When flying into Puerto Rico’s capital, San Juan, it’s not hard to see why this became the location that solidified Thompson’s distrust of the greed-driven, expansionist, Uncle Sam. High-rise totems litter the city, casting their skeletal shadows over the beaches whose halcyon days are surely behind them. Fast food chains beckon on every corner, like a humid L.A. Thomson was here in the 60s, with the book set a little before this. Thus the novel captures the sleepy island becoming a magnet for burgeoning cruise ship, casino tourism and the usual development, corruption and obesity that accompanies it.

Sound bleak? Thankfully the island extends beyond the clutter of San Juan and Thompson lays out a bit of a blue print on how to avoid being bought.

My advice, head straight for the Northwest coast and hole up somewhere between Isabela and Rincon. Here you will find regularly crowded but quite often pumping waves rolling over sun drenched coral setups. Between November to February chances are high that there will be some heat in the juice.

Ron and The Rum Diary in hand, under the shade of a palm in between sessions, was where the concept for the Lost Boys’ Book Club was birthed. Familiar places appearing on the page before me. The nature of my current location captured, like I was being swallowed into the story or reminded to create my own. A revelation! One should always be reading a novel set in the place they find themselves. Whether on the beach or back at the bamboo tree house, Thompson’s maniacal characters and their rum fuelled rampaging were the perfect companion. The natural beauty and the ugliness of the American influence so crisply captured.

There is an extract in the novel where the not-so-loosely autobiographical protagonist, Paul Kemp, is trying to cover and make sense of the exodus of Puerto Ricans to the U.S. mainland. In doing so he is forced to further ponder his own itchy feet. I refuse to spoil it but for me it is the most poignant moment of the novel. Something of a manifesto. Not wanting to be too much of a tease though I’ll leave you with this quote to make sure that your next bookmark is a boarding pass to San Juan, lodged firmly between the pages of Thompson’s second novel:

“Like most others, I was a seeker, a mover, a malcontent, and at times a stupid hell-raiser. I was never idle long enough to do much thinking, but I felt somehow that some of us were making real progress, that we had taken an honest road, and that the best of us would inevitably make it over the top. At the same time, I shared a dark suspicion that the life we were leading was a lost cause, that we were all actors, kidding ourselves along on a senseless odyssey. It was the tension between these two poles - a restless idealism on one hand and a sense of impending doom on the other - that kept me going.” 
― Hunter S. Thompson, The Rum Diary