Diana Lambdin Meyer a RoamRight Blog Author

Exploring The Cayman Islands – From Classy To Kitschy

Cayman Islands are a British Overseas Territory in the western Caribbean Sea.

As winter grays and browns loom the seasonal palette, the inner VanGogh deep in us all craves an infusion of color and warmth. The cure is most certainly a turquoise kaleidoscope of ocean colors, white powder sand beaches and a rainbow explosion on structures of all sizes. Top it off with color in your food, language and drink, and you need look no farther than the Cayman Islands.

Located in the Western Caribbean about 500 miles south of Miami and 200 miles north of Jamaica, the Caymans are just about the closest and easiest of the Caribbean islands for Americans to access. They are also renowned for being among the safest and cleanest of island nations for visitors.

Three islands make up the Caymans although about 90 percent of travelers only find their way to Grand Cayman, and most of those visit during a one-day port of call at George Town via cruise ship. That's a shame because the little sisters of Cayman Brac and Little Cayman have equally beautiful beaches, dive spots and offer plenty of relaxation.

But no matter which island you end up on, here are some key things to do and experience to get the most out of your colorful VanGogh-esque getaway.

First of all, pronounce the islands like the locals do. Most Americans want to say CAY-mun, but instead, both syllables receive equal emphasis: CAY-MAN.

Good Eats

To eat with the locals, head out to West Bay in search of the chartreuse and purple building that houses Timbuktuu. It's on the right side of the road as you're heading west. Try the lemon garlic grouper or the barbecued pork. To see and be seen while enjoying a great meal, seek out Michael's Genuine in Camana Bay. Michael Schwartz, originally of Miami, is the first James Beard Award winning chef to open a restaurant on Grand Cayman.


Finding the best buzz on the beach can be a delightful challenge. The local brew is Caybrew, served everywhere, but a tour of the brewery on Shamrock Road is the only place to buy really cool souvenir T-Shirts. Head out to Rum Point on the island's northeast end for the Wreck Bar's famous Mudslide. The bar at Sunshine Suites, a boutique hotel property across the road from the Westin in George Town, serves a spectacular Painkiller using Pusser's Rum.

Please drink responsibly and use a designated driver, as your RoamRight policy does not cover loss resulting from or caused by being under the influence of alcohol.

Activities Worth The Money

Stingray City is actually a shallow area in the Caribbean, about a 10-minute boat ride from Grand Cayman where the very gentle southern stingray and their babies allow you to feed them by hand and will pose for photos. You can dive or snorkel here or just splash in the water with new friends. Dozens of tour operators offer trips and one is as good as the next. Depending on the season, it will cost about $45 per adult, but it's worth the money.


Miss Lassie's House was once the home of a local legend and a fourth generation Caymanian everyone called Miss Lassie. A self-trained artist in her later years, Miss Lassie painted images on every surface of the house, which is now owned and recently opened for tours by the Cayman National Cultural Foundation. Find it just north of George Town on Church Street.


Hurricane Ivan in 2004 was the most devastating hurricane to ever hit the Cayman Islands. After the hurricane, tons of debris washed up on the beaches, including lots of shoes and flip flops. Somebody just haphazardly nailed a couple of mismatched flip-flops to a dead tree on South Church Road. Since then, contributing a flip-flop to the dead tree has become one of THE things to do while on Grand Cayman. The Cayman Shoe Tree even has its own Facebook page.

Get Away From It All

The two smaller islands, Little Cayman and Cayman Brac, have more than 100 dive sites between them and therefore cater primarily to divers so there's not a lot of other entertainment options or distractions. The Little Cayman Beach Resort and its Beach Nuts Bar is a good choice on that island. Cayman Brac has some nice caves to explore and the Tipsy Turtle Bar hums all day and night, but otherwise, if you want to lie on the beach and be undisturbed by anything, either of the little islands is where you need to be.

Authentic Cayman

An authentic souvenir representing Caymankind is anything woven from silver thatch palm, the country's national tree. Local artists weave these pliable fronds into baskets, handbags and some jewelry and can be found in outdoor markets all along the harbor. Also look for Caymanite jewelry, a semi-precious stone cut from the bluffs of Cayman Brac. It's the only place in the world where this rusty red stone can be found. For a selection of any number of hand-crafted products made by locals, visit Pure Art just north of George Town.


Go to Hell. It's certainly the kitschiest thing to do on Grand Cayman, but everyone does it. Located in West Bay, the place receives its name from the barren, black limestone formations poking through the soil in this tiny area. There really is nothing to DO there except look at it. Go, get your picture made, buy a T-shirt and say you've been to Hell and back.

Have you been to the Cayman Islands? What else would you add to this list?

Note: Available plans and coverages may have changed since this blog was published.


About the Author

Diana Lambdin Meyer

Diana Lambdin Meyer, a RoamRight Blog Author A Midwest farm girl at heart, Diana Lambdin Meyer caught the roaming bug early in life. Diana married well - to a photographer who also has the travel bug and whose work in still and video complements her words. Now based in the Kansas City area, Diana is a member of the Society of American Travel Writers who makes a full-time living on the road and at the keyboard. Read about Diana's adventures on her blog, Mojotraveler or follow her on Twitter or Google Plus.

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