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.
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Timestamps
00:00 Introduction to Solo Travel
02:22 The Pros and Cons of Solo Travel
10:23 Cultural Awareness and Adaptability
19:29 Memorable Encounters and Lessons Learned
25:49 Unexpected Encounters in Puerto Rico
33:13 The Importance of Travel Connections
36:06 Solo Travel vs. Group Travel
39:30 Navigating Travel with Friends and Partners
43:55 Embracing Solo Adventures
48:02 Reflections on Travel and Personal Growth
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Produced by Winging It Productions - https://www.wingingitproductions.com
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Winging It Travel Podcast Credits
Host/Producer/Creator/Composer/Editor - James Hammond
Contact me - jameshammondtravel@gmail.com
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Cheers James.
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