Anguilla Off the Beaten Path: 6 Days
Six days in Anguilla is two days past the point where the island still has new sights to hand out, and this itinerary says so upfront instead of padding the schedule to look busy. The first four days cover the headline beaches, the first offshore cay, and the island loop ending at Scilly Cay’s wave-down lobster lunch; day five trades Anguilla for a Sint Maarten day trip, and day six gives you nothing new on purpose. Prices run on the East Caribbean dollar, pegged at a flat EC$2.70 to US$1 since 1976, so the arithmetic stays simple even when the total does not. This is a British Overseas Territory that prices itself like one, not a St Martin suburb and not a bargain.
This route nests inside the 5-day plan with a full Sint Maarten day trip promoted to its own day six; the 7-day version stretches the same spine with more deliberately empty beach time, not more sights, since six days is already past the point where Anguilla runs out of fresh checklist items. Starting from scratch, the 2-day through 4-day plans cover the beaches, the first cay day, and the island loop without ever needing a passport stamp for St Martin.
Book these before you go:
- A Sandy Island or Prickly Pear cay tour : calm-weather days fill the outbound boats fast, so lock in the cay day before you land rather than hoping for a spare seat at Sandy Ground.
- An Anguilla snorkeling or reef boat trip : worth booking if you’d rather skip the cliffside rope scramble down to Little Bay and arrive by boat instead.
- A Meads Bay or Rendezvous Bay stay : six nights on the west-end resort row sells out first in the December-April dry season, exactly when a longer trip needs a fixed base for the whole stay.
| 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 | Sint Maarten day trip via ferry | ~25 min ferry each way, plus taxis on the other side | ~150-250 |
| 6 | Unstructured repeat beach day, Prickly Pear optional | as little or as much driving as you like | ~80-140 |
Day 1: Shoal Bay East and the No-Cruise-Ship Coastline
The typical Anguilla arrival doesn’t touch Anguilla at all for the first hour. You land at Princess Juliana International Airport (SXM) on Sint Maarten, then continue on the public ferry from Marigot to Blowing Point, a crossing of roughly 20-25 minutes with eight scheduled sailings a day and no reservation needed. Budget a separate taxi between the airport and the Marigot pier, since SXM sits on the Dutch side and the ferry leaves from the French one; Anguilla’s own airport, Clayton J. Lloyd (AXA), handles a smaller slate of regional flights and, some years, a Miami nonstop, worth checking directly if the ferry route sounds like one leg too many.
Settle into a base on the west end, Meads Bay or Sandy Ground both suit a six-day trip, then give the rest of day one to Shoal Bay East, two miles of pale sand with a reef close enough to snorkel from the shore. Entry is free here, and at all of Anguilla’s 33 beaches , because charging for sand was never the plan: no cruise dock, no casino, no high-rise hotel, all by policy rather than accident. Pick a beach shack, order whatever is on the grill, and let day one end there.
Day 2: Meads Bay, Rendezvous Bay and the Sunday Jump-Up
Meads Bay is the glossiest stretch on the island, turquoise water backed by the 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 somewhere in the next six days, since a cheap Anguilla dinner isn’t 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 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 trusting 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, and it’s also where day six can circle back to if a second cay lunch beats a second beach afternoon.
A cay day beats a fourth beach day on a trip this length. 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 days five and six both lean on that same logic, just off-island and unhurried instead of off-shore and scheduled.
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 can’t: 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 for non-guests, 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 it.
Finish the loop at Island Harbour on the east end for Scilly Cay, the kind of place that doesn’t really run on 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. Driving is on the left here, a British-territory habit that catches out plenty of visitors arriving straight from right-hand-drive St Martin.
Day 5: Sint Maarten, the One Day You Leave Anguilla
Day five sends you off-island entirely, back across the same ferry route you arrived on, this time toward Marigot’s French-side cafes and Philipsburg’s Dutch-side duty-free strip and casinos, a genuinely different register from anything Anguilla itself offers. Anguilla has no casino and no cruise dock by design, so a taste of louder, glossier Caribbean tourism is a Sint Maarten specialty, not an Anguilla one, and that contrast is the actual reason to spend a day on it rather than a fifth beach day back home.
A packaged Sint Maarten day trip from Anguilla bundles the ferry crossing with a driver on the other side, worth it if two currencies, two languages and two sides of one island in a single afternoon sounds like more logistics than a vacation day should ask of you. Budget the same 20-25 minute crossing each way, plus whatever departure tax happens to be charging that day, since the fare tables genuinely disagree with each other on that one number.
Day 6: Repeat Beach Day, Deliberately
Day six has no new landmark on it, and that’s not an oversight. By now you’ve covered the beaches that earn the reputation, the first cay, the island loop, and one full day entirely off Anguilla, so the honest move is to return to whichever beach won the week rather than manufacture a sixth attraction the island doesn’t have. Shoal Bay East for one more snorkel, Rendezvous Bay for one more sunset with the Dune Preserve’s speakers going, or a return trip to Prickly Pear for Johnno’s or Agatha’s if a second cay lunch beats a second beach afternoon, all count as a legitimate day six. The point of a six-day Anguilla trip isn’t more checklist items, it’s this exact kind of unhurried repeat, and pretending otherwise is how itineraries end up inventing attractions that don’t exist.
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 and day five’s destination, are separate jurisdictions entirely. The mix-up is understandable since nearly every visitor flies into St Martin’s airport and ferries over from there, twice on a trip like this one, but Anguilla was briefly grouped with St Kitts and Nevis instead, until a 1967 revolution ended that arrangement for good.
Is the Sint Maarten Day Trip Worth a Day of Your Trip?
Yes, specifically because it’s different, not because Anguilla runs short on beaches by day five. Casinos, duty-free shopping and a livelier restaurant scene don’t exist on Anguilla by policy, so a day trip is the only way to get them without a flight home, and it breaks up a week that would otherwise be five nearly identical beach days back to back. Skip it only if you’d rather spend that day on a second cay or a favorite beach instead, which is also a legitimate six-day plan.
Is Anguilla Safe for Six Days?
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, don’t resist during a robbery, keep valuables out of sight. None of that describes a typical six-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 and cross-reference it against anguillaferrytimes.com , since fares and departure taxes are cited differently across sources and genuinely disagree with each other. 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 six-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’s 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 go stand on the beach for it instead of booking a third cay day.