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

Check out the new Smart Travel PodcastThis episode is supported by Smart Travel a new podcast from Nerd Wallet. Travel smarter — and spend less — with help from NerdWallet. Follow Smart Travel wherever you get your podcasts.Smart Travel PodcastBack 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!Support Winging It Travel PodcastIf you enjoyed this episode:⭐ Leave a 5-star rating or review on your podcast app☕ Support the show at buymeacoffee.com/wingingit🌍 Explore more episodes at wingingittravelpodcast.com✈️ Check out more great travel podcasts at https://voyascape.com📺 Now also on YouTube - https://www.youtube.com/@wingingittravelpodcastTimestamps00:00 — Introduction: Recalling My Strange, Unscripted 2014 Trip to Puerto Rico00:40 — Welcome to Winging It with James Hammond02:17 — Why Puerto Rico? Navigating Complex Territories and Finding Cheap Flights05:05 — Hostel Drama: Helping a Crying Traveler &amp; Finding Legendary Starbucks Oreo Cheesecake09:40 — Local Rum Bars: Drinking in Residents' Living Rooms in San Juan11:15 — Sunday Morning Rain: Running Through Town to Track Down a Football Match12:20 — Exploring Culture: Visiting Castillo San Felipe del Morro &amp; Walking Old San Juan13:50 — Enter the Irish Solicitor: Relentless Jokes and Taking Phone Calls from Criminal Clients15:40 — Live Salsa Bands, Trip Highlights, and Heading Off to Toronto17:05 — Next Week's Teaser: Heading to St. Kitts and Nevis17:47 — Outro &amp; Where to Find More Content at WingingItTravelPodcast.com--------------------------------------------------------------Produced by Winging It Productions - ⁠https://www.wingingitproductions.com⁠Voyascape: Travel Podcast Network - https://voyascape.com/Winging It Travel Podcast - Website--------------------------------------------------------------Winging It Travel Podcast CreditsHost/Producer/Creator/Composer/Editor - James HammondContact me - jameshammondtravel@gmail.com or james@wingingitproductions.comSocial Media - follow me on:InstagramTikTok Facebook--------------------------------------------------------------Affiliate Links If you click one of the below to book something, I get a tiny commission, which helps the podcast.Book Flights with Skyscanner - HereUse Revolut Travel Card - HereBook Hostels With Hostelworld - <a href="https://hostelworld