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Island Hop

Exclusive Resorts CEO James Henderson discovers the charm of Anguilla.

The irony of being the CEO of a luxury travel company is that I’m typically not very good at vacationing. I’m also not very good at planning them. At Exclusive Resorts, we often call my type the “‘we really should” traveler — meaning we really should take that trip or vacation, but something (usually work related) always seems to get in the way.

I have no excuse, however, as I'm fortunate to have an Exclusive Resorts membership and a fabulous Vacation Ambassador, Erin, who executes all planning and organizing for me. As a last-minute planner, I tend to only book trips around 60 days out. As such, I was thinking about a four-day trip to Kiawah in South Carolina, yet while perusing the monthly availability report, I noticed the Club had a week available in Anguilla, followed by a few days in St. Barts and a week in Nevis. Many discerning travelers consider the Caribbean solely for peak season — December to April — but the Caribbean islands are also fabulous between May and September. Temperatures don't change that much throughout the year, and during the summer months the resorts, activities, and beaches are quieter, making it easier to secure top restaurant reservations. So while I have never been to Anguilla, St. Barts, or Nevis, I figured what could be better than an island hopping adventure? So we booked the trip... and a potential four-day trip to Kiawah turned into a two-week island escape to the Caribbean.

Gorgeous colors are on display all over Anguilla
The Club homes are beautiful on the inside and out

Club homes in Anguilla are set on a bluff overlooking the bay, and our first experience was witnessing a beautiful sunset across the tranquil Caribbean Sea. Each home is approximately 7,000 square feet with spacious outdoor areas, large kitchens and chic dining rooms, complete with huge windows overlooking the private pool and a separate living room with a balcony.

Homes also have two spacious master suites with large, en-suite bathrooms and outdoor showers. You’ll find a third room with a king bed and a fourth bedroom with two queen beds, which can easily accommodate three to four couples with plenty of space. Each home also has a large roof deck with an outdoor dining terrace, sun loungers, and a jacuzzi tub. 

We had plenty of breakfast items, snacks, and wine for the week. What’s more, the Four Seasons team thoughtfully prepared a beautiful charcuterie board and bottle of iced Veuve Clicquot as a welcome amenity. After freshening up, we headed to the resort's Sunset Lounge for a cocktail and light dinner. I have a penchant for a great Old Fashioned cocktail, however, the islands have a particular take on the Old Fashioned and serve it with rum — which gives it a slightly sweeter, more buttery and smoother taste — I would highly recommend it! 

Anguillans take pride in hospitality and there is a genuine sense of community found throughout the island. Locals look out for each other and this natural friendliness is extended to visitors. Due to their natural, relaxed confidence, it’s easy to chat with them for hours. Considering Anguilla is a British Overseas Territory, many locals have spent time living and working in the UK before returning to Anguilla for the simplicity of island life.

Conversations inevitably turn to island cuisine and favorite restaurants — a hotly debated topic. Sharky’s, Blanchard’s, and Jacala usually vie for the top spot on the island's west end.

Sharky’s is a private roadside home turned restaurant. The bizarre mix of wooden chairs and patio furniture is quickly forgotten once food arrives. Proprietor Lowell Hodge is a gracious host, and house specialties include lobster cakes, calamari, and lobster risotto. Blanchards first opened its teal shutters in 1994 and has been owned and operated by proprietors Bob and Melinda Blanchard ever since. Expect a relaxed beach atmosphere with big windows and a terrace overlooking tropical gardens. Cuisine incorporates an infusion of Caribbean, Asian, and American influences, and highlights include the Brussels sprout caesar, red curry mussels with lemongrass, jerk shrimp, and char-siu ribs. Their exceptional wine list received Wine Spectator's "Best of Award." My personal favorite local restaurant? Jacala. Owned and operated by Chef Alain Laurent (named one of the Caribbean's top chefs), his locally inspired dishes are infused with French flair and the snapper carpaccio and crayfish were absolutely superb.

Food is absolutely a highlight on this island
Innovative and fresh cusine from top-rated restaurants

Anguilla is a relatively small island — 16 miles long and three miles wide — so it's easy to explore in a day by renting one of the ubiquitous Mini Mokes. Beaches are spectacular and Maundays Bay is one of the best beaches in the entire Caribbean. Drive to the Belmond Cap Shack which houses Cips by Cipriani and Pimm's, both open for cocktails and dinner and overlook a beautiful bay, as well as UCHU; unwind and soak up the Caribbean atmosphere at Chef Cesar Soto's Peruvian spot with sophisticated dishes and amazing ceviche bar.

Sunset Lounge at the Four Seasons is the best island perch to watch the sun dip over the horizon. Featuring a wonderful bar and service, you can sit by the pool, watch the sun go down, and look for the elusive green flash. Salt is the Four Seasons' signature restaurant (named for the island's salt-mine history), and cuisine is consistently excellent. Servers prepare fresh ceviche table-side, and the seafood is divine. I would also recommend Chef Darren's award-winning pork chop with parsnip puree, served with pineapple and rum sauce, it was cooked to perfection.

The Four Seasons in Anguilla is an easy place to spend a full week. Unwind at three pools or enjoy resort access to fabulous Meads Bay Beach and Barnes Bay. The Half Shell restaurant on Barnes Bay is ideal for lunch and you cannot leave Anguilla without having Dean's Green Supreme. Created by the restaurant manager, it's billed as a health drink, as it's made with moringa plant leaves, yet also features a generous amount of rum and is supposed to be good for your back (or maybe it was that it puts you on your back!).


For being a small tropical island, Anguilla boasts 33 of the most stunning beaches in the world — from wide stretches of white sand to hidden coral covered coves. Expect ocean-inspired cuisine, local calypso bands, world-class diving, and endless water excursions. With sweeping views of the ocean, our four, stand-alone luxury villas at The Four Seasons Resort, are perfectly suited for large family gatherings, with accommodations for up to ten guests, private plunge pools, sun decks, and a gourmet kitchen.