It was a long road to the decision to visit Grand Cayman. The original idea was to charter a small live-a-board for a week. But there were only four of us, and so that got expensive. And our window of when we could travel got shorter and more specific – mid-Oct. Unfortunately, this is right in the middle of hurricane season. And I got a little squeamish about multiple nights on a boat (I’ve never done that). And so, we switched to land based but water focused … But it is still Oct… And we wanted somewhere with enough to do for 5 nights, but not so much that we’d feel like we were missing out with such a short trip.
Thus – Grand Cayman!
I was pretty curious about Grand Cayman. It is a British Overseas Territory and the UN lists it as one of the 17 remaining non-self-governing territories following decolonialization. I was curious what a little slice of the UK would feel like in the middle of the Caribbean.

After 5 days there, I have more questions than answers.
They drive on the left and speak English … I only saw one picture of the King and one British Flag. Speed limits are in miles per hour, they use the U.S. electrical socket, they accept USD, and you buy gas by the gallon. When I asked locals where the biggest influences came from, I was told Jamaica and the U.S. Locals are authorized both a Caymanian and British passport. As a general rule, to be a citizen you have to be born there and your mother has to be a citizen. Those who live there (even born there) but refer to the UK as “home” are considered paper Caymanians. And interestingly, those there from the UK need a visa to work. There was a very strong sense of Caymanian identity but no push for independence.
But most importantly … if ordering a cup of tea you might as well be at Denny’s in the US. There is no way this is part of the UK or even the commonwealth based on the tea!!!
We decided to rent a car and are glad we did. While there are public buses there is not a lot of public transportation and getting to see the entire island would be difficult without your own transportation.



We also stayed in West Bay which is roughly in the “middle” of the island. It isn’t particularly close to anything but it is away from the crowds and you can get anywhere in an hour. However, regardless of where you stay, beware of the morning and evening commute. Give yourself extra time.
Things to do while in Grand Cayman:
Of course, spending time at the beach is always an option. But I like to be more active.
The Cayman Turtle Center was a favorite for our eclectic group. Turtles are an important part of the island’s history and even current culture. The center is both the world’s oldest rescue and a current farm to raise turtles as meat. And frankly I love seeing them up close.



The Cayman National Museum is right downtown and a great resource to help answer some of the questions about the history and culture. It is small and we were there about 45 minutes (for most people you probably only need 30 minutes).
Time on the Water. You can take a tour to see the sunset, go fishing, go see the bioluminescent, or to swim with the stingrays. Or you can rent a private boat and do them all. Since there were 4 of us, we rented a boat for the day through Y Knot. It was perfect!!!

Cayman Cigars is a non-profit with locally rolled cigars. And you can find Cuban cigars at Las Casa del Habano.


We went diving with Ocean Frontier and Living the Dream. We all preferred Living the Dream. While I am glad we went diving, I wouldn’t consider the Grand Cayman a “diving destination.” We also went snorkeling several times but unfortunately most of the coral is bleached.
Queen Elizabeth Botanical Garden was lovely and I would definitely recommend it.
Starfish point was a great place to see lots of starfish and the nearby Memorial of 10 sails gave us another part of Cayman history.
Of course, eating and drinking is always a favorite activity….


Eating and Drinking:
Vivo: We went here twice. They have both fish and vegetarian options. My husband declared it the best veggie burger EVER.
Cassanova: They had something for everyone, seafood, pizza, and pasta. They had a lovely deck on the water. My friends declared this the best ceviche on island.
Rackam’s: This was my favorite sunset spot. They had good food and a casual vibe.
Red Hills Jerk Chicken: This is where you go if you are hungry and looking for local and looking for a deal. It is an outside BBQ (pass Hurleys on left, pass two gas stations, and look for the smoke). The chicken was better than the pork but both are good and plentiful.

Baraco: This is on the other end of the spectrum. White table clothes and on the water for a fancy night out. You’ll need a reservation. Their brussels spouts were pretty good (unfortunately I don’t like fish or seafood).
Silverside Rum Bar at Edens Rock was a great place to hang out for a drink and to watch the water. It was nothing special but still one of my favorite spots.
Macabuca has a big menu and other great spot to watch the sunset. I preferred Rackam’s.
Over the Edge is where you can find a big American breakfast.
Rum Point and Kaibo both have a very “club med” feel. I would not go back to either spot.
Head to Tukka to feed the frigates at 5 pm every night.
Finally, we heard great things about the Czech Inn but didn’t make it there.
Some Other Considerations and Pro Tips:
Even though the island is small, you don’t want to waste time by driving back and forth. Plan your stops based on where they are on the island. Also account for the morning and evening commute which will definitely affect your travel times.
Likewise, the sunsets are beautiful, so plan your day so you will be facing west at Sunset.
Most things are closed on Sunday. This is a great day to be on the water.
Check out the cruise ship schedule so you can avoid some of the popular excursion spots while they are in port.
Swim and dive at your own risk. There were no lifeguards and even the dive masters were not very attentive.
