Magazine photospreads of floury sand and ocean, glinting like turquoise glass, had won me over to the idea of vacationing on Anguilla—but I never imagined it could be cheap. This is, after all, a little British West Indies isle, population 14,000, that’s favoured by jetsetters who seek seclusion on its 90 square kilometres, studded with five-star resorts and about 150 millionaire villas.

Yet here I am, booked into Anacaona Boutique Hotel, a family-owned charmer that’s priced like a Best Western.

No need for a front-desk wakeup call when there’s sunlight filtering through the curtains of my simple white room and a rooster crowing by the courtyard fountain. For US$160 in the summer “low season”—the cheapest time of year to travel to the Caribbean—I get to share my hotel’s near-empty public beach with a handful of reclusive gazillionaires, Hollywood powerbrokers and designer-bikinied supermodels peeking out from Sunbrellas. But five minutes by car deposits me on the deep, bleached arc that’s been in my mind’s eye ever since cracking open an issue of People years ago; it’s the beach that put Anguilla on celeb-seeker maps, when Jennifer Aniston and Brad Pitt broke up there while staying at a US$75,000-a-week villa.

The busy cruise port of St. Martin/St. Maarten, where WestJet touches down, is worlds away. Anguilla is so relaxed, it’s practically in fetal position. There are no casinos, duty-free shopping streets or all-inclusive resorts. Jet Skis and fast-food joints are banned. There’s a lone banana boat guy. And just a few (über-posh) cruise ships anchor each year at the same port, quaintly named Road Bay, next to the yachts of the Abramoviches and Armanis. I’d heard rumours of LeBron James playing pickup hoops in town when he visited, and of Janet Jackson arriving uncharacteristically without her entourage, while Bruce Willis is said to have asked here, “Doesn’t anyone know who I am?”

Of all the world’s islands, superstars flock to the one that couldn’t muster electricity, running water or paved roads until the 1980s, but offers the rare luxury of being able to turn the spotlight off.

Here’s how to get the most out of Anguilla, a destination rich in contrasts and prices—and one that, refreshingly, lacks in pretension:

Get there


Arrive by Funtime Sea Shuttle’s 25-minute service from St. Martin/St. Maarten. (US$65/person, with free drinks)


Charter your own seven-minute flight on a Britten Norman Islander BN-2, with Anguilla Air Services. (US$500)




Canadian expat Mimi Gratton lists budget-friendly stays on her website, including Lloyds Bed & Breakfast. (US$99/single occupancy; 264-497-2351,



The Kelly Wearstler-designed Viceroy Anguilla, a Miamiesque fave of Sofía Vergara and Sandra Bullock, charges US$800 (minimum) nightly during the peak winter season.


The Canadian-owned Villa Kishti is an example of a prize-winning four-bedroom oceanfront stunner that rents for US$8,000 a night in high season.

Get around


Anyone whose previous experiences of the Caribbean have taken place behind resort gates will find Anguilla liberating. Given its low crime rate, tourists can safely roam the low-lying, dusty roads crisscrossed by goat herds and lined with naturally formed salt ponds, cinderblock homes, churches and tucked-away villa entrances. Buy a US$20 temporary driver’s permit from any car rental agency or negotiate a day rate with taxi drivers, such as Wilmoth Hodge (264-584-4616).




Anguilla’s screaming deal is the John T. Memorial cycling race, a 140-km event held in July that attracts pan-Caribbean competition. For a US$20 entry fee, riders stay free for three nights at host Anacaona Boutique Hotel, inclusive of breakfast and two dinners.


The Anguilla Tennis Academy charges US$80/hour for private lessons, and runs day clinics encouraging Anguillian children to play together with children staying at the resorts and villas.



Using X-Acto knives and chisels, Cheddie Richardson of Cheddie’s Carving Studio whittles away at driftwood to reveal its inner seabird, stingray, eel or shipwrecking siren. The self-taught sculptor’s pieces, priced from a few dollars to US$5,000, are in private collections worldwide, including Queen Elizabeth II’s.



Sipping “Duneshine” (a fermented ginger drink) while listening to reggae recording artist Bankie Banx at his Dune Preserve beach bar, ranked No. 1 worldwide by CNN Travel, is the ideal sign-off for a laid-back trip to Anguilla. Keep an eye out for celebs in the audience of this Swiss Family Robinson-style tree fort cobbled together from driftwood and shards of old wooden Anguillian fishing boats.



Calgarian Denise Carr rose to become one of the Caribbean’s first female executive chefs working at a five-star resort, the CuisinArt, which she left to open SandBar, a tapas bar in the nightlife area of Sandy Ground, with husband Joash Proctor. Most of Carr’s nibbles are less than $10 each —that may sound cheap, but her tapas are so yummy, it’s hard not to keep on ordering plate after plate until the tab starts to add up.

Lunch and Learn

Leandro Rizutto, owner of Conair Corporation and CuisinArt appliances, built CuisinArt Golf Resort & Spa, and it is Rizzuto’s continuing creative experiment. It now has the Caribbean’s largest spa, and its first “hydroponic farm”: an 18,000-sq.ft. greenhouse full of Styrofoam floating rafts of lettuce, tomatoes and bell peppers are grown. Guests at the resort can book a complimentary greenhouse tour/cooking class combo. Guests can also take a professional three-course class using ingredients from the hydroponic farm (US$65 per person).