REVISITED in 2025 - Episode 5 - To Travel Solo Or Not?

REVISITED in 2025 - Episode 5 - To Travel Solo Or Not?In this episode, I go back to one of the earliest recordings I ever released on the Winging It Travel Podcast. My original episode, To Travel Solo or Not, captured a moment when I was still finding my voice, building the show from my bedroom, and trying to make sense of my own travel experiences. Now, years later, I’m revisiting those stories with fresh eyes.I take you through some of the pivotal solo travel moments that shaped who I am as a traveller today — from navigating Bolivia on my own after a last-minute change of plans, to driving around Antigua as the only tourist in sight, to the chaotic hostel scenes in Puerto Rico where life happened right in front of me. I also look back on the randomness of meeting a QPR legend in St. Kitts, getting stranded in Toronto with no way out, and being rescued by a friend I’d met years earlier on the road.These stories reminded me why solo travel can be so powerful. It gives you freedom, vulnerability, unexpected friendships, and moments of real growth. But I also talk honestly about the challenges — the loneliness, the missteps, the uncertainty — and how I see those experiences differently now in 2025.I also reflect on how travelling with friends and partners has shaped me, and how those dynamics contrast with going it alone. Revisiting this episode felt like opening an old journal and realising just how much has changed… and how much hasn’t.If you’re thinking about travelling solo this year, or if you’re curious about how our perspectives evolve as we keep exploring, I think you’ll get something out of this one.If you enjoy the episode, come say hello on Instagram at @wingingittravelpodcast, and check out more at wingingittravelpodcast.com. I’d love to hear your own solo travel stories.To finish, I am not sure what to think of my early episodes; they are a tad cringe from me in terms of the sound and production, but a reminder of the progression I have made in five years.Want to travel with me to El Salvador? Click this link to hear more - https://podcasts.apple.com/ca/podcast/winging-it-podcast/id1559489384?i=1000734952340Click here to book - https://intrepid.wetravel.com/i/68fa168c8d157da799033142❤️ Support the ShowIf you enjoyed this episode, please rate and review on your favourite podcast app — it helps new listeners discover the show. And share this episode with a friend who loves adventure, travel and big ideas.Timestamps00:00 Introduction to Solo Travel02:22 The Pros and Cons of Solo Travel10:23 Cultural Awareness and Adaptability19:29 Memorable Encounters and Lessons Learned25:49 Unexpected Encounters in Puerto Rico33:13 The Importance of Travel Connections36:06 Solo Travel vs. Group Travel39:30 Navigating Travel with Friends and Partners43:55 Embracing Solo Adventures48:02 Reflections on Travel and Personal Growth--------------------------------------------------------------Produced by Winging It Productions - ⁠https://www.wingingitproductions.com⁠Voyascape: Travel Podcast Network - https://voyascape.com/Winging It Travel Podcast - WebsitePlease leave a review and a 5-star rating wherever you get your podcasts!--------------------------------------------------------------Winging It Travel Podcast CreditsHost/Producer/Creator/Composer/Editor - James HammondContact me - [email protected] Social Media - follow me on:InstagramTikTok Facebook --------------------------------------------------------------Support My Podcast - MembershipsPatreon - HereBuy Me A Coffee - HereAffiliate 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 - HereBook Your E-Sim With GigSky - Here Book Hostels With Hostelworld - HereBooking.com - HereBook Experiences With Viator - HereDiscovery Car Hire - HereBook Buses With Busbud - HereBook Trains With Trainline - HereTravel Insurance with SafetyWing - HereBook Flights With Expedia Canada - HereBuy my Digital Travel Planner - Here--------------------------------------------------------------Thanks for supporting me and the podcast!Cheers James.Mentioned in this episode:Check out all of our other travel podcasts from around the worldThis podcast is part of Voyascape, a podcast network that brings together the world's best travel podcasts. You can find all of our podcasts from around the world at Voyascape.com. If you are interested in advertising or sponsored content on any of our shows you can find out more at the link below.Voyascape Podcast Network