Anguilla 4 Day Itinerary

Most visitors to Anguilla never touch down on the island itself. You’ll fly into Sint Maarten, then cross by ferry, and that single detail shapes the whole first day more than any beach list does.

Day 1: Arrival and The Valley

  • Most travelers land at Princess Juliana International Airport on Sint Maarten, then take a taxi to Marigot on the French side and catch the public ferry to Anguilla’s Blowing Point terminal. The crossing itself takes about 25 minutes and runs eight times daily, with no advance reservations available, so arrive at least 30 minutes before your chosen departure. The one-way fare is 30 USD for anyone 12 and older, plus a separate departure tax that runs 28 USD on the French side. Budget close to 60 USD each way once fees are added up, more than most first-time visitors expect.

  • Before you even book flights, apply for the UK Electronic Travel Authorization if you’re a US citizen or from another non-exempt country, since Anguilla is a British Overseas Territory and this requirement has been enforced since January 2025. Sort it online well ahead of the trip; it is not something you can arrange at the ferry dock.

  • Check into your hotel and grab lunch in The Valley, the low-key capital. Fish stew, conch fritters, and fungi and peas (a cornmeal side dish, not literal fungus) are the dishes to look for on a local menu rather than a resort one.

  • Wallblake House, the last surviving plantation-era great house on the island, dates to 1787 and gives a quieter, more honest sense of Anguillan history than the beach-brochure version. A short guided walk through takes maybe 30 minutes.

  • Dinner in town, then an early night if the ferry crossing wore you out; Anguilla runs on island time and nobody will judge you for it.

My opinion on Day 1: don’t skimp on trip insurance here specifically because of the multi-leg travel. A missed connection through Sint Maarten with an inflexible ferry schedule can eat a full vacation day.

Day 2: Shoal Bay and the Outer Cays

  • Shoal Bay East earns its reputation honestly, powder-soft sand and startlingly clear water, and it’s busiest late morning through early afternoon. Get there before 10am if you want a stretch of beach to yourself.

  • Madeariman Bar and Restaurant sits right on the sand at Shoal Bay and does a lunch worth planning around, not just a quick bite; some evenings bring live music too. Tropical Sunset a bit further down the beach is the other name locals mention unprompted, particularly for the crusted snapper.

  • In the afternoon, book a boat out to Sandy Island or Prickly Pear Cays. Social catamaran trips with lunch and open bar run around 140 to 150 USD per person; a bare-bones local boat transfer to Sandy Island from Sandy Ground can be closer to 50 USD round trip if you just want the sandbar and snorkeling without the full package. Sandy Island is genuinely tiny, a strip of sand with a couple of palm-thatched bars, so temper expectations if you’re picturing a full island.

  • Dinner at leisure back near your hotel; nothing on Anguilla runs late by design, and most kitchens close by 10pm.

Day 3: Heritage and the North Coast

  • The Heritage Collection Museum in East End is a one-room, deeply personal museum built by a local historian rather than a government institution, and it’s a better primer on pre-colonial and colonial Anguilla than anything online.

  • Crocus Hill, the island’s high point at just 65 meters, still delivers a genuinely good panoramic view given how flat the rest of Anguilla is.

  • Big Spring, near Island Harbour, is a freshwater cave and petroglyph site rather than a beach stop, worth the detour if you’re interested in the island’s Amerindian history, which predates European contact by centuries.

  • Evening at Meads Bay or Maundays Bay for calmer swimming than Shoal Bay’s open Atlantic side. Both have beachfront restaurants worth booking ahead in high season, December through April, when the island fills up with a wealthier crowd and reservations tighten.

My opinion on Day 3: Meads Bay at sunset beats Shoal Bay for the golden-hour photo, the beach faces west and the water goes a color that doesn’t quite show up right in photos anyway, so just watch it.

Day 4: Departure

  • Keep the morning loose. A spa treatment at your hotel or a slow walk through a local farm stand beats cramming in one more attraction on a travel day.

  • Work backward from your outbound flight through Sint Maarten. The ferry back to Marigot, the taxi to the airport, and check-in add up faster than they seem to, especially with the departure tax queue at Blowing Point, so leave more buffer than feels necessary.

  • Keep small bills in East Caribbean dollars or US dollars on hand for the ferry terminal; card machines there are unreliable and the line moves slower for anyone fumbling for exact change.