
What if the key to planning your dream trip isn't choosing the right destination, but first figuring out what you actually need right now in your life?
Kelly Tolliday is the founder of Transform With Travel, a professional travel advisor and wellness travel expert with over a decade of industry experience, a retreat facilitator and 500-hour registered yoga teacher, and a podcast host. She has traveled to more than 45 countries and lived across four continents, including extended time in Australia, Thailand, and Costa Rica.
In this episode, Kelly walks through the step-by-step system she uses to plan bucket list trips and how anyone can apply the same framework to start planning their own dream trip today.
Kelly reframes the entire planning process in a way that most of us haven't considered, and it changes not just where you end up going, but how you show up when you get there. She also makes a strong case for why the best travel experiences often come from letting go, even when every instinct is telling you to hold on tighter. You'll not only get Kelly's framework, but destination recommendations and a call to action at the end that I hope you follow through on.
What's one destination that's been sitting on your bucket list for way too long, and what's actually been stopping you from booking it? I'd love to hear what they are, and I hope you’ll share them by sending me an audio message.
Tune In To Learn:
Why asking "what do I need right now?" is the most important first question in trip planning
How to use urgency as a real planning tool, and why some destinations carry a genuine now-or-never factor
Why mapping out your full route, including transfer time and cost, is often the step that saves the most money
How slow travel creates more space for the unscripted moments that people end up talking about for decades
Why booking independent, locally-owned tour operators almost always leads to more memorable experiences than going with the bigger names
How to approach accommodations with a "sense of place" mindset
Advice on when hiring a professional travel advisor makes sense versus planning a bucket list trip on your own
Why we both agree that physically demanding adventures should move to the top of your list sooner rather than later
Hidden gem destinations worth visiting now, including a little-known Thai island that has somehow stayed off the radar
How to reset your mindset when things go sideways on a trip
And so much more
Resources:
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Live Your Bucket List w/ Ryan Jacobson
Curiosity As Your Travel Guide + Exploring Overlooked Destinations with John McKenzie
7 Must-Visit Destinations for 2026 (Get There Before the Crowds Arrive!) with Lyn Hughes
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Apr 21
1 hr 25 min

What would you do if your bus driver bought six Coca-Colas at the border, cost you your exit stamp, and forced you to sleep outside in malaria country between two countries?
Co-hosts Gunnar Garfors and Jacqui Kunz are back to share part two of their overland travel adventure through West Africa, covering the final stretch of their seven-country journey through Sierra Leone, Liberia, and the Ivory Coast.
If you've ever been curious about what it actually takes to travel overland through West Africa, this episode gives you the unfiltered picture. You'll walk away with concrete tips on visa strategy, border navigation, shared transport logistics, and honest guidance on when to push through and when to bail and book a flight. Beyond the tactics, Gunnar and Jacqui model what it actually means to travel slowly and patiently through challenging terrain, staying flexible when things go sideways. If you're considering overland travel in West Africa or anywhere similarly complex, this episode cuts through the romance and gives you the real picture.
Have you ever had a travel experience where everything went wrong and it somehow turned into the best story you came home with? I'd love to hear your thoughts, and I hope you’ll share them by sending me an audio message.
Gunnar Garfors is a Norwegian traveler, journalist, and author who became the first person to visit every country in the world twice. He is known for seeking out unusual routes and lesser-visited destinations, often traveling far beyond typical tourist paths. Jacqui Kunz is a full-time traveler who has explored more than 100 countries and was named “World’s Most Intrepid Traveler” in 2023, recognizing her commitment to exploring challenging destinations and traveling well off the beaten path.
Tune In To Learn:
Why Sierra Leone's land border crossing was a surprisingly smooth and welcoming experience
What Freetown is really like to explore, from the historic Cotton Tree to its beaches and police checkpoints
Why the city of Bo is worth a stop, and where to go nearby to see diamond mining
How a fellow passenger buying Coca-Cola at the border kiosk resulted in an overnight stay between two countries in mosquito country
Why Monrovia has a surprisingly American feel and where to stay, eat, and get cash
When it makes sense to give up on overland travel and just book a flight
How paying for an extra seat in a shared taxi can save your sanity, and why the "imaginary bag fee" is a negotiation you can usually win
Why timing your trip just after the rainy season can make roads far worse than expected
How Gunnar ended up in a Norwegian hospital with malaria, and why taking preventatives seriously is not optional
And so much more
Resources:
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Gunnar’s website
Gunnar on Instagram
Jacqui on Instagram
iOverlander
Want More?
Overland Travel in West Africa Across 7 Countries (Part 1) with Gunnar Garfors & Jacqui Kunz
5 Surprising Experiences in Africa, How to Transition to a New Career After Travel, and Exploring the African Diaspora With Jay Cameron
Adventure and Conservation - A 6,000 km Tuk-Tuk Journey Through Africa
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Apr 14
53 min

What if the secret to a truly meaningful travel experience starts not when you land, but long before you ever pack a bag?
Dr. Kristina Wachter is an award-winning professor, bestselling author, and CEO of Cross-Culture Connections. With over 25 years of experience in cross-cultural communication and education, she developed the Culture SPIN Method, a four-step framework trusted in 54 countries to help individuals and organizations turn cultural differences into genuine human connection.
In this episode, Dr. Wachter walks us through her Culture SPIN Method and how it applies directly to travelers who want richer, more meaningful experiences on the road. She uses real-world business stories, her own travel mishaps, and a live case study with Jason to bring the whole thing to life.
If you've ever shown up somewhere and felt like you were missing something, like you were skimming the surface of a place rather than really getting into it, this conversation is for you.
Dr. Wachter breaks down the cross-cultural communication tips every traveler can actually use, from how to research a culture before you go, to how to recover gracefully when you inevitably get something wrong. Whether you're planning a two-week trip or building a life abroad, there's a lot here to chew on.
What's a cultural moment from your own travels that surprised you or changed the way you see things? I'd love to hear your thoughts, and I hope you'll share by sending me an audio message.
Tune In To Learn:
Why the Culture SPIN Method starts with looking inward at yourself before you ever look outward at another culture
How to build a personal "cultural Venn diagram" that maps your interests onto a new destination to create real connection opportunities
Why one U.S. executive unknowingly drank $300,000 worth of tea in a single business meeting, and what he did next that actually saved the deal
How a single joke in South Korea cost a businessman millions of dollars in 30 seconds, and what that means for travelers too
Advice for doing genuine cultural research before a trip, including reading fiction, watching local media, and finding primary-source content
Why "winging it" is one of the most common and costly mistakes people make when traveling or moving abroad
How to handle cultural mistakes with humility and recover without losing the connection you're trying to build
Why cultural agility, the ability to pivot and adapt without beating yourself up, is one of the most valuable skills any traveler can develop
What "cultural courage" really means and how acting deliberately outside your comfort zone invites reciprocity and deeper human connection
Why Rick Steves' idea of traveler responsibility hit home for Dr. Wachter
And so much more
Resources:
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Cross-Culture Connections
Culture SPIN: Your 4-Step Toolkit for Global Leadership and Cross-Culture Success
Get Dr. Wachter's free Cultural Courage Guide: info@crosscultureconnections.com
Want More?
7 Mistakes to Avoid When Moving Abroad (Or Traveling Long-Term) with Chrishan Wright
Top 10 Challenges Of Living Abroad with BoTik Quest
Building a Life Abroad, Culture Shock, and Big Leaps with Traveling Jackie
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Apr 7
1 hr 5 min

What are you really looking for when you travel?
Sarika Bansal is a travel writer, editor, and former editorial director of Afar magazine. Her work has appeared in The New York Times, The Guardian, and Vice, and she focuses on ethical storytelling, global perspectives, and the deeper impact of travel. She currently lives in Nairobi, Kenya, with her family.
In this episode, Co-host Paige McClanahan talks with Sarika Bansal about how travel shapes us, from living in Kenya to trekking in the Everest region, and how those experiences influence the way we think about travel itself.
This conversation explores what happens when we shift from collecting places to truly engaging with them, and how that shift can completely change the way we experience travel. Sarika shares stories from her own journey, from trekking in the Everest region to building a life in Kenya, and reflects on how stepping outside your comfort zone can reshape your worldview in unexpected ways. We also get into the idea of country counting, the value of returning to places, and how different stages of life influence not just where we go, but how we show up when we get there.
What do you think matters more in travel, the number of places you visit or the depth of your experiences? I'd love to hear your thoughts, and I hope you'll share by sending me an audio message.
Co-host Paige McClanahan is a writer, editor, and former journalist based in Paris, France. As the author of The New Tourist: Waking up to the Power and Perils of Travel, Paige is passionate about making sure our travels have a positive impact on the world. Get in touch and follow her on Substack.
Tune In To Learn:
Why Sarika’s move to Nairobi reshaped her daily life, pace, and perspective
What drove her to travel writing and how growing up between the U.S. and India influenced her approach to storytelling and travel
What a “questionable” volunteer trip taught her about ethics in travel early on
How trekking in the Everest region while pregnant forced her to slow down
What it’s like exploring quieter trails, monasteries, and local life beyond the Everest “highway”
How climate change is visibly impacting fragile destinations like Everest Base Camp
Why the idea of “country counting” breaks down when you question what it means to visit a place
Sarika’s analogy between travel metrics and personal health, and why both can become misleading
How different life stages, like traveling with kids, change how and where you explore
Unexpected ways to experience Kenya, from DIY safaris to birdwatching and coastal towns
And so much more
Resources:
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Castle Forest Lodge
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Ethical Wildlife Tourism With Kristen Diederich
The World’s Most Traveled Person on the Ethics of Gamifying Travel, Best Regions in the World, and Why To Keep Traveling With Harry Mitsidis of NomadMania
How To Be a “New Tourist,” the Powers and Perils of Tourism, Embracing Tourist Traps, and the Impact of Travel With Paige McClanahan
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Mar 31
1 hr 6 min

If you need some inspiration to make those travel dreams a reality, look no further! We're resharing some of our Transition to Travel episodes this month to help kickstart your plans in 2026. In this series, we interview a guest both before and after their travels (or during if it's long-term), so we can see how it all panned out and how travel has changed them.
Sofia and Teague are a couple who left behind demanding careers, including law and personal training, to travel the world for a year. This conversation gives you a full arc of a transition to travel story, from fear and uncertainty to growth, burnout, perspective shifts, and ultimately redefining what “home” and “work” mean. You’ll hear how they saved money quickly, traveled on a budget, worked abroad, navigated relationship dynamics, and what surprised them most along the way.
What part of your life might be ready for a transition, even if you don’t know exactly what comes next? I'd love to hear your thoughts, and I hope you'll share by sending me an audio message.
Tune In To Learn:
Why the hardest part of long-term travel often happens before you ever leave
How they saved $25K in a year to fund their trip (and what made it possible)
What it actually feels like in the first few weeks on the road, including the uncomfortable parts
How their expectations of travel compared to the reality after a full year abroad
Why working abroad became the key to slowing down and enjoying the experience
What happened when they decided to travel separately for part of the journey
How letting go of identity, jobs, and “normal life” reshaped how they see themselves
The moment they realized travel had changed their relationship in a lasting way
What they didn’t expect about returning home after a year of travel
Why knowing you can always leave again changes how you approach life and work
And more!
Resources:
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Vagabonding by Rolf Potts
Workaway
Couchsurfing
Trail Wallet
WhatsApp
MapsMe
Trekking Nepal- Audio Adventure Series
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Transition To Travel: From Big Salary to Frugal Travel Life
Transition To Travel: Single Mom + 3 Kids Move to Mexico (Jenita's Story)
Transition To Travel: Radical Life Change For World Travel w/ Jordan & Tyler
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Mar 26
2 hr 5 min

Have you ever felt the pull to do something BIG, but weren’t sure if you were “that kind of person?” What if the bravest thing you could do is take the first step before you feel ready?
Lauren Roerick is a long-distance hiker who has traveled more than 12,000 kilometers on foot across countries and continents. Since 2019, she has completed trails like the Pacific Crest Trail, the Colorado Trail, the Hexatrek in France, Te Araroa in New Zealand, and sections of the Transcaucasian Trail. Through her solo journeys and films, she shares stories about resilience, self-trust, and choosing a life shaped by curiosity and courage.
Co-host Dianni Hall talks with Lauren about how to start thru-hiking, what solo trail life actually feels like, and how to move through fear, discomfort, and self-doubt one step at a time.
You’ll hear how Lauren went from zero backpacking experience to long-distance trails by breaking intimidating goals into smaller, doable pieces. She shares what training really matters, what gear is actually worth prioritizing, how trail community works, and why thru-hiking can build self-trust in a way few other experiences can. If you’ve been curious about how to start thru-hiking but feel intimidated, this episode will give you a realistic way in.
What’s one uncomfortable thing you’ve been wanting to try, and what would your version of the first step look like? I'd love to hear your thoughts, and I hope you'll share by sending me an audio message.
Co-host Dianni Hall is a queer, second-generation Latina, solo budget backpacker, freelancer, and host of the While She’s Away podcast, where she interviews women on their travel experience and expertise to help women live their best lives exploring the world. Learn more about her work here.
Tune In To Learn:
How doing a 100K with only six weeks of training (and despite hating running) changed her confidence
Why Lauren often takes a “how hard can it be” approach to new challenges
How she went from having no backpacking experience to taking on the Pacific Crest Trail
Why breaking big goals into smaller steps makes thru-hiking feel possible
What the mental challenges of solo hiking really look like, and how she works through them
How thru-hiking builds self-trust and strengthens your intuition
What role fear plays on the trail, and how to move through it instead of avoiding it
How to start small, even if it’s just sleeping outside for one night
How to choose your first trail based on your goals, time, and experience
What kind of training and gear actually matter, and what you can skip
How Lauren approaches content creation on trail without losing presence in the moment
And so much more
Resources:
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Instagram
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Hiking the West Highland Way in Scotland with Lynne Nieman
A 2,190+ Mile Mother-Son Adventure: Thru-Hiking the Appalachian Trail after a Decade of Nomadic Family Travel with Jessica and Largo Sueiro
Hiking the Camino De Santiago, Painting Your Travels, Letting Curiosity Rule, and Tiny House Living with Kari Gale
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Mar 24
1 hr

Do you have dreams of long-term travel? What are you willing to "give up" in pursuit of it?
If you need some inspiration to make those travel dreams a reality, look no further! We're resharing some of our Transition to Travel episodes this month to help kickstart your plans in 2026. In this series, we interview a guest both before and after their travels (or during if it's long-term), so we can see how it all panned out and how travel has changed them.
Becca Hall is a long-term traveler who left a high-paying nonprofit tech job in San Francisco to pursue a life of indefinite travel. We talk about how she saved $30,000 in just a year and a half, why she travels as if she doesn’t have that cushion, and the psychology behind adopting a frugal travel mindset. She also shares what surprised her most after leaving her job, including the months it took to mentally decompress from work stress. Later, we catch up a year and a half into her journey to hear how things actually unfolded, from bartending and working festivals in Australia to building out her own van and redefining what freedom looks like on the road.
What surprised you the most in Becca's journey? What was your biggest takeaway from today's episode? I'd love to hear your thoughts, and I hope you'll share by sending me an audio message.
Tune In To Learn:
Why Becca chose to act like her savings didn’t exist, even after putting away $30,000
How a no-frills travel mindset helped her save money long before she ever left home
What happened when cheap travel started costing her more energy than it was worth
Advice for navigating solo female travel, couchsurfing, and gut-check moments on the road
The surprising emotional hangover that followed quitting a job she was desperate to leave
Why earning less money ended up feeling like a better deal
How festival work and bartending became part of her long-term travel strategy
What pushed her from backpacking burnout into building a van in Australia
The unexpected lessons she learned from creating a home on wheels by herself
Why taking a break can feel strangely difficult when you’re traveling full time
How she decided whether bringing a laptop was freedom or just extra baggage
What indefinite travel taught her about pace, pressure, and finding her own version of flow
And so much more
Resources:
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Becca on Instagram
Mint.com
Want More?
Transition To Travel with Lance Wright
Transition To Travel: Radical Life Change For World Travel w/ Jordan & Tyler
Transition To Travel: Single Mom + 3 Kids Move To Mexico (Jenita's Story)
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Mar 19
1 hr 24 min

What happens when talking to strangers while traveling becomes the thing that helps you feel less alone?
Adam Schluter is an award-winning, National Geographic published photographer and writer, and the founder of Hello From A Stranger, a project built around spontaneous travel, portraits, and conversations with people he has just met. Through that project, he has traveled across 21 countries, created thousands of conversations and portraits, given a TEDx talk, published a book based on the work, and is now making a documentary.
In this episode, Adam shares how a period of heartbreak, depression, and isolation pushed him to buy the cheapest ticket he could find and start talking to strangers while traveling. That simple decision eventually turned into Hello From A Stranger, Monday Night Dinners, and a larger mission to help people feel seen.
We get into what travel can open up when you use it intentionally, not just to see a place, but to connect more deeply with the people in it. Adam talks about what he learned from being an introvert in unfamiliar places, why vulnerability worked better than trying to sound polished, and how genuine conversations helped him find purpose when he needed it most. We also talk about how he brought that same spirit home by inviting strangers to dinner, eventually building a recurring community gathering that now draws hundreds of people. If you’ve ever felt lonely, wondered how to meet people more naturally, or wanted to recreate a little of that hostel-kitchen magic back home, there’s a lot in this one.
Trigger warning: This conversation includes honest discussion of depression, suicidal thoughts, and suicide. If you’re struggling, call or text 988 for support.
What would change if you approached one stranger this week with a little more curiosity and a little less fear? I'd love to hear your thoughts, and I hope you'll share by sending me an audio message.
Tune In To Learn:
The breaking point in Adam’s mental health, and how he navigated depression and isolation
Why buying the cheapest flight he could find became the start of an unexpected journey
The importance of creating a framework around his travels and what happened when he started intentionally talking to strangers
Why Adam’s first attempt at approaching strangers failed, and what finally worked
How vulnerability and awkward honesty opened the door to deeper conversations
Why solo travel can still feel lonely, and how to move beyond “ghost mode” while traveling
The story behind Monday Night Dinners, and how inviting strangers over changed his community
Why a simple conversation might matter more than you think
And so much more
Resources:
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Hello From A Stranger
Documentary Trailer
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100 Documentaries Project: Traveling the Globe to Find Extraordinary Humans + Changing the World One Story at a Time with Robin Danehav
How to Be a “Supercommunicator” and Connect with Anyone (At Home or on the Road) with Charles Duhigg + The Best of Baltimore, MD
Bicycling Across the USA Without Money in Search of Human Connection With Daniel Troia
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Mar 17
1 hr 1 min

Dreaming of quitting your job and becoming a digital nomad? Planning a career break to travel the world? If you need some inspiration to make those travel dreams a reality, look no further! We're resharing some of our Transition to Travel episodes this month to help kickstart your plans in 2026. In this series, we interview a guest both before and after their travels (or during if it's long-term), so we can see how it all panned out and how travel has changed them.
Lance Wright is a longtime higher education professional and the creator of The Midlife Crisis Traveler, where he shares the story behind taking a major travel leap in midlife. At the time of this episode, he stepped away from his role at Colorado State University to take a seven-month trip, and that experience led him to rethink work, identity, and how he wanted to live.
This conversation gets into the real stuff behind long-term travel. Lance shares what it was like to ask for time away from a job he actually loved, how he and his wife navigated his decision to travel solo, and what helped him through the lonely stretches on the road. We also talk about minimalism, masculinity, identity, and the surprising clarity he had when he got home.
What chapter in your life might be ready to close so a new one can begin? I'd love to hear your thoughts and hope you’ll share by sending me an audio message.
Tune In To Learn:
Why Lance finally stopped waiting and committed to a seven-month trip
How he negotiated a leave of absence from a job he genuinely enjoyed
Advice for talking with your spouse about a solo long-term trip
What Albania taught him early on about connection and loneliness
How local tours, cooking classes, and Workaway helped him meet people
Why travel pushed him toward minimalism and a simpler lifestyle
How the trip reshaped his thinking about work, masculinity, and identity
What happened when he came home and realized he needed a new chapter
Why trusting your own travel style matters more than following someone else’s plan
And so much more
Resources:
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The Midlife Crisis Traveler
Tours By Locals
Want More?
Transition To Travel: Radical Life Change For World Travel w/ Jordan & Tyler
Transition To Travel: Single Mom + 3 Kids Move To Mexico (Jenita's Story)
Transition To Travel: From 9-5 To Biking The USA with Joe Ferrara
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Mar 12
1 hr 34 min

What happens when you try overland travel in West Africa across seven countries using only local transport?
Gunnar Garfors is a Norwegian traveler, journalist, and author who became the first person to visit every country in the world twice. He is known for seeking out unusual routes and lesser-visited destinations, often traveling far beyond typical tourist paths. Jacqui Kunz is a full-time traveler who has explored more than 100 countries and was named “World’s Most Intrepid Traveler” in 2023, recognizing her commitment to exploring challenging destinations and traveling well off the beaten path.
In this episode, co-hosts Jacqui and Gunnar share stories from the first leg of their West Africa adventure across seven countries, covering Senegal, The Gambia, Guinea-Bissau, and Guinea.
They talk about what it’s really like to travel overland in West Africa, from chaotic border crossings and broken buses to incredible landscapes, unexpected friendships, and the patience required to move through the region.
If you’ve ever wondered what travel in this part of the world actually feels like on the ground, this conversation gives you a candid look at the challenges, surprises, and rewards of exploring West Africa slowly.
What kind of travel experiences become possible when you stop rushing and embrace the unpredictability of the journey? I'd love to hear your thoughts, and I hope you’ll share them by sending me an audio message.
Tune In To Learn:
Why traveling overland in West Africa requires a completely different mindset about time and planning
How local minibuses work, and why you may be waiting a while to get going
What it’s like traveling upriver in The Gambia to visit River Gambia National Park and see chimpanzees
Why going inland in The Gambia offers a very different experience from the coastal resort areas
How to navigate crossings, visas, and illegal stamp fees that travelers are sometimes asked to pay
What happened when their bus broke down and the driver abandoned it on a remote road
How unexpected delays led to shared rides, new friendships, and memorable moments with local travelers
Why Guinea-Bissau ended up being the biggest surprise and favorite country of the trip
What it’s like traveling through Guinea’s highlands on roads compared to a motocross track
Why slow, overland travel creates deeper connections with people and places along the way
And so much more
Resources:
Sign up for our FREE newsletter
Gunnar’s website
Gunnar on Instagram
Jacqui on Instagram
Want More?
9 Ways Travel Will Change You + Lessons from Cycling Africa and Visiting 95 Countries with Alex Hennock
5 Surprising Experiences in Africa, How to Transition to a New Career After Travel, and Exploring the African Diaspora With Jay Cameron
Adventure and Conservation - A 6,000 km Tuk-Tuk Journey Through Africa
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Mar 10
47 min
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