Grand Cayman Travel Tips from an Oyster Hotel Expert

See recent posts by Guest Contributor

Mary sets up her camera to shoot a panorama of the beach.
Mary sets up her camera to shoot a panorama of the beach.

At, we're all about bringing you honest hotel photos and reviews. How do we do that? Well, we have an amazing team of hotel experts and they travel the world visiting and photographing hotels in person so when you arrive, what you've seen is what you get. But our hotel experts' skills go beyond hotels, and throughout their travels, they pick up quite a few tips and tricks. Fortunately, they like to share as much as we do, and Oyster investigator Mary chronicles her trips and what she learns along the way on her blog, A Wandering Reader. Here's all the dish she had on what's what in Grand Cayman, where Oyster now covers a slew of gorgeous hotels.

Hotels in this story

Cayman is very safe

Unlike many Caribbean destinations, Cayman can be considered a ‘developed’ (or first world) destination. Poverty and crime is low and it doesn’t really have a bad part of town. One hotel concierge told me that in the nine years he’s been working at the large, popular resort, they’ve never even had so much as a car break-in. You should always exercise safety when traveling, of course, but Cayman feels like a more secure destination.

Cayman offers high-quality travel ‘products’

Hotels, restaurants, shops, excursions, and amenities are of excellent quality — and you pay for it. It makes sense, as Cayman is the place where all the rich people go to hide their money. Cayman tourists tend to be older than folks who visit other Caribbean locations, and comprises mostly couples, older retired folks, and well-to-do families. As a bartender explained to me, you have to have a good product on this island. Tourists expect a certain quality and if you don’t have it, someone else will. I agree with this — the food was excellent, there are a plethora of fantastic accommodations to stay in, and the excursions were superb.

This all comes at a price. Dinner entrees start at $20-25 at a sit down-restaurant, and drinks, food at the grocery store, and other amenities are priced accordingly. Also, the local currency is Cayman dollars and the exchange rate is not in our favor (at the time of this writing, it is 80 cents Cayman to 1 American dollar). American dollars are accepted everywhere.

Cayman is a foodie destination

Fish tacos at Sunshine Grill

Fish tacos at Sunshine Grill

See above — ritzy travelers want to eat well and the island has fabulous food. Italian and seafood cuisines are the shining stars here.

To drive or not to drive?

The best way to explore Cayman is by renting a car. The island is small, flat, and driving is relatively easy. Taxis and buses can get expensive, and hiring a car is usually the cheapest option. If you are staying on the Seven Mile Beach area, a car is not needed but if you want to explore other parts of the island, then a car is recommended.

Cayman drives on the LEFT side of the road. There’s only one highway and it’s relatively quiet. The roads are well-maintained and clearly marked. Drivers are mostly courteous. On my work trip, I drove for 10 days by myself with no GPS and I did ok — I don’t think I killed anybody.

Cayman — more diverse than NYC?

Cayman is an awesome melting pot of a bunch of cultures. Most people working in Cayman aren’t actually from Cayman. I was amazed at the number of foreigners I met, in particular, British, Americans, Canadians, Irish, Phillipinos, and Australians, in addition to others. Many come here for the scuba diving, working as diving instructors or in dive shops, although I met plenty of food staff, bartenders, and hotel workers from other countries as well.

Other facts:

  • Cayman is a big hub for business. At the Comfort Suites, for example, there were just as many people in business suits as there were folks in shorts and T-shirts.
  • Cayman is a religious island so a lot of businesses are closed on Sunday. For example, there may not be maid service in your hotel on Sundays. Most grocery stores are open, however.
  • A tip for the partying crowd: do not go out on Saturday night! Bars and clubs must close at 12 by law, so these places are very quiet. Most folks go out on Friday night. 
  • Speaking of partying, Cayman is not really a rowdy/partying destination. If you are looking for a spring break vacation with your friends, or want to go out and meet guys with your single girlfriends, this is not the island for you. The high price keeps a lot of young people out. Go for a quiet, relaxing vacation, not for a rowdy romp with friends.

All products are independently selected by our writers and editors. If you buy something through our links, Oyster may earn an affiliate commission.