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 resorts, stunning private villas, lovely beaches, excellent golf and some of the best food in the Caribbean. Indagare can advise on the best resort and villa options on the island.

  • Perfect for
    Families | Foodies | Romantics | Ultimate Indulgers
  • When to go
    December-February | March-May
  • Ideal length of stay
    3-5 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-LP

    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.

  • Member Stories

    “We loved our trip to Anguilla. The resort was fabulous ­– we felt so pampered! It was just the right amount of "busy."­ The restaurants, excursions, and spa treatments were excellent. Anguilla is my new favorite island”
    Elaine Ventola, member since 2016
Indagare's Lizzie McGirr
“Anguilla has long been a favorite of laid-back sophisticates looking for a beach escape. Boasting five-star hotels, private villas, fantastic local restaurants and more than 30 quiet stretches of talcum-powder sand beaches, the Caribbean island offers something for everyone.”
Sue and Robin Ricketts, developers of the Malliouhana
“It’s all about the people. Remember to chat to them, and you will learn a lot. New restaurants are sprouting up all the time, so check those out, too. Look for anything new that retains the cultural aspect of Anguilla.”

What To Read

Everything we recommend is sourced first-hand by our well-traveled team and incredible network of insiders and resources around the world. Here are some the latest articles, interviews, and book and film recommendations not to be missed.

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