Madeariman Bar and Restaurant

Ernest Benjamin Harrigan opened this on Shoal Bay East in 1984, back when there was no electricity out on that beach and the shacks ran off generators.

Olas is a wooden shack in the middle of Shoal Bay East, run by Bev, who also runs the Fountain resort, and his partner Eulandy. Tacos and Mexican plates instead of the ribs-and-crayfish standard of this beach, plus a fresh margarita Eulandy makes herself and topped tostones large enough to count as lunch on their own.

Gwen’s has survived beach erosion, a fire, and Hurricane Irma, relocating and rebuilding each time with a little more concrete and zero drop in spirit. Owner Gwen Webster’s resilience alone earns the place a spot on the island, and Shoal Bay East genuinely wouldn’t be the same without it. Expect a slow pace by design: pick your own spot among picnic tables, deck chairs, or hammocks, and don’t expect hovering service. Gwen’s rum punch has a real reputation, made with better rums than most beach bars bother with. Sunday afternoons bring the local Anguillan Scratch Band for a proper beach dance party. A genuine Anguilla institution.

Tropical Sunset is on Shoal Bay East, west along the sand from Madeariman and Elodia’s, running as a restaurant and bar with chair service. Seafood, rum punch, and the same water everybody else on this beach is looking at.

Elodia’s is the last stop at the eastern end of Shoal Bay East, past the umbrellas and the crowd and just short of The Point. That walk is the whole pitch: the same famous beach, far fewer people on it.