5 Days in Anguilla: First-Timer Itinerary

5 Days in Anguilla: First-Timer Itinerary

Five days is where an Anguilla itinerary stops chasing new sights and starts protecting pace. The first four days cover the headline beaches, a first offshore cay, and Scilly Cay’s grilled lobster at Island Harbour; day five is deliberately open, a repeat visit to whichever beach won you over, plus a Little Bay snorkel if the mood strikes. Anguilla is a British Overseas Territory, not a corner of neighboring St Martin, and almost every visitor arrives through Sint Maarten’s Princess Juliana Airport (SXM) before finishing the last leg by ferry. Prices run in East Caribbean dollars pegged at EC$2.70 to the US dollar, though menus quote USD directly, and this island is upscale by deliberate policy, not a cheap one. Only have a few days? See the 2-day , 3-day and 4-day itineraries. Staying longer? The 6-day and 7-day versions add a St Martin day trip on top of this same route. Our Anguilla travel guide covers the planning details this post doesn’t repeat.

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Day-by-day at a glance

Day Focus Travel time Daily cost (approx)
1 SXM arrival, ferry over, settle in, Shoal Bay East Ferry 20-25 min Marigot to Blowing Point; taxi hops 15-20 min roughly $150-250
2 Meads Bay morning, Rendezvous Bay beach-bar evening Taxi hops 15-25 min around the West End roughly $150-300+
3 Offshore cay day: Sandy Island or Prickly Pear Boat transfer 5-15 min from Sandy Ground roughly $200-300
4 Scilly Cay lobster lunch, full island loop by car Drive loop roughly 45 min end to end roughly $200-350
5 Little Bay snorkel, repeat your favorite beach Whatever’s closest, or nothing at all roughly $100-200

Day 1: landing, the ferry hop, and Shoal Bay East

Most first-timers touch down at Princess Juliana International Airport (SXM) on Sint Maarten, then taxi across to the ferry pier at Marigot: the airport sits on the Dutch side, the boat leaves from the French side, so budget a separate transfer between the two. The public ferry runs eight scheduled crossings a day, takes 20 to 25 minutes, and costs roughly $30 for an adult one way plus a departure tax that genuinely varies by source, confirm the current figure at gov.ai before you plan the day’s spending. Flew American’s nonstop from Miami straight into Clayton J. Lloyd instead? Then you skip the ferry entirely.

Clear customs, collect a rental car if the day four island loop is on your list (a temporary local driving permit is required, roughly $25 for three months or $15 for a short stay, bought through the rental company, and driving here is on the left, the British-territory rule that catches out first-timers given right-hand-drive St Martin sits a short ferry ride away). Drop your bags at a West End base near Meads Bay or in Sandy Ground, then head straight to Shoal Bay East for the afternoon: a two-mile run of powder-white sand with reef right off the shore and a line of beachfront bar shacks for lunch. Stay put for dinner at one of those shacks and let day one set the pace for the rest of the trip.

Day 2: Meads Bay’s morning into Rendezvous Bay’s beach-bar evening

Spend the morning at Meads Bay, the glossiest stretch of sand on the island and home to Blanchards, whose casual Beach Shack arm runs 11:30am to 8pm and skips Sunday, no reservation needed, though the main restaurant next door does want one. By early afternoon, move to Rendezvous Bay on the south-west coast, a long, quiet beach with a clear sightline across the channel to St Martin and two genuine destination bars of its own, Sunshine Shack and the Dune Preserve, the latter owned by reggae musician Bankie Banx and home to the annual Moonsplash festival. If your dates land on a Sunday, several beach bars island-wide run a weekly “jump-up,” a live-music beach party worth chasing down.

Day 3: your first offshore cay, Sandy Island or Prickly Pear

This is the day a 5-day trip earns its keep over a shorter one. Sandy Island is a tiny sandbar islet roughly a 5-minute boat ride from Sandy Ground, with its own restaurant, hammocks, and loungers right on the sand. Prickly Pear is a slightly bigger cay with two long-running beach restaurants, Agatha’s and Johnno’s, plus better snorkeling and shade under thatch umbrellas. Either works, book the crossing above rather than showing up and hoping for a spot.

Back on the mainland by mid-afternoon, swing through The Valley, the low-key capital, and the Heritage Collection Museum if it’s open, hours and admission for this small, locally-run museum aren’t reliably published, so treat a visit as a bonus rather than a fixed plan. Close the day with dinner near your base, you’ve earned a quiet one after a full day on the water.

Day 4: Scilly Cay’s lobster lunch, then a full loop of the island

Head to Island Harbour on the quieter east end for Scilly Cay, the island’s classic wave-it-down lunch spot: stand on the pier and a dinghy motors across to collect you, no phone booking involved. Grilled lobster and crayfish are the reason people build a day around this place, but it historically opens only a few specific days a week, commonly cited as Wednesday, Friday and Sunday, so confirm the current open days before you commit an afternoon to it.

Spend the rest of the day taking the rental car (with that temporary permit from day one) on a full loop of the island, an easy 45 minutes end to end, swinging past Maundays Bay’s exclusive curve of sand on the far west end and back along the East End’s quieter fishing-village stretch. It’s the one day on this itinerary built around covering ground rather than sitting still, and with five days to work with, you can afford it.

Day 5: Little Bay, a repeat-favorite beach, and no fixed plans

This is the day that separates a 5-day trip from a 4-day one, and it isn’t about adding another sight. Anguilla simply doesn’t have enough distinct headline attractions to fill a fifth day with fresh checklist items, so the honest move is to slow down instead. Start with a Little Bay snorkel if you want one: a secluded north-coast cove with genuinely good visibility, reachable by boat or a rope-assisted scramble down the cliffside, treat the rope route as needing a current-conditions check rather than a guaranteed DIY option.

After that, go back to whichever beach won you over earlier in the week. Loved Shoal Bay East’s reef? Return for a longer swim. Preferred Meads Bay’s sunset or Rendezvous Bay’s beach-bar scene? Do it again, slower, with no boat to catch and nowhere else on the list. A repeat afternoon on a beach you already know beats a rushed first visit to a fourth or fifth beach you don’t, and five days is exactly enough runway to prove it.

Is 5 days too long for a first Anguilla trip?

No, but it changes what the trip is for. Anguilla has no interior sights, no mountains, and a roughly 45-minute end-to-end drive, so four days genuinely covers the headline beaches, a cay, and Scilly Cay. The fifth day buys pace, not more ground, a repeat beach visit or a Little Bay snorkel rather than a new must-do stop. If that sounds like padding, a 4-day trip covers the same substance in less time.

Is Scilly Cay worth building day four around?

Yes, more than a second straight beach day would be. It’s a genuine local institution, wave-down pickup, grilled lobster, heavy-handed rum punch, and it only runs a few days a week, so it earns a dedicated slot rather than a maybe-if-we-pass-by mention. Just confirm its current open days before you lock day four in around it.

Is Anguilla safe for a first-timer?

Mostly yes, with one caveat worth stating plainly. The UK Foreign Office’s current advisory for Anguilla flags a documented 2025 uptick in gang-related gun crime and robbery alongside its otherwise routine guidance, so check the current advisory before you go and keep ordinary city-level caution. Day to day, strong sun, rip currents on windier stretches, and cost are the more likely issues for a beach-focused first-timer.

What to sort before you land

The East Caribbean dollar (EC$/XCD) is the official currency, pegged at $1 to EC$2.70 since 1976, but US dollars work everywhere and most tourist prices are quoted in USD directly, so you rarely need to think in EC$ at all. What you do need to plan for is cost: Anguilla runs no cruise ships, no casinos, and no high-rise hotels by deliberate policy, which keeps it upscale and genuinely pricier than most of its neighbors, not a budget stop. Check ivisitanguilla.com for current beach and cay-transfer details before you lock the schedule in, and keep a bit of physical cash on hand for the cay boats and Scilly Cay’s dinghy pickup.