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They sold the farm, let go of the stuff, and pushed off the dock lines with a shared promise: sail around the world together. From their boat in French Polynesia, award-winning author and lifelong sailor Alison Gieschen joins us with her husband Dan to tell the full story behind their liveaboard sailing life on their 43-foot sailboat, Equus, including what it takes to keep moving when the dream gets expensive, exhausting, and genuinely scary.

We dig into the turning points that make a circumnavigation real: how Alison’s horsewoman roots and an early “out of nowhere” sailing vision turned into skills, how they met during a sailboat race, and why they decided to sell everything and commit. Then we go straight into the hard part, including their worst storm experience in the Gulf Stream, the damage that forced a turnaround, and the PTSD that lingered long after the repairs. Alison also shares the moment a trusted mentor helped reframe the fear, and why that single conversation kept them out there for eight years and counting.

We also talk about the quieter day-to-day realities that rarely make the highlight reels: staying close to kids and grandkids from far away, how minimalism changes your priorities, and how life at sea can create the focus to write books across memoir, children’s literature, and adult fiction. We wrap with their current route plans across the South Pacific, favorite stops like the Azores, and a practical travel-planning lesson from our own Europe prep about booking early when thousands of travelers hit the same ports and airports.

Subscribe for more conversations about long-term travel and real-world ways to make it happen, and if you found value here, share the episode and leave a quick review so more travelers can find us.

Alison's Website: https://alisongieschen.com/

Also check out: https://sailmates.org/

YouTube: https://www.youtube.com/@sailingequus

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"Wherever We May Roam: Finding Your Travel Style" - On Amazon

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Life doesn’t follow a map, and neither do the journeys that shape us. We’re joined by Shannon Lamkin, author, speaker, and host of the internationally listened to podcast Travel Time Stories with Shannon, for a conversation that starts with travel and quickly gets more honest. Shannon shares how a show built around destinations evolved into a space where people tell the stories that changed them, and why one good conversation can be the first step toward healing.

We talk about what it means to rebuild yourself after trauma, including surviving abusive relationships and learning the hard truth that leaving isn’t the same as being healed. Shannon opens up about anxiety and panic attacks, and how a first solo trip to New Orleans became a surprising milestone in confidence and self-trust. We also get into parenting through serious mental illness, the lifelong ripple effects of childhood experiences, and Shannon’s adoption story and search for birth family long before DNA kits and social media made it easier.

Caregiving and identity come up in a big way as Shannon describes supporting a spouse through chronic illness, kidney failure, and dialysis, plus the pressure of holding everything together without losing yourself. From there, we shift back to the power of travel as reinvention, including cruising as a way to explore and a Scotland road trip that raised the bar for what felt possible. Shannon also shares what she’s writing now, including her memoir "Map Back to Me" and her novel "Wrong Turns, Right People", built around the idea that detours can bring the right people into your life.

If you’re drawn to travel, midlife reinvention, storytelling, mental health, and finding your own travel style in the real world, this one’s for you. Subscribe, share this with a friend who needs it, and leave a quick review so more listeners can find us.

Shannon's Website: https://www.traveltimestories.com/

Shannon's Podcast: https://podcasts.apple.com/us/podcast/travel-time-stories-with-shannon-real-journeys-real/id1821032644

Download full-color PDFs of my book at prices below Amazon paperbacks. Visit my store at https://shop.jimsantosbooks.com

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"Wherever We May Roam: Finding Your Travel Style" - On Amazon

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You can’t “budget” your way to a better trip if you don’t know where the money leaks actually happen. We sit down with Australia-based author, travel writer, and travel coach Linda King to unpack a practical approach to budget travel that feels empowering, not restrictive: save with intention so you can travel more often and for longer stretches.

We get tactical on the big pre-trip wins, including smarter research, price monitoring, and why paying upfront can sometimes unlock better rates and extras. Then we move into real-world daily strategies that keep your travel budget intact, like free activities, free walking tours, and the simple meal math that adds up fast: breakfast included, supermarket meal deals, and choosing when to splurge on restaurants. If you’ve ever come home to a painful post-trip bill, this conversation is built to prevent it.

Next, we dive into points and miles and credit card rewards without the hype. Linda explains how to choose loyalty programs, learn partner options, and build a redemption strategy that fits your routes. We also talk about the non-negotiables that make travel hacking work: understand annual fees, use the card enough to justify it, and always pay in full so interest doesn’t erase your rewards. We even address those “point multiplier” offers and why doing your own research usually wins.

Finally, we explore AI travel planning, solo travel confidence, and what mindful travel and sustainable travel look like in practice, from better prompts to “leave no trace” habits. Subscribe, share this with a travel buddy, and leave a quick review so more people can find the show.

Linda King's Website: https://www.thesmarttravelista.com/

YouTube Channel: https://www.youtube.com/@thesmartravelista

Facebook Page: https://www.facebook.com/Thesmartravelista

Instagram: https://www.instagram.com/thesmartravelista/

The Smart Travelista Guide Series: https://www.amazon.com/dp/B0F5NHMYGQ

Antics Abroad Series: https://www.amazon.com/dp/B0GRV1YT5F

Download full-color PDFs of my book at prices below Amazon paperbacks. Visit my store at https://shop.jimsantosbooks.com

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jim@jimsantosbooks.com

"Wherever We May Roam: Finding Your Travel Style" - On Amazon

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You can live overseas for years and still feel your stomach drop the first time you travel alone. That tension between “I want to go” and “what if I can’t handle it” drives our conversation with Paula Barnes, the travel creator and expat storyteller behind Truly Expat Travel, joining us from Sydney.

Paula shares how a “six-month” move from Australia turned into nearly two decades across Asia, raising three kids in places like Taiwan, Singapore, and Hong Kong. We talk about the real-life logistics that shape confident travelers: language barriers before smartphones, how Google Translate changed everything, and why cultural context matters more than snap judgments. Along the way, we compare notes on how travel reshapes kids, families, and the meaning of home.

Then we get practical for anyone considering solo travel, especially women over 45. Paula breaks down how to start small, when a tour can be the perfect bridge, and how to handle the surprisingly hard parts like eating alone at restaurants. We also dig into the tools that make modern travel smoother and safer, from WhatsApp communities to TripIt itineraries and using AI like ChatGPT and Claude without letting it overstuff your days. Plus, Paula gives guidance on planning Australia the right way and shouts out destinations that deserve more attention, including Sri Lanka and Bhutan.

Subscribe for more thoughtful travel stories, share this with a friend who needs a nudge to book the trip, and leave a quick review so more travelers can find us.

Paula's Website: https://trulyexpattravel.com/

Facebook: https://www.facebook.com/trulyexpat

Podcast: https://podcast.trulyexpattravel.com/

Download full-color PDFs of my book at prices below Amazon paperbacks. Visit my store at https://shop.jimsantosbooks.com

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"Wherever We May Roam: Finding Your Travel Style" - On Amazon

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You can spend a fortune on a “once-in-a-lifetime” family vacation and still come home thinking, we barely connected. That’s why we sat down with Paul Partridge, a former financial advisor and retirement planner who now designs multigenerational trips as a different kind of investment: time together that turns into stories your family repeats for years.

Paul shares the planning mindset behind his company, Travel Villa Guide, including a simple but powerful tool he calls travel type matching. He breaks down four common travel styles immersers, adventurers, experiencers, and relaxers and explains how conflict happens when one style sets the agenda for everyone. We talk about how to give each person space to enjoy what they love, then pull the group back together for the moments that actually matter, like meals, mornings, and unhurried time under one roof.

We also dig into the practical side of group travel planning: why starting with the people and the purpose beats starting with the destination, how to avoid the “vacation from vacation” feeling, and when a villa rental can deliver more value than booking multiple hotel rooms. Paul explains why vetted homes and local travel concierge support reduce risk, fix problems faster, and keep small issues from hijacking the whole trip.

If you care about family reunion travel, legacy, and building memories that last, this conversation will give you a clearer plan and a better reason to travel. Subscribe, share this with your favorite travel planner, and leave a quick review so more people can find us.

Visit Paul's Site: https://www.travelvillaguide.com/

Get a Free Guide!: https://gift.travelvillaguide.com/

Download full-color PDFs of my book at prices below Amazon paperbacks. Visit my store at https://shop.jimsantosbooks.com

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"Wherever We May Roam: Finding Your Travel Style" - On Amazon

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Travel technology is changing so fast that it can feel like you need a new degree just to book a flight. We sit down with Madison Rolley, a travel content creator and entrepreneur with a tech background, to bridge that gap and make modern trip planning feel simple, practical, and worth your time.

Madison shares how studying abroad sparked her travel confidence, how she became a digital nomad at 22, and why moving too fast can burn out even the most excited traveler. From there, we dig into the real reason her audience grew: people kept asking how she could afford it. That question led to clear, repeatable tactics that anyone can use, including price alerts, deal subscription emails, and smarter ways to search when you care more about value than a perfect date.

Then we get into AI travel planning and what is actually changing right now. Madison explains why Google’s AI overviews increasingly pull from video platforms like Instagram, TikTok, and YouTube, and how that shifts the way we discover destinations, hotels, and experiences. We compare tools like Google Flights beta and ChatGPT for itinerary building, including how AI can quickly suggest routes, pacing, side trips, and free activities, while still requiring human judgment to confirm details and avoid bad assumptions.

We also talk about solo travel, the rise in female solo travelers, and how social media can reduce fear by showing real experiences and practical safety context. You’ll leave with a better framework for using travel tech without feeling overwhelmed: start small, ask better questions, and treat AI as a tool that saves research time, not a robot that replaces your instincts.

If this helps you travel longer or travel better, follow the podcast, share this with a friend who’s planning a trip, and leave a quick review so more people can find us.

Madison's Website: https://hoo.be/madisonrolley

Madison' YouTube Channel: https://www.youtube.com/@madisonrolleytravel

Madison's TikTok: https://www.tiktok.com/@madisonrolley

Madison's Instagram: https://www.instagram.com/madisonrolley

Download full-color PDFs of my book at prices below Amazon paperbacks. Visit my store at https://shop.jimsantosbooks.com

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jim@jimsantosbooks.com

"Wherever We May Roam: Finding Your Travel Style" - On Amazon

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Weeks of travel planning can come down to one stubborn problem: turning a big dream into a realistic route that fits your time, energy, budget, and check-in times. We’re Jim and Rita Santos, and we’ve built plenty of complicated itineraries the old-fashioned way with spreadsheets, tabs, and too many “wait, what day do we check out?” mistakes. This time, we try something different: we hand AI a tight set of rules and see if it can draft a trip that actually matches our travel style.

We walk through a 53-day Europe overland itinerary starting in Madrid and ending in Hamburg, using trains, buses, and ferries with ride times capped at about six and a half hours. AI spits out a full outline in about 87 seconds, then surprises us with extra travel research like top highlights, typical weather, and the big “book early” reminders that can make or break a trip (Anne Frank House, Sagrada Familia, Louvre timed entry, tulip season tickets). We also share where we still tweak the plan, like cutting expensive stays and avoiding too many two-night stops.

Then we run a smaller experiment: a senior-friendly 2–3 night getaway within a 5.5-hour drive from Knoxville that avoids heavy crowds. The results are genuinely useful, but we also talk about the fine print: AI can be wrong, schedules change, and personalization can feel both exciting and a little unsettling. If you’re curious about AI travel planning, Europe train travel, or just traveling smarter, hit play, then subscribe, share the show with a travel buddy, and leave a quick review so more listeners can find us.

Download full-color PDFs of my book at prices below Amazon paperbacks. Visit my store at https://shop.jimsantosbooks.com

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jim@jimsantosbooks.com

"Wherever We May Roam: Finding Your Travel Style" - On Amazon

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That $895 annual fee can either buy you real travel freedom or it can quietly drain your budget while you chase perks you never use. We put premium travel credit cards under a practical microscope and share what happens when you treat points like a tool instead of a hobby.

We walk through the exact cards we carry and why: what Amex Platinum is good for when you’re traveling heavily, why Amex Gold can be the smarter long-term play for dining and groceries, and why you still need a Visa like Chase Sapphire Preferred when you’re overseas and merchants refuse American Express. We also talk about booking travel through credit card portals, including when the multipliers and customer service make it worth it, and when you give up flexibility or hotel loyalty benefits. And yes, we tell the truth about airport lounge access, because “included” does not always mean “available.”

Then we get into the details that actually protect your wallet: how to think about a 3% credit card surcharge, what point values really look like in dollars, and how point maximizer services and award travel tools work behind the scenes. We share safer ways to find partner award redemptions, plus the biggest rule we follow when transferring points so you don’t get stuck with a one-way, non-reversible mistake. Finally, we cover underrated perks like foreign transaction fees, paying in local currency, rental car insurance options, trip interruption coverage, and purchase protection, along with scam red flags you should never ignore.

If you like practical travel strategies and real-world money decisions, subscribe, share this with a friend who loves points, and leave a quick review so more travelers can find us.

Download full-color PDFs of my book at prices below Amazon paperbacks. Visit my store at https://shop.jimsantosbooks.com

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https://www.buzzsprout.com/2292506/supporters/new
http://jimsantos.net
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https://www.youtube.com/@jimsantos508
jim@jimsantosbooks.com

"Wherever We May Roam: Finding Your Travel Style" - On Amazon