6 Days in Anguilla: First-Timer Itinerary

6 Days in Anguilla: First-Timer Itinerary

Six days is enough to run Anguilla’s entire spine, then know exactly when to stop inventing new stops. Days one through five cover the headline beaches, your first offshore cay, Scilly Cay’s grilled lobster, and a full island loop by rental car, the same route the shorter trips use with room to actually enjoy it. Day six leaves Anguilla altogether for a ferry over to Sint Maarten, because by then the checklist has genuinely run dry and a change of pace beats a manufactured fourth beach. Anguilla is a British Overseas Territory, not a piece of neighboring St Martin, and prices run in East Caribbean dollars pegged at EC$2.70 to the US dollar, though this island is upscale by deliberate policy, not a cheap one. Shorter trip? See the 2-day , 3-day , 4-day and 5-day itineraries, this route builds straight on top of all four. Got a full week instead? The 7-day itinerary adds one more unstructured day, not a longer checklist. 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 First offshore cay: Sandy Island or Prickly Pear, then The Valley Boat transfer 5-15 min from Sandy Ground roughly $200-300
4 Scilly Cay lobster lunch, Little Bay snorkel Taxi or drive 20-30 min to Island Harbour roughly $180-300
5 Full island loop by rental car, Maundays Bay, East End About 45 min for the whole loop roughly $150-250
6 Sint Maarten day trip: shopping, casinos, livelier dining 20-25 min ferry each way, plus a taxi between Marigot and Philipsburg roughly $120-220

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

Land at Princess Juliana International Airport (SXM) on Sint Maarten first, a genuine first-timer surprise, then taxi to the ferry pier at Marigot: the airport sits on the Dutch side and the boat leaves from the French side, so budget a separate transfer between them. 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 budget the day. Flew American’s nonstop from Miami into Clayton J. Lloyd instead? Then you skip the ferry entirely.

Clear customs, and if the day-five island loop is the plan, pick up a rental car and the temporary local driving permit now, roughly $25 for three months or $15 for a short stay, bought straight through the rental company, with driving here on the left, the British-territory rule that catches first-timers off guard 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 get 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. Six days means you don’t have to cram day one, stay put for dinner at one of those shacks and ease into the trip.

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

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, generally held around March. If your dates land on a Sunday, several beach bars island-wide run a weekly “jump-up,” a live-music beach party genuinely worth chasing down.

Day 3: your first offshore cay, then The Valley

This is the day that separates a short Anguilla trip from a real 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 turning up and hoping for a spot on a boat.

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 anywhere, so treat a visit as a bonus rather than a fixed plan. Close the day with dinner back near your base.

Day 4: Scilly Cay’s lobster lunch, then Little Bay

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, and don’t trust the venue’s own website for current hours, its domain currently resolves to a parked page. Grilled lobster and crayfish are the reason people build a whole 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 to it.

With a full lobster lunch behind you, ease into the afternoon at Little Bay, a secluded north-coast cove with genuinely good snorkeling, 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. Six days buys you the luxury of a slow Little Bay afternoon instead of rushing it in behind an island loop, that comes tomorrow instead.

Day 5: the full island loop, and the day the checklist runs dry

Take the rental car (with that 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, effectively the private beach of the Cap Juluca resort and worth a look rather than a beach day unless you’re staying there, and back along the East End’s quieter fishing-village stretch. Be honest with yourself about what today actually is: a scenic drive that ties together beaches you’ve mostly already seen, not a new checklist item. That’s fine, that’s the point of a fifth day on an island this size.

Spend the rest of the afternoon back at whichever beach from days one through four pulled at you hardest, or use the free time for a second cay run if Sandy Island and Prickly Pear both tempted you on day three. Anguilla genuinely doesn’t have five distinct days of fresh sights, and pretending otherwise is how itineraries end up padded with filler. A slower afternoon repeat is the honest move here.

Day 6: the day that isn’t about Anguilla at all

Take the ferry back over to Sint Maarten, but treat it as a genuine change of pace rather than a rerun of your arrival day. The public ferry lands at Marigot, on the French side, good for boutique shopping and a proper lunch in Grand Case; the Dutch side, Philipsburg, is a short taxi away and has the casinos, the cruise-ship boardwalk, and a noticeably livelier restaurant and nightlife scene, none of which Anguilla has by design. There’s no border checkpoint between the French and Dutch sides, so combining both halves in one day is a straightforward taxi hop, not a second immigration queue. This day works precisely because it’s nothing like the rest of the trip, casinos, cruise crowds, and duty-free shopping are the opposite of what brought you to Anguilla in the first place.

Is 6 days too long for a first Anguilla trip?

Not if you use day six honestly. Anguilla has no interior sights, no mountains, and a roughly 45-minute end-to-end drive, so its own headline beaches, one offshore cay, and Scilly Cay’s lobster lunch fill four solid days on their own. Days five and six earn their keep only by adding pace and a genuine Sint Maarten change of scene, not by manufacturing more Anguilla checklist items the island doesn’t actually have.

Is the Sint Maarten day trip worth giving up a beach day for?

Yes, specifically this late in a trip. Anguilla’s own beaches and cays are genuinely better than anything Sint Maarten offers for sand and snorkeling, so day six isn’t an upgrade, it’s a deliberate change of pace: shopping, casinos, and a livelier restaurant scene Anguilla doesn’t have by policy. By day six you’ve already covered the island’s headline sights, so the day trip costs you nothing you hadn’t already banked.

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 across a full six-night stay, 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.