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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:  Sign up for our FREE newsletter  Transform with Travel  Instagram  Want More?  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  Thanks To Our Sponsors  Earn Cash Back and rewards on nearly every purchase with Rakuten. Learn more about your ad choices. Visit megaphone.fm/adchoices

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:  Sign up for our FREE newsletter  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  Thanks To Our Sponsors  Earn Cash Back and rewards on nearly every purchase with Rakuten.  Learn more about your ad choices. Visit megaphone.fm/adchoices

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:  Sign up for our FREE newsletter  Cross-Culture Connections  Culture SPIN: Your 4-Step Toolkit for Global Leadership and Cross-Culture Success  Get Dr. Wachter's free Cultural Courage Guide: ⁠[email protected]⁠  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  Thanks To Our Sponsors  Earn Cash Back and rewards on nearly every purchase with Rakuten.  Learn more about your ad choices. Visit megaphone.fm/adchoices

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:  Sign up for our FREE newsletter  Castle Forest Lodge  Want More?  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  Thanks To Our Sponsors  Earn Cash Back and rewards on nearly every purchase with Rakuten.  Learn more about your ad choices. Visit megaphone.fm/adchoices

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: Sign up for our FREE newsletter Vagabonding by Rolf Potts Workaway Couchsurfing Trail Wallet WhatsApp MapsMe Trekking Nepal- Audio Adventure Series Want More? 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 Thanks To Our Sponsors Earn Cash Back and rewards on nearly every purchase with Rakuten. Go to https://surfshark.com/zerototravel or use code ZEROTOTRAVEL at checkout to get 4 extra months of Surfshark VPN! Learn more about your ad choices. Visit megaphone.fm/adchoices

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:  Sign up for our FREE newsletter  YouTube  Instagram  Want More?  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  Thanks To Our Sponsors  Earn Cash Back and rewards on nearly every purchase with Rakuten.  Go to https://surfshark.com/zerototravel or use code ZEROTOTRAVEL at checkout to get 4 extra months of Surfshark VPN!  Learn more about your ad choices. Visit megaphone.fm/adchoices

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:  Sign up for our FREE newsletter  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)  Thanks To Our Sponsors  Earn Cash Back and rewards on nearly every purchase with Rakuten.  Go to https://surfshark.com/zerototravel or use code ZEROTOTRAVEL at checkout to get 4 extra months of Surfshark VPN!  Learn more about your ad choices. Visit megaphone.fm/adchoices

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:  Sign up for our FREE newsletter  Hello From A Stranger  Documentary Trailer  Want More?  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  Thanks To Our Sponsors  Earn Cash Back and rewards on nearly every purchase with Rakuten.  Go to https://surfshark.com/zerototravel or use code ZEROTOTRAVEL at checkout to get 4 extra months of Surfshark VPN!  Learn more about your ad choices. Visit megaphone.fm/adchoices

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:  Sign up for our FREE newsletter  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  Thanks To Our Sponsors  Earn Cash Back and rewards on nearly every purchase with Rakuten.  Go to https://surfshark.com/zerototravel or use code ZEROTOTRAVEL at checkout to get 4 extra months of Surfshark VPN!  Learn more about your ad choices. Visit megaphone.fm/adchoices

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  Thanks To Our Sponsors  Earn Cash Back and rewards on nearly every purchase with Rakuten.  Go to https://surfshark.com/zerototravel or use code ZEROTOTRAVEL at checkout to get 4 extra months of Surfshark VPN!  Learn more about your ad choices. Visit megaphone.fm/adchoices

Join Caitlin and Janessa in this Remote Roundup as they catch you up on where they’ve been lately, the travel mistakes they’re learning the hard way, and the systems that keep long-term travel from turning into financial and emotional whiplash.  Remote Roundup is a monthly series hosted by Zero To Travel’s associate producer, Caitlin Sunderland, and partnerships manager, Janessa Klatt. Explore what's new in remote work and travel, including helpful tools and resources, need‑to‑know trends, destinations, and insight into what it really means to live and work around the world.  In this episode, Caitlin and Janessa share what it’s like spending a season in a southern hemisphere coastal hub and time in a vibrant Latin American capital known for culture, markets, and museums. You’ll get Caitlin’s solo travel hot take and the #1 travel mistake she keeps repeating so you don’t have to, and hear from Janessa on her perfected expense tracking system with tips for self-employed travelers.  What’s one “comfort” you’re keeping in your travel life right now, even if it costs a little more or takes up a little more space? I’d love to hear your thoughts, and I hope you’ll share by sending me an audio message.  Tune In To Learn:  Considerations for making Cape Town a long-stay base, what to expect in the cultural capital of Mexico City, and a magic town you may want to add to your Mexico itinerary  Why it’s so easy to keep falling for the budget airline trap and more hidden fees you need to be aware of   Why you should always check your entry stamp and never assume you’ve been granted the maximum tourist stay  Janessa’s system for remote work and travel budgeting, including expense tracking apps, annual reviews, tax set-asides, and building a DIY PTO fund  Why Caitlin says she hates solo travel (yet still thinks everyone should do it), and why we need to redefine what “solo” means  A common travel mistake and what it can reveal about the expectations we carry into travel  And so much more  Resources:  Sign up for our FREE newsletter  Caitlin on Instagram  Janessa on Instagram  TravelSpend  Trabee Pocket   Want More?  Going Nomad with Jason Robinson  Joys of Solo Travel with Manjinder Kang  Remote Roundup: True Costs of Long-Term Travel, Taxes & Borderless Living, an Underrated Productivity Habit, + More (October 2025)  Thanks To Our Sponsors  Earn Cash Back and rewards on nearly every purchase with Rakuten.  Go to https://surfshark.com/zerototravel or use code ZEROTOTRAVEL at checkout to get 4 extra months of Surfshark VPN!  Listen to the Planet Visionaries podcast on Apple and Spotify.  Learn more about your ad choices. Visit megaphone.fm/adchoices

How would your life change if you decided to take a mini-retirement to travel the world, instead of waiting?  After saving for two years, Helen Lin and her former husband, Tim, put their life into storage, rented out their home, and quit their 9–5 jobs to take off on a mini-retirement traveling around the world. They documented their 25+ month adventure across 26 countries on their YouTube channel, Helen and Tim Travel. Along the way, their relationship was reshaped by the experience, and they ultimately returned home divorced, still grateful for the journey they shared.  In this episode, Helen shares what it actually looked like to plan and take an extended trip as a mini retirement, including the practical runway, the emotional realities, and the unexpected ways long-term travel can impact your relationships.  If you’ve ever dreamed of taking months off to travel, this conversation gives you a grounded look at what it takes to make it happen and what you might learn about yourself along the way. Helen talks about building a financial runway, using local guides to lower the friction of adventure travel, and why campervan trips can be their own logistical puzzle. We also get honest about the parts people rarely post, stress, mental health, and the way constant proximity can intensify relationship dynamics. Plus, Helen shares destination recommendations and the practical systems that helped them stay on the road, including earning 1.5 million credit card points over five years to offset major travel costs.  If you took a mini retirement, what would you want it to help you rethink about your life right now? I’d love to hear your thoughts, and I hope you’ll share by sending me an audio message.  Tune In To Learn:  Why Helen thinks “mini retirement” beats waiting for traditional retirement  How increasing your savings rate can create a real travel runway  Advice for choosing destinations around seasonality and the adventures you want most  How guided trips can reduce risk and planning overwhelm for big hikes and outdoor goals  What Helen learned from campervanning in Norway and New Zealand, and what she’d plan differently  How long-term travel can amplify relationship patterns, for better or for worse  Why “wherever you go, there you are” applies to mental health on the road  How to think about boundaries and personal space when traveling with a partner  How Helen and Tim earned about 1.5M points and miles over time to support their travels  What it looks like to come home and build a new chapter after a life-shifting trip  And so much more  Resources:  Sign up for our FREE newsletter  Instagram  Helen and Tim Travel  Waves of Color  Want More?  How to Win at Travel with “The Points Guy” Brian Kelly  Travel Is Your Birthright: Breaking Free from “Too Broke to Travel”, Travel Hacking (Without Credit Cards), and Solo Travel in 90+ Countries with Shakeemah Smith  How to Plan Your Camino + Going Beyond the Camino Frances (Secret Routes, Donkey Highways, and Spain’s Hidden Village Network) with Shawn and Lainey  Thanks To Our Sponsors  Listen to the Planet Visionaries podcast on Apple and Spotify  Go to https://surfshark.com/zerototravel or use code ZEROTOTRAVEL at checkout to get 4 extra months of Surfshark VPN!  Earn Cash Back and rewards on nearly every purchase with Rakuten.  Learn more about your ad choices. Visit megaphone.fm/adchoices

Shakeemah Smith, aka The Passport Abuser, is a solo traveler who has visited 92 countries and helped more than 12,000 people ace their first solo trip. A former social worker from East Orange, New Jersey, she built her platform, Travel Like a Bawse, to teach practical strategies for traveling more affordably and flipping everyday bills into airline miles. She later relocated to Antigua and Barbuda, where she now lives as an expat.  In this episode, we talk about the personal shift that makes solo travel possible, how to travel for free without credit cards, and what it’s really like to move abroad and build a life in the Caribbean.  Shakeemah opens up about calling off her wedding three months before the big day, boarding her first solo flight to Paris in the middle of heartbreak, and realizing she didn’t know how to be alone. What follows is a conversation about self-trust, identity, and deciding to meet the “2.0 version” of yourself instead of waiting for permission.  We also get tactical. Shakeemah shares the exact systems she used to earn airline miles through everyday expenses like gas, groceries, utilities, and dining. And we talk honestly about leaving the U.S., adjusting to island life, and what it means to create safety and belonging on your own terms.  If you’ve been waiting for the right time, the right money, or the right person to travel with, this one might challenge that story.  Who would you become if you stopped waiting and just went? I'd love to hear your thoughts, and I hope you’ll share by sending me an audio message.  Tune In To Learn:  How growing up near New York City shaped her worldview and early curiosity about the world  Why ending her engagement forced her to confront her fear of being alone  The insights and exercises that helped Shakeemah move from emotional dependence to independence and from fear to self-trust  Why she believes solo travel is a fast track to trusting your instincts and enjoying your own company  The moment she decided to build a framework to help others take their first solo trip  How she turned 34 countries’ worth of lessons into a structured framework for new travelers  The overlooked airline shopping portals that generate miles without opening new credit cards  How to earn flights from gas, electricity, and everyday bills you’re already paying  The mindset behind “bills to boarding passes” and why it works long term  Why she moved to Antigua and Barbuda during 2020 and what that decision taught her about safety and lifestyle design  The cultural adjustments of living on island time and navigating life as an American expat  And so much more  Resources:  Sign up for our FREE newsletter  Travel Like a Bawse  Bills to Boarding Passes FREE masterclass  Instagram  Want More?  How to Win at Travel with “The Points Guy” Brian Kelly  Seizing Your Opportunity to Travel, Saving Money as a Solo Traveler, Lessons from a Career Break, and How to Figure Out What You Want (In 60 Seconds) with Leslie McKellar  7 Mistakes to Avoid When Moving Abroad (Or Traveling Long-Term) with Chrishan Wright  Thanks To Our Sponsors   Listen to the Planet Visionaries podcast on Apple and Spotify  Experience an audio guide to the world's strange, incredible, and wondrous places with Atlas Obscura Podcast  Go to https://surfshark.com/zerototravel or use code ZEROTOTRAVEL at checkout to get 4 extra months of Surfshark VPN!  Learn more about your ad choices. Visit megaphone.fm/adchoices

How do you experience the Louvre Museum in a way that actually feels enjoyable, not stressful? And what makes this museum so much more than the Mona Lisa?  Elaine Sciolino is a veteran journalist and author, former Paris bureau chief for The New York Times, and the writer of several books about France, including The Seine, The Only Street in Paris, and Adventures in the Louvre. She has lived in Paris for over two decades and brings history, culture, and personal insight into every story.  Elaine joins co-host Paige McClanahan to explore Adventures in the Louvre: How to Fall in Love with the World’s Greatest Museum, diving into the history, hidden artworks, and practical strategies for making the most of your visit.  You’ll hear why the Louvre is more than just a building with the Mona Lisa and how its role in French history makes it extraordinary. Elaine demystifies visiting the museum, from understanding crowds and lines to discovering lesser-known works like Titian’s Man With a Glove and what she calls the “undiscovered Mona Lisa.” She shares crowd-beating strategies, best days and times to visit, and surprising places within and around the Louvre where peace and beauty await. You’ll get insider stories on heists, hidden collections, and how even children can be captivated by Egyptology and Islamic art sections that most tourists miss out on.  When you visit a major museum like the Louvre, do you tend to focus on the most famous works, or do you prefer to explore what’s less obvious? 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. Learn more about her work here.  Tune In To Learn:  How the Mona Lisa came to dominate the Louvre’s identity, and why that fame is both a blessing and a burden  How the 1911 theft of the Mona Lisa helped turn her into a worldwide obsession  The surprising historical roots of the Louvre as a royal palace and revolutionary museum  Lesser-known treasures, “undiscovered” masterpieces, and quieter sections of the Louvre worth seeking out  The unexpected history of France’s crown jewels, including how many were sold off and ended up in the United States  The story behind the recent crown jewels heist and what it reveals about museum security  How the right membership, 1:1 consultation rooms, and alternative museums can transform your experience of Parisian culture  Future plans for the Louvre’s expansion and what that could mean  And so much more  Resources:  Sign up for our FREE newsletter  Elaine’s website and books  Louvre Museum  Want More?  5 Unexpected Things to Do in Paris and 3 Hidden Gems in France with Paige McClanahan  How To Explore Paris Like a Local, Working on Hospital Ships, and Becoming an Expat on a Mystery Visa With Jay Swanson  9 Best United States Museums and Advice for Fostering Your Creativity with Bob Eckstein  Thanks To Our Sponsors  Listen to the Planet Visionaries podcast on Apple and Spotify  Experience an audio guide to the world's strange, incredible, and wondrous places on the Atlas Obscura Podcast  Go to https://surfshark.com/zerototravel or use code ZEROTOTRAVEL at checkout to get 4 extra months of Surfshark VPN!  Learn more about your ad choices. Visit megaphone.fm/adchoices

What are the best hidden gems and local experiences in Ljubljana, Slovenia, that some travelers completely miss?  Sharon Kaufman is a licensed local guide in Ljubljana, Slovenia, and founder of MyLjubljanaTour.com. Originally from Israel, she moved to Slovenia with her family on what was meant to be a one-week vacation and ended up building a new life there. Today, she leads free and paid tours focused on helping travelers experience Ljubljana through local stories, food, and everyday culture.  In this episode, Sharon shares about her spontaneous family move to Ljubljana, how she built a life and business there, and her top hidden gems and local tips for experiencing the city like a resident, not a tourist.  If you’re planning a trip to Slovenia or curious about what makes Ljubljana special, this episode is packed with practical recommendations. Sharon walks us through lesser-known places to explore, affordable ways to get around, unique food experiences, art districts, scenic viewpoints, and easy nature escapes right from the city. You’ll also hear how her perspective as a local guide shapes the way she helps travelers connect more deeply with the city.  Which of these Ljubljana, Slovenia, experiences would you want to explore first? 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:  How a one-week family vacation unexpectedly turned into a move to Slovenia  What Sharon quickly learned about daily life, culture, and work-life balance in Ljubljana  How intuition and local conversations shaped her decision to stay  How she transitioned from online coaching to becoming a licensed local guide  One of the most affordable and fun ways to explore the city  Where to get sweeping views of Ljubljana without crowds or ticket lines  A hidden market area with local food and unique vending machines that most visitors walk right past  A hidden alley filled with public art, symbolism, and a secret pub  An alternative art district shaped by activism, creativity, and nightlife  A cafe locals love for great coffee, healthy food, and a relaxed vibe  An easy forest hike just minutes from the city center, plus what to eat at the top  The best times of year to visit Ljubljana and where to go beyond the city  And so much more  Resources:  Sign up for our FREE newsletter  MyLjubljanaTour.com  Want More?  Top 10 Iceland Hidden Gems (Highlands, Hot Springs, and Hidden Canyons) + Building a New Life Abroad with Jewells Chambers from All Things Iceland  7 Mistakes to Avoid When Moving Abroad (Or Traveling Long-Term) with Chrishan Wright  Top 10 Reasons to Love Living Abroad with Botik Quest  Thanks To Our Sponsors  Listen to the Planet Visionaries podcast on Apple and Spotify  Experience an audio guide to the world's strange, incredible, and wondrous places on the Atlas Obscura Podcast  Go to https://surfshark.com/zerototravel or use code ZEROTOTRAVEL at checkout to get 4 extra months of Surfshark VPN!  Learn more about your ad choices. Visit megaphone.fm/adchoices