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(2019 - Spring Issue)


Yearning for life in the laid-back lane? On Anguilla, the day’s most pressing question may be which beach to try next.

Even if you’ve heard of Anguilla, you might not be sure how to pronounce its name. (For the record, it “rhymes with vanilla,” as locals are quick to inform you.)

However, you could be forgiven for being unaware of this off-the-beaten-track Caribbean island. For one thing, it’s tiny—you could fit 120 Anguillas into Jamaica, with room to spare. For another, it’s very quiet. There are no casinos. Huge cruise ships pass it by. You’d be hard-pressed to rent a Segway or find a posh jewellery boutique.

So why go?

One word: Escape.

Long a discreet haven for rich and famous travellers—Derek Jeter, Sandra Bullock, Jay-Z and Beyoncé have all dropped by—the island is famous for its privacy, opulent resorts, great food and at least 33 beaches.

Although it can be pricey, the 91-square-kilometre British overseas territory has an endearing lack of pretention. For instance, the capital of Anguilla is simply called The Valley—not surprising on an island where you’ll also find communities with straightforward names like West End, East End, North Hill, South Hill, Little Harbour and Island Harbour.

The island is that sort of place where you can let down your guard, kick off your shoes and forget about making an impression. And one great way to get into Anguilla’s state of mind is to step aboard Tradition, a sleek wooden sailboat built on Carriacou in 1978 to transport cocoa and other goods around the islands. Laurie Gumbs and his partner, expat Albertan Deb Vos, now use it to run day trips and private charters.


They greeted my group with sparkling mimosas and made sure we weren’t thirsty for the duration of our “sundowner sail,” however our outing was far from a raucous booze cruise. If anything, you could call it a “nosh cruise,” as the couple’s idea of hors d’oeuvres ranges far and wide. I loved the cheese board, piled high with fromages purchased on the French side of neighbouring Saint Martin/St. Maarten. Depending on what’s seasonally available, you might also nibble on charcuterie, devilled eggs, hummus, tapenade or gorgonzola-stuffed figs wrapped in bacon as you watch pelicans swoop and dive for their own dinner.

Taking care of the gleaming vintage ship is clearly a labour of love for Gumbs and Vos, who sail it back to Carriacou periodically for a bit of TLC. “As you’re repairing one part of the ship, another part is saying goodbye,” Gumbs said wryly, noting they replace roughly half the ship each year. Fortunately, he had enough warning of Hurricane Irma in September 2017 to sail Tradition out of harm’s way. It survived the storm unscathed, and the couple used it in the ensuing months to ferry supplies to the devastated island.


For an island with a permanent population of just 15,000 people, Anguilla boasts a surprising number of upscale resorts.

If cooking is your passion, the two-year-old Reef by CuisinArt (yes, the kitchen appliance company) may be just your cup of gazpacho. Menus at the Reef’s two restaurants highlight ingredients from the hydroponic farm the Reef shares with its nearby sister property, CuisinArt Golf Resort and Spa. My favourite menu items included a spectacular caprese salad at the beachfront Breezes restaurant and an unusual appetizer of peekytoe crab on a funnel cake at the more formal Yacht Club. After dinner, I happily wound down in a huge guest suite featuring a standalone oval tub, walk-in closet and many CuisinArt appliances (in-room espresso, anyone?).

The Reef’s sleek esthetic glitters with marble and glass, however if your idea of luxury leans more toward wood and natural materials, check out a relatively new resort at the opposite end of the island. At Zemi Beach House Hotel & Spa, the food is also outstanding, from the curried pasta salad with crispy chickpeas I enjoyed by the beach to the chilli-orange salmon with coconut rice I’m still dreaming about. The adults-only tranquillity pool, perched a bit above the main resort buildings and offering a sweeping ocean view, is well named. Thoughtful touches, such as baskets of sunscreen by the pool, make Zemi a soothing haven.

My favourite place on the property was the spa. Housed in a 300-year-old Thai building that was shipped to the island and reassembled years ago, the spa is home to one of the largest Turkish-style hammams in the Caribbean, along with five treatment rooms. Yes, it sounds like a jarring combination of international themes, but it worked for me. The pools and hammocks were relaxing, my grapefruit-and-rosemary massage eased the aches from my shoulders, and the mud-bath ritual—coat yourself in mud, bake in the sun, rinse off in an outdoor shower—was surprisingly refreshing.


While Anguilla doesn’t have as many tourist attractions as some other Caribbean islands, that doesn’t mean you’ll be bored—especially if you like to exercise under the tropical sun.

Not surprisingly, watersports are popular. I spent an enjoyable hour kayaking in the waters off the Reef, and the hotel also offers its guests complimentary snorkelling and paddleboarding.

Looking for land-based fun? The elegant CuisinArt Golf Resort & Spa next door to the Reef is home to an 18-hole golf course designed by Greg Norman. Elsewhere on the island, you can polish your backhand at the Anguilla Tennis Academy or go horseback riding with Seaside Stables.

And for the ultimate escape, book a trip to Sandy Island, a tiny islet just offshore, where you can swim or snorkel to work up an appetite, then devour giant servings of lobster, crayfish or barbecued chicken. You can’t get much farther from a Canadian winter than that.

Travel Planner

Most Canadians reach Anguilla via St. Maarten, then take a ferry to Anguilla. For more details on Anguilla, go to ivisitanguilla.com.

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