Anguilla 4 Day Itinerary (No Tourist Traps)

Anguilla runs on East Caribbean dollars pegged at EC$2.70 to the US dollar, but almost nothing here is EC$2.70 cheap. It’s a British Overseas Territory built deliberately around no cruise ships, no casinos, no high rises, and it is not part of St Martin even though nearly everyone flies into Sint Maarten first and takes the ferry across. Four days is enough for the two beaches that genuinely earn the hype, one offshore cay, and Scilly Cay’s grilled lobster, without inventing a fourth “must-see” the island simply doesn’t have.

This plan builds on our 3-day itinerary with a full extra day for a rental-car loop and Scilly Cay; go longer with the 5-day itinerary for a second cay day or a Sint Maarten detour.

Book these before you go:

Day Focus Travel time Daily cost (USD, roughly)
1 Arrival via SXM + ferry, Shoal Bay East ferry ~20-25 min, taxi 10-15 min to beach 100-160
2 Meads Bay, Rendezvous Bay beach bars 15-20 min taxi between beaches 90-150
3 Prickly Pear or Sandy Island, The Valley ~10-15 min boat to the cay 120-190
4 Scilly Cay lunch, island loop by rental car ~45 min end to end by car 140-220

Day 1: Shoal Bay East, once the ferry lands you

Most visitors fly into Princess Juliana International Airport on Sint Maarten, then take a taxi to Marigot and the public ferry to Anguilla’s Blowing Point terminal, a crossing of roughly 20 to 25 minutes with eight scheduled departures a day and no advance booking. Fares run around $30 one way plus a departure tax that varies enough between sources that it’s worth confirming the current figure on the ferry terminal’s official page before you travel. American Airlines flies direct from Miami into Anguilla’s own Clayton J. Lloyd airport, though confirm the current weekly frequency before you build a schedule around it; a handful of newer seasonal carriers serve the route too. Drop your bags at a Meads Bay or Sandy Ground base, then head straight to Shoal Bay East, a roughly two-mile run of powder-white sand on the north coast that shows up on more than one “world’s best beach” list and has genuinely good reef snorkeling right off the sand. Eat at the beachfront shack row rather than walking back to your hotel for lunch; nobody comes here for the service speed.

Ferry or fly direct into Anguilla?

The ferry is cheaper and runs all day without a reservation, but it adds an extra taxi leg on the Sint Maarten side and a second wait at immigration on arrival. A direct flight into Clayton J. Lloyd skips both of those, landing you closer to your hotel in under an hour from Miami, but only works if the current schedule lines up with your dates and budget. Most first-time visitors do the ferry once for the novelty and fly direct on a repeat trip.

Day 2: Meads Bay’s resorts, Rendezvous Bay’s beach bars

Meads Bay in the morning is the glossiest stretch of the island, turquoise water backed by the highest concentration of luxury resorts on Anguilla, and it’s worth a stop at Blanchards Beach Shack for lunch (11:30am to 8pm, closed Sunday) rather than the main restaurant if you want something casual and unreserved. In the afternoon, move to Rendezvous Bay on the west end, a long, quiet stretch with a clear sightline across the channel to St Martin, and post up at Sunshine Shack or the Dune Preserve, the beach bar owned by Anguillian reggae musician Bankie Banx and home to the Moonsplash festival most years around March. If your Day 2 happens to land on a Sunday, ask locally whether that week’s beach “jump-up” is running; it’s a recurring weekly tradition, not a one-off event, and worth building an evening around if the timing works.

Day 3: Your first cay day, plus The Valley

Book a short boat out to Prickly Pear or Sandy Island in the morning, both a matter of minutes from Sandy Ground rather than a half-day commitment. Prickly Pear has two long-running beach restaurants, Agatha’s and Johnno’s, plus chairs and shade already set up; Sandy Island is a genuinely tiny sandbar with one bar-restaurant, loungers, and reliably good snorkeling just offshore. Back on the main island by mid-afternoon, swing through The Valley, Anguilla’s low-key capital, for Wallblake House, a restored 1787 plantation great house that’s a quieter, more honest read on the island’s history than anything a resort brochure offers. The Heritage Collection Museum nearby covers the same history in more depth, though call ahead, since its hours and admission price aren’t consistently published anywhere.

Prickly Pear or Sandy Island, which cay first?

Prickly Pear wins if you want a proper sit-down lunch and real shade without paying for a full catamaran package; Sandy Island wins if you want the postcard sandbar-with-one-bar experience and don’t mind it being genuinely small. Neither is a wrong choice on a 4-day trip, and both beat spending the day on a third or fourth stretch of the same beach sand.

Day 4: Scilly Cay, a rental-car loop, and the ferry back

Scilly Cay off Island Harbour is the island’s best lunch, grilled lobster and crayfish reached by waving from the pier for a dinghy pickup rather than booking online; it’s historically open only a few specific days a week, so confirm the current schedule with Anguilla’s official tourism site before you build your last day around it. If it’s closed, use the morning instead for a full loop of the island by rental car, a genuinely easy drive given Anguilla runs tip to tip in about 45 minutes, taking in Maundays Bay (effectively Cap Juluca’s private beach, worth a look even if you’re not staying there) and the East End. Renting requires a temporary local driving permit, bought through the rental company, and remember driving is on the left, the British-territory convention that catches people off guard coming from right-hand-drive St Martin. Squeeze in a Little Bay snorkel if you have energy left; it’s reached by boat or a rope-assisted scramble down the cliffside, and the rope route is worth a local check before you rely on it. Work backward from your outbound flight or ferry: the crossing back to Marigot, the taxi to Sint Maarten’s airport, and the departure tax queue at Blowing Point add up faster than they look on paper.

Is a rental car worth it for four days?

Only if you want to drive yourself to Maundays Bay or the East End on your own schedule; a fixed-rate taxi covers the same 45-minute-long island perfectly well without the permit paperwork or left-hand-drive adjustment. Travelers who’d rather not think about logistics on a short trip are better off with taxis and saving the rental for a longer stay.

Before you go

Carry both East Caribbean and US dollars; USD is accepted everywhere and most menus quote it directly, but the actual currency is the EC dollar, not the euro and not a free-floating local unit, so don’t expect this to be a budget island just because the math is easy. The UK Foreign, Commonwealth and Development Office’s current advisory notes a 2025 uptick in gang-related gun crime and robbery alongside the usual advice to avoid isolated areas after dark and keep valuables out of sight; ordinary tourist caution is enough, but it’s no longer accurate to call the island crime-free. Hurricane season runs officially June through November, with August to October carrying the highest storm risk, so travel insurance is a sensible add if your dates fall in that window.