Gwen’s Reggae Grill

Elvis built this entire Sandy Ground institution through sheer force of personality, no gimmicks, just strong rum punch and decades of irrepressible Anguillian warmth.

Anguilla has the finest beaches in the Caribbean and some of its most genuine bars to match, and Sunshine Shack proves both claims with cold Carib beer and zero pretense.

Bankie Banx himself might pick up a guitar and start playing at any moment, a driftwood compound on Rendezvous Bay where the music comes first and the rum punch is basically along for the ride.

The first (and likely only) beach bar on Maundays Bay – one of the Caribbean’s most photographed stretches of sand – opened in 2019 as part of the Belmond Cap Juluca resort. A converted vintage Citroen food truck marks the spot, backed by a small thatched bar and a scatter of egg-shaped loungers. Non-guests are welcome, prices are resort-premium, and the view back along the bay to Cap Juluca’s white buildings is genuinely stunning. AXA – Anguilla’s self-proclaimed first local beer – is on the menu. Creative small plates round out an elevated but still relaxed resort-bar experience.

The French side of St. Martin runs at a noticeably calmer pace than Dutch Sint Maarten, and Karibuni captures exactly that relaxed rhythm with cold rose on the island’s quieter eastern shore.

Nat Richardson’s Palm Grove is the only building on Junk’s Hole, at the end of a mile and a half of dirt and coral road on Anguilla’s eastern end. There is no electricity out there, which is why everything comes off a grill.