The Winging It Travel Podcast is your weekly ticket to the world—dropping every Monday and hosted by me, James Hammond, proudly part of the Voyascape Network.
This is more than just a travel podcast—it's a cinematic audio experience that takes you deep into the heart of each journey. Through rich immersive soundscapes, on-the-ground reactions, and authentic storytelling, I bring you right alongside me—whether I’m hiking up volcanoes in Guatemala, navigating the chaos of a city market in India, or camping under the stars in British Columbia.
With over fifteen years of travel behind me, I've met incredible people, seen breathtaking places, and collected unforgettable stories—and now I get to share them with you. Expect a mix of:
🎧 Immersive-Audio episodes that let you hear the world as I experience it
🎙️ Raw, reflective solo episodes filled with insights, tips, and honest travel tales
🌍 Guest conversations with some of the most diverse and well-travelled people I've encountered on the road
Every episode blends anecdotes, practical advice, cultural insight, and moments of pure adventure. This podcast is for travellers, dreamers, backpackers, and anyone who’s ever thought, what if I just went for it?
So, if you're looking for stories to tell, tips to share, and experiences to inspire, you're in the right place.
There’s so much travel content coming your way, it just might spark that trip you’ve been dreaming about for years.
Welcome to a world of travel! Thank you for listening in. Please get in touch with us below.
Produced by Winging It Productions - https://www.wingingitproductions.com
Finally, please rate the podcast five stars on your podcast app and give a positive written review. This helps the podcast grow, for free.
Website - https://www.wingingittravelpodcast.com
Buy Winging It a coffee - buymeacoffee.com/wingingit
Voyascape - https://voyascape.com
Linktree - https://linktr.ee/jameshammondtravel
Email - jameshammondtravel@gmail.com
Roaming with Hammo YouTube channel - https://www.youtube.com/@roamingwithhammo
Happy Winging It!
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Winging It On Location – Days 2-3-Tallinn: A Trendy Old Town, Estonian History and Monopoly Deal
Saturday, August 8, 2026 • Duration 15:29
Winging It On Location – Days 2-3-Tallinn: A Trendy Old Town, Estonian History and Monopoly Deal
In this second instalment of my Winging It On Location series from the Baltics, I spend two full days exploring Estonia’s capital beyond the first evening impressions. From avocado toast in one of Tallinn’s trendiest cafés to a deep dive into the country’s Soviet history, this episode blends food, culture, history and the small moments that make a trip memorable.
I wander through the cobbled streets of the Old Town in the sunshine, join a free walking tour to learn about Estonia’s path to independence, and take in panoramic views across the city. The next day I head out to the seaside district of Pirita, visit the Soviet memorials and cemetery, and reflect on how Estonia preserves difficult parts of its past.
There’s also excellent coffee, cardamom buns, goulash in a bread bowl, jazz at Philly Joe’s, and the beginning of a travel obsession that may last the rest of the trip: Monopoly Deal.
If you’re considering a European city break that feels safer, quieter and less crowded than many of the continent’s major capitals, Tallinn might be the perfect choice.
In this episode:
Exploring Tallinn’s Old Town, cafés and bakeries
Learning about Estonia’s history on a free walking tour
Visiting Soviet memorials and Pirita Beach
Jazz, wine and final thoughts on Tallinn as a city break
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Winging It On Location – Day 1: 5-Hour Layover in Amsterdam & Arriving in Tallinn
Wednesday, August 5, 2026 • Duration 12:12
Winging It On Location – Day 1: 5-Hour Layover in Amsterdam & Arriving in Tallinn
The European tour is officially underway.
In this first on-the-road episode, I take you through my journey from Toronto to Tallinn via Amsterdam, including what you can realistically do with a 5-hour layover at Schiphol Airport. I share the exact train route into the city, why I chose the Jordaan district, and the coffee stop that made the short visit worthwhile.
After a quick wander through Amsterdam’s canals, bridges, and tree-lined streets, I head back to the airport for my flight to Estonia. Once in Tallinn, I give my first impressions of the city, explain the easiest tram connection from the airport, and meet up with friends for dinner in the heart of the Estonian capital.
If you’re planning an Amsterdam layover, a Tallinn city break, or simply enjoy hearing authentic travel stories from the road, this episode is for you.
In this episode:
How to do Amsterdam on a short layover
Using contactless payment on Dutch trains
The best area to wander for 2–3 hours in Amsterdam
Coffee recommendation in the Jordaan district
Arriving in Tallinn and getting into the city for €2
Hotel information
Dinner, drinks, and the start of the Baltic adventure
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How Celiac Disease Changed the Way We Travel | My Appearance on The Gluten Free Advocate Podcast
Monday, July 27, 2026 • Duration 43:38
A year ago, my partner Emma was diagnosed with celiac disease, completely changing the way we think about travel. In this special episode, I'm sharing my conversation with Leigh Francis from The Gluten Free Advocate Podcast about what it's really like adapting to gluten-free travel while still chasing adventure.
We discuss the emotional side of a diagnosis, how our travel style has evolved from spontaneous backpacking to careful planning, and why destinations like Victoria, BC and parts of Europe have given us confidence that incredible travel is still possible.
We also dive into my recent adventures through El Salvador, Guatemala, Mexico and Bhutan, my future plans for French Polynesia, Central Asia and Africa, and how this experience is changing the content I create on both the Winging It Travel Podcast and YouTube.
Whether you have celiac disease yourself, travel with someone who does, or simply love hearing honest travel conversations, this episode offers practical advice, encouragement and plenty of wanderlust.
In this episode you'll hear:
Emma's unexpected celiac diagnosis and how it changed our lives
Why travelling with celiac disease requires a completely different mindset
The challenges of avoiding cross-contamination while travelling
The best gluten-free destinations we've experienced so far
Planning our upcoming trip to French Polynesia
How this journey is changing my podcast and YouTube content
Bucket list destinations still waiting to be explored
Why travel is still absolutely worth it—even with dietary restrictions
If you want to be able to listen to our conversation from Season 1 - check out this episode: https://www.youtube.com/watch?v=ynv84AuSkek
If you have any questions or fun stories to share, feel free to reach out at hieatexplorelove@gmail.com.
Some travel memories fade over time, but others stay with you forever.
In this solo episode of the Winging It Travel Podcast, I'm sharing ten very specific travel moments from the past 15 years that instantly take me back whenever I think about them. These aren't just favourite countries or famous landmarks—they're the unexpected moments of peace, achievement, freedom and awe that remind me exactly why I love travelling.
From watching the sunrise over the Himalayas after hiking to Poon Hill in Nepal, to discovering paradise in the Cook Islands, exploring Thailand and Myanmar by scooter, reflecting after completing the Inca Trail, standing alone at Petra before the crowds arrived, watching hot air balloons drift over Cappadocia, experiencing the Canadian Rockies at sunrise, and witnessing Volcán Fuego erupt in Guatemala, these are the memories that continue to inspire me to keep exploring.
I'd love to hear your own unforgettable travel memories after listening to this episode.
In this episode you'll hear:
Why a tiny tea house in Nepal became one of my favourite travel memories
REVISITED - Episode 25 - 10 Things I Would Advise A New Traveller
Tuesday, July 14, 2026 • Duration 01:00:29
Five years ago, I recorded one of the earliest solo episodes of Winging It, sharing ten pieces of travel advice that I wished someone had told me before I set off exploring the world. Since then, I've visited many more countries, built a travel podcast, launched a YouTube channel, started a podcast production business and experienced everything from hiking to Tiger's Nest in Bhutan to travelling through Guatemala, Mexico and El Salvador.
So I decided to revisit that episode and ask a simple question: Would I still give the same advice today?
In this episode, I react to each of my original ten travel tips, discussing what's changed, what I've learned over another five years of travelling and whether my opinions still hold true. From embracing flexibility and getting outside your comfort zone to documenting your travels, packing efficiently and making the most of working holiday visas, this is an honest look at how both travel—and I—have evolved.
Whether you're planning your very first backpacking trip or you've already caught the travel bug, I hope these updated reflections help you travel smarter, more confidently and make the most of every adventure.
If you've got your own travel advice that you'd give to a first-time traveller, I'd love to hear it. Get in touch on social media or leave a comment on YouTube.
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Why the World Cup Proves Travel Brings People Together | My Updated 2026 Travel Plans & Recovering From Kidney Stones
Wednesday, July 8, 2026 • Duration 17:27
Why the World Cup Proves Travel Brings People Together | My Updated 2026 Travel Plans & Recovering From Kidney Stones
This week I'm sharing a more personal update as I recover from kidney stones, reflect on the incredible atmosphere surrounding the FIFA World Cup, and look ahead to an exciting second half of the year packed with travel.
After a slower start to 2026, I'm finally getting ready to hit the road again with trips to Toronto, Estonia, Finland, Paris and French Polynesia. I also share how this period away from travelling has helped me rethink my content, my business and what I want the future of Winging It to look like.
I also explain why I believe the World Cup is one of the greatest examples of how travel brings people together. From the incredible hospitality shown by Mexican fans to England supporters, to thousands of people from different cultures celebrating side by side, it's a reminder that travel creates understanding, respect and unforgettable memories.
Finally, I open up about dealing with kidney stones over the past couple of weeks, what it's taught me about appreciating everyday life, and why I'm looking forward to getting back out into the world once I'm fully recovered.
If you've been thinking about booking your next adventure, hopefully this episode gives you the inspiration to finally go for it.
In this episode:
• Why the World Cup is about far more than football.
• The incredible hospitality between travelling fans.
• My upcoming trips to Canada, Estonia, Finland, France and French Polynesia.
• How I've been rethinking my travel content and podcast plans.
• Recovering from kidney stones and what the experience has taught me.
• A look ahead to what's coming next on Winging It Travel Podcast.
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⏱️ Timestamps
15 Reasons Why You Should Travel From 15 Previous Guests
Thursday, July 2, 2026 • Duration 15:13
This week is a little different.
I went back through the Winging It archives and handpicked 15 previous guests, asking each of them the same quick-fire question:
"What would you say to someone who's nervous about travelling and why they should go?"
Their answers are honest, inspiring, funny and thought-provoking. Whether you're dreaming about your first solo trip, planning a career break, or simply need a reminder of why we explore, these 15 reasons might be exactly what you need.
Featuring adventurers, authors, broadcasters, travel creators and industry experts, this episode is the perfect way to kick off the summer.
Why You Should Stop Waiting for the “Right Time” to Take a Career Break (Taking A Career Break with Katrina Crossover)
Monday, June 22, 2026 • Duration 33:12
Why You Should Stop Waiting for the “Right Time” to Take a Career Break (Taking A Career Break with Katrina Crossover)
This week on Winging It, I'm sharing a special crossover episode from my other podcast, Taking A Career Break with Katrina McGhee. I really feel our two audiences do crossover, so I am sharing one of our most popular episodes with you. Please check out the rest of the catalogue for everything relating to a career break.
Episode 67 - Why You Should Stop Waiting for the “Right Time” to Take a Career Break Shownotes
If you've ever dreamed of taking a career break, travelling the world, changing direction, or simply pressing pause on the life you've built, you've probably told yourself the same thing many of us do:
"I'll do it when the timing is right."
The truth is, there may never be a perfect time.
In this episode, Katrina and I dive into one of the biggest reasons people never take a career break: waiting for the mythical "right time." We explore why life will always present obstacles, why fear often disguises itself as practicality, and how delaying your dreams can lead to years of wondering "what if?"
Is there ever a right time to take a career break—or are you just waiting forever?
From economic uncertainty and job market fears to internal pressure and workplace guilt, they unpack why it always feels like the wrong time—and why that thinking is keeping you stuck.
Katrina introduces the concept of PHOBO (Fear of Becoming Obsolete) and explains how this fear shows up both before and during a career break—often preventing people from fully committing to the change they need.
You’ll learn why the “perfect moment” doesn’t exist, how your brain is wired to keep you in survival mode, and what it actually takes to create a good enough time to step away and reset your life.
If you’ve been telling yourself “maybe next year” or “once things settle down,” this episode will challenge that narrative—and help you take your first real step toward a career break.
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Why Travel Changes Everything - A Deep Dive with James Hammond on the Island Vacation Travel Podcast
Monday, June 15, 2026 • Duration 01:00:37
Why Travel Changes Everything - A Deep Dive with James Hammond on the Island Vacation Travel Podcast
Hello guys!
Another guest appearance on another travel podcast today, and this time it is the Island Vacation Travel Podcast with Al Philogene, as we take a deep dive into the impact of travel on our daily lives, as a lifestyle choice and the impact on me personally too.
You can watch this episode on YouTube here (please subscribe to Winging It) - https://youtu.be/XWfXoSQ5r7c
I loved speaking with Al on his podcast, so please check it out below, too. Enjoy!
Apple Podcasts - https://podcasts.apple.com/ca/podcast/island-vacation-travel-podcast/id1579773196
Website - https://islandvacationpodcast.com/#
Island Vacation's Shownotes below.
James Hammond shares his unforgettable travel experiences in Bhutan, Japan, and Bolivia, highlighting the importance of practical budgeting and lifestyle centered around exploration. He emphasizes the significance of people, culture, and food in each destination, and provides valuable insights on planning a six-month backpack trip to South America, including budgeting, route planning, and avoiding common travel mistakes.
The conversation covers topics related to visa rules and immigration, the difference between hidden gems and tourist-heavy spots, the choice between travel and a traditional career path, financial trade-offs and the balance between freedom and stability, and the impact of COVID-19 on travel. The conversation covers the impact of COVID on travel, the rise in travel costs, the experience of over-tourism, and the financial considerations of long-term travel. It also delves into the importance of cultural familiarity when starting to travel and the need to adapt to changing travel costs and conditions.
Takeaways
• Unforgettable travel experiences in Bhutan, Japan, and Bolivia
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Wellington Travel Guide: Why I Spent a Year Living in New Zealand's Capital
Monday, June 8, 2026 • Duration 30:04
Wellington Travel Guide: Why I Spent a Year Living in New Zealand's Capital
Wellington is one of my favourite cities in the world, and in this episode I'm sharing exactly why.
I first visited New Zealand's capital in 2013 on the Kiwi Experience and instantly connected with the city. In 2017, when Emma and I arrived in New Zealand on a working holiday visa, we spent weeks road-tripping around both islands before deciding where to settle. I already had my sights set on Wellington, and thankfully Emma fell in love with it too. We ended up spending nearly a year living there, giving us the chance to experience the city far beyond the typical tourist highlights.
In this Wellington travel guide, I share the places, experiences and local tips that made the city so special to us. From riding the iconic Wellington Cable Car and exploring Te Papa Museum to walking the waterfront, climbing Mount Victoria and discovering all parts of the city, I cover the attractions that I think every visitor should experience.
Of course, no episode about Wellington would be complete without talking about coffee and brunch. This is the city where my love of coffee began, and over the course of 11 months I worked my way through more cafés than I can count. I share my favourite spots for brunch, great coffee, waterfront views and local atmosphere, including some long-time Wellington institutions that I still think about today.
I also dive into the practical side of visiting and living in Wellington, including where to stay, the best neighbourhoods to base yourself, transport options, day trips, travelling between the North and South Islands, and what it was like finding work while on a New Zealand working holiday visa. If you're considering moving to Wellington or spending time there as a backpacker, digital nomad or working holiday traveller, there's plenty here for you.
Along the way, I share some personal stories from our time living in the city, including working in government ministries, surviving a late-night earthquake, becoming known as the office "serial monster", buying a $1,000 road-trip car and somehow making a profit when it was written off.
Whether you're planning your first visit to Wellington, preparing for a New Zealand working holiday, or simply looking for inspiration for your next trip, this episode will give you an honest look at one of the most creative, quirky and liveable cities I've ever experienced.
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00:00 Intro & recording live from Tallinn
01:38 Toronto to Amsterdam: the journey begins
02:20 Getting through Schiphol and heading into the city
03:15 The fastest train from Amsterdam Airport to Central Station
04:05 Why I chose the Jordaan district for a short layover
05:30 Canals, bridges, sunshine, and wandering without a plan
06:40 Coffee stop recommendation: KOF Café
07:30 The unexpected challenge of finding a public toilet
08:10 Where to see the famous houses sitting on the water
09:05 Is a 5-hour Amsterdam layover actually worth it?
09:45 Flying to Tallinn and first impressions of Estonia
10:20 Tallinn hotel, tram tips, and city-centre arrival
10:55 Dinner with friends and Estonian food prices
• Practical budgeting and lifestyle centered around exploration Visa rules and immigration are important considerations for travelers, and it's essential to research and understand the rules of each country.
• Choosing hidden gems over tourist-heavy spots can lead to a more unique and less crowded travel experience.
• The decision to prioritize travel over a traditional career path involves a trade-off between stability and freedom, and the pursuit of experiences over material possessions.
• The impact of COVID-19 on travel has led to increased costs and a surge in travel to popular destinations, highlighting the importance of exploring hidden gems and off-peak travel periods. COVID has impacted travel costs and led to a rise in expenses.
• Cultural familiarity is important when starting to travel, and it's advisable to start small and gradually explore different cultures.
• Adapting to changing travel costs and conditions is crucial for long-term travel.
If you enjoyed this episode:
⭐ Leave a 5-star rating or review on your podcast app
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