February 14th, 2019

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Happy Valentine’s day from the middle of the Caribbean ocean, ya’ll! As I’m sure you’ve heard, Team dRiFFt set off this week on an intrepid journey to attend the inaugural KAABOO Cayman music festival – the first of its’ kind (and certainly the biggest) on Grand Cayman island this Friday and Saturday. We arrived a day and a half ago, after a 3am start in Austin, long airport lines and an extended layover in Miami because the incoming flight struck a flock of birds. I’d complain about this, but considering the plight of the birds in question… we fared pretty well. And for the first time in my life, I must actually commend American Airlines for their handling of the situation. They were able to find a new plane and send us on our way with minimal pain and suffering. Also, there are worse places to be stuck than behind an octogenarian paying for crummy Miami airport coffee in dimes and nickels. Yes that happened. And then I also paid for mine in kind. Because, when in Rome… 

​Regardless, airport delays and customs lines had us in Cayman a mere three hours later than expected, which was fine because I was unashamedly not OK about our car rental pickup. My nerves were fried even before I attempted an opposite-side-of-the-road drive while deciphering cryptic foreign road signs along endlessly winding roads with rogue Caymanian buses zipping in and out, pedestrians that didn’t seem to notice that vehicles were also on the roads, and chickens… chickens everywhere. It was mildly harrowing, but we made it. Except for my inability to adapt to the indicator and windshield wipers flipped to opposite sides of the steering wheel. No, Kail, it is not sufficient to indicate that you are turning left by flipping your wipers on and off in frustration-slash-panic. 

In a tired haze, we managed to find our incredible Coconut Bay AirBnB, acquire food and rum (very important) and get some rest.

The next morning, we woke to sunshine, birdsong and crowing wild roosters (this is an experience). We grabbed something caffeinated and stepped off the back porch for some tidepooling, coffee in hand. Coconut Bay Condos are located directly on the waterfront, adjacent to some of the best diving and snorkeling on the island. The water is warm, crystalline turquoise blue and teeming with sea life. We spotted sea urchin, hundreds of crabs and small fish while sipping our coffee and clambering around on the sharp rocks like enthusiastic fourth graders, looking for aquatic treasures. Heaven.

But it was time to go to Hell. 

The first stop on our touristy Wednesday was a little middle-of-the-island limestone rock formation that is razor sharp, black as night and treacherous as hell. It’s also the butt of endless terrible jokes (sorry, not sorry), and a truly excellent and authentically Caymanian low-key tourist attraction. And it is 100% really actually called Hell. 

We then took a lovely left-side drive to the north side of West Bay; through the ‘burbs and into Barkers National Park. There were still chickens everywhere, though the roads were certainly not paved and civilization felt miles away. We parked and trekked ourselves and the cameras on to a pristine beach. I felt like I’d stepped into the set of Pirates of the Caribbean. I may actually have done exactly that, who knows? We snapped and swooned, found a weathered log for a (ridiculous) glamour shot portrait sesh; the results of which may or may not ever see the light of day. Don’t ever take a troop of goofy photogs to a deserted island locale and expect nothing but galleries of pristine beaches and perfectly poised palms. 

Beach glamour queens satisfied, we trekked back to our vehicle discovering (many) more wild chickens along the way and a herd of unsupervised fully saddled trail ponies tied to scraggly beach trees, not a soul in sight.

It was high time for some lunch and a refresher in the civilized world. Now confident in my wrong-side-of-the-road driving situation, we meandered back to Seven Mile Beach for a taste of tourist trap Cayman. Calico Jacks, a beachside shack bar, packed to the hilt with cheesy pirate-inspired decor and sweaty overweight cruise ship patrons was the perfect layover. We grabbed a crisp can of CIB Mango Tango – the perfect craft beer for the situation – and found a picnic table among sandy, salty beachgoers and roaming chickens. 

Post-beer, we took a sandy stroll to the north side of the Kimpton Seafire, where KAABOO festival grounds were starting to take shape. The now sold-out beachfront festival commences this Friday; it’s the first and largest full-scale music festival on the island featuring not only a stellar musical lineup, but food, comedy, art and luxury indulgences comprising their “Five Senses Under the Sun” programming. With big shoes to fill and the backlash of Fyre Fest still rampant, KAABOO Cayman is the talk of the town – both within the Caribbean and across north american shores. We were wildly curious to take a coveted sneak peak and I can verify, without hesitation, that this will be no Fyre-y repeat. From the towering stages with sound and light systems already in place and being tested, to incredible art installations, scenically stunning BASK beachside club ready and raring, or the stone-faced security-guarded entry gates concealing soaring tents and sumptuous surprises. This is going to be quite the festival. 


​After our sneak peek we bundled our exhausted selves back to West Bay to partake in a waterfront happy hour at The Cracked Conch. Fish and chips, Pina Coladas, scuba divers climbing out of the water and straight to the bar with scuba tanks still on their backs (not even kidding here) and an incredible sunset vista to enjoy between the warm glow of tiki torches and old ship’s lanterns.

We have one more day of sunshine, touristy temptation and pristine beach exploration before it’s festival time. We’ve an ambitious itinerary, so it’s time to sign off. From paradise to yours truly, have a wonderful dRiFFty tropical day, and I’ll report back tomorrow from KAABOO… can’t wait!


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