About the island
The quietest island in the northern Caribbean.
Anguilla is a long, low, narrow coral island lying just north of St. Martin in the Lesser Antilles. Sixteen miles end to end and just over three at its widest, with thirty-three white-sand beaches and a population of around fifteen thousand. It is a British Overseas Territory and one of the most discreet upper-end destinations in the region — the kind of place that does not need to announce itself.
The defining feature of the island is the sand. Because Anguilla is coral rather than volcanic, its beaches are unusually white and unusually fine — the result of centuries of reef erosion deposited along a leeward coast protected from the open Atlantic. Shoal Bay East regularly appears on lists of the world’s finest beaches; Meads Bay, Rendezvous Bay, and Maundays Bay run it close. Most are quiet enough to be walked end-to-end without seeing another person.
Anguilla’s character is shaped by what it does not have — no high-rise development, no chain hotels at scale, and a single set of traffic lights on the entire island. What it does have is a long-standing British Caribbean culture, a deep musical heritage, and a restaurant scene that punches well above the island’s size. Recent years have brought direct flights from Miami; before that, Anguilla was reached only by ferry from St. Martin — an arrival that filtered out a particular type of guest.
“Anguilla is the rare Caribbean island that has chosen, deliberately, not to develop in the way the others have — and it is all the better for it.”
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When to go
Anguilla enjoys a stable tropical climate that is comfortable throughout the year. The high season runs from mid-December through April, with consistent trade winds and very low humidity. May and November are excellent shoulder months — warm, quiet, and meaningfully better value. The summer months bring more heat and the chance of a passing tropical system; Anguilla sits within the main hurricane belt and Irma made a direct strike in 2017, though the island has rebuilt comprehensively.
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Feb
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May
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Aug
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Oct
Nov
Dec
Peak season
Shoulder
Green Season
Getting there
Clayton J. Lloyd International Airport (AXA) was extended in 2024 and now accepts a wider range of jet aircraft, including direct service from Miami. The majority of guests still arrive via Princess Juliana International (SXM) on St. Martin and connect by a 25-minute ferry crossing.
Things to do
Anguilla rewards a particular kind of stay — long beach days, slow lunches, and quiet evenings at restaurants that take their work seriously. There is enough on the island to fill a fortnight without ever feeling busy.
The thirty-three beaches define the island. Shoal Bay East is the most photographed; Meads Bay, Rendezvous Bay, and Maundays Bay are the others most guests circulate through. The east-end beaches — Captain’s Bay, Savannah Bay — are quieter and require a short drive on rough road.
The Anguilla restaurant scene is exceptional for an island this size. Blanchard’s at Meads Bay has been the standard-bearer for thirty years; Veya, Straw Hat, the Place, and Cuisinart at the Aurora all sit at the upper end. Mango’s, Tasty’s, and the seafood barbeques on the east end are part of the rhythm.
Anguilla’s offshore cays — Sandy Island, Prickly Pear, Scilly Cay — are essential day trips. Sandy Island lunches and the snorkelling at Prickly Pear are well-established island rituals.
Anguilla has a deep music tradition. Bankie Banx’s Dune Preserve on Rendezvous Bay is the legendary venue; the Moonsplash festival in March and the August carnival (Summer Festival) anchor the calendar.
Anguilla’s national sport is wooden boat racing, with traditional sloops sailed by local crews. Anguilla Day (30 May) is the year’s main race; the August Monday races at Sandy Ground are equally serious.
The waters around Anguilla are clear and warm, with several wreck dives offshore. Shoal Bay East provides excellent snorkelling directly from the beach; the offshore reefs around Prickly Pear are reliably populated.
The major hotels — Cap Juluca, Four Seasons, Aurora, Malliouhana, Quintessence — all operate spas open to villa guests by reservation. A morning at Cap Juluca followed by lunch at the bar is one of the standing pleasures of the island.
Anguilla’s eastern half is largely undeveloped — quiet roads, salt ponds, and the windward beaches. The fish at Smokey’s at the Cove and a slow drive out to Captain’s Bay are a full afternoon.
Our Anguilla villa portfolio is concentrated along the leeward coast between Meads Bay and Rendezvous Bay — the protected, calm-water side of the island where most of the major beaches sit. A small number of properties on the east end offer something more remote and self-contained. Every villa has been visited and assessed by our team.
Long Bay Beach . Anguilla
Sea
12 Guests
6 Beds
Sun Loungers
Air-Conditioning
Heated Pool
Fully Equipped Kitchen
Communal Gym
Courtesy Bath Amenities
From
$ 5500 / night
Long Bay Beach . Anguilla
Sky
10 Guests
5 Beds
Parking
Sound System
WI-FI
Communal Gym
Air-Conditioning
Courtesy Bath Amenities
From
$ 4700 / night
Limestone Bay . Anguilla
Sandcastle Beach House
8 Guests
4 Beds
Sun Loungers
Jacuzzi
Parking
Private Garden
Fully Equipped Kitchen
Beach Access
From
$ 2448 / night
Practical information
Entry requirements
UK, US, EU, and Canadian passport holders. Six months’ passport validity required.
Currency
Eastern Caribbean Dollar, pegged at 2.70 to USD. USD universally accepted.
Climate
26–30°C year-round. Sits within the main hurricane belt; September is peak risk.
Electricity
US-style plugs (Type A/B). UK and European devices require adaptors.
Driving
British convention. Temporary local licence required, issued at car hire offices.
Time zone
Atlantic Standard Time. No daylight saving observed.
Connectivity
4G/LTE island-wide. All Simply Islands villas have fibre WiFi.
Healthcare
Princess Alexandra Hospital handles routine care. Serious cases transfer to Miami or Puerto Rico. Travel insurance essential.
A note from our team
Every Simply Islands villa in Anguilla has been personally visited by our team on the ground. We know which Meads Bay villas catch the afternoon light at the right angle, which Rendezvous Bay properties suit larger groups, and which of the east-end estates work for those wanting genuine seclusion. Call us if you would like honest guidance on the right pocket of the island for your group.
