Anguilla: The Caribbean's Most Beautiful Beaches, Deliberately Uncrowded

Shoal Bay East is the definitive Anguilla beach and one of the finest beaches in the Caribbean — a 2-kilometer crescent of the most powdery white coral sand in the Lesser Antilles, with turquoise water of extraordinary clarity and warmth, backed by sea grape trees and accessible from the road. The beach has a handful of beach bars and restaurants (Uncle Ernie's Beach Bar is the most beloved local institution) but no overdevelopment — its beauty is largely uninterrupted. Snorkeling at the far eastern end of the bay (past the reef marker) is among the finest accessible snorkeling on the island.

Meads Bay on Anguilla's northwest coast is the island's second-most celebrated beach and the home of its finest hotels — the Four Seasons Resort Anguilla (on the beach's southern end) and the Malliouhana Resort (on the cliff above the northern end) are both world-class properties. The beach itself is approximately 1 kilometer of fine white sand with calm water and the finest hotel beach infrastructure on the island.

The live music scene on Anguilla is disproportionate to the island's size — the Moonsplash Music Festival (annual, held at Dune Preserve) has attracted performers including Jimmy Buffett, the Rolling Stones, and major Caribbean artists. Dune Preserve (Bankie Banx's beachside venue on Rendezvous Bay) is the most culturally important music venue on the island. Sandy Island (a tiny uninhabited sand cay accessible by 10-minute boat ride from Sandy Ground) is the most picturesque day excursion.

Grilled spiny lobster is Anguilla's signature dish — pulled from the surrounding Caribbean waters and grilled at beachside shacks and resort restaurants alike. At Falcon's Nest (Island Harbour — a local beach shack on the eastern coast), grilled lobster with your feet in the sand costs approximately $35 to $50. At resort tasting menus, the same lobster might form part of a $250 per person dinner. The gap in price does not reflect a gap in quality — Anguilla's local lobster is excellent at every price point.

The island's restaurant scene per capita is among the highest in the Caribbean. Straw Hat (Meads Bay — consistently Anguilla's most acclaimed casual fine dining, beachside), Blanchard's (West End — one of the Caribbean's most celebrated restaurants, white-tablecloth tasting menu, James Beard-adjacent quality), and Zemi Beach House's 20 Knots (Shoal Bay East — sophisticated Caribbean cuisine, beachside setting) represent the most acclaimed dining options.

The island's rum punch — made with Pyrat rum, lime juice, and local fruit — is the signature cocktail. Pyrat Rum (a Anguilla-associated brand, orange-infused, in the distinctive orange sailor's head bottle) is the most distinctively Anguillian spirit. The beach bars of Shoal Bay (Uncle Ernie's, Gwen's Reggae Grill) and Sandy Ground's marina strip provide the most social low-key drinking settings.