Anguilla 5 Day Itinerary
Most visitors do not fly directly into Anguilla, they fly into St. Maarten and take the ferry across, and that detail alone should shape your first day. Also worth knowing before you book anything: the dolphin encounter facility that used to operate at Blowing Point closed after Hurricanes Irma and Maria hit in September 2017 and never reopened, so drop it from your plans regardless of what an older blog post promises.
Day 1: Arrival and Relaxation
Places to Go
Most travelers land at Princess Juliana International Airport in St. Maarten, then take the public ferry from Marigot to Blowing Point, a 20-minute crossing that runs roughly eight times a day, with one-way tickets around 30 dollars for adults, 15 for children, plus a 7 euro passenger fee payable only in euros or by card at the counter. Anguilla’s own Clayton J. Lloyd International Airport handles smaller regional flights, mostly from Puerto Rico and other nearby islands, so check which route your itinerary actually uses before assuming a direct flight exists. Once you clear customs, head straight to your accommodation, whether that is Malliouhana, CuisinArt Golf Resort and Spa, or Cap Juluca, and spend the rest of the day doing nothing more ambitious than finding the pool bar.
Things to Know
Anguilla is a British Overseas Territory and uses the Eastern Caribbean Dollar, though US dollars are accepted almost everywhere and often quoted directly on menus. English is the official language. The island runs on Atlantic Standard Time, one hour ahead of US Eastern time, and does not observe daylight saving, so the gap narrows to zero in summer.
Day 2: Sandy Ground and Shoal Bay East
Places to Go
Sandy Ground is the closest thing Anguilla has to a nightlife strip, a stretch of bars, restaurants, and small shops right on the water, good for a laid-back lunch rather than any organized attraction, since the dolphin center that used to draw crowds here shut down years ago. In the afternoon head to Shoal Bay East, consistently ranked among the best beaches in the Caribbean for its pale sand and clear turquoise shallows. Skip trying to pick one restaurant in advance and just walk the beach: Uncle Ernie’s at the east end does simple grilled lobster and conch well, Madeariman leans more toward Italian-Caribbean fusion with a full bar, and Hank’s does the best breakfast plate on the beach if you time it right.
Activities
Book a half-day boat charter out of Sandy Ground to reach the offshore cays like Prickly Pear or Sandy Island, both better snorkeling than anything directly off Shoal Bay. Jet ski and paddleboard rentals are easy to find right on Shoal Bay East, though prices run higher than similar rentals on nearby islands, worth knowing before you commit to a full day.
Day 3: Cultural Exploration and Heritage Tour
Places to Go
Wallblake House in The Valley, built in 1787 and generally considered the oldest surviving structure on the island, is free to walk the grounds, though seeing the restored kitchen and slave quarters requires calling ahead to arrange a guided tour, it is not a walk-up experience. For actual museum exhibits on Anguillian history and culture, the Heritage Collection in East End Village is the real destination, not a generic “Museum of Anguilla,” admission is 5 dollars for adults and 3 for children 11 and under, open weekdays 10am to 4pm only. Round out the day with a walk through The Valley, the capital in name only, since it is really a compact village center with a handful of shops and the pretty Anglican church.
Activities
A guided cultural walk through The Valley area is worth the money if you want context on Anguilla’s 1967 revolution against federation with St. Kitts, a piece of history most visitors never hear about. Several small galleries showing local artists are worth a browse, particularly around the Wallblake House area.
Day 4: Adventure and Nature
Places to Go
Rendezvous Bay stays quieter than Shoal Bay even in high season and is the better pick if you want a full beach day without crowds. Scrub Island, the uninhabited islet off the northeast tip, is a genuine wildlife area best reached by chartered boat rather than a casual paddle out, currents around it can be stronger than they look.
Activities
The trail up Shoal Bay West’s hillside gives a solid payoff view over the western half of the island for relatively little effort. A guided kayak trip through the mangroves on the island’s calmer bays is a good change of pace from beach lounging, and most operators run these as half-day trips out of Island Harbour.
Day 5: Departure
Places to Go
Use the last morning for one more beach session or anything you skipped, then head back to whichever airport or ferry terminal matches your outbound route, Blowing Point if you are routing back through St. Maarten, Clayton J. Lloyd if flying direct on a regional carrier.
Visa Requirements and Transportation
Citizens of the US, Canada, the UK, and most EU countries do not need a visa for stays up to 30 days, though always confirm with your own country’s guidance since rules do shift. A departure tax applies when leaving by ferry, roughly 28 dollars for anyone staying more than 12 hours and a lower rate for day visitors, payable at the terminal. Taxis are the default way to get around and drivers post fixed rates by destination rather than metering, so confirm the fare before getting in. Renting a car or scooter is common and reasonably priced, just remember Anguilla drives on the left, the opposite of what most US visitors expect, and roundabouts take some getting used to on the first day.