It was, without question, the most ambitious music, art and entertainment festival the Cayman Islands had ever seen. KAABOO Cayman, staged on a purpose-built site that stretched from Seven Mile Beach to the Esterley Tibbetts Highway, saw international A-list bands, DJs and comedians performing over the 14-15 Feb. weekend to thousands of islanders.

The months of teasers, advertising and social media posts leading up to KAABOO Cayman created eager fans and skeptics alike. The tickets were not cheap, with general admission Thatch passes costing a few hundred dollars, up through VIP tickets that cost thousands apiece. Even as the venue began to take shape, visible to anyone who drove past it, it all seemed too good to be true. The Chainsmokers? Wanda Sykes? Duran Duran? With the spectacular failure of the 2017 FYRE festival still fresh in everyone’s minds (thanks in part to two rival documentaries from Hulu and Netflix that were released just a month prior to KAABOO’s debut in Cayman), some decided to hang on to their Benjamins until the last minute. Others figured they would let the first year work out its kinks without them and they would plump for tickets for the next one in 2020, assuming reports were positive.
The first hiccup came when the sneak peek preview on
13 Feb. for VIP ticket holders was postponed due to bad weather, which might have rattled a few; but in the end, it was just that – a hiccup.

What followed was two days of impressive coordination and extraordinary performances, with a couple of teething problems but no major issues.
Yes, the site became a telecommunications Bermuda Triangle, as thumbs descended on mobile devices in record numbers; and the lines for the bars were one of the biggest complaints. Apparently, phones, they could live without; beer, they could not. The music from one of the stages also had a habit of bleeding into the Humor Me tent, but then that was no great loss when ‘SNL’ alumnus Darrell Hammond mumbled his way through his set.
However, when it came to the performance schedule, no one could fault the military precision with which it was executed. Acts began their sets when they were supposed to and finished on time. One award-winner after the next brought the energy, from Blondie to Flo Rida and Maxi Priest to Zedd.
The site was easy to negotiate and was well laid-out, with local artists also getting their moment to shine. Not only did bands like Suckerbox have the opportunity to play on a huge professional stage – they also had unprecedented backstage access, giving them an enviable behind-the-scenes concert experience.
By the end of the final night, Cayman’s audiences were well-and-truly sold on KAABOO. Everyone raved about the festival, making those who had missed it green with envy.
If there had been any lingering questions about its level of success, they were soundly stifled when the loyalty pre-sale for 2020 was announced on 21 Feb. It seemed even the organisers had underestimated the monster they had created when the site crashed under the volume of ticket requests. Future attendees, desperate to take advantage of the limited, special pricing being offered online, entered their credit and debit card details multiple times as web pages kicked them out or froze. The result was an unintended run on bank accounts with withdrawal amounts far greater than the customers had planned – some being charged for 10 tickets when they had only ordered two. Resulting phone calls to financial institutions clogged the lines for hours and social media lit up with complaints.
That same day, KAABOO sent out an email suspending all online purchases, promising to contact customers once the sale was reinstated.
People’s monies for the faulty transactions were slowly but surely returned to them, yet there was silence from the KAABOO Cayman camp regarding further ticket sales. Confirmation communications were sent regarding those already purchased, but beyond that, it appeared that the organisation had gone to ground.
As the months passed with still no announcement of the next year’s lineup or information about local auditions, rumors began to swirl as to whether KAABOO Cayman 2020 was actually going to happen. Perhaps someone somewhere with a calculator had crunched the numbers and subsequently suffered an aneurysm. Whatever was going on, the small island seagrape tree-vine was running rampant, focussed on the radio silence from the organisers.
On 1 Sept., the word finally came out: KAABOO Cayman 2020 was cancelled. Dart, which had partnered with KAABOO, had made the business decision to step back. As a result, Jason Felts, then chief brand and marketing officer for KAABOO, announced that the sequel was not moving forward.
Those who had bought tickets had their money refunded yet expressed disappointment at the news that the festival would not be returning to Cayman.
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