Only 16 miles long and three miles wide, tiny Anguilla can surprise travelers with the breadth and variety of its luxury amenities. As part of the British West Indies, this flat island, whose name derives from the Spanish word for “eel,” is the northernmost Leeward Island and sits just 12 miles north of St. Martin. It is one of our favorite destinations in the Caribbean, with five-star hotels, stunning private villas, lovely beaches, excellent golf and some of the best food in the Caribbean. Like many islands in the region, Anguilla was hit hard by Hurricane Irma in September 2017, and some properties are still undergoing renovations. Indagare can advise on the best resort and villa options on the island.
Perfect forFamilies | Foodies | Romantics | Ultimate Indulgers
When to goDecember-February | March-May
Ideal length of stay3-5 Nights
Designing Your Journey
Work with Indagare to design the perfect itinerary for an immersive journey. Our travel experts know the destination inside and out, and they can make recommendations based on your travel needs and preferences.
3 Days: Essential Anguilla
Craft a customized itinerary that includes special access, touring and exclusive reservations. Here is just one example of what our destination experts can create for you.
Day One: The Beachfront
After checking in, enjoy a light lunch at your hotel and head down to the beach. Go for a walk, soak in the sunshine and explore your surroundings, then treat yourself to a massage before dinner at a local hot spot like the Sunset Lounge.
Day Two: Island Activities
Start your morning with fresh fruit and a bike ride around Anguilla. After lunch at Hibernia on the far eastern end of the island, explore the restaurant’s exquisite art gallery. Finish off the day with a private boat tour, followed by dinner at the classic restaurant Blanchard’s.
Day Three: Ultimate Relaxation
Indulge in a leisurely brunch at your hotel before walking to the beach for an afternoon of swimming and lounging, or else head to the CuisinArt’s 18-hole golf course. End the day with a beachside cocktail at one of Anguilla’s chic open-air properties, then dine at an Indagare-recommended local restaurant.
Where To Stay
We only feature hotels that we can vouch for first-hand. At many of them, Indagare members receive special amenities, including upgrades, early check-in, breakfast, spa credits and more. Look for the Indagare Plus logo in the reviews.
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Thirty years after Malliouhana became the standard-bearer for luxury in the Caribbean, it emerged in 2014 from a massive renovation as an Auberge Resort, with a new relaxed sophistication, updated design and major (and welcome) restaurant reboot.
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Four Seasons Anguilla
While it lacks the sense of place of Anguilla’s classic properties, the Four Seasons offers a sleek design, spacious accommodations, a large spa and gym and pampering service for both families and couples.
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