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 organization for me.

As a last-minute planner, I tend to book trips around 60 days out. As such, I was thinking about a four-day trip to Kiawah. Yet while perusing the monthly availability report, I noticed the Club had a week available in Anguilla, followed by a few days in St. Barths and a week in Nevis. Many discerning travelers consider the Caribbean solely for peak season, from December to April. But the Caribbean islands are also fabulous between May and September. Temperatures don’t change much throughout the year, and during the summer months the resorts, activities, and beaches are quieter and it’s easier to get secure top restaurant reservations. So while I had never been to Anguilla, St. Barths, 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 escape to the Caribbean.

In a Covid-cautious world, preparing for trips, particularly with multiple destinations, can be slightly daunting. Rules and regulations, especially in the islands, change regularly and many locations have pre-arrival forms and testing. At Exclusive Resorts, we closely follow these requirements. Working with my Ambassador, Erin, and our in-destination teams, I was able to assemble all the forms and schedule all pre-arrival tests for each location. Before I knew it, we were headed to the airport and jumped an overnight flight from SFO to Miami. After a connection through St. Martin and a speedboat shuttle across the channel, we took a private boat charter to Anguilla. I quickly changed into shorts and a tee-shirt and the Captain passed me a bottle of Carib Lager. Finally, a vacation! All the meticulous organization and planning by my Exclusive Resorts Ambassador and our local destination teams had come together perfectly. After a quick transfer, we rolled into the manicured grounds of the Four Seasons in Anguilla and were greeted by General Manager Diego Angarita, who welcomed us to the fabulous Exclusive Resorts homes.

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, featuring outdoor areas, large kitchen and dining rooms, 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 queens, 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 and on the ground floor with large private pools. 

One of the wonderful benefits of traveling with Exclusive Resorts is that our Concierge teams provision the home with groceries based on personal preferences. 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 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 taste (I highly recommend it!). 

Anguillans take pride in their 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. Anguillans have a natural, relaxed confidence and 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 yet return to Anguilla for the simplicity of island life.

Conversations inevitably turn to island cuisine and favorite restaurants — a hotly debated topic. Sharky’s, Blanchards, and Jacala vie for 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 Brussel Sprout Caesar, Red Curry Mussels with Lemongrass, Jerk Shrimp, and Char-Siu ribs, while an 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. 

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 Juluca and savor ceviche at the Peruvian-inspired Uchu or have lunch at the more relaxed Cap Shack. The Belmond also houses Cips by Cipriani and Pimm’s — both are open for cocktails and dinner and overlook a beautiful bay. 

Another short drive is the Malliouhana Hotel, which sits on the cliffs at Turtle Cover overlooking Meads Bay. Opened over 30 years ago, the Malliouhana feels like stepping back in time; the vibrant décor reminds me of the Polo Lounge at the Beverly Hills Hotel and feels like the sort of place to sit and write a book. 

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 tableside, and the seafood is divine, but 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!). The off-menu tacos at the Half-Shell are also an absolute must. Though it can feel a bit odd eating tacos in the Caribbean, they are some of the best tacos I have ever had.

Diego, his team, and our Concierge host CJ did a super job in bringing out the charm of Anguillan hospitality in a fantastic setting with beautiful homes. There is plenty to explore and I can’t wait to go back.

For more information visit the Exclusive Resorts website here.

Photographs by James Henderson.