Winging It Travel Podcast

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

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.

Taking A Career Break with Katrina McGhee

Apple Podcasts - https://podcasts.apple.com/ca/podcast/taking-a-career-break-with-katrina-mcghee/id1772602758

Spotify - https://open.spotify.com/show/1lRPigXIghYUw82Eqak0mF?si=b956d5b826df4cf1

YouTube - https://www.youtube.com/@TakingaCareerBreakwithKatrina

Ready to stop "running on empty" and start running toward a life you actually love?

📞Schedule a call with Katrina - ⁠⁠⁠⁠⁠⁠⁠https://kmcgheecoaching.as.me/freeconsult⁠⁠⁠⁠⁠⁠⁠

🫶🏼Join the BreakSpace community - ⁠⁠⁠⁠⁠⁠⁠www.gobreakspace.com⁠⁠⁠⁠⁠⁠⁠

🎁Order Katrina's book (w/ special bonus!) - ⁠⁠⁠⁠⁠⁠⁠https://www.kmcgheecoaching.com/book⁠⁠⁠⁠⁠⁠⁠

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

00:00 Introduction – Why this career break episode matters for travellers

02:08 Winging It Travel Podcast intro

03:47 Welcome to Taking A Career Break with Katrina McGhee

04:39 Why do we keep waiting for the "right time"?

06:34 The fear of becoming obsolete and falling behind

08:13 Is there ever a good economic time to take a break?

10:59 Why hard times don't mean you can't make a career break happen

13:00 James shares his own fears about timing and entrepreneurship

15:27 The "worst time fallacy" explained

17:13 Why guilt keeps people stuck in jobs

18:52 Break Space: Support for your own career break journey

19:28 The target keeps moving – there will always be another excuse

22:58 When has life ever truly felt certain?

24:39 Planning versus endlessly postponing your dreams

26:23 Why the perfect moment doesn't exist

27:15 How fear of falling behind keeps you in survival mode

29:32 Building the bridge before taking the leap

31:05 Stop waiting and start making your career break happen

32:17 Final thoughts and outro

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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.

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.

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

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!

Spotify - https://open.spotify.com/show/6IKCiUg5sZstUia5vOpK62?si=d9c56d650b754e28

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

• 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
• ☕ 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

00:00 - Introduction & Welcome

02:02 - Meet James Hammond: Building a Travel Lifestyle

02:56 - Top 3 Countries: Bhutan, Japan & Bolivia

05:32 - Memorable Travel Experiences from Around the World

08:14 - Why People Matter More Than Food or Culture

09:12 - Why Everyone Should Travel at Least Once

10:39 - Planning a 6-Month Backpacking Trip

13:41 - Essential Gear Every Long-Term Traveller Needs

15:14 - Travel Budgets: How Much Money Do You Really Need?

17:33 - Route Planning Across South America

19:21 - Biggest Travel Mistakes to Avoid

22:31 - Hidden Gems vs Tourist Hotspots

25:46 - Why I Chose Travel Over a Traditional Career

30:07 - Freedom vs Financial Stability

37:42 - Upcoming Trips: Finland, Estonia & French Polynesia

38:51 - Travel After COVID: What's Changed?

43:21 - My Least Favourite Destination (And Why)

46:55 - Countries Still on My Travel Bucket List

49:19 - How Much Money Do You Need to Travel the World?

54:07 - Advice for First-Time Travellers

58:00 - Where to Find Winging It Travel Podcast & Roaming with Hammo

59:43 - Final Thoughts & Outro

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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.

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.

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

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.

In this episode:

• Why Wellington became our home for nearly a year

• The best things to do in Wellington

• My favourite cafés, brunch spots and coffee roasters

• Where to stay and the best neighbourhoods to explore

• Working holiday and job-hunting advice

• Transport tips and South Island connections

• Road-trip recommendations and day trips

• Stories from everyday life in New Zealand's capital

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

00:00 Why Wellington became my favourite city

02:30 Wellington explained: location, culture and first impressions

03:20 The "Serial Monster" work story

05:50 Working holiday jobs and finding work in Wellington

08:10 Best things to do in Wellington

10:50 Waterfront walks, Mount Victoria and local neighbourhoods

12:05 Day trips, sporting events and road trips

13:30 Where to stay in Wellington

15:55 Support the podcast

16:40 Earthquake experiences in Wellington

17:50 Best cafés, brunch spots and coffee in Wellington

22:15 Food markets and eating on a budget

23:15 Wellington travel and transport tips

25:40 Kiwi Experience and travelling New Zealand

26:40 Buying a car and road-tripping New Zealand

28:05 Why Wellington is still one of my favourite cities

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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.

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.

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

Welcome to this special episode where I am on the other side of the mic!

I recently joined the Temporary Locals Podcast to share my experience travelling through the fascinating Himalayan kingdom of Bhutan. In this conversation, we dive into what makes Bhutan one of the most unique travel destinations on Earth, from its strict tourism policies and sustainable tourism model to its rich Buddhist culture and breathtaking mountain scenery.

We discuss the realities of planning a trip to Bhutan, including costs, guided tours, and the famous Sustainable Development Fee. I share stories from hiking to the iconic Tiger's Nest Monastery, staying with a local family in a traditional homestay, attending Bhutanese festivals, exploring the capital Thimphu, and experiencing the country's deep spiritual culture.

Along the way, we talk about Bhutanese food, local customs, mountain life, and even the surreal experience of flying home on the same flight as the King and Queen of Bhutan. If you've ever wondered what it's really like to visit one of the world's most exclusive and mysterious countries, this episode is packed with practical advice, cultural insights, and memorable travel stories.

Temporary Locals' Shownotes

In this episode, Jared and Megan welcome travel vlogger James Hammond to discuss his recent trip to Bhutan. They explore Bhutan's unique culture, geography, and the requirements for visiting this lesser-known Himalayan destination. James shares his experiences hiking to the famous Tiger's Nest Monastery, staying with a local family, interviewing a Lama, nightlife of Thimphu and ending up on the same flight as a King.

Please check out Megan and Jared's Temporary Locals Podcast below. I love their style, content and approach to travel.

Apple Podcasts - https://podcasts.apple.com/ca/podcast/temporary-locals-podcast/id1845249694

Spotify - https://open.spotify.com/show/3pQ3gIDSRfd4Ep9zqZ2YoK?si=f4997bb0755b4997

YouTube - https://www.youtube.com/@TemporaryLocalsPodcast

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

00:00 Introduction and why Bhutan captured my attention

03:50 Where Bhutan is located and why I finally decided to visit

05:55 Why Bhutan remains one of the world's most underrated destinations

07:24 How Bhutan's tourism system works, tour requirements, and trip costs

12:00 Previous Himalayan adventures and first impressions of the region

14:00 Flying over Everest and the Himalayas on the way to Bhutan

15:51 Arriving in Bhutan and adjusting to life at altitude

23:23 Working with Bhutan Tourism and creating travel content in the country

26:38 Staying in a Bhutanese homestay and meeting Amma Om

28:30 Milking cows, making cheese, and authentic cultural experiences

33:43 Experiencing Bhutan's colourful festivals and celebrations

37:06 Unexpectedly attending Bhutan's National Day celebrations

38:41 Sharing a flight with the King and Queen of Bhutan

41:09 Hiking to Tiger's Nest Monastery and what it's really like

47:44 Why I cancelled a Himalayan camping trek in Haa Valley

51:40 Exploring Thimphu, nightlife, breweries, and local culture

56:38 Buddhism, spirituality, and daily life in Bhutan

59:00 Getting around Bhutan and travelling between Paro and Thimphu

01:01:24 Bhutanese food, chilli cheese dishes, and coffee culture

01:06:25 My top recommendations for a first-time trip to Bhutan

01:12:32 Final thoughts and where to find my travel content

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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.

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.

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

In this immersive episode of the Winging It Travel Podcast, I head over to beautiful Gabriola Island in British Columbia for a peaceful weekend of camping, beaches, coffee shops, sunsets, ferries, and slow island living. Located just off the coast of Nanaimo on Vancouver Island, Gabriola is one of BC’s hidden gems and the perfect nature escape from Vancouver.

Gabriola Island is a scenic, tranquil Gulf Island in British Columbia, Canada, located just a 25-minute ferry ride from Nanaimo on Vancouver Island. Known as the "Isle of the Arts," the island is celebrated for its lush forests, rugged coastline, and vibrant community of working artists.

This episode is a mix of travel guide, solo storytelling, and immersive soundscape audio as I share exactly how to get to Gabriola Island, ferry costs, campsite information, what to do on the island, where to eat and drink coffee, and why this laid-back Gulf Island completely won me over.

From camping at Descanso Bay Regional Park and relaxing at Sandwell Provincial Park to visiting local cafes like Mad Rona’s and Ground Up Cafe, this trip was packed with wholesome moments, nature, and plenty of ocean views. I also share practical travel tips, ferry advice from Horseshoe Bay and Nanaimo, and honest thoughts on whether Gabriola Island is worth visiting.

If you’re planning a weekend getaway in British Columbia, looking for Gulf Islands travel inspiration, or simply want an immersive travel podcast experience, this episode is for you.

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

00:00 – Introduction to Gabriola Island

01:05 – What this episode will include

02:18 – BC Ferries information & travel costs

04:45 – Nanaimo parkrun & pre-island stop

05:40 – Brunch at Black Rabbit in Nanaimo

06:40 – Ferry from Nanaimo to Gabriola Island

07:05 – Gabriola farmers market & alpaca farm

07:50 – Exploring the island hub & Nestors Market

08:20 – Camping at Descanso Bay Regional Park

09:15 – Sunset by the bay & campsite vibes

10:45 – Morning sounds & camping breakfast

11:15 – Coffee stop at Mad Rona’s Cafe

12:05 – Sandwell Provincial Park beach visit

13:05 – Gabriola Sands Provincial Park & The Twins

13:50 – Ground Up Cafe & more island coffee

14:20 – Ravenskill Orchards cidery visit

15:00 – Sunset reflections & island atmosphere

15:40 – Leaving Gabriola Island & ferry tips

16:15 – Final thoughts on Gabriola Island

17:00 – Why Gabriola Island is worth visiting

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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.

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.

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

Why Waiting Until Retirement To Travel Will Be Your Biggest Regret

Have you ever said to yourself, “I’ll travel when I retire”? In this solo episode of the Winging It Travel Podcast, I dive into why I believe waiting until retirement to travel could become one of your biggest regrets.

After travelling to more than 75 countries over the last 15 years, I’ve realised that there will always be another excuse not to go — another promotion, another bill, another responsibility, another reason to delay your dreams. In this episode, I explore why so many people postpone travel until “someday,” and why I think that mindset can be dangerous.

I talk about the realities of health, time, energy, work culture, fear, and the societal expectations that keep people trapped in routines they don’t actually enjoy. I also share personal stories and reflections from my own travels through places like Central America, Ukraine, Canada, and the USA, alongside lessons I’ve learned from years of backpacking and long-term travel.

This is a deep, honest, and motivational episode about creating freedom, prioritising experiences, and making travel part of your life now — not decades into the future.

In this episode, I discuss:

• Why retirement is never guaranteed
• How the “someday” mentality leads to regret
• Why travel becomes harder later in life
• The importance of time freedom and flexibility
• How geopolitics can suddenly change travel opportunities
• Why memories mean more than possessions
• The employee mindset vs lifestyle freedom
• Why taking a sabbatical or career break can change your life
• How travel improves confidence, perspective, and personal growth
• Why meaningful experiences matter more than material things

If you’ve ever dreamed of taking a career break, backpacking the world, travelling long term, or escaping the traditional 9-5 lifestyle, I hope this episode gives you the motivation to stop waiting and start planning your next adventure.

Need help taking a break to travel? Check out my other podcast, Taking A Career Break with Katrina McGhee below.

YouTube - https://www.youtube.com/@TakingaCareerBreakwithKatrina

Apple Podcasts - https://podcasts.apple.com/ca/podcast/taking-a-career-break-with-katrina-mcghee/id1772602758

Spotify - https://open.spotify.com/show/1lRPigXIghYUw82Eqak0mF?si=30ab153333794e19

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

00:00 – Why “I’ll Travel When I Retire” is dangerous

02:23 – Introduction to the podcast

04:03 – Reason #1: Retirement and life are never guaranteed

06:30 – Why health and energy matter for travel

07:55 – The employee mindset and time freedom

10:18 – Why geopolitics can change travel forever

12:30 – Ukraine, Central America & travelling while you can

13:47 – The danger of the “someday” mentality

15:55 – Quick podcast break & ways to support the show

16:39 – Reason #5: Memories are worth more than possessions

18:55 – Why travel memories stay with you forever

20:28 – Are jobs really worth sacrificing your life for?

23:20 – How travel improves confidence and worldview

24:45 – The value of career breaks and sabbaticals

26:05 – Doing things outside your comfort zone

26:58 – Alex Garland quote from The Beach

27:45 – Why millennials should travel now, not later

28:40 – Final thoughts and listener takeaway

29:27 – Outro

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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.

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.

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

IMMERSIVE - The Soundscapes of Oaxaca, Mexico - Colourful Streets, The Zocalo, Busy Markets + A Local Food Tour

Oaxaca, Mexico, had been on my travel list for years, and in 2024, I finally got the chance to experience it for myself. In this immersive soundscape episode of the Winging It Travel Podcast, I take you with me through the colourful streets, lively markets, rooftop cafés and buzzing Zócalo of one of the most atmospheric cities I’ve ever visited.

This episode is all about slowing down and soaking in the vibe of Oaxaca through sound, food and real-time reactions. You’ll hear church bells echo through courtyards, market vendors shouting across packed stalls, sizzling street food being cooked fresh in front of me and the energy of locals and travellers filling the city streets from morning until night.

I wander through the historic centre trying incredible coffee, exploring famous landmarks like the Oaxaca Cathedral and Templo de Santo Domingo de Guzmán, before diving headfirst into Oaxaca’s legendary food scene. From tlayudas and mole to mezcal tastings and local market snacks, this city absolutely lived up to every bit of hype I had built up in my head over the years.

Honestly, this became one of my favourite cities I visited during my Central America and Mexico trip. The colours felt brighter, the food tasted richer and the atmosphere was unlike anywhere else I’ve travelled before. Oaxaca gave me that rare feeling where a destination genuinely exceeds your expectations.

So put your headphones in and come walk the streets of Oaxaca with me.

🎙️ In this episode:

• My first impressions of Oaxaca, Mexico
• Exploring the famous Zócalo and colourful streets
• Trying traditional Oaxacan street food and mezcal
• Visiting Mercado Benito Juárez
• Coffee stops at Muss Cafe and Boulenc
• Historic churches and colonial architecture
• An immersive Oaxaca food tour experience
• Why Oaxaca completely won me over

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

00:00 – Arriving in Oaxaca, Mexico

02:13 – Hostel vibes and first impressions

03:57 – Coffee and breakfast at Mas Cafe

06:04 – Experiencing the Oaxaca Zócalo

06:58 – Trying traditional tlayudas

08:10 – Walking the colourful streets of Oaxaca

08:31 – Oaxaca Cathedral explained

09:03 – Templo de Santo Domingo de Guzmán

10:15 – Why Oaxaca’s streets feel so unique

11:17 – Coffee stop at Boulenc

11:55 – Mercado Benito Juárez food tour begins

12:30 – Trying ceviche and dried insects

13:49 – Rosa de Jamaica tasting

14:24 – Mezcal tasting in Oaxaca

14:45 – Visiting a local chocolate factory

15:10 – Trying traditional Oaxacan mole

16:01 – Wandering Oaxaca at night

16:25 – Why Oaxaca exceeded every expectation

17:14 – Final reflections on the city

18:30 – Outro

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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.

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.

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

10 EPIC Campervan Road Trips We’re Planning Around the World

In this episode of the Winging It Travel Podcast, I’m sharing 10 incredible campervan road trips that are firmly on our bucket list for the next decade. From the dramatic fjords of Norway and the remote highways of Northern Canada to the deserts of Utah, the coastline of Western Australia, and even a possible campervan adventure across Japan — these are the road trips we genuinely cannot stop thinking about.

If you love freedom, open roads, wild camping, national parks, tiny coastal towns, and the idea of waking up somewhere completely different every morning, this episode is for you.

I talk through why each route stands out, the best time of year to go, how long you’d realistically need, and what makes these journeys unforgettable. Whether you’re planning your own campervan adventure or just dreaming of future travels, this episode should give you plenty of inspiration.

Expect epic scenery, practical road trip thoughts, and a lot of wanderlust.

Road trips featured include Norway, Western Australia, Arctic Canada, Newfoundland & Labrador, Scotland’s NC500, Utah’s Mighty Five, Iceland, Ireland’s Wild Atlantic Way, South Africa to Namibia, and Japan by campervan.

If you enjoy the episode, please leave a 5-star review on your podcast app and share it with someone who loves travel and adventure.

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

00:00 – Intro & why campervan road trips feel like ultimate freedom

02:49 – Norway: Oslo to the Lofoten Islands

05:55 – Western Australia: Esperance to Darwin

08:52 – Vancouver to Tuktoyaktuk via the Dempster Highway

11:01 – Labrador Highway & Newfoundland Loop

14:21 – Scotland’s NC500 & the Scottish Highlands

16:48 – Utah’s Mighty Five & Valley of the Gods

18:53 – Iceland Ring Road & Golden Circle

21:05 – Ireland’s Wild Atlantic Way

22:53 – South Africa to Namibia road trip dreams

24:29 – Japan by campervan? The wildcard road trip

26:18 – Final reflections on slow travel & future road trip plans

27:30 – Outro & support the podcast

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

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.

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.

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

Ep 193 w/ Amanda Kendle - Should You Travel to Antarctica? Ethical Travel & The Cruel Reality of Wildlife Tourism

In this thought-provoking episode of the Winging It Travel Podcast, I’m joined by Amanda Kendle from The Thoughtful Travel Podcast to unpack two of the most controversial topics in modern travel: Antarctica tourism and wildlife experiences.

We dive deep into the ethical dilemma of visiting one of the most fragile places on Earth. With Antarctica losing billions of tons of ice every year and tourism numbers rising fast, is it still justifiable to go? Or are we contributing to the very destruction we claim to care about?

Then we shift to wildlife tourism—an industry many travellers engage with without fully understanding the consequences. From elephant riding in Thailand to tiger encounters and zoo ethics, we explore what’s really happening behind the scenes and how travel has evolved over the years.

This isn’t about guilt—it’s about awareness. We both reflect honestly on our own past travel experiences, mistakes included, and discuss how travellers can make better, more responsible choices moving forward.

If you’ve ever questioned the impact of your travels, this episode will challenge your perspective and help you think more critically about how you explore the world.

Amanda Kendle/The Thoughtful Travel Podcast

Website - https://www.notaballerina.com

Apple Podcasts - https://podcasts.apple.com/ca/podcast/the-thoughtful-travel-podcast/id1269489189

Spotify - https://open.spotify.com/show/3AwRGIPRytKa9Txnz1cGBK?si=644319aec60f4f92

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

00:00 – Intro & welcome to Amanda Kendle

02:15 – Perth vs Vancouver: travel memories & lifestyle chat

06:45 – Topic 1: Should we travel to Antarctica?

09:50 – Shocking facts about Antarctica’s ice loss

11:15 – Tourism boom & rising visitor numbers

12:30 – The real cost of visiting Antarctica

14:30 – Carbon footprint & environmental impact explained

17:05 – Why even scientists are choosing not to return

20:00 – Can tourism ever be justified in Antarctica?

23:00 – The problem with regulation & greenwashing

25:20 – Final thoughts: would we go?

26:10 – Topic 2: Wildlife tourism ethics

26:30 – Personal stories: elephant rides & tiger encounters

31:00 – The brutal reality behind elephant tourism

34:50 – How wildlife tourism has evolved (and still needs to change)

36:00 – Seeing animals in the wild vs captivity

38:00 – Cultural differences & lack of awareness globally

39:30 – Elephant riding bans & progress in Southeast Asia

41:00 – Sanctuaries vs exploitation: what’s real?

43:00 – Are zoos ethical? The grey areas explained

46:10 – Can wildlife tourism ever be responsible?

49:30 – Safari tourism vs trophy hunting debate

51:20 – What should be banned immediately?

54:00 – Final reflections on ethical travel choices

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

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.

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.

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

What if a song could take you somewhere you've never been? Or transport you straight back to a beach, a bus ride, or an open road on the other side of the world?

In this solo episode I'm sharing the songs that have shaped my travel life — from the early days of dreaming about the world from my bedroom, through my first big adventure in 2013, all the way to life on the road today.

Some of these songs painted pictures of places before I'd ever set foot there. Others are locked forever to a specific moment — a sweaty dance floor in Thailand, a hungover bus ride through New Zealand, a road trip across Canada that changed everything.

Seven songs. A lifetime of wanderlust. And one or two choices that might genuinely surprise you.

Whether you're a seasoned traveller or still dreaming of that first big trip, this one might just make you want to book a flight, hire a campervan and disappear.

🎵 Matt Monro 🎵 Kid Francescoli 🎵 David Guetta feat. Sia 🎵 Jim Reeves 🎵 Sérgio Mendes 🎵 Percy Faith 🎵 Tiësto

What songs do this for you? Drop me a message — I'd love to know.

📍 Next solo episode: 10 Campervan Road Trips on the Winging It Bucket List

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

00:00 – Intro: Songs That Invoke Travel Memories

01:05 – Why Music & Travel Are Deeply Connected

02:35 – Song #1: On Days Like These – The Italian Job & The Alps Inspiration

04:20 – Song #2: Moon (And It Went Like) – Ultimate Road Trip Anthem

06:05 – Song #3: Titanium – Southeast Asia Party Memories (2013)

07:55 – Bonus Mentions: Swedish House Mafia & Avicii

08:35 – Song #4: Welcome to My World – Early Travel Dreams & Tropical Escapes

10:15 – Song #5: Mas Que Nada – Australia Mine Job & Brazil World Cup Motivation

12:20 – Song #6: Theme from A Summer Place – Dreaming of Paradise & Cook Islands

14:05 – Song #7: Elements of Life – New Zealand Bus Journeys & Backpacker Life

15:25 – Bonus: XFM Podcast – Road Tripping New Zealand Laughs

16:10 – Reflections: Road Trips, Beaches & Travel Themes

17:20 – Why “Moon” Is My Defining Travel Song

18:15 – Outro + Next Episode (Future Road Trips List)

19:10 – Final Outro & Call to Action

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

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.

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.