Anguilla Off the Beaten Path: 5 Days
Five days in Anguilla is where the itinerary logic quietly flips. By day five you have already covered the two beaches that earn the hype, taken the boat out to a cay, and looped the island by car, so the honest move is to stop hunting for a fifth attraction and slow down instead. This route runs the same spine as the four-day trip through Scilly Cay’s wave-down lobster lunch, then hands day five back to whichever beach won you over. Prices still run on the East Caribbean dollar, pegged at a flat EC$2.70 to US$1 since 1976, and five slow days do not make this British Overseas Territory any cheaper.
This route nests inside the 4-day plan with a fifth day of deliberately unstructured time bolted on; the 6-day through 7-day versions add a St Martin day trip for a genuine change of scene, since Anguilla runs out of fresh checklist items well before day six. Starting from scratch, the 3-day plan covers the same ground minus the wave-down lunch and the repeat day.
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 arrive by boat than take the cliffside rope scramble down to the cove
- A Meads Bay or Rendezvous Bay stay : the west-end resort row sells out first in the December-April dry season, exactly when a five-day trip needs a fixed base for the long haul
| 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 |
| 5 | Unstructured repeat day, favorite beach or Wallblake House | none required | ~60-120 |
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 five-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 five 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. 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 before day five pulls back on purpose.
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 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.
Day 5: The Slow Day, Because Pace Beats a Fifth Sight
Anguilla does not have a fifth headline sight waiting for day five, and pretending otherwise is how itineraries end up padded with a stop nobody actually wanted. The honest plan: sleep in, skip the taxi, and go back to whichever beach earned your loyalty on day one or two, Shoal Bay East for the reef, Meads Bay for the resort-row polish, or Rendezvous Bay if the Sunday jump-up won you over. If a slow morning still needs one small stop, the Wallblake House in The Valley, a restored 1780s plantation house turned local history site, is a genuinely low-key half-hour rather than a full excursion.
Skip anything that needs a boat reservation or a rental-car return deadline. Day five works precisely because nothing on it is time-boxed, and a five-day trip that tries to squeeze in a second cay run usually just means less time actually sitting on the beach you came for.
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 Five Days in Anguilla Buy You More Than Four?
Not more sights, just more pace. The island’s short list of headline beaches and cays is fully covered by day four, so a fifth day buys a slow morning and a repeat visit to a favorite spot instead of a new attraction. Three or four days covers the same ground faster; five just leaves room to sit still, which on an island this small is a genuine feature, not padding.
Is Anguilla Safe for a Five-Day 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 five-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 five-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 spend your slow fifth day on the beach watching for it instead of booking another cay day.