Cayman Cowboys

Who would have guessed that cowboys range the shores of Grand Cayman island? What do cowboys know of honeyed sand and aquamarine waters? To say nothing of Frigate birds silently gliding on seven-foot wing spans buoyed above on ascending thermals? Even Sergio Leone would be hard-pressed to conjure up a cowboy in the Caymans.


Grand Cayman, a 22-mile-long island, was discovered by Captain Drake in 1568 – some years after Columbus discovered Grand Cayman’s sister islands in 1503. Given the multitude of crocodiles living here, Drake named the island “Los Camanos.” Today, Grand Cayman is awash with tourists – day-trippers off the cruise ships sheltered in the welcoming arms of the George Town harbor. The tourists come in all shapes and sizes… many tourists are older and economy-sized. Multiple cruise ships (occasionally as many as six at one time) disgorge the tourists, and the small town (maybe three blocks by ten) feels suffocatingly small.

Less monied and aventurous tourists stay in town buying postcards,  tee-shirts, and souvenir shot glasses. They fuel up on McDonald’s, Burger King and Kentucky-fried chicken before heading back to the ship. Those who have more money and are more active head for the glitz of Seven Mile beach where swimming, snorkeling and scuba dives are on-offer. Stingray City is a draw as is the turtle farm which monitors and protects a green turtle population that was, at the turn of the century, threatened with extinction. Shopping is also an attraction. Diamonds are big… very big. And high-end watches.  International banking is big. So big that global banking is a larger part of the economy than tourism.

Given that our stay at The Reef resort is at the far east side of the island an

d we have chosen not to rent a car, going into George Town calls for taking what I choose to call a “cowboy” bus. I am unsure if these white vans are regulated by the local government or not. The buses are white vans, and they do have route numbers on the front, but they have no meters, no seatbelts, and no tickets. No fees are posted. The buses are a mystery, and the lack of over-sight invites abuse. Tourists are sheep waiting to be fleeced.

The concierge told me that because the resort so remote, buses don’t routinely pass by. I could, however, plan on a 9:00 bus going to town and a 3:00 return. Drop-off and pick-up would be in front of the Hard Rock Café. The round trip charge would be $12.50 U.S. dollars. It sounded simple enough. I was lulled into passivity.


nine sharp, the driver (hereafter referred to as “the cowboy”) picked me up in the resort lobby. J

umping on his skittish horse, the steely-eyed cowboy dug in his spurs, cr

acked the whip, and we bolted out onto the road. In no time the horse was lathered and frothing. The cowboy was in a hurry: he slowed down only to pick up passengers standing along side the road. Jumping on quickly was the riders’ only choice; hesitating was not an option. As the only white rider on the bus, I felt very much a novelty act. Surprise was written over every black face. The women were dressed up for shopping – very civilized… very 1950s.

Tropical vegetation pressed in on every side. Bougainvillea bloomed in red, pink, and orange. Not to be outdone, the modest eastend houses held their own dressed in psychedelic green, Gummy worm green, teal, sage,  egg yolk yellow, Pepto Bismol pink, mint, lime, tourquise, sky blue, tangerine,  and baby nursery pink. Calypso music and Bob Marley played over the radio.

The cowboy’s speed on the narrow, twisting road had me planting my feet wide at acute angles. Why stay in your lane when you can go faster by taking the shortest radius on the curves? I fell into a zone… if this was my day to die, so be it. My fate was out of my hands. I wasn’t anxious; I was ready.

Passengers left the bus one by one. I was the last when the cowboy reined in at the station. I asked if he would be picking me up at three… at the Hard Rock Cafe? After a long thoughtful pause, the cowboy told me that I could return to the bus station… at any time and look for a number nine or five. And I owed him 14 U.S. dollars… one way. I recognized that this was a hold-up. Sheepishly,  I thought, “whatever.”

On my return to the station (just a paved lot covered with a worse-for-wear awning and two Porta-potties) I waited for some time. Across the way was the public library. For over a good half hour, black patrons streamed through the doors, but not one white person. I found this disturbing. Yes, probably all the white residents had computers at home, and it is likely that they order their books through Amazon… but shouldn’t the library be a great melting pot? Apparently not in the Caymans. F

inally, a numbered nine van drew up beneath the canopy. I asked the driver if he would be driving as far east as The Reef. He took a long time to think it over. Meanwhile, I was thinking that I had myself another cowboy and he was figuring how much he might be worth. At last he agreed to take me.

The hot-rodding magazine stashed in the pocket behind the driver’s seat alerted me that my life and wallet were in the hands of another cowboy. And his driving didn’t disappoint. Never in his designated lane, he took the curves on the shortest radius.  His passing one motorcycle and three cars in one go was equally impressive. I e

xpected to be victimized again. The charge? Four American dollars.

This driver was a white-hatted cowboy.

postscript: Sorry about the wonky paragraphs and the absence of photos. I am working off a Tablet… always a challenge. Pictures to come later.

About timeout2

I have lived 100 lives. I write essays, short stories, poetry, grocery lists and notes to myself. If I am ever lost, look for a paper trail, but be careful not to trip over any books that lie scattered here and there. I am a reader. I am a reader in awe of writers. When I don't live in Westcliffe, Colorado, I live in London where I am a long-time member of Word-for-Word - Crouch End.
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2 Responses to Cayman Cowboys

  1. Drew B says:

    I spent some time in Cost Rica a few years back and had an odd experience with the transport there as well. I had purchased a Blue Moon travel guide (book) in advance and read several warnings about not taking “unofficial” cabs as they would gouge one’s wallet and take extended paths to run up the meter. I ended up taking one anyway as they seemed to be much more present and convenient. I believe I used them about four times around San Jose and each time was more impressive and helpful than the last. The final cab I took was back to the airport to meet with friends who were coming in a few days after myself. Once we arrived I realized I may have messed up their arrival time but had no good way to check it. The cabbie drove me to an internet cafe that he knew of and got me set up. When I was done the owner wouldn’t let me pay because I was a “friend” of the cab driver. Once we arrived back at the airport the cab driver wouldn’t let me pay for the last leg of the cab ride because it, politely, “wasn’t necessary”. I ended up showing the driver the book I had read and what it said about his profession. As expected he wasn’t very happy about it. We spoke about it for a few minutes while I waited for my company and I thanked him and was off. I love being pleasantly surprised by innate good in people, particularly when you’re told to expect otherwise.
    Travel is about new experiences and losing preconceived notions of other people and places, learning whats going on outside our bubble. Even in researching other countries I run into misconceptions from the mouth of those whose business it is to know better. Maybe they had a bad experience? Turns out travel itself is more educational than expectations & singular experiences. Only one way to find out…

    • timeout2 says:

      Dear Drew, I love your comment about experiencing life outside our bubble. So true – the trick is to visit as a traveler rather than a tourist. I love it all – the good, the bad, and from time to time… the ugly. Mostly good. As for the bad, I come home with something to think about, so that’s good.

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