Anguilla 7 Day Itinerary

Most visitors don’t fly straight into Anguilla at all. Clayton J. Lloyd International only handles small regional aircraft, so the more common route is to land in St. Maarten and take the ferry across from Marigot to Blowing Point, a twenty to twenty five minute crossing. Budget around 65 to 75 dollars round trip once you stack the ticket price with the separate port fees charged on each side, and bring exact cash since parts of the fee structure are euros-only at the ticket window.

Day 1: Arrival and Settling In

British Overseas Territory rules mean U.S., Canadian, and EU passport holders enter visa-free for stays under 30 days, provided the passport itself is valid. After clearing the ferry terminal or airport, check into a resort like Cap Juluca or CuisinArt Golf Resort and Spa if you’re going all in on the barefoot-luxury reputation Anguilla has built, or book a villa through a rental site if you’d rather cook some of your own meals, since dining out here is not cheap by Caribbean standards.

Spend the rest of the day doing nothing ambitious. Walk Sandy Ground in the evening for a first look at the island’s low-key beach bar scene, and don’t expect a bustling duty-free shopping strip, Anguilla’s charm is quiet rather than commercial.

Day 2: Rendezvous Bay and Meads Bay

Rendezvous Bay’s long stretch of sand and calm, clear water make it one of the best swimming beaches on the island, and it’s quiet enough on weekday mornings that you can walk long stretches without passing another person. In the afternoon head to Meads Bay, home to Blanchard’s, open since 1994 and still one of the Caribbean’s most consistently well-reviewed restaurants, known for its bread pudding and a menu that mixes Caribbean, Asian, and Mediterranean influences. The attached Beach Shack next door does the same setting at a fraction of the price if you want fish tacos instead of a tasting menu.

Day 3: Shoal Bay East and a Coastal Drive

Shoal Bay East regularly lands on best-beach-in-the-world lists and it earns the reputation, powder sand and a reef close enough to reach with a short swim straight off the beach in front of the Manoah Hotel, with a second good entry point further east. Spend the morning here, then drive the coast road toward Island Harbour, stopping at Crocus Bay along the way. If you want to see Little Bay, note that it’s boat-access only, a local operator based at Crocus Bay will run you over and back for around fifteen dollars, and the cove’s cliffside snorkeling is worth the short detour.

Day 4: Heritage Sites and the East End

Anguilla’s Heritage Collection links several small restored sites that track the island’s colonial and pre-colonial history, worth a couple of hours if you want context beyond the beaches. In the afternoon, push out toward Island Harbour village, still a working fishing community rather than a resort strip, and the dramatic rock formations near Scrub Island offshore. This is the least touristed corner of Anguilla and it shows in the pace of everything.

Day 5: Fine Dining and the Dune

Book a table at Veya in Sandy Ground Village if you haven’t already, a treehouse-style dining room built around what the kitchen calls Cuisine of the Sun, using produce from organic farms on the island. Reservations matter here, especially in high season. In the evening head to the Dune Preserve, the beach bar and music venue built by Anguillian musician Bankie Banx, not, contrary to a story that circulates among visitors, a former Bob Marley residence. Banx knew Marley and shares some of his era’s reggae lineage, but the Dune is entirely his own creation and was voted the world’s best beach bar by CNN in 2013. Go on a night with live music if the schedule lines up.

Day 6: Reef Trips and Dolphin Watching

Book a snorkeling trip out to Prickly Pear Cays or Dog Island in the morning, both a short boat ride offshore and considerably less crowded than the mainland beaches, with reef structure that rewards a full morning rather than a quick dip. In the afternoon, join a boat tour looking for spinner dolphins, sightings aren’t guaranteed on any given day, but Anguilla’s waters are genuinely one of the better spots in the eastern Caribbean for it.

Day 7: Departure

Save your last morning for whichever beach you liked best rather than trying to squeeze in something new, Anguilla rewards repeat visits to the same stretch of sand more than checklist tourism. If you’re leaving via the ferry, get to Blowing Point with real buffer time, the port tax and boarding process at a small terminal can take longer than the crossing itself during busy periods.