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 Podcast
This 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 Podcast
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!
Support Winging It Travel Podcast
If 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/@wingingittravelpodcast
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
05:05 — Hostel Drama: Helping a Crying Traveler & Finding Legendary Starbucks Oreo Cheesecake
09:40 — Local Rum Bars: Drinking in Residents' Living Rooms in San Juan
11:15 — Sunday Morning Rain: Running Through Town to Track Down a Football Match
12:20 — Exploring Culture: Visiting Castillo San Felipe del Morro & Walking Old San Juan
13:50 — Enter the Irish Solicitor: Relentless Jokes and Taking Phone Calls from Criminal Clients
15:40 — Live Salsa Bands, Trip Highlights, and Heading Off to Toronto
17:05 — Next Week's Teaser: Heading to St. Kitts and Nevis
17:47 — Outro & Where to Find More Content at WingingItTravelPodcast.com
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Produced by Winging It Productions - https://www.wingingitproductions.com
Voyascape: Travel Podcast Network - https://voyascape.com/
Winging It Travel Podcast - Website
--------------------------------------------------------------
Winging It Travel Podcast Credits
Host/Producer/Creator/Composer/Editor - James Hammond
Contact me - [email protected] or [email protected]
Social Media - follow me on:
Instagram
TikTok
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 - Here
Use Revolut Travel Card - Here
Book Hostels With Hostelworld - Here
Booking.com - Here
Book Experiences With Viator - Here
Discovery Car Hire - Here
Book Buses With Busbud - Here
Book Trains With Trainline - Here
Travel Insurance with SafetyWing - Here
Book Flights With Expedia Canada - Here
--------------------------------------------------------------
Thanks for supporting me and the podcast!
Cheers James.
Check out all of our other travel podcasts from around
the world
This podcast is part of the Voyascape Network, a collection of some of the world’s best travel podcasts. Explore more at Voyascape Podcast Network . For advertising or sponsorship opportunities on this show and across the network, email [email protected] or you can find more information at Voyascape Ads.
This 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 Podcast
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!
Support Winging It Travel Podcast
If 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/@wingingittravelpodcast
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
05:05 — Hostel Drama: Helping a Crying Traveler & Finding Legendary Starbucks Oreo Cheesecake
09:40 — Local Rum Bars: Drinking in Residents' Living Rooms in San Juan
11:15 — Sunday Morning Rain: Running Through Town to Track Down a Football Match
12:20 — Exploring Culture: Visiting Castillo San Felipe del Morro & Walking Old San Juan
13:50 — Enter the Irish Solicitor: Relentless Jokes and Taking Phone Calls from Criminal Clients
15:40 — Live Salsa Bands, Trip Highlights, and Heading Off to Toronto
17:05 — Next Week's Teaser: Heading to St. Kitts and Nevis
17:47 — Outro & Where to Find More Content at WingingItTravelPodcast.com
--------------------------------------------------------------
Produced by Winging It Productions - https://www.wingingitproductions.com
Voyascape: Travel Podcast Network - https://voyascape.com/
Winging It Travel Podcast - Website
--------------------------------------------------------------
Winging It Travel Podcast Credits
Host/Producer/Creator/Composer/Editor - James Hammond
Contact me - [email protected] or [email protected]
Social Media - follow me on:
TikTok
--------------------------------------------------------------
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 - Here
Use Revolut Travel Card - Here
Book Hostels With Hostelworld - Here
Booking.com - Here
Book Experiences With Viator - Here
Discovery Car Hire - Here
Book Buses With Busbud - Here
Book Trains With Trainline - Here
Travel Insurance with SafetyWing - Here
Book Flights With Expedia Canada - Here
--------------------------------------------------------------
Thanks for supporting me and the podcast!
Cheers James.
Check out all of our other travel podcasts from around
the world
This podcast is part of the Voyascape Network, a collection of some of the world’s best travel podcasts. Explore more at Voyascape Podcast Network . For advertising or sponsorship opportunities on this show and across the network, email [email protected] or you can find more information at Voyascape Ads.