Anguilla is a firm favourite with the Original Travel team thanks to the seductive sense of relaxation that pervades this laid-back and sleepy backwater. That said, Anguilla is also home to some of the finest beaches and hotels in the Caribbean. We recently revisited this island after a couple of new hotel openings, and are delighted to say that the high standards have more than been maintained, making Anguilla holidays a great Caribbean option.

Anguilla holiday ideas

A few suggestions to get the holiday planning process started

Why visit Anguilla with Original Travel

Travelling with us to Anguilla means enjoying some of the Caribbean’s best beaches on a trip that has been crafted by our team of experts. Tailor-made with originality, quality and cultural immersion in mind, we can customise itineraries based on your taste, whether you’re a sun worshipper or food fanatic (Anguilla boasts the best food in the West Indies, in our opinion). Working with local guides, we’ll uncover places that are perfect for you. From hip beach bars to snorkelling spots, our curated suggestions are supported by an array of additional services, including a 24-hour helpline and an app full of recommendations.

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A few of the benefits of travelling with us to Anguilla

  • The Original Travel app
  • Airport lounge access
  • Destination Dossier
  • 24-hour helpline
  • Expert guides
  • 100% carbon absorption

Our Anguilla holiday collections

Discover different ways to explore Anguilla

Anguilla Guide

Practical advice and inspiration to help you prepare for your holiday

Anguilla Testimonials

1 reviews
4.5 / 5
"We had a dream stay in Anguilla that perfectly met our request for a holiday somewhere relaxing and beautiful. Our consultant arranged high quality services throughout, and the smartphone app was a great help in discovering great local restaurants and bars. We highly recommend it."
Ellen - Liverpool
Published on 2nd October 2019

Our Anguilla
specialists

Who better to entrust with your Anguilla travel plans than our team of passionate Caribbean consultants? With regular research trips, we stay up to date on the hippest beach bars and newest seaside properties – and our expertise doesn’t end there. While you’re away, we’ll hook you up with the best guides around, teeming with contagious passion for their beloved 15-mile-long country. They will be clued up on your likes and dislikes, for personalised tours and recommendations. In short, we’ve covered every possible travel-related base in Anguilla.

Need to know about Anguilla

The tiny island of Anguilla is the most northerly of the British Leeward Islands in the Caribbean. A British crown territory, the island is just sixteen miles long, three miles wide and shaped like an eel - or 'anguilla' in Spanish. We commend the choice of name - Eel Island doesn't have quite the same ring to it.


What you can find in Anguilla that you won't find anywhere else?

The island's real claim to fame, aside, that is, from Chuck Norris being a former resident, is the outstanding food on offer at the various hotels, restaurants and even beach shacks that dot the island. St Barths might have something to say about that, but on Anguilla the quality of food is in evidence far beyond the elegant confines of the hotels - in fact arguably the best restaurant on the island is Scilly Cay, a tiny island restaurant in the middle of a bay serving the delicious fresh lobster, caught that day, chosen by you and then barbecued to perfection and served with owner Eudoxie's extremely punchy rum punch.


What is there to do in Anguilla?

To burn off the inevitable holiday pounds, Original Travel can arrange fishing, windsurfing, waterskiing, sea kayaking, snorkelling (you can even snorkel round Scilly Cay after lunch) and diving. We can also organise a private yacht charter so you can explore Anguilla's hidden bays and more secluded beaches. And if the bright lights of neighbouring St Maarten catch your eye, the shops and casinos of Marigot Bay are just a few miles away.

Best places to go in Anguilla



100% tailor-made holidays

Understanding Your Needs

Our team of destination experts will get to know you and your unique requirements for your holiday

Personalisation

We work with you to build an ultra-personalised holiday itinerary with your choice of accommodation, experiences and activities

Our Services

All of our holidays include little extras designed to make a big difference to your trip, from fast-tracking you through airport check-in and security to our network of local Concierges