A 7-Day Guide to Anguilla: Where Luxury Meets Laid-Back

There are two ways to get to Anguilla: take a direct flight from Miami or fly into St. Martin and either take a boat or a flight over. It’s a bit harder to access than most of the Caribbean islands, but that’s part of what adds to its charm.

After you’ve arrived at the airport or port, be whisked away to Zemi Beach House, where the slow pace of life allows for ultimate relaxation. Spend three days here eating breakfast with your toes in the sand and cooling off in the crystal-clear blue waters.

Start your day off by taking a refreshing swim in Shoal Bay, known for its crystal-clear blue water.

Walk down to Gwen’s to grab lunch on the beach, listen to live music, and truly feel that Caribbean vibe. This is where the locals hang out! This is a Caribbean BBQ spot where they grill up fresh meats and seafood, adding a Caribbean vibe. We loved the chicken and rib plate, which had a curry rub. Make sure to wash it down with an ice-cold Red Stripe.

Treat yourself to a massage and hammam treatment at the traditional Thai House Spa at Zemi. Each treatment room is in an individual, authentic wooden hut. They start out by washing your feet, which is traditionally done in Thailand. I felt thoroughly relaxed after my massage here—one of the best I’ve had.

Take a quick drive to Arisan for dinner, a traditional Napoli-style pizza with a pizza oven flown in from Naples. This gem is tucked away in a far corner of the island, just a five-minute drive from Zemi, and is truly an experience. Both the pizzas and pastas were fantastic.

Take a quick 30-minute drive and check in to the Four Seasons Anguilla. Revel in the beauty of the property, with its unique location on the apex of two beautiful (but very different) beaches.

Take a relaxing beach walk down Mead’s Bay and pop into Blanchard’s Beach Shack for a quick lunch. Make sure to grab an ice cream cone for the walk back.

Visit the Four Seasons’ own Sunset Lounge for drinks and dinner, with live music. We loved the cuisine and vibe here. On certain nights, this place can turn into a party.

Borrow some (complimentary) snorkel gear and swim out to Barnes Bay to view nature’s playground. Each small inlet of sand has rocks that fish swarm. It’s much calmer on this side, with a more adults-only feel—if that’s what you’re into.

Walk along Mead’s Bay and head down to Leon’s on the beach at the Malliouhana to listen to live music with your toes in the sand and a cocktail in your hand. If you have kids, there’s a cute little pirate ship playground here that the kids can play on while you enjoy the sunset.

Casually stroll back and stop at Straw Hat for an elevated Caribbean dinner experience. The curry here was fantastic!

Rent a Moke to explore the island—they have them parked right at the Four Seasons. This is so fun to drive—it's a mix between a go-kart and a golf cart.

Visit the Anguilla Arch and Sandy Ground to watch a boat race. Head to the south side of the island to ride horses down Maunday’s Bay at sunset, then grab drinks and dinner at Uchu on the beautiful Belmond property. During our visit to the Belmond, they were having a champagne sabering contest.

Spend your day sunning and reading by the adults-only sunset pool, where the Four Seasons staff will pamper you to no end by bringing you cold treats and cleaning your sunglasses.

Take a quick walk down to Picante, a local Mexican eatery with the best enchiladas.