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There’s nothing better than a week in paradise, you’ll be able to probe deeper into the island diverse offerings while interacting with the warm personalities of the people.

It is recommended to rent a car, or engage the services of one of our knowledgeable Tax Operators to execute this itinerary. Be sure to always walk with your beach wear, towel and snorkeling gear as you will always be enticed to jump right in.


Type: Historical Cultural Seeker


Duration: 4 Days

Welcome to Anguilla

  • Arrival into Anguilla

    Step foot onto Anguilla and you’ll quickly find that this island has a wonderful and rich historical and cultural element to it, thanks in large part to our wonderful people. To truly experience this facet of the island, we encourage you to attend our local festivals and events. Or, relax and unwind in the hospitality suite of your accommodation. Indulge yourself in a welcome cocktail, refreshments and then grab some rest as tomorrow begins the real Anguilla Historical and Cultural experience.

  • Dinner

    Your first dinner is an important one as you fuel yourself for the wonderful and adventurous experiences that await. Anguilla offers many different dining options, so be sure to choose one that complements your style and taste.

  • Breakfast

    Start your history-rich day with an equally rich breakfast. Fuel up at any of our delicious restaurants or cafes before embarking on your journey.

  • Hiking Adventures

    Hike North Hill to Sandy Ground

    One of the best ways to experience Anguilla is through a guided hiking experience, facilitated by Anguilla National Trust. Hike the slinks down to the rocky coast, and traverse century-old trails to discover the ruins of a well-known sugar plantation estate. It’s an enriching experience all set against the backdrop of Sandy Grounds blue waters and the limestone cropping at Road Bay.


    Coastline Walk

    Rendezvous Bay to Maunday’s Bay
    Soak up the natural beauty of Anguilla’s turquoise waters while you stroll along the coastline of four breathtaking breaches.

  • Lunch

    Stop by one of Anguilla’s famed beachside restaurants for a casual barefoot lunch.

  • Anguilla Historical Tour

    Uncover Anguilla’s rich Amerindian history through a self-guided tour that combines driving and a little walking. This adventure will take you to the Big Spring Heritage Site with its 1000-year-old petroglyphs, the Old Valley Well, the Ebenezer Methodist Church, the Warden’s House (Koal Keel), the Old Court House, Sandy Ground, Road Pond, and Wallblake’s Plantation House.

    Tour the historical Lower Valley by walking alongside points of interest and buildings of national and historical importance, such as The Valley Well, Landsome Bowl Cultural Centre and St. Mary’s Anglican Church.

  • Dinner

    Stop by one of Anguilla’s famed beachside restaurants for a casual barefoot lunch.

  • Entertainment Pleasures

    Experience authentic Anguillian nightlife on Sandy Ground. Order a cocktail and dance the night away to the local Caribbean sounds.

  • Breakfast

    Fuel up for the day with a delicious breakfast on your outdoor patio or at any of our delicious restaurants and cafes.

  • Caves

    The adventure begins at the caves, an experience you won’t soon forget. These natural wonders present amazing views you won’t find anywhere else. And the tours are family friendly, an excursion all generations can enjoy.

  • Lunch

    Choose from the island’s wide variety of authentic Anguillian dining spots.

  • The Big Spring

    Mystical and captivating, Big Spring is one of Anguilla’s most famous historical sites. Frequented by the Amerindians as far back as 600AD, it offers a unique glimpse into Anguilla’s rich history.

  • Dinner

    As night falls, make your way to one of Anguilla’s local eateries. This time, may we suggest you seek out eclectic cuisine prepared by Anguilla’s master chefs.

  • Entertainment Pleasures

    Experience authentic Anguillian nightlife on Sandy Ground. Order a cocktail and dance the night away to the local Caribbean sounds.

  • Breakfast

    Sadly, it’s your last day here on the island with us. Get an early start and grab some fresh coffee and pastries with the family at any of our delicious cafes or restaurants. And while we don’t want you to leave, we understand you have to. So, be sure to pack up your things before departing.

  • Lunch

    Your last lunch with us should be magical. We recommend savouring something you’ve enjoyed eating while on Anguilla that will leave you energized for your travels back home.

  • Leaving Anguilla

    It was great having your entire family here with us. We hope you make plans to return in the future.

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