San Juan, Puerto Rico - Hostel Break-Up Drama, Local Rum Bars in Houses & A Drunk Solicitor Advising 'Clients' On The Phone

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Back in 2014, I was working my way through the Caribbean as a solo traveller and my last stop was Puerto Rico. It was an interesting time to say the least!

In this episode of the Winging It Travel Podcast, I'm taking you back to an unexpected four-day trip I took to San Juan, Puerto Rico. Moving away from a standard travel guide, I'm sharing a raw, storytelling experience as I can't remember anything else from this trip bar the stories, ha!

Tune in as I recount comforting a fellow traveler after a shocking hostel heartbreak over the best Oreo cheesecake I’ve ever had in Starbucks, bar-hopping through local residents' makeshift rum-houses, dodging torrential downpours during the rainy season, and sharing a dorm with an Irish solicitor who was drunkenly managing his criminal clients over the phone.

A weird and wonderful experience in Puerto Rico and I wouldn't have it any other way!

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Timestamps

00:00 — Introduction: Recalling My Strange, Unscripted 2014 Trip to Puerto Rico

00:40 — Welcome to Winging It with James Hammond

02:17 — Why Puerto Rico? Navigating Complex Territories and Finding Cheap Flights