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How to Improve Your Retirement Travel – As Featured on the Retirement Answer Man Podcast

Published: June 4th, 2025

What does it really mean to travel well in retirement? That's the heart of a recent conversation between Roger Whitney, host of the award-winning Retirement Answer Man podcast, and Andrew Motiwalla, founder of The Good Life Abroad. Episode 594, titled "How to Improve Your Retirement Travel," is a thoughtful and wide-ranging discussion that goes well beyond bucket lists — exploring the deeper why behind travel in retirement and how to make it truly meaningful.

Why Do Retirees Want to Travel?

Roger opens the episode by sharing a conversation with a client who was deeply passionate about hiking the Camino in Spain. When asked why, the client offered all sorts of explanations, but it ultimately came down to three words: "I feel awake." Roger uses that phrase as his working thesis throughout the episode — travel, at its core, wakes us up.

He goes on to explore several reasons retirees are drawn to travel: making up for missed opportunities during working years, expanding your world and gaining new perspectives, creating lasting memories, and perhaps most unexpectedly, self-care. As Roger reflects from his own experience, changing your environment — getting out of the routine, being more social, engaging with new things — is genuinely good for your mental health.

He also touches on something less obvious: that we may simply like ourselves more when we're in traveler mode. We bring our "great attitude," we're more open, more flexible, more present. And then there's what Roger calls the teleological nature of travel — the joy of the full cycle, from dreaming and planning, through the trip itself, to coming home with stories and new perspectives, then starting all over again.

What Gets in the Way

Roger doesn't shy away from the obstacles either. He identifies several common ones: inertia (maybe next year…), anxiety about navigating unfamiliar places, differing preferences between partners, safety concerns, financial worries, family obligations, and health limitations. None of these are insurmountable, but they're real — and acknowledging them honestly is the first step to moving past them.

Rethinking What "Travel" Even Means

One of the episode's most practical moments is Roger's invitation to broaden how we think about travel altogether. Not everyone needs to book a transatlantic flight. Travel can mean international adventures, yes — but also U.S. road trips, regional exploration, or even local discovery. Roger describes his own approach: spending a season in Colorado and making a point to visit new restaurants, hikes, and neighborhoods without ever leaving the state. He also shares the example of a friend who keeps a running Google Maps list of nearby breweries and trails — never leaving his zip code, but always feeling like an explorer.

The point: the feeling of being awake doesn't require a passport.

Living Abroad Like a Local — The Good Life Abroad

That said, for those who are drawn to international travel, the conversation with Andrew Motiwalla offers a genuinely different model for how to do it.

Andrew's background spans three decades in group travel — starting with student travel, then family programs, and eventually noticing that the grandparents on those family trips kept asking the same question: "Why isn't there something like this just for us?" What they wanted wasn't a tour bus. They wanted to slow down, live at their own pace, and actually inhabit a place rather than race through it. That insight became The Good Life Abroad.

The program places adults 55 and older in vetted, furnished apartments in European cities — Lisbon, Florence, Barcelona, Rome, Palermo, and more — for a month or two at a time. Each program includes a local Community Manager who acts as an on-the-ground concierge and friend, plugging participants into local events, activities, and hidden gems. Participants live near a cohort of fellow travelers, gathering for happy hours, dinners, cooking classes, and spontaneous adventures — while retaining full independence to explore on their own terms.

Andrew is clear that The Good Life Abroad isn't a tour. As he puts it, it's a blank canvas with support — everyone paints their own picture. One traveler in Florence spent a month immersing himself in Renaissance art and learning to paint, fulfilling a dream he'd carried through a whole career as an accountant. In Palermo, one participant traced her family genealogy while another went deep into Sicilian cooking. Same city, same cohort, completely different and deeply personal experiences.

Who Is It For?

About 75% of Good Life Abroad participants simply want the experience of living like a local abroad — they have no intention of becoming expats, and they're not giving up their homes. The remaining 25% are genuinely exploring a permanent move and use the program as an informed, supported way to scout neighborhoods and get a real feel for daily life in a city.

Roughly 30% of participants are solo travelers, drawn specifically by the community aspect — the comfort of having neighbors, a local guide, and a built-in social circle, while still maintaining the independence to do what they want, when they want.

What Actually Takes Travel to the Next Level

When Roger asks Andrew what separates a good travel experience from a transformative one, Andrew's answer is worth sitting with. Beyond the logistics — the right apartment, medical coverage, safety — the most important ingredient is introspection. Taking a moment before you travel to ask yourself who you are and what you actually want out of this chapter of life, then letting that shape how you travel, leads to something far more satisfying than checking off a list of sights.

As Andrew puts it, running through a checklist can still leave you feeling a little empty. But doing something that feeds your soul — that's what makes the difference.


Listen to the Full Conversation

🎧 Listen to the full episode: #594 - How to Improve Your Retirement Travel


About the Retirement Answer Man Podcast

Hosted by Roger Whitney, CFP®, CIMA®, CPWA®, RMA, the Retirement Answer Man is a two-time PLUTUS Award-winning podcast that tackles both the financial and personal sides of retirement. From Social Security and healthcare to travel, purpose, and lifestyle planning, Roger helps listeners build the confidence to not just survive retirement — but to rock it. Learn more at rogerwhitney.com.

About The Good Life Abroad

The Good Life Abroad is a travel program designed for adults 55 and older who want to experience Europe not as tourists, but as temporary locals. With vetted apartments, on-the-ground community support, and a built-in cohort of like-minded travelers, The Good Life Abroad makes extended travel abroad more accessible, social, and meaningful than ever.

Curious what a month in Europe could look like for you? Explore our destinations or request a free catalog to get started.

Andrew Motiwalla

Andrew is the Founder of The Good Life Abroad and has worked in the travel industry for over 30 years. His first experience living abroad was as a Peace Corps volunteer.

He is also the Founder of Discover Corps, a company specializing in meaningful vacations for families.

Learn More about Andrew Motiwalla