A Long Weekend in Anguilla: Offbeat Plan

Three days in Anguilla is not a rushed preview of a bigger trip: it is two full beach days at Shoal Bay East and Rendezvous Bay, then a third day that trades a fourth stretch of sand for a five-minute boat hop to Sandy Island. Prices run on the East Caribbean dollar, pegged at a flat EC$2.70 to US$1, and the tidy math is not a bargain signal. This is a British Overseas Territory, not a St Martin suburb, and it prices itself accordingly.

This route nests inside the 2-day plan with one cay day bolted on; the 4-day through 7-day versions add Scilly Cay’s wave-down lobster lunch, a full island loop by rental car, and eventually a St Martin day trip for a change of scene, since Anguilla runs out of fresh checklist items well before day six.

Book these before you go:

Day Focus Travel time Rough daily cost (USD)
1 Arrival via SXM and ferry, Shoal Bay East ~25 min ferry, then taxi ~120-180
2 Meads Bay, Rendezvous Bay, the Sunday jump-up taxi hops, 10-20 min each ~130-200
3 Sandy Island cay day ~5 min boat from Sandy Ground ~90-150

Day 1: Shoal Bay East and the No-Cruise-Ship Coastline

Most Anguilla trips start at Princess Juliana International Airport (SXM) on Sint Maarten, not on Anguilla at all; the island’s own airport, Clayton J. Lloyd (AXA), handles only a handful of regional flights and, some years, a Miami nonstop, so the standard route is SXM first, then the public ferry from Marigot to Blowing Point, roughly 20-25 minutes across open water with eight scheduled crossings a day and no reservation needed. Budget a separate taxi transfer from the airport to the Marigot ferry pier, since the airport sits on the Dutch side and the boat leaves from the French one, a small daily reminder that Anguilla and its neighbor are two different jurisdictions sharing one arrival route.

Settle into a base on the west end, Meads Bay or Sandy Ground both work, and give the afternoon to Shoal Bay East, a two-mile run of pale sand with a reef close enough to snorkel from the beach. There is no entry fee here, or at any of Anguilla’s 33 beaches, because charging for sand is not really the local style: the island has no cruise dock, no casino and no high-rise hotel by deliberate policy, and the row of beach shacks along Shoal Bay East is about as crowded as this coastline gets. Order whatever the shack next to you is grilling and let day one end there.

Day 2: Meads Bay, Rendezvous Bay and the Sunday Jump-Up

Meads Bay is the glossiest stretch on the island, turquoise water backed by a resort row that includes Blanchards, the closest thing Anguilla has to a landmark restaurant. Its casual Beach Shack arm runs 11:30am to 8pm, closed Sunday, no reservation needed for a walk-in table; save the formal dining room for a splurge night, since “a reasonably priced Anguilla dinner” is not really a category this island offers.

Cross to the south-west coast for Rendezvous Bay in the afternoon, a long quiet beach that keeps making Caribbean best-beach lists for reasons that have nothing to do with amenities, just sand and a clean sightline across the channel to St Martin. Two beach bars anchor it: Sunshine Shack, and the Dune Preserve, owned by Anguillian reggae musician Bankie Banx and home to the Moonsplash festival most years around March. If your three days happen to land on a Sunday, ask around for the island-wide jump-up, a running tradition of live-music beach parties hosted at several bars at once, not a single event tied to one venue.

Day 3: Sandy Island, the First Cay Day

Skip a third straight beach afternoon and take the boat instead. Sandy Island is a sandbar islet about five minutes off Sandy Ground, small enough to circle on foot in a few minutes, with its own bar and restaurant, hammocks strung between the handful of palms, and, genuinely, a masseuse who sets up on the sand some days. Boat operators running the crossing change from season to season, so ask at Sandy Ground or your hotel desk for whoever is currently running it rather than assuming a fixed timetable; this is a small-operator island where “the schedule” is closer to a suggestion. Prickly Pear, a slightly bigger cay with two long-running beach kitchens, Agatha’s and Johnno’s, is the fallback if Sandy Island’s boat is full.

This is the trade worth making on a three-day trip: a cay day beats a fourth beach day, because the boat ride and the lunch are genuinely different from anything on the mainland, in a way another stretch of the same white sand is not.

Is Anguilla Part of St Martin?

No. Anguilla is a British Overseas Territory, King Charles III its head of state through a resident Governor, with its own elected House of Assembly running domestic affairs. St Martin and Sint Maarten, the French-Dutch island 12 miles south, are entirely separate jurisdictions. The two get lumped together constantly, mostly because nearly every visitor flies into St Martin’s airport and ferries over from there, but Anguilla was never administered as part of either side of it; it was briefly grouped with St Kitts and Nevis instead, until a 1967 revolution ended that arrangement for good.

What Does a Long Weekend in Anguilla Actually Cost?

More than most Caribbean trips, and that is by design, not an accident of currency confusion. The official currency is the East Caribbean dollar, pegged at a flat EC$2.70 to US$1 since 1976, and US dollars work everywhere, so the arithmetic is simple even when the total is not small: a beach-shack lunch runs perhaps $20-30 a head, a Blanchards dinner considerably more, and the Meads Bay resort row prices itself against its own reputation, not against a backpacker budget. Free beach access at every one of the island’s 33 beaches (ivisitanguilla.com ) and casual beach-bar meals are the real cost levers here, not a hidden cheap tier waiting to be found.

Is Anguilla Safe for a Long Weekend?

Yes, with one caveat worth stating plainly rather than glossing over. The UK Foreign Office’s current Anguilla safety advisory notes a spike in gang-related crime involving guns and robbery, serious enough that the island held a community anti-gun-violence march in August 2025, and its standard precautions apply: avoid isolated areas after dark, do not resist during a robbery, keep valuables out of sight. None of that describes the profile of a typical three-day beach itinerary, and Anguilla stays low-key by regional standards, but check the current advisory before you fly rather than assuming a quiet boat-racing island carries no advisory at all.

Practical Notes

Driving is on the left, a British-territory habit that can catch out anyone arriving straight from right-hand-drive St Martin; most three-day visitors skip the rental car and the temporary driving permit entirely and use Anguilla’s fixed-rate taxis instead, no meters involved, and more than a few drivers moonlight as informal island guides for the ride. Check the current ferry schedule before you fly, since fares and departure taxes are cited differently across sources and are worth confirming rather than guessing at the pier. Pack for a genuinely dry, sunny island with no rainforest interior to duck into if a shower rolls through, so sun protection matters more than a raincoat. And if the racing flags along Sandy Ground’s harbor front look oddly serious for a beach vacation, that is because they are: sailing locally-built wooden boats is Anguilla’s national sport, a tradition traced to early-1900s laborers racing each other home from work on neighboring islands, not a photo op staged for the itinerary crowd.