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.

Image of Alexandra Heriot Maitland
Image of Will Boocock
Image of Saskia Wilson

Saskia, Will and Alexandra are here to help give you the inside track.

Why we think you’ll love it

  • Miles and miles of beautiful white beaches, incredible resorts and the best restaurant scene in the Caribbean right now make Anguilla a fabulous holiday destination
  • For the amazing beach bbq lunches over on Scilly Cay - take the boat over to the island for a day of fresh fish and rum punch on the beach
  • There are no direct flights - but this just makes the island that little bit more exclusive than its neighbours

Luxury Anguilla Holidays: The Detail

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.

The architecture is sophisticated and the hotels subscribe to the island's determination to remain the finest gastronomic destination in the Caribbean.

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.

Did you know

  • Anguilla was discovered by Christopher Columbus in 1493
  • He also named the island 'Anguilla' for its 'eel-like' shape


Original Highlight

Image of Saskia Wilson

If you're lucky enough to be on Anguilla on a Sunday, don't miss heading to Jonno's beach bar on Sandy Ground for the afternoon to enjoy fresh snapper and live jazz music on the beach.

Saskia, Original Traveller

A note on price

Luxury Anguilla holidays aren't cheap, but if you travel out of season, the top hotels have rooms starting from around £320 a night. If you want to splash out and take the whole family at Christmas, you could easily spend several thousand a night. Learn more about our pricing

Weather in January January December February March April May June July August September October November
  • Average Temp. — 28°C / 82°F
  • Rainfall — 6cm / 2.7 inches
  • Water Temp. — 26°C / 78°F
Flight from London

8:00 hrs

Time Difference

GMT -4 hrs

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Emma & Tim

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