Empty Calories & Male Curiosity, #20
Travelogue #2: A Biggie Smalls Inspired Trip To The Cayman Islands
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I can’t believe it’s taken me twenty weeks to recommend one of my favorite writers, but here goes: Macho Man: The Untamed, Unbelievable Life of Randy Savage written by Jon Finkel is an absolutely amazing biography of the life and times of the former wrestler. Lenny Poffo (Macho Man’s real name) is brought alive in Finkel’s fun and heartfelt portrait of a man gone too soon. You don’t need to be a wrestling fan to appreciate this book! Jon has written a ton of other stuff you should check out, including this new venture: Midlife Male.
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GOING DEEP:
Travelogue #2: A Biggie Smalls Inspired Trip To The Cayman Islands
Recently we spent seven days in paradise and the first thing I’m going to do is complain. I figure it's the quintessential American thing to do. And it is regarding another quintessential American thing to do: be oblivious to all human beings other than yourself.
How often have you been waiting to get off an elevator only to see the doors open and some slug of a person standing six inches on the other side of the door? Do these people not understand that elevators operate in both directions?
Once the doors open they give you a surprised look and then hop out of the way. I don’t remember this being as prevalent years ago as it is today. It’s almost as though our society has been overrun by objectively stupid narcissists.
Upon arrival in a foreign country I find it imperative to exert my dominance. It is always a bonus if I can embarrass my family in the process. Our visit to the island of Grand Cayman was no different. Within minutes of arriving at customs I was accosted by the type of inane bureaucracy I thought only existed in the lands of uppity white people.
As we walked towards customs there was a literal fork in the road.1 Turn right and we’d enter customs, turn left and there were bathrooms. My wife and daughter decided to use the restrooms while I waited outside. As I waited I could feel the beady eyes of a female security guard staring me down.
Eventually Princess Melania of the Cayman Isles instructed me that I was not allowed to stand there. No, I needed to join the queue immediately. I was not inclined to leave my family and enter a foreign country without them so I declined her invitation. I’m pretty sure she intended it not as an invitation but rather as a demand as she was none too happy with my failure to comply.
Our back and forth about my inability to stand five feet closer to her came to a head with her telling me I was being ridiculous:
“Sir, you are being ridiculous.”
My response of:
“No, YOU are being ridiculous” was not well received. I was hoping my wife would swoop in and agree. She did not.
I’ve never been escorted out of anywhere by security, but I’m guessing being escorted by your wife is slightly more embarrassing. Luckily we were traveling with good friends so I won’t have to worry about this story being told over and over again for the rest of my life.
Ah, memories.

The Cayman Islands are a self-governing British Overseas Territory consisting of three islands: Grand Cayman, Little Cayman, and Cayman Brac. Located in the Caribbean just below Cuba many Caymanians see the ancestral home of Gloria Estefan as a go-to for the butt of their jokes. Questions from tourists like “where is that, “what is that” and “where is that from” are often answered with some version of ‘from Cuba.’
Have you seen the latest stand-up special on Netflix from that Caymanian comedian?
Yeah, me neither.
The thing most people know off-hand about the Cayman Islands is the ability of rich people to stash their money there. Over the course of the week I asked several locals about this. They were about as helpful as I would have been if they’d have asked me about taxes in the US.
I.E. not very.
Further research since the trip has not yielded better results.
While the uber rich may be able to squirrel away their Benjamins in the Caymans us rabble that visit are inundated with fees. I wouldn’t be surprised if Ticketmaster had their corporate offices on the island. After signing every receipt my wallet felt less and less Puffy. In the echoes of my signature I could hear the Cayman treasury department screaming ‘gimme the loot, gimme the loot’ in my head.
Another interesting fact about the Caymans is that unlike most other Caribbean Islands they were uninhabited before being truly discovered by European explorers. At least, this is what the internet informs us. The internet also tells people that Michelle Obama is a man and Hillary Clinton eats babies so maybe we should just stick to facts. Not alternative facts.
#consideredafoolcauseIdroppedouttahighschool
Anywho, on the second day of our trip we took a three hour boat tour of the island2. Jason, our skipper, was a fifth generation Caymanian whose grandfather was one of the first islanders to develop land for tourism. Rooms in his first building sold for $500/pounds at the time. When we sailed past it later that day he pointed it out…those same rooms (which have been converted to condos) now sell for $8-10 million.
Jason also shared with us was how invasive iguanas are on the island. So much so that several years ago the government placed bounties on them. You can turn in iguanas, dead or alive, and get paid for it. I checked the veracity of this claim when we returned to the states. Not only was it true, but point of fact: the Caymanian government has paid out roughly $10 million over the course of the past seven years in return for two million kidnapped and/or murdered iguanas.
Strangely, it is just the green iguana they are hunting. There is also apparently a very beautiful and rare blue iguana on the island. It is endangered and protected. Jason neglected to tell us this. Luckily for him no one in our party went iguana hunting. Had we done so we may have inadvertently killed the wrong type of iguana as two people in our group were color blind (#notjoking).
If you are wondering if we considered impaling some iguanas while we were there…
Yes. Yes we did.
All in all it was a wonderful trip. The country was super safe, no need to carry Mase. There were no bad bad men. Nobody called me fatso. The food was great…no sardines for dinner3. We sipped Moet while we were thirsty. (Are you getting these?)
And with any luck, we’ll have one more chance to return to the island someday.
I realize this sentence is problematic on two levels. First, I hate all forms of the word literally. Second, I know that “fork in the road” is an idiom so my use of literal is appropriate. However, being an idiom means that there really isn’t a ‘literal’ fork in the road (i.e. an instrument you eat with). If you’re wondering what kind of insanity runs through a writers brain as they write…this would be an example.
If you think I can write a piece about visiting a tropical island without referencing Gilligan’s Island I don’t think you know me well enough yet.
Biggie and my grandfather, who we ironically called Popi, are the only humans I’ve ever heard say they ate sardines. Coincidence? I think not.










My images of the Caymens come from reading The Firm. A lot of money laundering in that book. Sounds like an eventful trip!
Henny, as you describe the bounty on iguanas, I'm picturing Crocodile Dundee rooting around the Caymans, rounding up dozens of them - might be a cottage industry lurking there. . .