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Wherever We May Roam - Travels With Jim and Rita

Jim Santos, travel writer and his wife, Rita
Travel
Florence, Italy
Rome, Italy
London
Sailing
Ireland
Panama City, Panama
Ecuador
Public Speaking
Slow Travel
Lisbon
Seville
Oxford
Edinburgh
Greece
Giant's Causeway
Roscommon
Galway, Ireland
Extended Getaway
Part-Time Roamer

Not all travel is created equal. Some people take a two-week vacation and call it an adventure. Others disappear for months—or years—without ever really “coming home.” We discuss the challenges, rewards, and drawbacks of travel both domestically and overseas. Information for the would-be expat, digital nomad, roving retiree, or just plain traveler. We can help you find the travel style that is ri... more

PublishesWeeklyEpisodes66Founded2 years ago
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Latest Episodes

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The fastest way to ruin a great trip is to assume the border rules will “work themselves out.” Jim and Rita Santos unpack the unglamorous but essential side of longer travel: visas, passport validity requirements, and the Schengen A... more

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Most people don’t skip long-term travel because they hate adventure, they skip it because the money math feels impossible. We challenge that assumption by showing how travel costs aren’t fixed at all, they’re driven by decisions: wh... more

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The fantasy of full-time travel is simple: sell the house, grab your bags, and go wherever you want. The reality is both better and messier. We talk through what “full-time roaming” actually means when there’s no reset button, no fa... more

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The digital nomad lifestyle looks effortless from the outside, but the moment you try to earn a living while crossing borders, you find out you are juggling two demanding worlds at once. We talk through the difference between “trave... more

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Recent Guests

Trevor Burrus, Jr.
Guest panelist discussed visa regions and policy context
Episode: The Schengen Shuffle Without The Panic
Aaron Powell
Guest panelist discussing visa administration tools
Episode: The Schengen Shuffle Without The Panic
Aaron Ross Powell
Guest participant noted in dialogue
Episode: The Schengen Shuffle Without The Panic
June Russell Chamberlain
Travel writer and photographer specializing in sailing, food, wine, culture, history
Episode: Episode 53 - Beyond Cruise Ships: The Freedom of Charter Sailing
Penny Zubula
Freelance travel writer based in Greenville, South Carolina; born legally blind, now totally blind; writes for travelers with disabilities
Independent writer
Episode: Episode 51 - Beyond Vision: The Sensory Art of Travel Writing
Simon Locke
Photographer, FAA-certified drone pilot; Penny's husband
Independent photographer
Episode: Episode 51 - Beyond Vision: The Sensory Art of Travel Writing

Hosts

Jim Santos
Host of Travels with Jim and Rita; extensive travel writing background and roving lifestyle experience.
Rita Santos
Co-host of Travels with Jim and Rita; shares experiences as part of long-term travel and expat life.

Reviews

4.6 out of 5 stars from 9 ratings
  • Great podcast for those looking for the travel lifestyle!

    I’ve listened to every episode, and love following their plan to slow travel to beat the housing market. It’s full of great information on where they travel, and you get great information about international health care, it’s not scary or dangerous, and the food and health benefits of certain areas. Keep up tje great work Jim and Rita, and lastly you’ve had some great guests, and look forward to more.

    Apple Podcasts
    5
    Dallas FlyZ
    United States2 years ago

Listeners Say

Key themes from listener reviews, highlighting what works and what could be improved about the show.

Quality guest appearances and thoughtful perspectives on healthcare abroad are recurring positives.
The hosts share relatable, candid stories from expat and roaming life.
Listeners appreciate practical, real-world travel tips and the emphasis on slow, immersive experiences.
The format blends narrative with actionable planning advice for long-term travel.

Chart Rankings

How this podcast ranks in the Apple Podcasts, Spotify and YouTube charts.

Talking Points

Recent interactions between the hosts and their guests.

Episode 53 - Beyond Cruise Ships: The Freedom of Charter Sailing
Q: What's the most attractive part of this mode of travel to you?
The freedom to choose destinations and timeframes, with the ability to stay longer in places they love and to discover lesser-visited, authentic locales.
Episode 53 - Beyond Cruise Ships: The Freedom of Charter Sailing
Q: When did you start actually chartering for vacations?
They began chartering about 15 years ago, advancing from racing on lakes to bigger boats and international charters, eventually with crews and instructors as needed.
Episode 53 - Beyond Cruise Ships: The Freedom of Charter Sailing
Q: How did you get involved in sailing? What was your first experience?
Her husband sparked their sailing interest, starting with a fast 16-foot laser-type boat, learning with a steep early learning curve, and progressively moving to bigger boats and formal sailing credentials.
Episode 53 - Beyond Cruise Ships: The Freedom of Charter Sailing
Q: So, June, give us a little bit of an idea of your background. What got you first interested in travel?
June describes a lifelong love of exploration, beginning with family travel in Oregon, early writing in school, and a start in journalism that evolved into travel writing and photography.

Audience Metrics

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Frequently Asked Questions About Wherever We May Roam

What is Wherever We May Roam about and what kind of topics does it cover?

Two longtime travelers share practical, experience-driven guidance for longer, smarter travel. The show contrasts fast itineraries with slower, immersion-focused approaches—living like locals, budgeting for extended stays, and navigating housing, healthcare, and logistics while roaming. Episodes cycle through personal roving lifestyles, expat considerations, digital nomad setups, and roving retirement, often with vivid on-the-road storytelling and actionable tips. A notable angle is the pair's evolving travel philosophy, their focus on authenticity over crowds, and occasional deep-dives into future books or rebrands that broaden the conversation beyond single trips. Potential listeners can expect candid reflections, useful planning tactics,... more

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Which podcasts are similar to Wherever We May Roam?

These podcasts share a similar audience with Wherever We May Roam:

1. Zero To Travel Podcast
2. Travel with Amateur Traveler Podcast
3. The Thrifty Traveler Podcast
4. Catching Up to FI
5. Retirement Answer Man

How many episodes of Wherever We May Roam are there?

Wherever We May Roam launched 2 years ago and published 66 episodes to date. You can find more information about this podcast including rankings, audience demographics and engagement in our podcast database.

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What guests have appeared on Wherever We May Roam?

Recent guests on Wherever We May Roam include:

1. Trevor Burrus, Jr.
2. Aaron Powell
3. Aaron Ross Powell
4. June Russell Chamberlain
5. Penny Zubula
6. Simon Locke

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