustique for the winter, so it’s easy to spot trends and see how we can assist them”.
Celebrities employ celebrity travel agents to get them there: power players such as India and Jason Couvillion at Bruvion Travel, who are famous in their own right thanks to their impeccable service and flair for logistics. The secret, says India, is to cut through the entourages and get straight to the VIPs themselves.
“I learned really early on in my career when I took George W. Bush out that his team spoke for him,” says India. There’s this wall around the celebrity. People are trying to protect the person but they’re just being annoying… so we try to get the celebrity more involved and they get excited about the trip”. Below, we take a closer look at some favourite A-list winter sun destinations – and the experts who arrange their holidays.
Unlike Aniston, many superstars know better than to let irritants like the public or paparazzi get in the way of a good break. For Caribbean sunshine, one of Kim Kardashian’s favourite getaways is Baker’s Bay on the Bahamian island of Great Guana Cay, which bills itself as “the Bahamas’ most exclusive members-only community”.
Justin Bieber reportedly proposed to wife Hailey there, and Reese Witherspoon and Justin Timberlake are said to own homes among its sprawling mansions. There’s a spa, a golf course, three restaurants and six miles of private beach. There are, however, no pesky photographers or gawking tourists: only members and their escorted guests are allowed in.
Baker’s Bay is part of a collection of posh resorts from Discovery Land Company, including one in Los Cabos, Aniston’s winter destination of choice. Among the latest is CostaTerra, a Portuguese outpost near fashionable Comporta where Princess Eugenie and her husband Jack Brooksbank now spend part of the year and where he works for the company.
Other celebrities prefer a different destination with royal connections. Mustique, once Princess Margaret’s island of choice, remains a perennial favourite. “Privacy and discretion are respected there,” says Sarah-Leigh Shenton of luxury travel company Red Savannah. “Private villas range in size from boutique to spectacularly vast, with residents equally comfortable hosting parties at ‘home’ or letting their hair down at the weekly Jump Up at Basil’s Bar”.
For total seclusion though, there’s an even better option – an island entirely to yourself. Johnny Depp used to have his own Bahamian one. Others prefer to rent those owned by fellow superstars.
David Copperfield transformed 11 islands in the Exumas into the fittingly magical Musha Cay and the Islands of Copperfield Bay, a super exclusive resort where five guest houses with their own private pools are scattered across one sprawling dollop (holidaymakers hop between the others by private boat). Oprah Winfrey and Bill Gates are said to have been among previous guests.
Then there’s Necker, Richard Branson’s private getaway which was rebuilt after being destroyed by a wildfire in 2011 (Kate Winslet escaped the blaze). It’s generally only open for exclusive hire, but the island does rent out rooms on certain weeks of the year so that less monied guests can check in too. It’s all relative though: they still cost upwards of £4,300 per night.
Meanwhile luxury travel company Red Savannah sends guests looking for total seclusion to Thanda Private Island, spread across 20 acres in the Indian Ocean off Tanzania. It has just one five-bedroom villa but loads of empty white sand. Rent it and you get a full team of staff as well as four private boats.
Other private-island getaways include Calivigny off Grenada and Banwa Private Island Resort in the Philippines, which costs around £80,000 per night for exclusive use but is still a big hit with clients according to Catherine Heald of Remote Lands, a purveyor of ultra-luxe trips to Asia.
Of course, some A-listers like to use holidays as potential PR opportunities, preferring to make themselves known rather than hide away. For them, there are accordingly high-profile and high-price hotels including the renowned Eden Rock in St Barths. “It’s often our first recommendation for those who don’t mind being seen,” said Red Savannah’s Sarah-Leigh Shenton.
The hotel is owned by the family of Pippa Middleton’s husband and it’s notoriously hard to get into. India block-books rooms for the world’s most exclusive places to stay in advance in order to ensure her customers are never disappointed.
Other particularly popular hotels include Las Ventanas al Paraiso in Cabo, where George Clooney is rumoured to have checked in. (“It’s really one of the best places,” says Couvillion.) Then there are the Aman Resorts, which famously sparked addictions in billionaire ‘Aman junkies’ when they first opened: Couvillion rates the brand’s outpost in the Turks and Caicos Islands, India loves their places in Sri Lanka and Bali and Catherine Heald of Remote Lands name-checks Amanpulo in the Philippines.
“It’s by no means a perfect brand,” says India. “But their growth has been slower. If you look at a Rosewood, there’s a thousand of them coming up. The Four Seasons has 2,000. Their mentality is growth. It’s not about service anymore”.
It’s not just about booking a hotel (or an entire island). Once they are on the ground, travel planners can help celebrities with the logistical issues of planning a true escape for those who are recognised wherever they go.
“We are always mindful of arranging accommodation that provides as much privacy as possible, which is why our staff inspection trips are so invaluable,” says Shenton. “Knowing which way a villa or suite faces is crucial for camera-shy celebrities. Security is a top consideration too, especially where family is concerned. We can arrange a security detail where necessary, or provide appropriate accommodation for accompanying security staff”.
Lastly, for an A-lister determined to remain elusive on a winter-sun jaunt, there’s one age-old celebrity trick: the fake name. For clients determined not to be seen, “we book them at hotels under an alias so very few staff in the hotel know they are actually there and we arrange for them to be met on arrival and taken through private or staff entrances, rather than walking right through the lobby,” says Couvillion.