Navigating the 3 Phases of Travel in Retirement with Andrew Motiwalla

Andrew Motiwalla explains how to prepare for long-term travel and how to incorporate travel into your retirement plan.

When I sit down with people to talk about retirement, one of the first things I hear is, “I want to spend more time with my grandkids and I want to travel.” And while grandkids may not need much planning, travel does—especially if you want to do it in a way that truly enriches your retirement years.

That’s why I was excited to sit down with Andrew Motiwalla, founder of The Good Life Abroad, on the Retire Today podcast. Andrew has spent 30 years in the travel industry and has built something unique for retirees who want more than just a quick trip. His company helps retirees live abroad for one or two months at a time, creating deeper, more immersive travel experiences.

From Checklist Travel to Immersive Experiences

Andrew described three “phases” of travel that many retirees experience. The first is what he calls checklist travel. This is when you finally make it to those bucket-list destinations—the Eiffel Tower, Machu Picchu, the Taj Mahal—and snap the pictures you’ve dreamed of for years. It’s exciting, it’s rewarding, and for many, it’s where retirement travel begins.

But then comes phase two—intentional travel. This is when you begin asking bigger questions: Who am I? What do I really want out of retirement? Maybe you’ve always loved art and decide to spend a month in Florence studying Renaissance masterpieces. Or perhaps your family roots are in Poland, and you want to show your children and grandchildren where your story began. It’s travel with a deeper purpose.

Finally, there’s immersive travel. This is when travel becomes more than just a trip—it’s part of your lifestyle. Retirees may take language or cooking classes at home, then use extended travel to practice and grow their skills. Instead of being tourists, they start to live like locals, even if just for a short time.

Why Living Abroad Is Different

One of the biggest differences Andrew sees between standard vacations and what The Good Life Abroad offers is time. When you live abroad for a month or two, you’re not rushing from one destination to another. You can settle into an upscale apartment, shop at local markets, and develop routines—like a favorite café or a walking route through your neighborhood. You start to feel part of the community.

Just as important, Andrew’s company helps retirees avoid some of the biggest pitfalls of going it alone, such as loneliness or confusion about local customs. They provide a “community manager”—someone who knows both the local culture and the American mindset—to guide you to hidden gems like university concerts or local cooking classes. They also bring together a community of like-minded retirees, so you’re never traveling alone unless you want to be.

The Benefits Go Beyond Travel

What struck me most in this conversation is how immersive travel can actually help retirees find new meaning and identity. For decades, your sense of self may have come from your job or raising your family. In retirement, those roles shift. Travel—done with purpose—can fill that space. You might start to identify as a “traveler,” a “culture lover,” or an “art enthusiast.” And along the way, you’ll meet others who share that passion.

This isn’t just about checking boxes; it’s about transformation. As Andrew put it, travel can be a vehicle for reinvention.

Practical Considerations

Of course, planning extended travel comes with questions. What about health care? What about visas? Andrew explained that for trips under 90 days, Americans can generally travel freely in most of Europe, and The Good Life Abroad includes travel medical insurance and access to English-speaking doctors in every city they serve. For longer stays, you may need to look into visas and local insurance, but for most retirees, a one- or two-month trip fits perfectly within the rules.

And if you’re traveling solo, Andrew reassured us that this model works just as well. Many of their travelers are single—widowed, divorced, or just pursuing retirement independently—and the built-in community makes it easy to form new friendships and connections.

Your Retirement, Your Way

Whether you’re a lifelong learner eager to expand your horizons or simply someone who’s always wanted to “live like a local,” immersive travel may be one of the best gifts you can give yourself in retirement. As Andrew said, it’s never too late to keep learning, growing, and exploring.

Retirement isn’t just about financial freedom—it’s about personal freedom. And travel