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  • Locations: 27
  • Villas: 49
  • Private Islands: 0

Warm & Welcoming 

Anguilla is a 15-mile island east of Puerto Rico and the Virgin Islands, separated from St. Martin to the south by the Anguilla Channel. Though close in proximity to St. Martin, Anguilla couldn’t be more different. St. Martin is known for its vibrant nightlife and cosmopolitan atmosphere, while Anguilla is its calm, easygoing, casual counterpart — where you go to truly get away from it all. Which is not to say that Anguilla doesn’t have its own brand of chic; Anguillans know how to relax in the utmost style and comfort.

Among the many attractions of this tiny island are spectacular coral reefs perfect for snorkeling and scuba diving, over 30 beautiful white-sand beaches, and an 18-hole championship golf course designed by Greg Norman.

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Advice from Villa Specialists 

Getting There

The villa team traveled to Anguilla via St. Martin, so we took the easy route and hopped on the public ferry. Tickets are about $15 per person plus a $5 departure tax, and boats depart every 45 minutes. The ride itself is only about 25 minutes, and the entire process—ticketing, embarkation, and customs—was simple and comfortable. An important piece of advice: sit inside the ferry if you don’t want to get splashed. A few members of our team sat on deck and felt some ocean spray.

Private ferries are also available, which are smaller, often include transportation to/from the airport, and are a bit quicker (we took a private ferry on the way back, and the ride was about 20 minutes). If you’re looking for convenience above cost, a private ferry is definitely the way to go. If you don’t want to travel from St. Martin, you can also fly directly to the Clayton J. Lloyd International Airport in Anguilla.

Once we arrived in Anguilla, our already-high spirits immediately soared—a testament to the island’s incredible hospitality. We received the warmest welcome imaginable (prompting one agent to declare Anguilla “the friendliest island ever”) before piling in our rented Escalade to head to our villa.

On the way, one of the agents asked our driver, Mr. Bennie, the one thing we should know about Anguilla, and we’ll never forget what he said: “Get to know our people first, then enjoy the beaches and take time to taste our food.” People, beaches, and then food: It became our Anguillan mantra. As we made our way to our villa, along streets dotted with well-kept one-story homes, people waved at us and smiled. Mr. Bennie told us that it only takes about 45 minutes to drive around the entire island. There is such a pervasive community spirit in Anguilla, and though we had just arrived, we already felt like part of their private island world.

Where to Eat

When you stay in a luxury villa, you have a guaranteed delicious gourmet experience at every meal. Anguilla is known for its vibrant international cuisine, influenced by native Caribbean, African, Spanish, French, and English traditions. Your private chef will serve up all the local classics Iike spiny lobsters, mahi-mahi, conch fritters, and Johnny Cakes tailored to your personal tastes. Chef Shermon at The Sea Villa, where we stayed on our latest trip to Anguilla, was no exception; his menus were extraordinary, and it was incredibly relaxing to eat a 5-star meal on the pavilion overlooking the water. We did manage to venture out of our villa to check out a couple very different, but equally excellent, establishments.

Picantes is a casual and fun Mexican restaurant in a colorful house off the road to the West End. We were seated at a candlelit table and met by Zoe, the chef at the Bird of Paradise Villa. Zoe’s daughter, Chloe, owns Picantes, and the mother-daughter team created the menu together. The food was wonderfully fresh, right down to the herbs grown outside of the restaurant. We highly recommend the spinach artichoke dip, calamari, guacamole, and fish tacos (they made West Coast tacos taste like Taco Bell). And of course, you can’t forget the margaritas.

For a great place to catch a sunset and sip champagne, head to Sunset Lounge at Viceroy. Set atop a coral point where Barnes Bay and Meads Bay meet, this high-end bar is ultra-modern and sophisticated. One agent summed it up perfectly: “The place for 30-something New Yorkers.” We snacked on sushi straight from the sea as we enjoyed a stunning view of the shimmering water.

On Anguilla, we found that magic blend of absolute luxury and laid-back, carefree living. The sand was the whitest, cleanest, and softest we’ve ever stepped foot on, and the food was as fresh and delicious as could be. But Mr. Bennie was absolutely correct in his advice—it was, in fact, the people that made the biggest impression on us. Friendly, kind, and open, the Anguillan people welcome you with open arms and are eager to share everything their tiny Caribbean gem has to offer. We’ll be back.