Quintessence Hotel, a new resort in Anguilla.Quintessence Hotel Anguilla
Let’s begin our investigation of luxury resorts and pickleball and their respective effects on the human soul with a few words about pickleball. Pickleball was invented in 1965 in Washington State when someone forgot to bring along the equipment for a children’s game of badminton. Today it’s the fastest growing sport on Earth. Some 38 million North Americans tried it last year. Major League Pickleball is owned by the likes of Tom Brady and LeBron James. Chris Evert is a fan.
Traditional tennis fans resent everything about the new game, from the loss of tennis courts to the plinky noise of the puny upstart. If tennis is the establishment’s favourite, the prince of racquet sports, pickleball is its middle-class, arriviste cousin.
Which brings us to Anguilla, not the first place you think of when you think of pickleball, or for that matter when you think of anything. A British Overseas Territory, Anguilla is one of the Caribbean’s last unspoiled havens, a sliver (25 kilometres long, five kilometres wide, 15,000 inhabitants) of white-sand beaches on the leeward end of the British West Indies, a 20-minute boat ride north of Saint Martin. The Arawak from South America who settled on it 3,000 years ago called it Malliouhana, because it resembled a sea serpent. If you say you’ve been to Anguilla, most people think you’ve been to Angola.
Anguilla didn’t begin to attract tourists in a serious way until the 1980s – adventuresome snowbirds and especially the superrich, who moored their yachts off its beaches or rented villas on its shores or booked into a handful of five-star hotels. Anguilla was their secret.
At the height of the high season, knockout villas and luxury hotel pads fetch upward of US$30,000 a night, sometimes with a 10-night minimum. Who can afford to spend a quarter of a million dollars on a Christmas vacation? The upper echelons of the Manhattan financial world and celebrities such as Madonna and Michael Jordan. Anguilla is where billionaires like Bill Gates go to be left alone. The island’s “high-end, low volume” style of tourism guarantees that even with 75-per-cent occupancy, you rarely see many people around.
The Aurora Anguilla Resort and Golf Club is home to five pickleball courts.Aurora Anguilla Resort & Golf Club/Supplied
In other words, a plebe in search of some pickleball coaching and playing would normally make his way to Naples, Fla., or Palm Springs, Calif., two hotspots for the jumped-up sport. But an unexpected development is taking place on Anguilla. Pickleball is emerging there as well, the pastime of a faction until now rarely mentioned – the middle class. It’s still a bit of a secret, but Anguilla now wants us all. Even pickleball players.
Let me say this about the luxury villas we stayed in while I hunted for a game of pickleball: They are as enticing as they are infantilizing.
The first palace we occupied, Villa Kishti on Black Garden Bay, is the private residence (when it isn’t rented out) of Suresh Bhalla, a retired Canadian banker. The villa hangs like a beautiful cave over the less populated north shore of the island.
The seaward proscenium of the main floor is a vast open-concept bedroom-living room-thinking space, encased in floor-to-ceiling windows that slide open to the ocean. Behind the bedroom is an acreage of marbled bathroom. Behind them both rambles an exquisitely appointed (sculpture, Sikh artifacts) indoor-outdoor living/dining space, finished in Italian marble and Turkish limestone.
There were so many dimming pot lights and electronic window blinds and television sets and sound systems controlled by so many remotes, I spent hours wandering around trying to figure out which one controlled what gizmo. There was a heated infinity pool on one level of the patio and a hot tub or two on another. I felt compelled to try them all, like a three-year-old.
Luxury (“Everything as it should be, without having to ask for it,” according to an Anguillan hotelier I met) is thrilling – everything is done for you – but also enervating. Before you know it, if everything is not done for you, you turn into a squalling brat.
“I have become Resort Woman,” my wife said to me at one especially plush Eden, where she had spent the day reading on a freshly sheeted chaise lounge under a vast umbrella, being waited on by a beach boy who brought her fresh towels and ice-chilled bottles of water and free snacks and anything else she desired. “And the transition was instantaneous.”
I kept hoping something would actually happen, but the purpose of extreme luxury is to insulate the all-important client from all potentially scarring occurrences, such as running out of Cheetos.
Two days later, we moved to the Bhallas’ other property, Villa Kishti Meads Bay. It goes for US$14,000 a night during high season and sleeps 10.
Meads Bay was one of the coves where Anguillans smuggled contraband – rum, flour, other essentials – to avoid hefty duties levied by their British overseers after the island was colonized in 1650. The British tried to grow tobacco and cotton and then, with enslaved Africans, sugarcane, but nothing really worked, and they were gone by the early 1800s.
To this day, if you step outside the hermetic luxury of your villa, you’re instantly back in old, predeveloped Anguilla. (You can find a beachside suite for less than US$500 a night, even in the high season, if you book with a local owner.) The Valley, the island’s only town, is (maybe) three kilometres wide. The rest is villages and space between the villages, and silence between the spaces.
Restaurants tend to be non-descript roadside joints that look like they fold up or blow away each evening. But you won’t find more sophisticated or delicious food than you do at Roy’s Bayside Grill or Tasty’s (whose Anguillan chef trained in Paris) or Sharky’s (the most perfectly grilled swordfish I’ve ever eaten) or the SunShine Shack (breathtaking beachside barbecue), to name just a handful.
Anguilla is teetering between the upscale and the local. Its elected government – currently the Anguilla Progressive Movement, led by Dr. Ellis Webster, a former ear, nose and throat doctor – is trying to walk the tricky path between the two. It has been lucky of late in that regard. Anguilla’s internet domain is dot “ai”, an address so much in demand the government made US$32-million last year (more than 10 per cent of the GDP) charging for its use. Hence the island’s new school, a longer runway at the airport (to accommodate more direct flights), free health care for those over 70, a new guaranteed minimum wage of $6 an hour, and – get this – two new public pickleball courts.
Chantal Lachlan, professional pickleball coach and player based in Naples, Fla., and Anguilla, prepares to coach Globe and Mail writer Ian Brown in the subtleties of pickleball at the Quintessence Hotel in Anguilla.Ian Brown/The Globe and Mail
My first pickleball lesson took place at Quintessence, a new Relais and Châteaux resort owned by Geoffrey Fieger, the trial lawyer who successfully defended Jack Kevorkian. On Instagram, the resort claims to understand pickleball not just as a sport, but “as a lifestyle.” Alas, its pickleball court is just its tennis court, adorned with additional hard-to-see pickleball lines.
Still, that layout was where I met Chantal Lachlan, my first pickleball coach, and therefore a genius. It was 11 in the morning, and swelteringly hot. Lachlan looked 25 and was 40. Her dog, a long-haired chihuahua that accompanies her most places, was in its gold-tinted dog pram/carrier, complete with a bed of ice to keep the pup cool. I instantly longed for a similar setup.
A competitive tennis player forced off the court by injuries, Chantal is now establishing her professional pickleball ranking, and splits her playing and coaching between Naples, Fla., and Anguilla. From the moment she started speaking, Chantal changed my game.
“Pickleball is the exact opposite of tennis,” she said gently but persuasively, by which she meant it entails less power and more finesse, less drive and more shot-by-shot strategy. She taught me to be patient, to “dink” (the short, over-the-net game that amateurs tend to avoid), to make transition lobs. She fixed my serve and softened my touch. “The cross-court shot is the highest percentage shot,” she told me, and I believed her.
Best of all, she invited me to Anguilla’s only regular private pickleball game. “It’s in Seafeathers,” she said, referring to a neighbourhood at the other end of the island. “At Nurse Dana’s.” That is all the address you need on tiny Anguilla.
Nurse Dana, I discovered the following evening, was Dana Ruan, a 67-year-old retired nurse. She was recovering with a new knee and desperate to get back on the court. A lifelong athlete, she grew up on old, predeveloped Anguilla, back when there was a total of three telephones on the island and everyone walked everywhere, unless someone with a car happened by, in which case they always – always – drove you wherever you needed to go. She was converted to pickleball six years ago by Kirk Layton, a long-time winter Anguillan (and former squash player) from Philadelphia who is universally acknowledged as the forefather of pickleball on Anguilla.
By 2018, Kirk had convinced what was then called the CuisinArt Resort to convert two tennis courts to pickleball. That’s where Dana and everyone on the island started playing. He convinced the Anguilla Tennis Academy to turn over two more. Nurse Dana and her husband Clement built their court, Anguilla’s fifth, in response to the pandemic, which Dana found crushing, physically and psychologically. “Pickleball,” she says matter-of-factly, “saved my life.”
The Seafeathers court has lights because Dana and Clement let anyone on the island play there three days a week, at 5:30 in the late afternoon. Local people work during the day. Anguilla’s white retiree pickleballers tend to play in the morning at the Tennis Academy, before it gets too hot.
The only white person at Dana’s the night I dropped by was Bob Powers, a retired banker from Massachusetts who visited Anguilla with his wife in 1998 and has been coming down for winters ever since. The level of play was the best I’ve ever seen – fast, aggressive, no breaks – thanks in large part to Chantal and a woman named Blondel.
There was a lot of chirping backchat, especially from the women. Bob always asks Dana before he invites a newcomer to the locals’ Seafeathers game; Dana keeps telling him he doesn’t need to ask. “Anybody can come and play,” she told me the evening I visited. “We want to support it. We want everyone to play.” This is one way Black and white people on Anguilla get along.
I had experienced my first Anguillan game of pickleball that very morning at the Tennis Academy. I played with Bob (who has 28 Anguillan pickleball players on his WhatsApp); Jen Godfrey, a 70-year-old retired investment manager; Kevin Smith, a judge from Maine; a deceptively spry 80-year-old, Jeet Mahal; and Blair Cobb, a 30-ish therapist from Tennessee who moved to Anguilla six months ago with her 13-year-old son, after her divorce and an affair with a surfer.
Despite Chantal’s brilliant advice, I was still the worst player on the court. Bob and I won two games, but Bob scored all the points.
A converted tennis court at the Anguilla Tennis Academy.Ian Brown/The Globe and Mail
The liveliest place to witness the almost imperceptible transformation of Anguilla from a billionaires’ luxury retreat into an (upper) middle-class-friendly destination is the Aurora Anguilla Resort and Golf Club, where we stayed for our last three days on the island named after an eel. We were escorted in a golf cart to a suite overlooking the beach. The suite came with a butler and hypoallergenic bed linens and a bathroom the size of my living room in Toronto.
Aurora is the largest property on Anguilla. The land was assembled by Leandro Rizzuto, the late billionaire who started Conair Corp. (hair dryers) and later bought Cuisinart (food processors). He built the CuisinArt Resort and Spa, emphasis on the ahh. Then he died. In 2020, the entire vast holding was purchased by Richard Schulze, the billionaire who founded Best Buy. He renamed it Aurora. You are now up to date.
Schulze has carefully poured hundreds of millions of dollars into Aurora and Anguilla, rebuilding the resort’s Greg Norman-designed golf course as well as the island’s hospital and its school lunch program. In the meantime, Aurora runs as two worlds: the more serene Rendezvous Bay oasis, and the adjacent playland of Merrywing Bay, which is family-centred and features the golf course, a waterpark, a climbing wall, a club house for teens, a minigolf course, and (as of this season) five dedicated pickleball courts, the fruit of Kirk Layton’s lobbying.
Some of these changes have offended exclusive Anguilla. The waterpark (which locals use half price) set off a public uproar. “People who don’t live here, and or only holiday here, kept saying ‘That’s not my Anguilla!’ ” Edmund Richardson, the resort’s general manager, told me. “But it’s not their Anguilla anyway.” The plan “is to create a family-friendly resort with a longer season, to be a form of affordable luxury.”
Aurora’s new Merrywing pickleball clinic was packed the next morning. Ryan Williams, Aurora’s pro, taught me how to block volleys, how to use topspin, how to pay attention. Then Chantal (she coaches there as well) and I played a brace of doubles games against Ryan and an older woman in her late 70s whose skills had clearly been matched to mine. I think her name was Joy. Ryan’s and Chantal’s lessons were sinking in: I was playing with more confidence. But I was still responsible for our team’s loss to Ryan and Joy. Joy, it turned out, was recovering from a stroke.
We left Anguilla the following afternoon, reluctantly. Before we did, I snuck in a last game at the Tennis Academy.
And suddenly, just like that, on my last day in pickleball paradise, I was unbeatable. My new pals didn’t seem to mind. One of the luxuries of Anguillan pickleball – even if you’re middle class – is that the people you play with feel like friends.
If you go
The easiest way to get to Anguilla from Canada is to fly to Saint Martin and, via airport shuttle, transfer to a 20-minute ferry or launch ride across the water to nearby Anguilla.
Accommodations range from high-end villas, such as Villa Kishti Meads Bay (kishtiblackgarden.com) and luxury resort hotels, such as Aurora Anguilla Resort and Golf Club (auroraanguilla.com) and the Quintessence Hotel (qhotelanguilla.com), to more affordable locally owned villas and hotels; the Anguilla Tourist Board supplies many suggestions at www.ivisitanguilla.com.
The two best places to play pickleball or take lessons are the Aurora Anguilla Resort activity centre, which has five dedicated courts and a pickleball clinic free to guests, with a charge for non-guests. For a fee, visitors can join the Anguilla Tennis Academy (anguillatennis.com), where pickleball mornings are held multiple days a week.
The writer was a guest of the Anguilla Tourist Board. It did not review or approve the story.