Anguilla 2 Day Itinerary

Thirty-three beaches on an island eighteen miles long means two days is really only enough to sample a handful properly, so the right move is picking a slow beach and a boat day rather than trying to circle the whole coastline.

Day 1: Beaches and The Valley

Most visitors reach Anguilla by ferry rather than flying direct, since Clayton J. Lloyd International Airport has limited connections; the public ferry from Marigot on the French side of St. Martin runs eight times daily, costs around 30 dollars one way for adults, and takes just 20 to 25 minutes. Private charter ferries from near Princess Juliana Airport on the Dutch side run faster and more flexibly but closer to 65 to 70 dollars one way. Clear customs at the ferry dock and grab a taxi or rental car (driving is on the left, a holdover from British colonial rule that still trips up American visitors). Head straight to Shoal Bay East, regularly ranked among the best beaches in the Caribbean for its pale sand and reef-protected turquoise water, and eat lunch beachside; Hank’s, a no-frills outdoor spot, does a fried egg and potato pancake plate that’s better than it sounds and worth the detour even off the tourist trail. Midday, drive to The Valley, the capital in name only, since it’s really a scattered low-rise town rather than a dense center. The Wallblake Estate House, an 18th-century plantation house still tied to the adjacent Catholic church, and the Heritage Collection Museum both give a clearer picture of the island’s Arawak and colonial past than most visitors expect from such a small stop. In the evening, Rendezvous Bay delivers one of the better sunset views on the island, looking straight across the channel toward St. Martin’s silhouette. For dinner, Veya’s treehouse-style dining room does a Caribbean fusion menu worth the splurge, jerk tuna and a shrimp cigar with Moroccan spice being the two dishes regulars order.

Things to know: Anguilla is a British Overseas Territory, so English is the official language and driving stays on the left. The US dollar is accepted everywhere alongside the East Caribbean dollar, and most resorts and restaurants take cards, though small guesthouses and beach shacks often want cash.

Day 2: Boat day and quieter coves

Skip any itinerary that sends you to a formal “Anguilla National Park” on Scrub Island; that’s not accurate, since Scrub Island is actually an uninhabited islet off the northeast tip reachable only by boat, known for varied coral, less skittish fish than the mainland reefs, and the odd reef shark sighting rather than any hiking trail system. Book a half-day charter out of Island Harbour or Crocus Bay for the crossing. Little Bay is the better call if you’d rather stay closer to shore: a small boat operator at Crocus Bay (look for Calvin’s boat near the cabana) runs the short hop for around 15 dollars round trip, dropping you into a sheltered cove backed by limestone cliffs where sea turtles show up reliably and there’s a modest cliff jump for anyone who checks the depth first. After lunch, Maundays Bay on the southwest coast has calmer, clearer water for casual snorkeling if the morning’s boat trip already covered the adventure quota; rent gear from any of the beachfront resorts there. My take: do Little Bay over a full catamaran tour to St. Martin if you only have the one afternoon free, since the payoff per hour spent is much higher on a fifteen-minute boat hop than a half-day round trip to another island you’ll barely see.

Evening winds down wherever you’re staying, whether a villa rental or one of the island’s higher-end resorts, before a final dinner at Straw Hat on Meads Bay, open seasonally and known for lobster, though it runs pricier than most Anguilla dining, so check the current seasonal hours before counting on it.

Visa requirements: Citizens of the US, UK, most EU countries, and Canada do not need a visa for stays up to 30 days, but confirm your specific nationality’s rules before booking, since requirements shift periodically for other passports.

Transportation: taxis meet every ferry and flight, and rates are largely fixed rather than metered, so confirm the fare before getting in. A rental car gives more freedom for beach-hopping over two days and costs less than repeated taxi fares if you’re covering more than two or three spots.