Comedian Sebastian Maniscalco
Sebastian Maniscalco continues to build upon arguably the most successful year of his career yet: In 2016 he was named Just For Laughs Stand Up Comedian of the Year, selected
Shades of aqua and turquoise swirl together below, like colors in a Pollock painting. My flight attendant serves me another complimentary rum punch—par for the course on Cayman Airways—as we glide high above the Caribbean Sea, the placid water glittering like glass 40,000 feet below us. It’s just a 70-minute flight from Miami, yet I already feel worlds away from the frenetic energy of Nashville. It sinks in: For the next five days, the Cayman Islands are my reality.
I’m in town for the British territory’s inaugural International Dive Week, slated to be held each October, though in truth any week of the year could be classified as such in what is widely considered to be the Caribbean’s birthplace of recreational diving. If you’ve never gone diving, there’s no better place to get your fins wet. Cayman boasts 100-foot underwater visibility, balmy sea temps that average 86 degrees—no wetsuit needed, though I still advise one—and a healthy reef awash in coral and marine life. There are more than a dozen or so operators on the island, with Red Sail Sports being one of the biggest.
Divers tend to gravitate toward Sunset House (three-day, two-night dive packages from $664 a night), one of the premier dive resorts in the Caribbean. For those seeking more luxurious digs, the Westin Grand Cayman (from $383 a night) occupies prime real estate on Seven Mile Beach.
The easiest, most direct route to Grand Cayman is to fly through Miami. From there, Cayman Airways offers two direct flights to George Town daily. American Airlines also services the island several times each week.
Abacus (Contemporary Caribbean/Seafood), Guy Harvey’s Restaurant (French Caribbean/Seafood), LUCA Restaurant (Italian), Michael’s Genuine Food & Drink (New American), Mizu Asian Bistro & Bar (Sushi/Asian fusion), Ragazzi (Italian); The Flavour Tour (progressive dinner starting at West Indies Wine Company and Caymanian cuisine via four courses at four different stops)
January 28 — National Heroes Day (free admission) in commemoration of Grand Cayman’s maritime history and culture, featuring a performance by the children’s choir, uniform parades, and music from the Brass Band of Battle Creek.
February 7 — Taste of Cayman ($35 a ticket) celebrates the diversity of the islands’ food scene as dozens of local restaurants compete to be named “Cayman’s Favourite Restaurant” and attendees taste the fruits of their labor.
March 18-21 — Cayman Arts Festival (from $30 a show) showcases classic performance arts and cross-cultural explorations via a host of events.
Year Round — Water fun from sailing to stand-up paddleboarding off of Seven Mile Beach; day trip to Stingray City to snorkel with stingrays; boat to the shallow sandbar with Captain Marvin’s
There’s only one road that rings Grand Cayman, and in under two hours—the island is just 22 miles long and an average of four miles wide, after all—you can take it to the other end of the island, Rum Point, where there’s an outdoor bar and plenty of hammocks and loungers available for complimentary use. If you time it right, on your way back through town you can park at the port in George Town and climb aboard the island’s lone pirate ship, the Jolly Roger, for an adults-only sunset cruise where the buccaneers are friendly and the rum punch flows freely.
Heading out from George Town the following Saturday, I see flights to the two other islands the territory comprises—Little Cayman and Cayman Brac—come up on the airport monitor, while marveling at the fact that one small piece of land just 76 square miles in size could keep me so satisfied for six solid days. Maybe on my next visit, I’ll have time to explore the island’s more remote parts in depth, but for now Grand Cayman has given me everything I wanted in a destination: photogenic landscapes, underwater excitement, culinary adventures, and a longing to return—soon.