5 Best Bars in Seven Mile Beach, Cayman Islands

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.

This chic sports bar has three billiards tables, classic arcade games (Space Invaders, Donkey Kong), air hockey, and large-screen TVs (nab a private booth with its own flat-panel job). Events are daily happy hours, trivia nights, and the Caribbean's reputedly largest Bloody Mary bar on Sunday. Along with sister "O" Bar, it's ground zero for the Wednesday Night Drinking Club. For a C$25 initiation (with T-shirt and personalized leather wristband, toga optional) and C$10 weekly activity fee, you're shuttled by bus to three different bars, with free shots and drink specials.

If you blink, you might miss this intimate speakeasy off West Bay Road. However, it offers an air of sophistication reminiscent of the Prohibition years. Famous for award-winning craft cocktails and a vast selection of spirits, it's a place to relax in a leather chair. Smokers can peruse the vast cigar humidor offering a diverse selection to suit even the most discerning cigar aficionado.

You can sit at the bar or swing under a century-old poinciana tree and watch the traffic go by. There are murals of apes everywhere, from gorillas doing shots to a baboon in basketball uniform (in keeping with management's facetious suggestion that you attract your server's attention by pounding your chest while screeching and scratching yourself). Friday swings with DJs and free happy hour munchies. Popular for breakfast.

This sports bar has a clubby, retro feel—Marilyn Monroe and Frank Sinatra photos channel glamour days, while scarlet booths and bubble chandeliers add oomph. Good luck wrestling a spot at the bar for pay-per-view and major sporting events, but 10 TVs, including two 6-by-8-foot screens, broadcast to every corner. Also an entertainment venue, Legendz books local bands, stand-up comics, and island DJs, and serves grilled fare at reasonable prices.