Anguilla Off the Beaten Path: 4 Days
Four days in Anguilla is enough to stop checking things off a list. Two beach days at Shoal Bay East and Rendezvous Bay, a boat hop out to Sandy Island, then a fourth day built around Scilly Cay, the Island Harbour lobster shack you summon by waving from the pier. Prices run on the East Caribbean dollar, pegged at a flat EC$2.70 to US$1 since 1976, so the math stays simple even when the total does not. This is a British Overseas Territory, not a St Martin suburb, and it prices itself accordingly.
This route nests inside the 3-day plan with a fourth day of small-operator cay culture bolted on; the 5-day through 7-day versions stretch the same spine further, adding a full St Martin day trip and deliberately unstructured beach time, since a longer Anguilla trip buys pace, not a longer checklist. Starting from scratch, the 2-day plan covers just the headline beaches.
Book these before you go:
- A Sandy Island or Prickly Pear cay tour : calm-weather days fill the outbound boats fast, lock in the cay day before you land rather than hoping for a spare seat at Sandy Ground
- A Little Bay or reef snorkel trip : worth booking if you would rather skip the cliffside rope scramble down to Little Bay and arrive by boat instead
- A Meads Bay or Rendezvous Bay stay : the west-end resort row sells out first in the December-April dry season, exactly when a four-day trip needs a fixed base
| 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 |
| 4 | Island loop by rental car, Little Bay, Scilly Cay lobster lunch | ~45 min end-to-end drive | ~110-180 |
Day 1: Shoal Bay East and the No-Cruise-Ship Coastline
Most Anguilla trips begin at Princess Juliana International Airport (SXM) on Sint Maarten, not on Anguilla itself. The island’s own airport, Clayton J. Lloyd (AXA), handles a handful of regional flights and, some years, a Miami nonstop, but the standard route for a first four-day trip is SXM first, then the public ferry from Marigot to Blowing Point: about 20-25 minutes across open water, eight scheduled crossings a day, no reservation required. Budget a separate taxi between the airport and the Marigot ferry pier, since the airport sits on the Dutch side and the boat leaves from the French one.
Base yourself on the west end, Meads Bay or Sandy Ground both work for four days, and spend the afternoon at Shoal Bay East, two miles of pale sand with a reef close enough to snorkel straight off the beach. There is no entry fee, here or at any of Anguilla’s 33 beaches , because the island has no cruise dock, no casino and no high-rise hotel by deliberate policy, not by accident. Pick whichever beach shack is grilling something that afternoon and call it day one.
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, walk-ins welcome; save the formal dining room for one splurge night, since a cheap Anguilla dinner is not really on the menu anywhere on this island.
Move to Rendezvous Bay in the afternoon, a long quiet beach that keeps landing on Caribbean best-beach lists for reasons that have nothing to do with amenities and everything to do with a clean sightline across the channel to St Martin. Two beach bars anchor it, Sunshine Shack and the Dune Preserve, the latter owned by Anguillian reggae musician Bankie Banx and home to the Moonsplash festival most years around March. Land on a Sunday and ask around for the island-wide jump-up, a running tradition of live-music beach parties hosted at several bars at once, not one fixed event at 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 a handful of palms and, some days, an actual masseuse working the sand. The boat operators running the crossing shift season to season, so ask at Sandy Ground or your hotel desk for whoever is currently doing the run rather than assuming a posted timetable; this is a small-operator island where the schedule is more of 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 fills up.
A cay day beats a fourth beach day on a four-day trip. The boat ride and the lunch are different from anything on the mainland in a way another stretch of identical white sand is not, and day four doubles down on exactly that logic.
Day 4: Little Bay, the Island Loop and Scilly Cay’s Wave-Down Lunch
Rent a car for day four. It needs a temporary Anguilla driving permit bought through the rental company, cited at roughly $25 for three months or $15 for a short stay, plus your home license, and it buys you the one thing a taxi cannot: a full loop of the island in a single unhurried morning, since Anguilla runs tip to tip in about 45 minutes flat. Drive west past Maundays Bay, effectively Cap Juluca’s private beach and worth a look even if you are not staying there, then cut across toward the north coast for Little Bay, a secluded cove reached by a rope-assisted scramble down the cliffside. Check current conditions on that rope before committing to the climb; a short boat transfer from Sandy Ground covers the same cove without the scramble.
Finish the loop at Island Harbour on the east end for Scilly Cay, the kind of place that does not really have a booking system so much as a pier. Stand at the water’s edge and wave, and a dinghy motors across to collect you for grilled lobster and a rum punch strong enough to explain why nobody rushes lunch here. Scilly Cay has historically kept limited hours, commonly cited as Wednesday, Friday and Sunday for lunch only, so confirm the current open days before building your whole afternoon around it. Remember driving is on the left, a British-territory habit that catches out plenty of visitors arriving straight from right-hand-drive St Martin.
Is Anguilla Part of St Martin?
No. Anguilla is a British Overseas Territory, with King Charles III as head of state through a resident Governor and its own elected House of Assembly running domestic affairs. St Martin and Sint Maarten, the French-Dutch island 12 miles south, are separate jurisdictions entirely. The mix-up is understandable, since nearly every visitor flies into St Martin’s airport and ferries over from there, but Anguilla was briefly grouped with St Kitts and Nevis instead, until a 1967 revolution ended that arrangement for good.
Do You Need a Rental Car for Four Days?
Only for day four’s island loop; the rest of this itinerary runs fine on Anguilla’s fixed-rate taxis, no meters involved, and more than a few drivers moonlight as informal island guides for the ride. A rental car needs the temporary local driving permit above plus your home license, and it only pays off if you actually want to cover Maundays Bay, Little Bay and Island Harbour in one morning. Renting for all four days just to sit parked at a beach resort is money spent on a permit you will not use.
Is Anguilla Safe for a Longer Trip?
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, with standard precautions attached: avoid isolated areas after dark, do not resist during a robbery, keep valuables out of sight. None of that describes a typical four-day beach-and-cay itinerary, and Anguilla remains 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
Check the current ferry schedule before you fly, since fares and departure taxes are cited differently across sources and are worth confirming at the pier rather than guessing. Pack for a dry, sunny island with no rainforest interior to duck into if a shower rolls through, so sun protection matters more than a raincoat, and note that hurricane season officially runs June through November even though a dry-season four-day trip will likely never notice it. If the racing flags strung 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. Ask when the next race is, and go stand on the beach for it instead of booking another cay day.