At a certain point, all the Caribbean islands can seem interchangeable—start with a white-sand beach, add crystal-clear azure water, insert rum punch. But the Cayman Islands, a three-island archipelago just south of Cuba, is one of the closer destinations to the United States, and worth more than just the quick pit stop offered by cruise ships, which are responsible for the majority of the country’s two million-ish annual visitors.
On the superficial level, there’s the undeniable appeal of the Cayman climate—the average temperature fluctuates between 82°F and 89°F, so there’s literally no bad time of year to go. Plus, its western location shields the Cayman Islands from the worst of hurricane season. But if you look a little deeper, there’s the “Caymankind” hospitality the islands are known for; with people from 135 nations calling it home, it’s one of the most welcoming places you could vacation.
It’s easy to waste away your Cayman days in Margaritaville (that’s an actual beachfront resort, although the cocktails flow everywhere here), but if you follow this Friday night through Monday itinerary, you can max out your relaxation time and still have a few adventures in the Caribbean sun. Here’s our ultimate four-day weekend guide.
How to Get There
It’s never been easier to get to Grand Cayman. At the end of November, Cayman Airways debuted their new Boeing 737 Max 8, which offers 30 percent more seating capacity than other planes and will be launching direct flights from Denver to Grand Cayman starting in March 2019. In October 2018, JetBlue launched daily nonstop service to Grand Cayman from Fort Lauderdale-Hollywood International Airport, which is directly accessible from major U.S. travel hubs. New Yorkers can fly nonstop from John F. Kennedy International Airport to Grand Cayman through April 29, 2019, and Chicago has nonstop American Airlines service on Saturdays to Grand Cayman.
Where to Stay
There’s really only one place to stay in Grand Cayman and that’s on Seven Mile Beach, which is actually a 5.5-mile stretch of powdery white sand and 50-shades-of-blue water. Most of the island’s major resorts can be found here, including the Ritz-Carlton, which has a nine-hole, Greg Norman-designed golf course called the Carribean Club, has just 37 one-, two- and three-bedroom suites and villas; the Westin, known for its award-winning Beach House restaurant; and the Grand Cayman Marriott Beach Resort, with jet skiing, sailing, kayaking, and paddle-boarding rentals available right on site.
At the northern tip of Seven Mile Beach, you’ll find the Kimpton Seafire Resort + Spa—the Cayman Island’s newest resort (it opened in 2016, making it the island’s first new property in over a decade). There are 266 rooms, almost all of which have private balconies and stunning views of the sea, and freestanding beachside bungalows if you want something more private. There are three restaurants (including an ever-changing, nine-seat chefs’ bar, Avecita), two pool bars, and the only Turkish-style hammam spa experience on the island. You won’t even have to leave the property for a thorough Cayman experience—but you should!
Afternoon: Get the weekend started right with a stop at Cayman Spirits Co., just an eight-minute drive from the airport. They’re the official rum of Cayman Airways (and, really, the whole island), but they’re most famous for their Seven Fathoms rum, which is actually aged at 42 feet—or seven fathoms—under the sea; the rocking motion of the ocean is what gives the rum its full-bodied flavor. Stop by for a tour of their facility and and taste the rum, vodka, gin, and liqueurs they distill on site. Tours are $15, and tastings are generously poured.
Evening: Soak up all that rum at Peppers Smokehouse, which is known for its authentic take on Jamaican jerk cuisine. It may not be local food, but it’s stellar. The restaurant, with its thatched roofs, bamboo railings, and wooden tables and chairs, was designed to be a great hangout spot, so don’t dine and dash. Linger over cocktails and Caybrews—a lager brewed right on the island—and let the live music bring on those Caribbean vibes.
Morning: The Cayman Islands’ crystalline waters make it a prime snorkeling and diving spot. Just south of Seven Mile Beach are two of the island’s most popular spots: Eden Rock and Devil’s Grotto. Book a shore or boat dive to both (you can just snorkel, too!) with Eden Rock Diving Center in George Town. You can also dive to the USS Kittiwake, an ex-U.S. Navy submarine that was sunk as an artificial reef in in 2011, with Ocean Frontiers or Cayman Turtle Divers. All of these sites are great dives for beginners, since they’re between 40 and 60 feet under the surface.
Afternoon: Catch a ride with Red Sail Sports out to Stingray City. Yeah, it’s one of the most popular tourist destinations in the Cayman Islands—but it’s worth the crowds. During the 3.5-hour excursion, you’ll sail a 65-foot luxury catamaran out to the sandbar, where you can get up close and personal with the area’s giant stingrays. They’re there because they’ve learned to expect food, but watching them fly through the water and literally nuzzle up to humans (they like to have their chins scratched) is a pretty cool experience. Just a heads up: They feel like wet mushrooms.
Evening: After spending the day in and on the water, that’s where you should look for your meal, too. At the Lobster Pot, you can order up fish so fresh you can tell it was swimming just that morning—in fact, early in the a.m., fishermen sell their catch practically right next door. Sit on the deck overlooking the ocean, and at 7:30 p.m. every evening, you’ll get to watch the restaurant feed the tarpon that swim below.
Morning: Wake up early for a road trip over to the northern side of the island (it’s really just 45 minutes or so from most hotels). Rum Point is famous for its white sand and turquoise sea, and you can lounge off your hangover in one of the many beach hammocks and huts. Or go for a little hair of the dog with a morning mudslide—it’s a combination of vodka, Kahlua, and Bailey’s ice cream—at the Wreck Bar. Nearby is Starfish Point, another beautiful beach area known for the huge numbers of wild star fish you can easily spot in the shallow water. Once you’re all set on sun exposure, check out Crystal Caves, a network of around 105 limestone caves (three of which are open to the public) on the way back to Seven Mile Beach.
Afternoon: The Boulangerie Brunch at the Grand Cayman Marriott Beach Resort is the place to be on Sunday afternoons, whether you’re a tourist or a local. It takes place at the hotel’s Anchor & Den restaurant, which is bright and airy. Gorge on imported charcuterie meat and regional cheese and scoop fresh seafood from the raw bar, all while sipping on unlimited champagne refills or DIY cocktails from 12 p.m. to 3 p.m. Make reservations; it gets rowdy.
Evening: After you’ve fully digested while sunning on Seven Mile Beach, get (slightly) fancied up and take a walk through Camana Bay, a planned development with tons of restaurants and shops, as well as a 75-foot Observation Tower. When you’re finally ready to eat again, head to Agua Restaurant. Like the name implies, there’s a distinct water theme throughout, and the main dishes are mostly Italian-inspired seafood with a Peruvian twist—although the organic chicken is top-notch, too.