4 Best Nightlife in Cayman Islands

New Yorker Terry Chesnard built his dream bar from scratch, endowing it with an almost 1960s Rat Pack ambience. Nearly everything is handcrafted, from the elegant bar itself to the blown-glass light fixtures to the drinks. Try the Barracuda shot special "if you dare," or the cocktails, though Terry takes the greatest pride in his top-of-the-line espresso machine. The kitchen elevates pub grub to an art form with pizzas, Reubens, and French melts. Locals flock here for free-pasta Friday, karaoke Wednesday, and live music on Thursday. You might walk in on a hotly contested darts, shuffleboard, or dominoes tournament, but the vibe is otherwise mellow at this charming time-warp hangout.

Known islandwide as Bussy's after the larger-than-life owner, La Esperanza overflows with drinks and good cheer. On weekends, seemingly half the island can be found here, when Bussy fires up the grill and hosts a huge beach jerk barbecue (he'll occasionally give impromptu jerk lessons). Shoot pool in the colorful lounge, or pass time at the alfresco bar or the covered pier jutting into the Caribbean. Drink in the sunset views (and cocktails in matching colors), and if available, try the luscious Key lime pie made by Bussy's wife, Velma. The music, heavy on the reggae with the occasional salsa tune thrown in, blares, encouraging everyone to sway along.

Pat's (previously Bucky's) is popular for its all-you-can-eat West Indian lunch buffets. But the real allure is free Wi-Fi and the cushy (if frayed) lounge adjacent to the restaurant, which resembles a small Vegas sports bar with leather armchairs, black-and-white photos, and team pennants and jerseys galore. Open until 11.

This pub overflows with good cheer and strong drinks. The mudslides are particularly potent, and there are usually some good Cubanos. The alfresco, split-level bar (great water views from the top) serves excellent pub grub (jerk chicken pizza, Caesar salad wrap, portobello-and-Swiss cheeseburger, messy and marvelous spareribs, tempura shrimp) for around C$10 a dish. It's the kind of casual, congenial hangout where almost everyone ends up buying a round at some point. Stop by for Tuesday bingo, Wednesday karaoke, or Friday barbecue with live music, which attracts large, enthusiastic crowds.