Anguilla rewards slowness, but seven days is enough to see all of it without hurrying. Distances are trivial — the longest drive on the island takes half an hour — so this plan is organised by mood rather than by geography.
Day 1 — Arrival and Sandy Ground
Most visitors land at Sint Maarten and take the twenty-minute ferry to Blowing Point. Settle in, then go to Sandy Ground for the evening: the harbour beach has the island's most relaxed bars and the sunset lands directly across the water.
Day 2 — Shoal Bay East
The full day at the island's best-known beach. Snorkel the reef at the eastern end in the morning while the water is stillest, eat at one of the beach bars, and stay for the light in the late afternoon.
Day 3 — The Valley and the interior
Wallblake House, St Gerard's Church, and the Heritage Collection Museum in East End. Eat lunch at a local restaurant in The Valley rather than on a beach. In the evening, the barbecue stands set up along the road.
Day 4 — Sandy Island or Prickly Pear
A boat day. Sandy Island is a sandbar with a few palms and one restaurant, ten minutes out from Sandy Ground. Prickly Pear Cays are further, wilder, and better for snorkelling. Boats leave in the morning and come back mid-afternoon.
Day 5 — The west end
Meads Bay, Maundays Bay and Rendezvous Bay in one slow loop, with a long lunch at one of the Meads Bay restaurants in the middle. This is the stretch of coast the island is famous for.
Day 6 — The east end
Island Harbour, the fishing village where the boats come in, and lunch at Scilly Cay if it is open — a tiny island reached by waving from the dock for the boat to come and collect you. Then Savannah Bay or Captain's Bay, both usually empty.
Day 7 — Little Bay and departure
Little Bay by boat in the morning is the best snorkelling on the island. Leave time for the ferry: Blowing Point to Sint Maarten runs frequently, but allow three hours before an onward flight.
Getting around
There is no bus network on Anguilla and taxis must be called rather than hailed, so a rental car is effectively required for this itinerary. Driving is on the left, a local permit is issued with the rental, and the whole road network amounts to a coastal loop and a few connecting lanes. Roads are unlit at night and goats have right of way in practice.
If you only have three days
Take days two, four and five — Shoal Bay East, a boat to Sandy Island, and the west end beaches with a long lunch. That is the island in miniature and leaves out only the quieter east.