Anguilla Holidays: An Overview

Anguilla is a firm favourite with the Original Travel team thanks to the sense of relaxation that pervades this laid-back and sleepy backwater, however it is also complete with 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 in 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.

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.

To burn off the inevitable 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.

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Map of Anguilla

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A Note on Price

All of our holidays are completely tailor-made and prices will vary based on things like when in the year you will be travelling, how far in advance you book and the level of accommodation you choose. The guide prices shown across this website are designed to provide you with a broad indication of how much to budget for your trip.

Itinerary Suggestions

A Week in Anguilla

7 Days

From $2,820pp