Beyond the Gates:  There was one byrning question on everyone’s mind when word first came of KAABOO Cayman. The world had just gleefully witnessed the shocking implosion of an attempted multi-million dollar luxury island festival, and the idea of someone attempting one in the Caribbean came with prejudgement by default. However, as mentioned in our lineup preview, the folks behind KAABOO are the farthest thing from Billy McFarland. After four years of success in Del Mar, they are proven, sincere, and determined. Their vision for a hospitality-focused destination extravaganza wasn’t an ego-inflating delusion; they saw a hole in the festival industry and sought to use their knowledge — and capital — to fill it.

Literally. KAABOO Cayman’s site along Seven Mile Beach was nothing more than marsh before founder Bryan Gordon, Virgin Produced’s Jason Felts, and their team of investors put millions into creating a brand new event space out of sand and stone. Intelligently designed over two years, the grounds are truly singular in the festival landscape, not only for their tropical location, but for their ease and comfort. Hell, extra care even went into the bathrooms, which were flushable portable facilities constantly being cleaned as opposed to porta potties getting refuse sucked out of them twice daily.

Occupying this fresh space was a lineup that would cause ordinary festival fans to scoff. There’s something laughable about seeing acts like Blondie and Zedd alongside names like Bryan Adams and Shaggy in an era when Childish Gambino and Tame Impala are headliners. Again, though, KAABOO purposefully set out to be different. They aren’t concerned with trendsetting bands as much as they are reliable stalwarts with guaranteed hits. It’s an undeniable strategy; no matter your vinyl collection, you too sing along when Counting Crows’ “Mr. Jones” comes on and shake that thing when Sean Paul tells you to “Get Busy”.


We already knew what such a mass-appeal bill could achieve thanks to KAABOO Del Mar, and anyone watching the site’s transformation could see the organizers gave the utmost heed to logistics. Yet still that fyre-y question remained. Would it work? Could someone really deliver a high-end destination event that felt exclusive, unique, and above all, fun?

If it could happen anywhere, of course it’d be the Caymans.

KAABOO Cayman, photo by Ben Kaye

KAABOO Cayman Festival Fashionista, photo by Ben Kaye

Festival Fashionista: Depending on your status, there’s a range of Caribbean-appropriate attire, and all of it was represented. But as far as geographically germane fashion goes, you can’t beat tropical flower prints and pirates, so you have to give it up to these scallywags.


Best of the Tiny Fonts: Many of the early acts either were reggae or had local connections. Alt-pop rockers Transviolet fell into the latter category, forming online while singer Sarah McTaggart was living just down the road from the festival site. Relative unknowns considering the mainstay names on the bill, their zealous delivery of accessible tunes started things rolling in the right direction on Friday.

Transviolet KAABOO Cayman, Ben Kaye-1

Transviolet, photo by Ben Kaye

Snap Poll: The local presence was felt strongest when Sean Paul called for Caymanians to make noise, and the majority of the (GA) audience’s hands went up. KAABOO obviously isn’t after your typical young, savvy music consumer, so I was curious as to who would end up buying tickets. Like the island population itself, it was noticeably varied: families on a KAABOO-centered vacation, the beautifully rich, the middle-aged elite of Grand Cayman’s temporary residents, and a strong local contingent. There were a surprising number of young kids and a trivial amount of teens, with the older set the clear majority.


Perhaps that demographic breakdown contributed to the general ease of the whole experience, as rowdy youth often force you to keep your head on a swivel at a standard festival. Sure, these wizened folks were still willing to drink till they literally dropped, but they also largely weren’t pushy, rushed, or inconsiderate. Regardless of who you were, it seemed everyone was there to enjoy themselves in a beautiful location with unfussy music, and that made for a homogeneously harmonious crowd.

Bryan Adams KAABOO Cayman, Ben Kaye

Bryan Adams, photo by Ben Kaye

Festival Karaoke: The KAABOO Cayman lineup could essentially be divided into two factions: party starters and karaoke standbys. With radio hitmakers abounding, it would actually be the Soundtrack King himself, Bryan Adams, who would draw the most voices from the crowd. People unironically ate up “Summer of ’69” and “(Everything I Do) I Do It for You”, belting along with each glorious note of staple rock.


Best Bites:Seafood is an iffy proposition in a festival environment, but in the Caymans, not only was fish plentiful (no fewer than four ceviche options!), the quality was as upscale as advertised. The tradeoff for taste was often comparatively smaller portions for the price, though with delicious delicacies like Capt. Ceviche’s tuna dish and the teriyaki marinated wahoo with crispy tortilla bits and seaweed salad from Grand Old House, cost wasn’t a major concern.

You could also hang out by the culinary stage to snag a cooking demo sample, like the homey lobster dish local chefs Cody Bush and Anthony Lawson of Smokin’ Bros served up after breaking down two of the biggest crustaceans you’d ever seen.

Why Can’t We Be Friends?: You’d think Maren Morris would’ve showed up to do “The Middle” with Zedd, but apparently scheduling didn’t allow it. The sole surprise collaboration was a pretty fun one for ’90s fans, though, as Blues Traveler’s John Popper popped in during LIVE’s set to wail on harmonica.


 John Popper blues traveler LIVE KAABOO Cayman, Ben Kaye

LIVE with Blues Traveler’s John Popper, photo by Ben Kaye

Humor Me: Cooly lit with attractive chandeliers and cooly kept with AC, the Humor Me tent continued the upscale vibes. Purchasable table seating pleased many, although a few more entitled guests were vocally put off by the strict no cell phone and no late entry policies (as well as Wanda Sykes’ Trump commentary), as I witnessed two temper tantrums that involved the phrase, “I paid $1,000 for my tickets…”

Kevin Nealon’s classic humor slayed (even with a wobbly Anthony Bourdain joke), Darrell Hammond’s scattershot set came off sloppy, and Norm MacDonald — while completely hysterical — proved too strange for the Cayman crowd. It was Natasha Leggero and Moshe Kasher who garnered the most laughs, their energetic performances the right fit for a festival and their millennial parent status aligning in a sweet spot for the audience. They also were the only ones to seamlessly fold in local references, and the fact that they wound up unexpectedly using one of the KAABOO partners for their final couples therapy bit made it an absolutely distinct set.


Richard Branson KAABOO Cayman, Ben Kaye-1

Richard Branson, photo by Ben Kaye

Phones Up: When you have an upper-class event put on by Virgin Produced, Richard Branson is bound to appear. He first danced with Flo Rida before returning later that night to introduce The Chainsmokers. “Who are you waiting for?” he asked the crowd, shoving a fistful of cigarettes in his mouth when everyone yelled “Chainsmokers.” See what he did there? Eccentric multi-billionaire, that Branson.

Chained to the Rhythm: They don’t call it dancehall music for nothing. As islanders themselves, Sean Paul and Shaggy were both greeted warmly by the crowd. The latter taught the out-of-towners about Jamaican whining, while the former’s litany of smashes defied you to stand still. If you came to KAABOO Cayman to party, you came for sets like Paul and Shaggy’s.


Basking on the Beach: A luxury festival is going to be as much about amenities as music, and KAABOO provided them in spades. Vitamin IV drips, massages, ocean-side lounging, and misting fans were available for all; those willing to drop a few extra bucks could enter various levels of exclusive areas. A cover charge would grant access to Bask, a beach club with DJs spinning all day, while wealthier attendees could spring for lounges featuring everything from open bars to cigar rolling classes, and even artist meet-and-greets. If you could afford it, the perks were a nice addition, but you could certainly get the most out of KAABOO Cayman with standard GA admission.

Don’t Believe the Hype: No one wholly disappointed over the two days, a result of the carefree, unpretentious vibes of the fest. If anyone left me wanting a bit more, it was Counting Crows. They sounded just fine, really, but frontman Adam Duritz seemed disinterested in being there. While other acts embraced the good times inherent in a festival like this in a location like this, Duritz came off as a bit of a downer.

Counting Crows KAABOO Cayman, Ben Kaye

Counting Crows, photo by Ben Kaye


That One Performance: The thing about making a festival for anyone is that everyone’s going to have a different highlight. If you polled the crowd, Zedd would’ve been a clear favorite. That said, Jason Derulo put on a hell of a show, and LIVE represented alt-rock in a big, big way. Blues Traveler tickled the nostalgia bone just right, and Salt-N-Peppa put on the perfect hip-hop mixtape. Duran Duran were nearly flawless, and Flo Rida, his bevy of hits in tow, trounced the idea of expectations with his high-octane performance. This wasn’t about one big show, it was about KAABOO, and it all delivered.

Coming Home: Few festivals can boast of such an impeccable first incarnation. Lines? Nonexistent. Transportation? Smooth and efficient, from public buses to ticketed shuttles. Capacity? Comfortably sold out without ever feeling close to crowded. Music? Consistently enjoyable.

Okay, the VIP sections were too large, left rarely half-filled while GA fans were forced to either crowd on one side or stand far behind a physical financial barrier. Organizers might also spring for quieter bleachers in Humor Me, as every early exit was audible. It was also probably a blessing that organizers had to deal with their first spat of poor weather early, as Thursday’s rainfall taught them valuable lessons.


Even so, besides a few patches of mud, you barely noticed those gripes. When you get over the whole Fyre thing, it’s not terribly surprising KAABOO pulled this off. Their programming was already validated, and any logistical issue can be solved by sparing no expense. Situating it on Grand Cayman, an island plenty familiar with deluxe hospitality, gave them a solid starting point. From there it was just making sure it all came together.

It had to. It had to prove doubters wrong, vanquish preconceived notions, and justify the massive investment. That KAABOO accomplished it is one thing; that it did so with such finesse was frankly a joy to experience.

With the cost of tickets, travel, and accommodations, it’s hard to say KAABOO Cayman is a festival for everyone, but it’s certainly a festival for anyone. In a stalling festival market, KAABOO has forged a different path. This welcome new experience works; expect it to continue doing so while everyone else plays catch up.