Such an easy trip in so many ways: Nonstop flight from JFK; English is spoken; taxis readily available; U.S. dollars widely accepted. I went in October, which is still hurricane season, but my four days there were absolutely glorious.
Lay of the Land
There are three islands that make up the Cayman Islands: Grand Cayman, Cayman Brac, and Little Cayman. They don’t like it when you call it “The Caymans.” I only went to Grand Cayman, which is flat and 22 miles by 8 miles.
I adore JetBlue and flew that airline there but Cayman Airways fit my schedule better for the return flight. I was pleasantly surprised with my first Cayman Airways flight. Everything ran smoothly and I even was served a hot lunch in coach!
If you’re comfortable driving on the left (it’s a British Overseas Territory), definitely rent a car. Taxis are expensive – at least $20 every trip in my experience. It’s great to have independence, and there are some experiences that are far from the main tourist areas. For example:
Kayaking in a Bioluminescent Bay

I am not terribly athletic but I figured since there are only a handful of places in the world where you can witness dark waters light up with the neon glow of tiny creatures, I had to experience it. Just like I had to say yes that time in India’s Thar Desert when I was asked if I wanted to run on my camel, who was by the way named Michael Jackson. But I digress…
I went with Cayman Kayaks and the evening was just as described on their website. Visitors of widely varying ages from Texas, Australia, and Connecticut filled a few sturdy two-person kayaks and headed into a serene bay that was surrounded mostly by homes. It was magical seeing the water where I pulled my oar swirling with purple and blue streaks. The best part of the evening was when the guide instructed us to cup water in our hands and blow on it. The result was like a scene from a Disney movie – Tinkerbell blowing pixie dust, thousands of tiny sparkles floating in the air and settling into the dark water to light again only when disturbed. Well worth the long drive.
Yo-Ho-Ho
Have any pirate buffs in your group? The Caymans Islands celebrate their pirate heritage in November with parties, parades, concerts (Wenches Gone Wild were playing at the Green Parrot), children’s fun fair, underwater treasure hunt, cardboard boat race, darts tournament, fireworks…you get the picture. Check out piratesweekfestival.com.
The Westin Grand Cayman Seven Mile Beach
The most famous beach on Grand Cayman is Seven Mile Beach, a white crescent fronting numerous hotels and private residences. The sand is soft, the water is warm, and I was surprised to find that the beach was uncrowded compared to other famous beaches I’ve visited. A stroll one night found not another soul for at least a mile.
The Westin is a great choice for a home base. It is right on the beach, has restaurants, bars (including a swim-up bar), and, for variety (and to save money), is located across the street from a little shopping plaza with a great breakfast place and a liquor store. I was not impressed with the room I was assigned (too close to a busy elevator and ice dispenser), so, with a big sheepish smile on my face and a $20 bill in hand, I asked the reservationist if perhaps there was something more quiet and with a better view. That paid off with a move to a different wing and a corner room with a balcony overlooking the ocean and this sweet little cabana. Room 301.
This was a couples’ getaway for us but this hotel has an active Kids’ Club and day and evening camps. Renovations to the public areas (e.g., lobby, pool) are due to be completed this month. Note: There is a $60/day resort fee. This is not a cheap destination.
Cayman Turtle Farm
The Cayman Islands have been known for their sea turtles since Christopher Columbus noted them in the early 1500s. At the turtle farm you can pick a little one up, snorkel with them, see a crocodile, tons of geckos and iguanas, and tour an aviary. There’s even a twirly water slide. There are approximately 7,000 turtles here but don’t get too attached: many end up on local dinner tables. Yes, Caymanians eat turtles. And yes, I had a turtle burger. When in Rome… The meat was fried like a hamburger, tasted chicken-y, and was dressed with lettuce, tomato, and a nicely spiced mayonnaise-based condiment.
Go to Hell
You can literally go to Hell and send a postcard home to prove it. In the West Bay is an area called Hell that consists of a post office and a souvenir shop built up surrounding a field of spiky black limestone that demonstrates the phenomenon of biokarst (don’t ask unless you’re really, really interested).
Other Fun Things
Swim with dolphins at Dolphin Cove or Dolphin Discovery; swim with rays at Stingray City; check out the original Batmobile and the world’s first car at the small Cayman Motor Museum; see rare orchids and blue iguanas at Queen Elizabeth II Botanic Park. Of course there are a million places to dive and snorkel; plus golf and a submarine ride.
I spent an hour or so wandering around the capital of George Town and came away wondering why people would waste their time going in and out of name brand stores with overpriced merchandise when they could be doing anything else listed here.
Tourism Boom
The islands’ status as a tax-free financial haven grew the population from 10,000 in 1970 to 55,000; and increased the number of visitors from 403 in 1970 to 1.2 million. When I learned that people from more than 100 countries live in the Cayman Islands, it made sense that I couldn’t put my finger on its culture.
I just spent a day in Grand Cayman as part of a cruise. Would love to go back and explore more!
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[…] Islands—I love saying I’ve been to Hell and back. You can claim that, too, if you go to the Grand Cayman town (really just a post office and souvenir shop) named […]
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