Despite Grand Cayman’s conservatism and small size, the nightlife scene looms surprisingly large, especially on weekends. Choices include boisterous beach-and-brew hangouts, swanky wine bars, pool halls, sports bars, jammed and jamming dance clubs, live entertainment, and cultural events. A smoking ban was instituted in 2010 for nightspots and restaurants (one preexisting cigar bar and a hookah lounge received special dispensation).
Most major resorts, clubs, and bars offer some kind of performance, including lavish rum-and-reggae limbo/fire-eating/stilt-walking extravaganzas. Local bands with a fan(atic) following include soft-rock duo Hi-Tide; the Pandemonium Steelband; reggae-influenced trio Swanky; hard rockers Ratskyn (who’ve opened for REO Speedwagon, Mötley Crüe, and Bon Jovi); blues/funk purveyors Madamspeaker; and neo-punk rockers the Blow Holes. Other names to look for are Musical Crew, Sucker Box, Ka, Noel’s Band, Wild Knights, Island Vibes, Exit, 45 C.I., Lammie, Heat, Gone Country, and Coco Red.
Consult the “Get Out” section in the Friday edition of the Caymanian Compass for listings of live music, movies, theater, and other entertainment. Local magazines such as Key to Cayman, What’s Hot, and Destination Cayman can be picked up free of charge around the island, sometimes providing coupons for discounts and/or freebies. Bars remain open until 1 am, and clubs are generally open from 10 pm until 3 am, but they can’t serve liquor after midnight on Saturday or permit dancing on Sunday. While shorts and sarongs are usually acceptable attire at beachside bars, smart casual defines the dress code for clubbing.
• A Smokin’ Time. Even if you’re not into stogies, Grand Cayman’s cigar and wine bars are civilized hangouts where you might see stars or overhear insider trading tips.
• Local Rhythms. Cayman’s musicians have fanatic followings; it’s worth a trip to The Reef for the hilarious Barefoot Man. Lammie, Coco Red, Karen Edie, Gary Ebanks & Intransit, and Hi-Tide are other memorable musicians.
• Fish Feedings. It’s touristy, but watching tarpons pirouetting for bait at sunset reels even locals into waterfront watering holes.
• Culture Vultures. If you want a real feel for Cayman life, take in an original play, particularly such annual special performances and festivals as Rundown and Gimistory.
• Full-Moon Parties. Various beach bars host celebrations with almost pagan abandon, and these parties are overflowing with cocktails and camaraderie.
• Tipsy Tips. Don’t drive and drink! Local police set sobriety checkpoints in heavily trafficked areas. The law is strict, the punishment (fine and/or prison) harsh. Revel away: The watering holes will happily pour you into a taxi. Or stick to the walkable cluster of bars in George Town and along Seven Mile Beach. Staggering isn’t illegal, just embarrassing.
Grand Cayman mounts special events throughout the year. The Cayman National Orchestra performs in disparate venues from the Cracked Conch restaurant to First Baptist Church. There’s a burgeoning theater scene. Many new works use religious themes as a launching pad for meditations on issues relevant to current events, such as the Cayman Drama Society (www.caymandrama.org.ky), which put on a provocative offering, The Judith Code, updating the biblical heroine’s story to a present-day London of TV talk-show hosts and terrorist coalitions; the company also produces stimulating children’s fare (Mort, based on Terry Pratchett’s Discworld novels about a young boy apprenticed to Death), as well as escapist crowd-pleasing revivals like Hairspray and Godspell.
Telling Tales. The Cayman National Cultural Foundation started “Gimistory” as a means of preserving the rich but vanishing oral-culture tradition once passed from generation to generation. Held annually the last week of November, it features storytellers, often in elaborate garb, from Cayman and the Caribbean “spinnin’ yarn” about old-time legends (duppies, spirits who return as bogeymen; or Pierrot Grande, the clown dressed in a colorful patchwork quilt of rags) as well as their travels and experiences. Free admission includes Caymanian delicacies like conch fritters and swanky (lemonade), part of a culinary competition.
Harquail Theatre.…This state-of-the-art facility seats 330 for theatrical performances, concerts, dance recitals, fashion shows, beauty pageants, art exhibits, and poetry readings sponsored by the Cayman National Cultural Foundation. | 17 Harquail Dr. | George Town, Grand Cayman | 345/949–5477.
Lions Centre.…The center hosts events throughout the year: “Battle of the Bands” competitions, concerts by top names on the Caribbean and international music scene such as Maxi Priest, stage productions, pageants, and sporting events. | Harquail Dr. | Red Bay, Grand Cayman | 345/945–4667, 345/949–7211.
Prospect Playhouse.…A thrust proscenium stage allows the Cayman Drama Society and its partner arts organizations to mount comedies, musicals, and dramas (original and revival) year-round. | 223B Shamrock Rd. | Prospect, Grand Cayman | 345/947–1998, 345/949–5054.