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Your vacation shouldn’t leave you more tired than your job. We dig into why so many trips feel rushed even when you “did everything right,” and the answer isn’t hustling harder or planning tighter. It’s choosing a different travel style. We call it the Extended Getaway: a three to six week trip designed to be realistic, affordable, and actually restorative.

We walk through the tradeoffs that make short vacations stressful: losing days to airports and check-ins, living out of a suitcase, and trying to cram too many destinations into a tiny window. We also share why we’re cautious about packaged tours, including a story where a simple day trip turned into hours of waiting and barely any time in the place we came to see. From there, we shift to what works better: fewer bases, more flexibility, and a rhythm that leaves room for culture instead of just landmarks.

To make it concrete, we tell the story of our first extended getaway in Italy, from renting an apartment in Florence to the kind of unplanned night in Venice you never could have scheduled. Then we break down a month in Panama City, Panama with real budget travel numbers: a condo with a kitchen, laundry, and a view for under $1,200, cheap rideshares, local mercados, and an average spend of about $100 a day for everything. Along the way we share practical long vacation planning tips like “zero days,” packing light, and building in adjustment time so the trip feels livable.

Subscribe for more travel style guidance, share this with a friend who always overpacks the itinerary, and if the extended getaway sounds like your kind of slow travel, leave us a review and tell us where you’d spend your first three to six weeks.

And if you want to go deeper, you can check out my book, "Wherever We May Roam, Finding Your Travel Style", where I walk through all of this in more detail. You can search for it on Amazon in Kindle, Paperback, and Audiobook, or just use the link on our podcast page. If you have any questions, a topic you would like discussed, or would like to be on our show, email us at jim@jimsantosbooks.com.

Be sure to enter the Goodreads Giveaway between May 10 and May 22nd, 2026 for your chance to win one of 100 free copies of "Wherever We May Roam: Finding Your Travel Style". Click here to enter!

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Most travel advice starts with destinations, but that’s not what makes a trip work, especially when you’re traveling for weeks or months. We’re Jim and Rita Santos, and after 16 years of everything from short trips to living abroad and experimenting with full-time roaming, we’ve learned the hard truth: long-term travel doesn’t fall apart because you “did it wrong.” It falls apart when you copy someone else’s travel lifestyle instead of building a travel style that fits your time, budget, and personality.

We’re back for a new season with a new name, Wherever We May Roam, along with our book Wherever We May Roam: Finding Your Travel Style. We break down four common long-term travel styles: extended getaways, part-time roaming, digital nomad life, and full-time roaming. We also unpack the biggest mistake travelers make, planning one style of trip with another style’s rules, and how a simple self-assessment can save you money, stress, and disappointment.

From there we get practical: how cash and payments work overseas now, what to do when accommodations go sideways, how visa rules and Schengen limits can surprise you, and why apps, travel insurance, and a flexible mindset matter more the longer you stay out. We share real stories, from unexpected delays to health care abroad, plus small cost-saving habits that make extended travel more sustainable.

Follow the podcast, share this with a friend who’s dreaming of longer travel, and leave a quick review so more travelers can find us.

And if you want to go deeper, you can check out my book, Wherever We May Roam, Finding Your Travel Style, where I walk through all of this in more detail. You can search for it on Amazon in Kindle, Paperback, and Audiobook, or just use the link on our podcast page.
If you have any questions, a topic you would like discuss, or would like to be on our show, email us at Jim at Jim@SantosBooks.com.

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

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

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A medical detour changed our itinerary, but it sharpened our belief in slow travel and why roaming creates better stories than any checklist. We close out season two by sharing a vivid sneak peek of our upcoming book on how to plan, budget, and savor longer stays without tour buses dictating your day. From an apartment steps from the Arno in Florence to a trust-the-chef feast in a tucked-away Venetian trattoria, we relive the small choices that turned into big memories—and the practical systems that made them affordable.

We walk through the core pillars of slow travel: choosing one meaningful focus per day, renting apartments with kitchens to cut costs and live like a local, and using trains and ferries to keep plans flexible. You’ll hear how a wrong turn near Livorno became a Mediterranean moment, why a spontaneous side trip to Lucca beat a packed itinerary, and how rain in Rome turned into a playful, poncho-clad wander across cathedrals, fountains, and welcoming neighborhood bars. We also tackle safety myths with grounded advice, from reading a city’s rhythm to staying present and letting common sense do more work than a lanyard ever could.

We’re taking a short break to finish the book and regroup for future travels, and we’d love your questions and stories as we write. Subscribe, share with a friend who wants more from their trips, and leave a review to help fellow travelers find the show.

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

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

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