So I went to Grand Cayman

April 2, 2019

Sometime in January, my friend Sarah called me and said, “Do you want to go to the Cayman Islands?”

“Yeah, sure,” I said casually, 100% pretending I knew where the heck the Cayman Islands are. (I get paid to write, not understand basic geography.)

While she explained the details, I pulled up my computer and asked Google, Where are the Cayman Islands?

If, unlike me, you have a socially acceptable knowledge of geography, you know we were heading to the Caribbean!

A week before I left, someone asked me, “Do they speak English there? And what kind of money do they use?” Well, I’ll be darned if I knew the answer to either of those questions. So I did some research so I wouldn’t accidentally stomp all over some basic island social norm and get banished to the wilderness.

Even though I dutifully read about Grand Cayman before I got on a plane and actually visited, I still learned quite a bit from actually exploring the place for myself. Without further ado, I present…

Five things I learned about Grand Cayman:

ONE: Stingrays can bite.

We went to Stingray City, a famous tourist attraction in Grand Cayman where visitors can hold, kiss, and feed stingrays. (Did you know kissing a stingray brings seven years of good luck?) Anyway, despite what the 15-year-old tour guide told me, stingrays DO, in fact, BITE! They don’t have any teeth, apparently. But I tried to feed Charlie the Stingray a squid, and he definitely sucked two of my fingers into his mouth and tried to eat them. (“Ouch, Charlie bit my finger!”) I escaped mostly unscathed. The beast just stole a chunk out of my pointer finger.

TWO: Scuba diving feels like a dream.

Have you ever noticed that when you are dreaming, usually at least one of your senses or basic human capabilities doesn’t work? You can’t move; you can’t speak; you can’t hear; you can’t see; or you can’t fly and fight off ninjas (that last one of the worst). Anyway, scuba diving feels like a dream because it’s pretty much silent! (Except, of course, when the Jaws theme plays as a Great White approaches). All I could hear was the sound of my own steady breathing. I felt like an astronaut, an alien intruder into the sea creatures’ home. It was easily one of the coolest things I’ve ever done.

THREE: The money looks like this.

Yes, I did learn in advance that the Cayman Islands circulates its own currency. But until I arrived, I didn’t know what it looked like. Also, one Cayman dollar is worth about 80 American cents.

FOUR: Reading in a hammock feels entrepreneurial.


I brought Tony Robbins’ Awaken the Giant Within, which already screams “I’m an entrepreneur, and my mindset now exceeds yours, and I will be able to change a pineapple into a million dollars using only my brain.” Reading it in a hammock made me feel like a real entrepreneur. We remote folks live for this stuff.

FIVE: People on Grand Cayman are super chill.

There are different levels of “chill.” Most people fall somewhere between Chill Level 1—”I noticed that your house burned down and you’ve been suffering from a life-threatening illness for eight months, so I’ll forgive you for being late”—to Chill Level 10—”Sure, go ahead and break into my house while I’m on vacation, eat all my food, sell my dog on Ebay, whatever man.” The Caymanians were so chill that they totally accepted my desire to learn how to sail dressed as Captain Jack Sparrow. (Can’t take me anywhere, right?)

I look forward to my return! Perhaps someday I will visit the other two Cayman Islands: Cayman Brac and Little Cayman. Only about 170 people live there year-round. How wild is that?!