Navigating the 3 Phases of Travel in Retirement – As Featured on the Retire Today Podcast

Published: October 8th, 2025

"I want to spend more time with my grandkids and I want to travel." It's one of the most common things people say when they sit down to talk about retirement. And while the grandkids part tends to take care of itself, travel — especially the kind that truly enriches your life — takes some planning.

That's exactly what Jeremy Keil, CFP® of Keil Financial Partners and host of the Retire Today podcast, set out to explore in a recent episode featuring Andrew Motiwalla, founder of The Good Life Abroad. The conversation, published October 8, 2025, goes well beyond the usual retirement travel checklist and introduces a genuinely thoughtful framework for how to approach travel across the full arc of retirement.

The Three Phases of Retirement Travel

The centerpiece of the episode is Andrew's concept of three distinct phases that retirees tend to move through in their relationship with travel — and recognizing which phase you're in can make all the difference in how satisfying your experiences are.

Phase one is checklist travel. This is where most people begin. You've finally got the time, and you're going to see the places you've always dreamed of — the Eiffel Tower, Machu Picchu, the Taj Mahal. It's exciting, it's deeply rewarding, and it's a natural and wonderful way to open this new chapter. There's nothing wrong with it. But for many retirees, after a few years of tours and cruises and bucket-list destinations, a quiet question starts to emerge: Is this all there is?

Phase two is intentional travel. This is where the deeper questions come in. Who am I now that I'm retired? What do I actually want out of this time? Travel becomes a vehicle for personal exploration rather than destination-ticking. Someone who has always loved art decides to spend a month in Florence diving deep into Renaissance masterpieces. Someone else realizes their family roots are in Poland and wants to bring their children and grandchildren back to where the story began. The destination serves a purpose beyond the postcard.

Phase three is immersive travel. Here, travel becomes woven into the fabric of retirement life itself. Retirees might take language or cooking classes at home, then use extended trips abroad to practice and deepen those skills in the real world. They stop being tourists in any meaningful sense. They start to live like locals — developing routines, favorite cafés, familiar walking routes — even if only for a month or two at a time.

Why Time Changes Everything

A recurring theme throughout the episode is the transformative power of simply having more time in one place. When you're living in an apartment in Lisbon or Barcelona for a month rather than passing through for four days, something shifts. You shop at the local market. You find your neighborhood bakery. You stop consulting the guidebook and start just living. The experience stops feeling like a performance and starts feeling real.

This is precisely the gap that The Good Life Abroad was built to fill. Andrew's program places adults 55 and older in vetted, fully furnished apartments in some of Europe's most beautiful cities — Florence, Lisbon, Rome, Barcelona, Palermo, and more — for one to two months at a time. Every apartment is personally checked to ensure it genuinely suits North American travelers: spacious, accessible, and comfortable in the way that matters most for longer stays.

Each program also includes a local Community Manager — someone who straddles both worlds, deeply knowledgeable about the local culture but also attuned to what American travelers need. This person guides participants to the experiences that don't show up in travel apps: a university concert, a neighborhood cooking class, a weekly market that locals actually use. They also help navigate the unexpected — logistical surprises, local disruptions, moments when you just need someone who knows how things work.

Travel as a Path to Reinvention

One of the episode's most thought-provoking threads is the idea that immersive travel can help retirees find new identity and meaning. For decades, a sense of self comes from a career or from raising a family. When those roles shift in retirement, travel — done with intention — can step in to fill that space in a meaningful way. A retired accountant who always dreamed of painting becomes, in Florence for a month, someone who paints. A family historian becomes a genealogist in Palermo. A home cook becomes a student of Sicilian cuisine. These aren't just trips. They're the beginning of new chapters.

As Andrew describes it, travel can be a genuine vehicle for reinvention — not just a reward for decades of hard work, but an active part of discovering who you are and want to be in this next stage of life.

Practical Considerations: Health, Visas, and Traveling Solo

Jeremy and Andrew also work through the practical side of extended travel abroad, which is often where hesitation sets in. On the visa front, Andrew notes that for stays under 90 days, Americans can move freely throughout most of Europe without needing to navigate any additional paperwork — and one to two months fits comfortably within that window for most travelers. The Good Life Abroad also includes travel medical insurance and access to English-speaking doctors in every city they serve, which removes one of the biggest sources of anxiety for retirees considering longer international trips.

For those traveling solo — a meaningful portion of Good Life Abroad participants, including many widowed or single retirees — Andrew is reassuring. The program's built-in cohort of fellow travelers and the presence of a local Community Manager means that going solo doesn't mean going alone. You have neighbors, you have a friendly face who knows the city, and you have a community to join for dinner or explore with on a whim — all while retaining the full independence to follow your own path.

Listen to the Full Conversation

🎧 Listen to the episode here: Navigating the 3 Phases of Travel in Retirement with Andrew Motiwalla

About the Retire Today Podcast

Retire Today is hosted by Jeremy Keil, CFP®, founder of Keil Financial Partners, a Milwaukee-based financial planning firm specializing in retirement. The podcast focuses on helping people navigate the financial and personal decisions that shape retirement — from Social Security and tax planning to the lifestyle questions that make retirement truly fulfilling. New episodes are released every Wednesday on Apple Podcasts and Spotify. Learn more at keilfp.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 furnished apartments, on-the-ground community support, and a built-in cohort of like-minded travelers, The Good Life Abroad makes extended travel in Europe more accessible, social, and meaningful than ever.

Curious what a month abroad could look like for your retirement? Explore our destinations or request a free brochure to get started.