Cayman Islands - Vacation Overview

My family wakes up to another lazy day on Grand Cayman, or so we think, until we begin discussing options for the day. I’m scheduled to take an Atlantis submarine ride with my daughter; my sister and niece want to go shopping in George Town, the capital; we’re all keen on the soup in huge, crusty bread bowls at Breezes by the Bay in town for lunch; and none of us want to miss the Black Pearl Skate & Surf for surfing on simulated waves. And so there we have it. There’s little time for just the beach with all that the Cayman Islands have to offer, including shopping, diving, fishing and hiking. The question is, how can we fit it all in on one vacation? It’s likely the reason I’m back for my eighth trip.

Three Islands

The Cayman Islands are a British territory made up of three islands: Grand Cayman, Cayman Brac and Little Cayman. The peaks of underwater mountains situated to the south of Cuba in the Caribbean Sea are a little more than an hour’s flight from Miami. The main island of Grand Cayman has long been known as a banking capital and signs of its affluence are omnipresent, albeit in an island sort of way, with luxury accommodations, fine dining and galleries, and the requisite ex-patriots at happy hour toasting, perhaps, to the Queen.

The “sister islands” of Cayman Brac and Little Cayman, in contrast, are small, rustic, not heavily inhabited, and definitely run on island time (not that there’s anything wrong with that). Visits to the sister islands typically revolve around scuba diving—some of the best in the world—and lounging and fishing. [Read our article on diving in the Cayman Islands]. But for action, it’s Grand Cayman.

• George Town is the capital of the Cayman Islands.
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Cayman History

Christopher Columbus sighted Cayman Brac and Little Cayman in 1503, during his last journey to the New World, and named the islands "Las Tortugas" after their numerous sea turtles. By 1530, the islands were known as the Caymanes, a name that’s believed to be derived from the Carib Indian word for the small crocodiles that lived on the island. Still later, Sir Francis Drake visited the islands and sailors also began frequenting them to replenish their food stock with the island’s abundance of turtle meat. (It’s easy to see why turtles are an integral part of the island’s history.)

A variety of people soon settled on the islands including British buccaneers, pirates, refugees from the Spanish Inquisition and slaves. Britain took formal control of the Cayman Islands from Spain in 1670, with the islands then becoming a formal British Overseas Territory in 1972 and are now overseen by a Governor appointed by Her Majesty Queen Elizabeth II.

• The Cayman Islands are a very popular port for cruise ships.
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Grand Cayman

Just about my favorite place to stay on Grand Cayman is the Westin Casuarina Resort & Spa, which features the main island’s longest, widest beach: the renowned Seven Mile Beach, a stretch of endless white sand on which most of the best resorts are located.

The Westin is a great halfway point for a vacation spot, just 10 minutes into George Town and 10 minutes to interesting attractions in West Bay like the Boatswain’s Beach Turtle Farm. [Read our Grand Cayman Environmental article.] Also at the Westin is Red Sail Sports, one of the premier water sports and scuba diving operators on Grand Cayman with dozens of dive sites just offshore. The Westin, where rooms start at $274 in summer low season and $362 in winter high season, also has one of the finest restaurants on Grand Cayman, Casa Havana, an oceanfront restaurant featuring intriguing Cuban fusion and Latino Caribbean cuisine in an elegant setting. www.westincasuarina.com

Many tourists are content to stay at one resort with an occasional taxi here and there, but cab fares add up quickly, so I prefer a rental car to explore Grand Cayman (about $40 per day; remember to drive on the left-hand side). That leaves my family free to dine and shop on a whim. George Town is especially known for its duty-free shopping, with everything from crystal to treasure coin jewelry, china and more. There are also plenty of stores filled with sarongs, island artifacts and scrumptious rum cakes—a Cayman specialty—in every flavor imaginable; my favorite is pineapple.

• Seven Mile Beach is one of the most popular beaches in the Cayman Islands and is known for its beauty.
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When in George Town, plan a ride on the Atlantis submarine—well worth it if you’ve never explored the undersea world. Operating since 1985, the 48-passenger tourist submarine submerges to 100 feet for a fish-eye view of the ocean. When a few people miss the turtle that swims by, our amusing guide laments, “The turtles are not on our payroll.” Shucks. Better luck at Stingray City, the ocean stomping grounds for groups of gentle stingrays that are sure to show up, on call, in search of tasty morsels from visitors. The snorkeling site draws dozens of tour boats daily and it’s an experience not to be missed, unless you strongly object to human interaction with wild animals. 

Family Friendly Information

Grand Cayman has activities to suit all ages, and even my 3-year-old was allowed to “snorkel” in Stingray City and pet the stingrays. (She put the snorkel on her head, and I held her.) Particularly fun for younger children is the Boatswain’s Beach Turtle Farm, a 23-acre turtle habitat located in West Bay, though all ages will find the farm interesting. The Black Pearl Skate & Surf Park is for ages 5 and older for skating, while the surf has no minimum age but is probably more appropriate for slightly older children as the waves, while fun, can be intimidating. Atlantis submarine rides are a delight for all ages, from 4 (minimum age) to 84.

Most of the major hotels on Grand Cayman have specific pool areas for younger children, along with either kids’ camps or babysitting services. At the Westin Casuarina, older kids go crazy with water toys like Aquatracks (a huge tricycle that floats in the water), Hobie Cats, kayaks and wave runners (must be 16 to drive).