4 Best Nightlife in Cayman Islands

This classic beach bar has a huge deck over the water, thatched roof, amazing mosaic murals of waves, spectacular sunsets (and sunset-color libations), and tiki torches illuminating the reef fish come evening. Macabuca means "What does it matter?" in the Indigenous Antillean Taíno language, perfectly encapsulating the mellow vibe. Big-screen TVs, live bands and DJs on weekends, excellent pub grub, and daily specials (C$9 jerk dishes on weekends; Monday all-night happy hour, DJ, and C$17 all-you-can-eat barbecue) lure everyone from well-heeled loafers to barefoot bodysurfers animatedly discussing current events.

This delightful seaside slice of old Cayman—grizzled regulars slamming down dominoes, fabulous sea views, old model cars, Friday-night dances to local legend Lammie, karaoke Saturday with Elvis impersonator Errol Dunbar, and reasonably priced red conch chowder and jerk chicken sausage—is also a big politico hangout. Fascinating photos, some historical, show local scenes and personalities. The juke jives, from Creedence Clearwater Revival to Mighty Sparrow.

It's easy to overlook this bar at the entrance to the Kimpton Seafire's main restaurant unless you're waiting for your table, but that would be a mistake. It's not the decor, which is surprisingly sterile despite the handsome driftwood sculpture hanging from the cathedral ceiling. Rather it's the gregarious mixologists who hold court, inventing cocktails on the spot based on your personality and preferences. You can also order dinner from the extensive regular Ave menu, including such standouts as crispy octopus with warm potato-and-white-bean salad or cavatelli with rabbit ragù.