Anguilla 5 Day Itinerary (No Tourist Traps)

Anguilla runs on the East Caribbean dollar, pegged at EC$2.70 to the US dollar since 1976, but almost every price you’ll see quoted is already in USD, and that price runs higher than you’d expect. No cruise ships, no casinos, no high-rise hotels, that’s deliberate policy, not an accident of underdevelopment, and it’s why this British Overseas Territory (its own jurisdiction, not a satellite of St Martin/Sint Maarten next door) reads as upscale rather than cheap. Five days here is enough to cover the headline beaches, two offshore cay days, and Scilly Cay’s grilled lobster, and still leave day 5 blank on purpose: a 33-beach island runs out of new things to show you well before it runs out of days.

This is the 4 day itinerary with a fifth day added on for a slower finish, and everything in the 3 day and 2 day routes still holds underneath it. Staying longer than 5 days? The 6 day and 7 day itineraries add a St Martin day trip rather than invent new Anguilla sights, because there genuinely aren’t enough left to invent.

Book these before you go:

Day Focus Travel time Rough daily cost (USD)
1 Arrival via SXM and ferry, Meads Bay settle-in, Shoal Bay East 20-25 min ferry, Blowing Point to Marigot $100-180
2 Rendezvous Bay, Sunshine Shack, the Dune Preserve, a Maundays Bay drive-by Short taxi or rental car, West End $80-150
3 First cay day: Sandy Island or Prickly Pear, Heritage Collection Museum 5-15 min boat from Sandy Ground $110-190
4 Scilly Cay lobster lunch, full island loop by rental car, Little Bay snorkel About 45 min for the whole island loop $120-200
5 Unstructured repeat beach day, your call which one None, you’re staying put $60-130

Day 1: Get In, Get to Meads Bay, Do Nothing Ambitious

Most visitors don’t fly into Anguilla directly. You land at Princess Juliana International (SXM) on Sint Maarten, then take the public ferry from Marigot to Blowing Point, about 20-25 minutes, roughly eight sailings a day, a one-way adult fare around $30 plus a separate departure tax that varies by category, confirm the current figure at gov.ai rather than trust whatever number an old blog quotes. Want to skip that transfer entirely? American Airlines flies Miami direct into Anguilla’s own Clayton J. Lloyd Airport (AXA), check the current weekly frequency at aa.com before you build a schedule around it, it’s changed more than once in the last few years. Settle into a Meads Bay or Sandy Ground base, then spend what’s left of the day at Shoal Bay East, a real 2-mile run of the kind of sand that keeps landing on “world’s best beach” lists, with a reef close enough to snorkel straight off it. Blanchards’ casual Beach Shack, right on Meads Bay, is walk-in only, save the main Blanchards dining room, reservations required, for a later night.

Day 2: Rendezvous Bay, Two Beach Bars, and Why Maundays Bay Isn’t Really for You

Rendezvous Bay is the quieter answer to Shoal Bay East, a long west-facing beach with a clear sightline across the channel to St Martin, plus two of the island’s best-known beach bars: Sunshine Shack and Bankie Banx’s Dune Preserve, home of the Moonsplash festival most years around March. Drive or taxi past Maundays Bay on the far west end while you’re out there, it’s genuinely one of the prettiest curves of sand on the island, but in practice it functions as the Cap Juluca resort’s private beach, so treat it as a look rather than a beach day unless you’re staying there or booked for a meal. Close the day back at Sandy Ground, the harbor town with the island’s real concentration of casual restaurants and the closest thing Anguilla has to a nightlife strip.

Day 3: The First Cay Day, Sandy Island or Prickly Pear

Book a short boat out of Sandy Ground to Sandy Island, about 5 minutes across, a sandbar islet with an on-site restaurant and bar, loungers, and a resident masseuse, or to Prickly Pear, where Agatha’s (running 20-plus years) and Johnno’s are the two beach restaurants worth choosing between, both with better snorkeling than anything directly off Shoal Bay. Either cay beats a straight fourth beach day: the food and the boat ride are real differentiators a repeat stretch of sand can’t offer. If there’s daylight left, swing through The Valley, Anguilla’s low-key capital, and the Heritage Collection Museum, a small, locally run museum covering the island’s history from the pre-Columbian period through the 1967 revolution against rule from St Kitts (a real, citable event, Anguilla isn’t part of St Kitts and Nevis either). Hours and admission shift, call ahead rather than trust an old figure.

Day 4: Scilly Cay’s Lobster, an Island Loop by Car, Little Bay

Scilly Cay, off Island Harbour on the east end, runs on the kind of informal system that trips up anyone expecting a normal restaurant: you wave from the pier and a dinghy motors over to collect you, no reservation line, no app. The draw is grilled lobster and crayfish with a heavy rum punch chaser, but it’s historically open only a few days a week for lunch, commonly cited as Wednesday, Friday, and Sunday, confirm before you plan a day around it, and don’t trust the venue’s own website for current hours, its domain currently resolves to a parked page. Pair the lunch with a full island loop by rental car (get the temporary Anguilla driving permit from the rental company first, roughly $25 for three months or $15 for three days, and remember driving is on the left), the whole loop runs about 45 minutes end to end, taking in Maundays Bay and the East End on the way. If you’d rather swim than drive, Little Bay is a secluded north-coast cove reachable by boat or a rope-assisted scramble down the cliff, worth confirming the rope’s still in good shape before you rely on it, with snorkeling as good as anywhere on the island.

Day 5: The Day With Nothing New On It

This is the day most 5-day Anguilla itineraries fake a new activity to fill, don’t. Go back to whichever beach from days 1 through 4 pulled at you hardest, Shoal Bay East for the reef, Rendezvous Bay for the quiet, and stay there. The honest case for a fifth day on an island this size was never more checklist, it’s pace: a slower morning, a repeat lunch at a beach bar you already liked, no new sights because the island doesn’t have enough distinct ones left to show you (that’s also why the 6 and 7 day versions of this route add a St Martin ferry day rather than more Anguilla). Head back through Blowing Point or AXA depending on which way you flew in.

Is Anguilla Part of St Martin?

No, and it’s a common mix-up given you’ll almost certainly fly into St Martin/Sint Maarten’s airport to get here. Anguilla is its own British Overseas Territory, a separate jurisdiction from the split French/Dutch island 12 miles south, run under its own House of Assembly and Chief Minister with a UK-appointed Governor retaining defense and policing. St Martin is a transit point and, on a longer trip, a deliberate day-trip change of pace, not part of Anguilla itself.

Is 5 Days Too Long for an Island This Small?

Only if you insist on filling every day with something new. Anguilla is roughly 45 minutes end to end with no interior sights or mountains to manage, so 2-3 days genuinely covers the headline beaches and one cay already. Five days works if you accept the honest trade you’re making: more pace, more repeat beach time, one more cay, not a longer list of checklist sights the island was never going to produce.

Is Anguilla Safe to Visit Right Now?

Mostly, with one caveat worth stating plainly rather than smoothing over. The UK Foreign Office’s most recent update flags a documented 2025 spike in serious gang-related gun crime and robbery, corroborated by a community anti-gun-violence march held on the island in August 2025, alongside the standard advice to avoid isolated areas after dark and keep valuables out of sight. That’s real and current, but violent crime aimed at tourists specifically stays rare. The bigger everyday risks for this itinerary are strong sun, rip currents on the windier north-coast beaches, and underbudgeting for an island that costs more than it looks like it should.

Pack a printed copy of your ferry confirmation and your accommodation’s address, phone signal drops mid-crossing between Sint Maarten and Blowing Point, and a taxi driver working off a name alone at the terminal wastes ten minutes you don’t need to lose on day 1.