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=1000734952340

Click here to book - https://intrepid.wetravel.com/i/68fa168c8d157da799033142

If 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.

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

--------------------------------------------------------------

Produced by Winging It Productions - ⁠https://www.wingingitproductions.com⁠

Voyascape: Travel Podcast Network - https://voyascape.com/

Winging It Travel Podcast - Website

Please leave a review and a 5-star rating wherever you get your podcasts!

--------------------------------------------------------------

Winging It Travel Podcast Credits

Host/Producer/Creator/Composer/Editor - James Hammond

Contact me - [email protected] 

Social Media - follow me on:

Instagram

TikTok 

Facebook 

--------------------------------------------------------------

Support My Podcast - Memberships

Patreon - Here

Buy Me A Coffee - Here

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 Your E-Sim With GigSky - 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

Buy my Digital Travel Planner - Here

--------------------------------------------------------------

Thanks for supporting me and the podcast!

Cheers James.

Mentioned in this episode:

Check out the Smart Travel Podcast

This week's show is supported by the new Smart Travel Podcast. Travel smarter — and spend less — with help from NerdWallet. Check out Smart Travel at the Link below:

Smart Travel Podcast

In this week’s episode, I sit down with my longtime podcasting friend and returning guest, Marie Walker, to pull back the curtain on what digital nomad life actually looks like. This is not a highlight reel. This is the real, messy, energising and exhausting truth of building a remote business while bouncing between continents. Marie opens up about leaving the USA with a plan, the crash-and-burn moments that forced her to return home, and the unexpected personal growth that came from rebuilding twice.

We talk about the difference between backpacking and being a digital nomad, the pressure to stay productive while constantly uprooting your life, and the emotional toll of trying to create community in a new country every few months. Marie shares the honest lessons she’s learned from Europe, Southeast Asia, Australia and Korea, why she needed to end her 10-month trip early, and how burnout changed the way she approaches business, travel and lifestyle freedom.

If you’re dreaming of working remotely around the world or already living the nomad lifestyle, this conversation gives you the reality check most digital nomad influencers skip. It’s raw, funny, vulnerable and full of valuable perspective from someone who has lived the ups and downs.

Stick around to hear why Marie is now focused on rebuilding her foundations, where she’s heading next, and how she plans to approach digital nomad life differently moving forward. This episode is a must-listen for anyone considering taking their work on the road.

Marie Walker

Your Girl Media - https://yourgirlmedia.com/

Culture Cult Travel Show

Apple Podcasts - https://podcasts.apple.com/ca/podcast/culture-cult-travel-show/id1603662928

Spotify - https://open.spotify.com/show/6Gfk2meDfzfmJIxybvoE6c

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=1000734952340

Click here to book - https://intrepid.wetravel.com/i/68fa168c8d157da799033142

If 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.

00:00 Intro

01:18 Marie joins the show

05:00 Digital nomad beginnings

10:12 Why she left the USA

15:44 Backpacking vs digital nomad life

22:00 Planning a long-term work-travel trip

26:14 The realities of burnout

30:42 Community, co-livings and connection

36:30 The loneliness factor

42:00 Digital nomads and overtourism

47:50 Dating while nomadic

55:00 What Marie would do differently

59:40 Lessons learned along the way

1:04:00 Closing thoughts

--------------------------------------------------------------

Produced by Winging It Productions - ⁠https://www.wingingitproductions.com⁠

Voyascape: Travel Podcast Network - https://voyascape.com/

Winging It Travel Podcast - Website

Please leave a review and a 5-star rating wherever you get your podcasts!

--------------------------------------------------------------

Winging It Travel Podcast Credits

Host/Producer/Creator/Composer/Editor - James Hammond

Contact me - [email protected] 

Social Media - follow me on:

Instagram

TikTok 

Facebook 

--------------------------------------------------------------

Support My Podcast - Memberships

Patreon - Here

Buy Me A Coffee - Here

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 Your E-Sim With GigSky - 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

Buy my Digital Travel Planner - Here

--------------------------------------------------------------

Thanks for supporting me and the podcast!

Cheers James.

Mentioned in this episode:

Check out the Smart Travel Podcast

This week's show is supported by the new Smart Travel Podcast. Travel smarter — and spend less — with help from NerdWallet. Check out Smart Travel at the Link below:

Smart Travel Podcast

IMMERSIVE - Hornby Island, British Columbia - A White Sand + Warm Clear Water Paradise

🌴 Episode Summary

In this immersive travel episode, join me, James Hammond, as I take you on a journey to Hornby Island, one of British Columbia’s most enchanting destinations — often called the “Hawaii of BC.”

Getting here isn’t easy — it takes three ferries, early mornings, and plenty of patience — but what waits at the end is nothing short of paradise. From tranquil ferry crossings and still turquoise waters to soft white sands at Tribune Bay, hidden calm at Whaling Station Bay, and live music and cider at Fossil Beach Farm, this episode captures the spirit of island life in sound and story.

You’ll hear the sea breeze, the crunch of sand, and the quiet hum of campfires as I explore Hornby’s beauty, culture, and community. It’s not just a visit — it’s a complete sensory escape into one of Canada’s most breathtaking coastal secrets.

Please sit back, pop on your headphones, and imagine you’re right here with me on Hornby Island. Picture the scenes as you listen — the waves, the wind, and the rhythm of island life. Throughout this episode, you’ll hear soundscapes, live reactions, music, and moments that will whisk you away on a perfect island escape. Enjoy.

• 🚢 The three-ferry journey from Horseshoe Bay, West Vancouver, to Hornby Island
• ☕ A caffeine stop at Courtyard Coffee anda breakfast burrito at Vorizo Café
• 🏖️ Discovering the paradise of Tribune Bay and its crystal-clear waters
• 🏕️ Camping at Tribune Bay Campground surrounded by island vibes
• 🏞️ Hiking to Mount Geoffrey’s panoramic viewpoints
• 🍎 Enjoying cider, live music, and sunset views at Fossil Beach Farm
• 🌅 Finding peace and solitude at Whaling Station Bay
• ❤️ Reflections on why Hornby Island might be my favourite place in Canada

Travel storytelling • Immersive soundscapes • Coastal adventures • British Columbia travel • Island getaways • Road trips

💌 Share your thoughts: What’s your vision of Hornby Island after listening?

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=1000734952340

Click here to book - https://intrepid.wetravel.com/i/68fa168c8d157da799033142

If 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.

00:00 – Introduction – “The Hawaii of BC” and setting off on the journey

01:10 – Ferry to Vancouver Island – calm seas and early-morning reflections

03:00 – Road trip north + quick coffee stop in Qualicum Beach

04:30 – Ferry crossings to Denman and Hornby – anticipation builds

06:20 – Arrival at Tribune Bay Campground + island first impressions

08:00 – Exploring The Hub – breakfast burrito, coffee, and local vibe

09:45 – Tribune Bay – white sand, warm clear water, paradise found

12:30 – Hike to Mount Geoffrey – forest trails and sweeping views

15:00 – Sunset music and cider at Fossil Beach Farm

17:00 – Whaling Station Bay – quiet reflections and goodbyes

18:30 – Closing thoughts + why Hornby Island stole my heart

--------------------------------------------------------------

Produced by Winging It Productions - ⁠https://www.wingingitproductions.com⁠

Voyascape: Travel Podcast Network - https://voyascape.com/

Winging It Travel Podcast - Website

Please leave a review and a 5-star rating wherever you get your podcasts!

--------------------------------------------------------------

Winging It Travel Podcast Credits

Host/Producer/Creator/Composer/Editor - James Hammond

Contact me - [email protected] 

Social Media - follow me on:

Instagram

TikTok 

Facebook 

--------------------------------------------------------------

Support My Podcast - Memberships

Patreon - Here

Buy Me A Coffee - Here

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 Your E-Sim With GigSky - 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

Buy my Digital Travel Planner - Here

--------------------------------------------------------------

Thanks for supporting me and the podcast!

Cheers James.

Mentioned in this episode:

Check out the Smart Travel Podcast

This week's show is supported by the new Smart Travel Podcast. Travel smarter — and spend less — with help from NerdWallet. Check out Smart Travel at the Link below:

Smart Travel Podcast

That’s right — I’m officially leading my first-ever guided group tour, and we’re heading to El Salvador from November 19 to 29, 2026!

This 10-night, 11-day adventure blends culture, hiking, beaches, food, and local connection — designed for curious travellers who want to see El Salvador, far beyond the headlines.

Here’s a sneak peek at what’s included:

🗺️ Highlights

• Explore San Salvador on a walking tour with local legend Dave Méndez
• Camp under the stars at Conchagua Volcano and wake up to sunrise views of El Salvador, Honduras and Nicaragua
• Learn to cook pupusas, the beloved national dish
• Discover the colonial charm of Suchitoto, visit Alejandro Cotto’s house, and enjoy lakeside sunsets.
• Experience the Civil War Trail in Cinquera with Daniel from Suchitoto Ecotours, ending at a jungle waterfall.
• Hike the stunning Santa Ana Volcano (3rd time lucky for me!) and enjoy coffee overlooking Lake Coatepeque.
• Wander colourful streets and artisan markets in Ataco on the Ruta de las Flores
• Tour a working coffee estate at El Carmen
• Chill by the Pacific coast in El Tunco and El Zonte — think surf, black-sand beaches, and good vibes

🏡 What’s Included

• 10 nights accommodation in twin share rooms (with private room upgrade available for USD 675)
• Private transport throughout the trip + airport transfers
• 10 breakfasts, 1 lunch, 5 dinners
• Local Intrepid-licensed guide, driver and me as your tour leader
• Activities, walking tours and unique local experiences

💸 Price:

• Early bird rate: USD 3,995 for the first six bookings and $4295 thereafter.
• Full group: 12 people maximum (6 minimum to go ahead)

Flights, insurance, and some meals not included — but I’ll definitely be buying a few rounds of lattes along the way ☕

👉 Book your spot: https://intrepid.wetravel.com/i/68fa168c8d157da799033142

This isn’t just a holiday — it’s an immersive experience that will change how you see Central America.

After years of helping other creators and brands bring their podcast ideas to life, I’ve launched Winging It Productions— a full-service podcast production business.

We offer:

🎙️ Podcast launch packages (from idea to release)

✂️ Audio editing for solo and guest episodes

👥 Guest and host management

📈 Marketing and growth support

If you’ve always wanted to start a show — or if you’re ready to scale an existing one — I’d love to help.

Learn more and book a free consultation at 👉 wingingitproductions.com

The rest of the year is stacked with adventure:

• 🇦🇺 Australia: Back to Brisbane for the Ashes cricket test and some coastal exploring around Queensland.
• 🇧🇹 Bhutan: A 10-day journey through the mountains with Breathe Bhutan — temples, trails and local festivals I’ve dreamed of for years.
• 🇹🇭 Bangkok: Rounding it off where my travel journey began back in 2013 — revisiting old spots, tasting street food, and recording fresh stories for you.

• Join the El Salvador Tour: https://intrepid.wetravel.com/i/68fa168c8d157da799033142
• Work with Me: wingingitproductions.com
• Follow My Adventures: Instagram
• Watch the Vlogs: Roaming with Hammo on YouTube

If 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.

00:00 Introduction

01:30 Announcing the El Salvador Guided Tour

06:51 Launching Winging It Productions

07:49 Upcoming Travel Adventures

10:13 Closing Remarks and Travel Resources

--------------------------------------------------------------

Voyascape: Travel Podcast Network - https://voyascape.com/

Winging It Travel Podcast - Website

Please leave a review and a 5-star rating wherever you get your podcasts!

--------------------------------------------------------------

Winging It Travel Podcast Credits

Host/Producer/Creator/Composer/Editor - James Hammond

Contact me - [email protected] 

Social Media - follow me on:

Instagram

TikTok 

Facebook 

--------------------------------------------------------------

Support My Podcast - Memberships

Patreon - Here

Buy Me A Coffee - Here

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 Your E-Sim With GigSky - 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

Buy my Digital Travel Planner - Here

--------------------------------------------------------------

Thanks for supporting me and the podcast!

Cheers James.

Mentioned in this episode:

Check out the Smart Travel Podcast

This week's show is supported by the new Smart Travel Podcast. Travel smarter — and spend less — with help from NerdWallet. Check out Smart Travel at the Link below:

Smart Travel Podcast

Ep 188 w/ Pauline Frommer (Frommer's Travel Guides) - From $5 a Day to the Digital Age: Why Travel Still Matters

In this week’s episode, I sit down with Pauline Frommer, the editorial director and the voice behind the legendary Frommer’s Travel Guides — a brand that has shaped how millions of people explore the world. From her father Arthur Frommer’s iconic Europe on $5 a Day to her own role in redefining modern travel, Pauline shares a fascinating journey through decades of changing travel trends and timeless wisdom.

We dive into the golden age of travel, the challenges of keeping guidebooks relevant in the AI and influencer era, and why authentic, local knowledge still matters more than viral posts or paid promotions. Pauline reflects on her early travels across Europe as a child, her father’s unexpected path from law to publishing, and how the Frommer family helped democratise travel for everyone—not just the rich.

We also unpack the realities of today’s travel media landscape — from fake reviews and corporate bias to AI scraping journalism — and what this means for travellers seeking honest advice. Pauline shares her insights on sustainable travel, mid-range budgets, and why travel remains one of the best ways to understand humanity, especially in divided times.

If you’ve ever carried a guidebook in your backpack, dreamed of exploring the world more meaningfully, or wondered how travel has evolved over the last 70 years, this episode is a must-listen.

Expect heartfelt stories, insider travel tips, reflections on modern society, and the enduring reminder that the world is still worth exploring — one honest adventure at a time.

🎧 Listen to The Frommer’s Travel Show: https://www.frommers.com/podcast

📚 Explore Frommer’s Guidebooks: https://www.frommers.com

📸 Follow Pauline Frommer on Instagram: https://www.instagram.com/frommers

☕ Support Winging It Travel Podcast: https://www.buymeacoffee.com/wingingit

00:00 – Why Pauline Frommer believes guidebooks still matter

04:00 – The Story of Arthur Frommer and Europe on $5 a Day

09:00 – Travelling through postwar Europe and lessons learned

13:00 – The power of travel to connect us beyond nationalism

15:00 – How influencers changed travel media (and not for the better)

19:00 – Why Americans don’t travel as much as they should

22:00 – What keeps Pauline passionate about exploring

30:00 – The best decades for travel and how COVID reshaped wanderlust

36:00 – Culture shock moments in China and India

37:30 – Who are Frommer’s guidebooks written for today

41:00 – How AI and algorithms are reshaping travel advice

47:00 – The truth behind energy use and AI’s environmental cost

48:00 – How podcasts keep travel storytelling real

53:00 – Pauline’s favourite destinations, cuisines, and experiences

59:00 – Why you should travel while you can

--------------------------------------------------------------

Voyascape: Travel Podcast Network - https://voyascape.com/

Winging It Travel Podcast - Website

Please leave a review and a 5-star rating wherever you get your podcasts!

--------------------------------------------------------------

Winging It Travel Podcast Credits

Host/Producer/Creator/Composer/Editor - James Hammond

Contact me - [email protected] 

Social Media - follow me on:

Instagram

TikTok 

Facebook 

--------------------------------------------------------------

Support My Podcast - Memberships

Patreon - Here

Buy Me A Coffee - Here

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 Your E-Sim With GigSky - 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

Buy my Digital Travel Planner - Here

--------------------------------------------------------------

Thanks for supporting me and the podcast!

Cheers James.

Mentioned in this episode:

Check out the Smart Travel Podcast

This week's show is supported by the new Smart Travel Podcast. Travel smarter — and spend less — with help from NerdWallet. Check out Smart Travel at the Link below:

Smart Travel Podcast

Welcome to this week's episode, where I share an episode where I was a guest on the Up In The Clowds Podcast with Adrian Ussling. Adrian's new podcast is a fantastic travel podcast sharing travel stories, tips, information, fun and much more. I loved being a guest, and hopefully, it provides you with some wanderlust.

Check out Adrian's podcast below.

Apple Podcasts - https://podcasts.apple.com/ca/podcast/wingin-it-ft-james-hammond/id1788205559?i=1000724621300

Spotify - https://open.spotify.com/episode/2M1CCDxcWDvBzwTwJ8DaLH?si=V8Ss8HssTFyxgS54dcbbmQ

Episode Shownotes

Joined today by fellow podcaster and travel enthusiast James Hammond. He has travelled to 70 countries and experienced a life that many of us dream of. His storytelling is immaculate and his memories are fascinating. A fun and memorable interview including:

• Going to a ping pong show in Bangkok
• Farm work and mining in Australia
• Almost losing a friend on the Death Road in Bolivia
• Experiencing life in the favelas of Brazil
• Embracing the organized chaos of Japan
• A series of unfortunate events in Bali
• & much much more!

Timestamps

00:00 Introduction and Life Update

10:40 Interview with James Hammond: Travel Experiences

19:01 Southeast Asia Adventures and Cultural Insights

25:46 Hidden Gems in Southeast Asia

28:01 Experiences in Australia: Work and Travel

30:29 Life in the Mines and Vineyards

33:10 Travelling Through South America

36:52 Adventures in Bolivia

40:08 Unique Experiences in Rio de Janeiro

45:01 The Thrill of Death Road

49:02 Reflections on Bolivia and the Inca Trail

53:19 Memorable Group Experiences

55:47 Travelling Without a Safety Net

58:13 Visa Strategies for Travellers

01:00:12 Hidden Gems and Favourite Destinations

01:01:38 The Allure of Japan

01:05:27 Lessons from Bali

01:10:04 Future Travel Plans and Aspirations

--------------------------------------------------------------

Voyascape: Travel Podcast Network - https://voyascape.com/

Winging It Travel Podcast - Website

Please leave a review and a 5-star rating wherever you get your podcasts!

--------------------------------------------------------------

Winging It Travel Podcast Credits

Host/Producer/Creator/Composer/Editor - James Hammond

Contact me - [email protected] 

Social Media - follow me on:

Instagram

TikTok 

Facebook 

--------------------------------------------------------------

Support My Podcast - Memberships

Patreon - Here

Buy Me A Coffee - Here

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 Your E-Sim With GigSky - 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

Buy my Digital Travel Planner - Here

--------------------------------------------------------------

Thanks for supporting me and the podcast!

Cheers James.

Mentioned in this episode:

Check out the Smart Travel Podcast

This week's show is supported by the new Smart Travel Podcast. Travel smarter — and spend less — with help from NerdWallet. Check out Smart Travel at the Link below:

Smart Travel Podcast

🎙️ Episode Title: Ep 187 w/ John Stuckey at Bear Hug Campers - Building the Perfect Campervan | Vanlife Design & Road Trip Freedom

In this week’s episode of The Winging It Travel Podcast, I chat with John Stuckey, the founder of Bear Hug Campers, a UK-based company known for crafting custom-built campervans that perfectly blend design, functionality, and adventure.

John shares how his passion for travel, craftsmanship, and freedom led him from building his first DIY campervan to launching a thriving business helping others bring their vanlife dreams to life. Based near the South Downs in England, Bear Hug Campers has become a go-to name for bespoke van conversions, off-grid living setups, and self-build support.

We unpack every stage of the campervan conversion journey — from early inspiration and learning the essential skills to understanding realistic build costs, materials, and layouts that actually work on the road. John also reveals the biggest rookie mistakes first-time builders make, the non-negotiables for safety and quality, and how to make smart choices that save money without cutting corners.

If you’ve ever dreamed of designing your own van, taking a road trip across Europe or North America, or simply embracing a more minimalist, nomadic lifestyle, this episode is packed with invaluable insight and encouragement. John’s experience offers both the creative inspiration and practical knowledge needed to start your own vanlife journey.

We also discuss the latest vanlife trends for 2025, including the rise of smaller, stealthy vans, clever space-saving designs, and why more people are turning to modular and off-grid builds. Plus, John explains how Bear Hug Campers supports the growing self-build community through his online van conversion courses, offering hands-on guidance, video tutorials, and a vibrant learning community for DIY builders.

This is a must-listen for vanlife enthusiasts, digital nomads, and travellers who want to combine creativity with practicality — and discover what it truly takes to build a home on wheels.

If you enjoyed this episode, please rate and review the show — it really helps others discover the podcast!

🔔 Subscribe, leave a ⭐️⭐️⭐️⭐️⭐️ review for Winging It, and support the podcast via Buy Me A Coffee!

00:00 Safety First: The Importance of Quality in Conversions

03:07 Budgeting for Your Dream Van: Cost Breakdown

06:01 Travel Tales: Exploring the UK and Beyond

08:55 The Allure of American Road Trips

12:03 Cultural Experiences: Japan and Its Unique Charm

14:49 The Journey to Van Conversions: Personal Experiences

18:06 Learning the Craft: Skills for Van Building

21:04 Bear Hug Campers: The Business of Custom Conversions

29:01 Building a Community Around Van Conversions

30:12 Budgeting for Van Conversions

34:35 Essential Features in Van Conversions

37:09 Cost-Saving Strategies Without Compromising Quality

41:07 Safety First: Where Not to Cut Corners

42:57 Common Rookie Mistakes in Van Conversions

48:35 Trends in Campervan Designs

51:06 Choosing the Right Van for Conversion

57:37 Must-Have Elements for a Successful Build

59:07 Designing the Perfect Van Layout

01:02:08 Understanding Customer Needs in Van Conversions

01:03:57 Training and Education for DIY Van Builders

01:06:05 Common Challenges in Van Conversions

01:08:37 Exploring the Van Life Community

01:10:00 Travel Destinations and Client Preferences

01:11:06 Unique and Challenging Requests in Van Builds

01:14:05 Future Projects and Innovations

01:16:05 Quickfire Travel Questions and Insights

• Website: bearhugcampers.com
• Instagram: @bearhugcampers

--------------------------------------------------------------

Voyascape: Travel Podcast Network - https://voyascape.com/

Winging It Travel Podcast - Website

Please leave a review and a 5-star rating wherever you get your podcasts!

--------------------------------------------------------------

Winging It Travel Podcast Credits

Host/Producer/Creator/Composer/Editor - James Hammond

Contact me - [email protected] 

Social Media - follow me on:

Instagram

TikTok 

Facebook 

--------------------------------------------------------------

Support My Podcast - Memberships

Patreon - Here

Buy Me A Coffee - Here

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 Your E-Sim With GigSky - 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

Buy my Digital Travel Planner - Here

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Thanks for supporting me and the podcast!

Mentioned in this episode:

Check out the Smart Travel Podcast

This week's show is supported by the new Smart Travel Podcast. Travel smarter — and spend less — with help from NerdWallet. Check out Smart Travel at the Link below:

Smart Travel Podcast

Magical Prague at Sunrise, My Cringe Oktoberfest Stories and Travel Fitness

In this week’s episode of Winging It Travel Podcast, I’m taking you through three very different parts of my travel life — the peaceful beauty of Prague at sunrise, the chaotic hilarity of my cringe Oktoberfest stories, and my personal reflections on something I call “travel fitness.”

I start with my recent trip to Prague, one of Europe’s most enchanting cities. After a sleepless overnight flight from Vancouver, I landed just in time to experience something truly magical — the city waking up at dawn. With the sun rising over the Vltava River and not a tourist in sight, I wandered across the Charles Bridge, through the Old Town Square, and soaked in that golden early-morning glow that made the whole city feel timeless. It reminded me why I travel — those quiet, unplanned moments that make everything worth it.

Then we move into a very different kind of travel experience — my cringe and hilarious Oktoberfest stories. I went to Oktoberfest for the first time back in 2014 at the end of my two-year backpacking trip, and to say it was messy would be an understatement. From falling off benches to accidentally soaking locals in beer, to somehow ending up cleaning my own disaster in a tent washroom — it was pure chaos. I also share what it was like to go back this year to meet some fellow travel creators, Chris and Sarah and Matt and Nat, and to see the festival from a slightly older (and more sober!) perspective. It’s a funny look back at my early travel days — the mistakes, the laughs, and the stories that stick with you forever.

Finally, I wrap up with a reflection on something I’ve been thinking about lately — travel fitness. It’s not just about being physically fit; it’s about having the energy, curiosity, and adaptability to keep exploring day after day. After walking nearly 27,000 steps in Prague, I realised just how much “travel stamina” it takes to be on the move — from early mornings, long days, and constant new experiences. I share a few honest thoughts on how I try to keep that balance and stay ready for whatever comes next on the road.

This episode is a mix of reflection, chaos, laughter, and travel insight — everything I love about sharing stories on this podcast. Whether you’re planning your next adventure, reminiscing about your own travel fails, or just dreaming of that next sunrise in a new city, I hope this episode inspires you to get out there and keep exploring.

00:00 – Intro and what’s coming up in this episode

01:10 – Why Prague blew me away at sunrise

03:20 – First impressions of the city and staying on a boat hotel

05:30 – Walking Prague’s empty streets and Charles Bridge at dawn

08:00 – Meeting a fellow traveler and reflecting on Prague’s vibe

10:30 – Travel tips: seeing Prague before the crowds

11:00 – Heading to Oktoberfest and meeting YouTube travel creators

12:45 – Throwback to my first Oktoberfest in 2014

15:00 – The infamous “bench collapse” story

17:30 – Falling asleep at a Bayern Munich game

19:40 – My worst Oktoberfest hangover ever

21:30 – Revisiting Oktoberfest as an older, wiser traveler

22:30 – What I’ve learned from embarrassing travel moments

23:00 – Introducing “travel fitness” — my personal theory

24:30 – Why travel stamina matters on long trips

25:20 – Tips for building your travel fitness before your next adventure

26:00 – Upcoming podcast news and future travel plans

🎥 Watch my vlogs on YouTube: Roaming with Hammo

🌍 Explore more travel podcasts at Voyascape.com

☕ Support the show → Buy Me a Coffee

🧳 Book Lucie's free walking tour on your next visit to Prague - https://www.guruwalk.com/walks/36530-welcome-to-prague-old-town-jewish-quarter-and-charles-bridge

--------------------------------------------------------------

Voyascape: Travel Podcast Network - https://voyascape.com/

Winging It Travel Podcast - Website

Please leave a review and a 5-star rating wherever you get your podcasts!

--------------------------------------------------------------

Winging It Travel Podcast Credits

Host/Producer/Creator/Composer/Editor - James Hammond

Contact me - [email protected] 

Social Media - follow me on:

Instagram

TikTok 

Facebook 

--------------------------------------------------------------

Support My Podcast - Memberships

Patreon - Here

Buy Me A Coffee - Here

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 Your E-Sim With GigSky - 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

Buy my Digital Travel Planner - Here

--------------------------------------------------------------

Thanks for supporting me and the podcast!

Cheers, James.

Mentioned in this episode:

Check out the Smart Travel Podcast

This week's show is supported by the new Smart Travel Podcast. Travel smarter — and spend less — with help from NerdWallet. Check out Smart Travel at the Link below:

Smart Travel Podcast

Ep 186 w/ Rachel Rudwall - From STA Travel to 80 Countries: Rachel's Journey as a Global Storyteller

In this episode of the Winging It Travel Podcast, I sit down with Rachel Rudwall, who is also known as Rachel Roams. Rachel is an Emmy-nominated on-camera Host, Producer, Camera Operator, Writer, and Award-Winning Photographer. Rachel has travelled to all seven continents, lived in three countries, and journeyed through over 80 nations. Rachel is also a Fellow of the Explorers Club and has an extensive social media following. I met Rachel last year at TravelCon, where she gave a very inspiring talk that captivated me, so I was eager to have her on the podcast for a conversation.

From her early days in Ohio dreaming of the wider world, to landing a life-changing internship with STA Travel, Rachel’s story is one of persistence, curiosity, and following her passion for exploration.

Rachel shares how her time with STA Travel opened the door to a career in travel media, taking her from study abroad experiences in Spain and Scotland to a globe-spanning role as a video producer and host. We dive into the challenges and lessons of producing content before the days of YouTube dominance, what it takes to capture and hold an audience, and why storytelling always begins with putting the listener or viewer first.

We also explore the reality behind the glamorous world of travel media — the grind of producing content, the countless hours behind the scenes, and the need to love the craft deeply enough to push through the hard days. Rachel discusses building her creative career in Los Angeles, collaborating with other storytellers, and carving out her niche in a male-dominated industry where persistence and proof of concept were crucial.

On a personal level, Rachel reflects on how travel has evolved for her as a mother, from multi-month shoots to family adventures across Italy and beyond. She offers powerful insights into balancing work and family life, finding joy in simple experiences like visiting playgrounds and local grocery stores, and instilling a spirit of adventure in her child.

This conversation is packed with travel inspiration, career lessons, and practical advice for content creators, adventurers, and dreamers alike. Whether you’re fascinated by travel TV, curious about breaking into storytelling, or simply love hearing about epic adventures across 80 countries, Rachel’s journey will spark your wanderlust and leave you inspired.

Rachel Rudwall

Website - https://www.rachelroams.com/

Instagram - https://www.instagram.com/rachelroams/?hl=en

X - https://x.com/RachelRoams

🔔 Subscribe, leave a ⭐️⭐️⭐️⭐️⭐️ review for Winging It, and support the podcast via Buy Me A Coffee!

Timestamps

00:00 The Power of Collaboration in Creativity

01:31 Embracing Travel: Overcoming Fear and Finding Joy

03:50 Introduction to Rachel Rudwell: A Journey of Exploration

12:10 Early Travel Experiences: Family Road Trips and Cultural Awareness

14:31 Defining Moments: The Internship that Changed Everything

20:55 Navigating the Media Landscape: From Intern to Storyteller

25:04 The Art of Storytelling: Learning from Experience

33:23 Proof of Concept: The Importance of Persistence in Content Creation

37:41 Creative Roots: Photography, Writing, and the Journey of Expression

41:54 Rediscovering Playfulness in Adulthood

46:21 The Joy of Travel and Family Adventures

56:18 Cultural Connections Through Travel

01:04:08 Moments of Reflection and Self-Discovery

01:10:24 Travel Tips for the Adventurous Spirit

--------------------------------------------------------------

Voyascape: Travel Podcast Network - https://voyascape.com/

Winging It Travel Podcast - Website

Please leave a review and a 5-star rating wherever you get your podcasts!

--------------------------------------------------------------

Winging It Travel Podcast Credits

Host/Producer/Creator/Composer/Editor - James Hammond

Contact me - [email protected] 

Social Media - follow me on:

Instagram

TikTok 

Facebook 

--------------------------------------------------------------

Support My Podcast - Memberships

Patreon - Here

Buy Me A Coffee - Here

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 Your E-Sim With GigSky - 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

Buy my Digital Travel Planner - Here

--------------------------------------------------------------

Thanks for supporting me and the podcast!

Cheers, James.

Mentioned in this episode:

Check out the Smart Travel Podcast

This week's show is supported by the new Smart Travel Podcast. Travel smarter — and spend less — with help from NerdWallet. Check out Smart Travel at the Link below:

Smart Travel Podcast

My Top 15 Travel Destinations I’d Return to Tomorrow in a Heartbeat (And Why They’re Unforgettable)

What makes a destination unforgettable? Is it the people, the food, the culture, or simply the feeling you get when you arrive? In this episode of the Winging It Travel Podcast, I take you through 15 of the most incredible places I’ve visited that continue to pull me back. These are the destinations I’d return to tomorrow if I had the chance, and each one has its own story, memory, and lasting impression.

Across this journey, you’ll hear about destinations that range from vibrant global cities to remote islands and peaceful mountain villages. Each one shaped my travels in different ways — whether through breathtaking landscapes, powerful cultural encounters, or spontaneous adventures that could only have happened elsewhere. These are the places that stay with you long after you’ve left, the ones that call you back no matter how many new countries you explore.

This list isn’t about checking boxes on a tourist itinerary. It’s about travel that feels personal and transformative. Some of these destinations are well-known icons of world travel, while others are tucked-away gems that left me speechless; yet all of them remain unforgettable. When I think about where I’d be happiest to go back to in a heartbeat, these 15 spots rise straight to the top.

If you’ve ever wondered which destinations are worth returning to, this episode will give you plenty to think about. Maybe it will remind you of a place you’ve already visited and loved, or perhaps it will spark your curiosity for somewhere new. Travel is about those moments that linger in your memory, and this countdown is all about the locations that have done precisely that for me.

So, whether you’re planning your next trip, looking for travel inspiration, or love hearing stories from around the world, join me as I share the places that I can’t stop thinking about. Some are across the ocean, some are closer to home, but every one of them has the power to inspire a return journey.

Press play and see how my list compares to yours. Which destination would you return to tomorrow in a heartbeat?

🔔 Subscribe, leave a ⭐️⭐️⭐️⭐️⭐️ review for Winging It, and support the podcast via Buy Me A Coffee!

Timestamps

00:00 – Introduction to the countdown of unforgettable travel destinations

02:17 – Starting with hidden islands and fiery landscapes

03:44 – Stories from vibrant streets and dramatic South American backdrops

06:08 – A journey through ancient temples and a golden coastline escape

08:54 – Mountain town magic and the charm of traditional culture

10:50 – A road trip through breathtaking natural wonders

12:44 – Two iconic cities filled with energy, history, and endless exploration

16:08 – Coastal drives, lighthouses, and a slower pace of life

17:35 – A buzzing metropolis full of flavours, markets, and surprises

18:35 – High-altitude trails, mountain villages, and unforgettable sunrises

20:33 – A dreamy finale in a place that feels like pure paradise

--------------------------------------------------------------

Voyascape: Travel Podcast Network - https://voyascape.com/

Winging It Travel Podcast - Website

Please leave a review and a 5-star rating wherever you get your podcasts!

--------------------------------------------------------------

Winging It Travel Podcast Credits

Host/Producer/Creator/Composer/Editor - James Hammond

Contact me - [email protected] 

Social Media - follow me on:

Instagram

TikTok 

Facebook 

--------------------------------------------------------------

Support My Podcast - Memberships

Patreon - Here

Buy Me A Coffee - Here

Affiliate Links 

If you click one of the links below to book something, I get a tiny commission, which helps the podcast.

Book Flights with Skyscanner - Here 

Use Revolut Travel Card - Here

Book Your E-Sim With GigSky - 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

Buy my Digital Travel Planner - Here

--------------------------------------------------------------

Thanks for supporting me and the podcast!

Cheers, James.

Mentioned in this episode:

Check out the Smart Travel Podcast

This week's show is supported by the new Smart Travel Podcast. Travel smarter — and spend less — with help from NerdWallet. Check out Smart Travel at the Link below:

Smart Travel Podcast