Caribbean - Nightlife - Posh Sips

Calle Fortaleza 364, Caribbean
787-977-3886

Dragonfly

One of the first "sceney" restaurants that helped transform Old San Juan into a bastion of trendiness, the original is still one of the best. The sensual gold, ruby, and black interior channels an ... read more

Sonesta Maho, Caribbean
599-545-3622

Bamboo Bernies

Recently moved from the Caravanserai Resort, the brand new Bamboo Bernies features a Buddha Lounge that serves sushi and specialty drinks late into the night. Focusing more on conversation and sult... read more

Caravanserai Resort, Caribbean
599-545-3936

Bliss

Reminescent of some of the more decadent Vegas clubs (think Pure or Lavo), Bliss is mega complex with two bars, a restaurant, a gigantic dance floor, a pool, and a boutique. While... read more

Holland House Hotel, Caribbean
599-542-2572

Ocean Lounge

Holland House Beach Hotel's brand new-ish open-air watering hole (with an adjoing restaurant) is the island's closest thing to Kelly Wearstler chic. Chi-chi bites like shrimp tempura with a t... read more

Frenchtown Mall, Caribbean
340-774-5348

Epernay Bistro

Epernay adds a much needed touch of class to the neighborhood. Named after the champers region, it's possible to order glasses of at least six different brands of champagne, and some rare win... read more

Salinja, Caribbean
5999.461.7707

Ole! Ole!

Live bands delight the crowds with jazz, calypso, and reggae. If you are self-conscious about your dancing then kick back with one of the house specialty drinks and enjoy the music. read more

Caracus Bai Street, Caribbean
599.9747.4489

Mi Dushi

Mi Dushi is a pontoon boat! Three bars hug the dance floor, where wobbly patrons attempt to keep their balance. If you feel woozy and need a bite to eat, there is a barbecue pit on this spectacular... read more

Cardinal Ave, Caribbean Grand Cayman
345-949-6274

Margaritaville

Pricey drinks and disco beats beckon to the young hot jet set crowd. There is a bit of a scene on Friday nights. This is a great place to people watch or socialize. read more

West Bay Rd., Caribbean Grand Cayman
345-949-6227

O Bar

Girls put on their little black dresses and Manolos while older sugar daddy types make table reservations. The drinks here are pricey but the hookups are usually guaranteed. Spend the money, have t... read more