Anguilla Destination Guide

The Island That Decided Not to Be Busy

Anguilla is a flat coral island in the northern Leewards, sixteen miles long and covered in low scrub, with none of the volcanic drama of its neighbors and roughly thirty three beaches that are among the finest in the world. There is no cruise port, no casino and no high rise development, and none of that is an accident. The island made a decision decades ago about what kind of place it wanted to be and has held to it, which is why a Tuesday in February on Shoal Bay East still means a long white beach with almost nobody on it. What it has instead of nightlife is food, and considerably more of it than an island this size should support.

The planning decision: getting there is the hard part

Anguilla has no long haul airport. Almost everyone routes through Princess Juliana on St. Maarten and then crosses, either by public ferry from Marigot or the Blowing Point service, by private boat transfer, or by a short hop on a small aircraft. The private boat and the charter flight cost more and remove almost all of the friction, and for a family arriving tired that is money well spent. There is also direct service into Anguilla's own airport from San Juan and increasingly from a few other points, which changes the calculation and should be checked for your dates. Whatever you choose, the last connection of the day is earlier than people expect.

Season, and a genuinely quiet calendar

The high season runs mid December through April, dry and breezy, with the peak at Christmas and New Year when the island fills with returning regulars. Spring is superb and quieter. The Atlantic hurricane season runs June through November and peaks from August into October, and Anguilla was hit hard by Irma in 2017 and rebuilt. A number of properties and restaurants close for part of September and October, so late summer travel needs the openings confirmed before anything is booked. Anguilla Summer Festival, with the boat racing, runs around the start of August and is the one week the island is genuinely loud.

Where to base, and which beach you want

Meads Bay on the north coast is the resort strip, a long curve of sand with several of the best hotels and restaurants on it, and it is the practical first choice. Shoal Bay East, further northeast, is the beach people photograph, with a handful of casual places on it and little else. Rendezvous Bay in the south is long and calm and looks across at St. Martin. Barnes Bay and Little Bay are smaller and quieter still. Sandy Ground is the harbor village and where the boats leave from. The island is small enough that a car turns all of it into a fifteen or twenty minute drive.

Stay strategy on a small, high end island

Belmond Cap Juluca on Maule Bay is the most recognizable property here, a line of white Moorish villas along the sand. Malliouhana above Meads Bay is the original grande dame, restored. Aurora Anguilla, the large resort and golf property at Rendezvous Bay, is the biggest thing on the island. Quintessence and Zemi Beach House are the small boutique end. Beyond the hotels, the private villa market is very strong and often the better answer for a family, since a house with staff on a quiet bay is precisely what this island is for.

When to begin

Six to nine months for the winter season, and a year for Christmas and New Year, when the returning regulars book their same weeks before leaving. Villas go earliest of all. The restaurants matter here as much as the room, and the handful of tables people travel for are reserved with the hotel rather than on arrival. Boat transfers, charters and any day sailing to the outer cays are arranged in the same conversation, because the schedules are limited and shared with St. Maarten traffic.

Four experiences worth building the days around

• A working through of the island's restaurants, which for a place this small is unreasonably good and the real reason people return.
• A boat day to Sandy Island or Prickly Pear, small sandbars off the north coast with a grill and nothing else.
• Shoal Bay East walked from end to end early, before anyone else is on it, which takes most of a morning.
• A crossing to St. Barths for a day or two, which is a short boat ride and a completely different atmosphere.

Who this trip suits

Anguilla suits couples above all, and it is one of the strongest honeymoon islands in the Caribbean for people who want privacy over scenery. It suits families in villas. It suits repeat Caribbean travelers who have tired of resorts with a thousand rooms. It suits anyone whose ideal day is a beach, a long lunch and a book. And it suits travelers who want St. Barths adjacency without the St. Barths scene.

When another plan may fit better

There is no nightlife to speak of, almost no shopping, and very little to see beyond the beaches, so anyone who needs a program will be bored by day four and should consider the Bahamas instead. Travelers wanting volcanic landscape, rainforest and things to climb should look at St. Lucia. And the connection through St. Maarten is a real cost in time that a direct beach trip to Turks and Caicos avoids entirely.

Plan it with one accountable advisor

Let us handle the arrival, because the St. Maarten connection is where most Anguilla trips go wrong and the fix is straightforward when it is planned rather than improvised. We set the villa or the hotel, the boat, the tables and the transfers together. Our luxury leisure travel planning covers it end to end.