The Good Life Abroad Alumni Roundtable

A Conversation with Paul Rand, Andrew Motiwalla & Program Alumni

Alumni Roundtable: What It's Really Like to Live Abroad with The Good Life Abroad

What does a month living abroad actually feel like? Not the highlight reel—the real thing. The moment you arrive jet-lagged in a rainstorm, the morning you become a regular at the corner café, the afternoon you find yourself at a rooftop bar with ten new friends you didn't know a week ago.

In this alumni roundtable, The Good Life Abroad founder Andrew Motiwalla was joined by five program participants—and guest moderator Paul Rand, creator of the intentional travel newsletter Nomadic Spirit—for one of the most honest, wide-ranging conversations we've hosted. The panelists had collectively experienced programs in Florence, Paris, Valencia, Lisbon, Porto, and Amsterdam, and they held nothing back.

Here's what they shared.

Meet the Moderator

Paul M. Rand is the founder and editor of Nomadic Spirit, a free weekly read for intentional travelers—particularly those over 50—who care as much about the why as the where. Through thoughtful essays, destination deep-dives, and an honest take on where the travel industry is getting it right and wrong, each issue helps readers travel with more intention and see places more deeply, not just pass through them. A longtime traveler himself, Paul also hosts The Big Brains video podcast at the University of Chicago.

Andrew came across Paul's newsletter and reached out immediately. "It was one of the most thoughtful, insightful travel newsletters I'd read," Andrew said. He's thinking about travel in much the same way that The Good Life Abroad does—specifically for travelers 55+, about intentional travel, about truly getting to know a place rather than checking sites off a list. The alumni roundtable format was actually Paul's idea, and he proved a natural at drawing out the honest, specific stories that make this conversation worth watching.

Meet the Panelists

Cynthia Ray, a retired pharmaceutical rep turned travel agent from Huntington Beach, California, did back-to-back programs in Lisbon and Porto—specifically to test whether she could live there. (Spoiler: she's moving to Lisbon.)

Julie Stevens, a self-described wanderer from the Kansas City area, had always wanted to spend a month somewhere instead of rushing through on a one-week itinerary. She's now done four programs—Florence, Paris, Valencia, and Nice—and has another trip booked.

Steven Chapman and his husband were in the very first Valencia group, more than a year ago. As a same-sex couple, they came in with some apprehensions—and left as enthusiastic advocates.

Bob Shoop, a retired professor of education law and ethics, traveled to Amsterdam with his wife Mary. He arrived to the webinar slightly late (Zoom had other plans), but made up for it with some of the conversation's most memorable observations.

Barry Parks, a retired architect and lifelong artist, became a widower in December 2023 and found himself, unexpectedly, on a solo trip to Florence in October 2024. He arrived as a planner—with spreadsheets and open browser tabs—and left with a painting he made for the first time in months.

On Going Solo—and Finding You're Never Really Alone

A recurring theme throughout the conversation: solo travel is far less isolating than it sounds, when the structure is right.

Julie put it simply. She couldn't quite imagine going off to live in Paris alone for three months. But an apartment already arranged, a few activities lined up, and a Community Manager there to help? That felt manageable—and it was. "There was just enough connections where I felt confident going and living there for a month."

Cynthia, who traveled as both a solo traveler and a woman of color, said her bigger concern going in was whether she'd be accepted. What she found instead was that her enthusiasm for exploring—skipping the tourist highlights to wander her own neighborhood, discovering a restaurant, leading a group to an African restaurant she'd found in Lisbon—made her a hub. "The next thing you know, you have ten people at a rooftop bar saying, 'How did you find this?'"

Barry, navigating his first solo trip after a major loss, described the experience as a kind of reawakening. He picked up a brush for the first time in months. The painting now hangs behind him on video calls.

On Traveling as a Couple—with Room to Breathe

Steven and his husband had, in his own words, different energy levels. Some days, one wanted a museum the other didn't. In a group of ten traveling units—couples and solo travelers alike—there was always someone who wanted to do what you wanted to do. "I could say, 'You go sit in the café for a day. I'm going to the beach,'" Steven said. (He may or may not have actually said that out loud.)

Bob and Mary found something similar in Amsterdam. "It was almost like staying in a family bed and breakfast for a month," he said. "You'd come down and someone would say, 'I found a restaurant,' or 'Let's go to the jazz club tonight.'" They had friends, but they also had privacy. The balance, he said, "worked really well."

On Living Like a Local—Through Routines

Andrew shared something he tells every prospective traveler: develop routines. "What do you do in Topeka, Kansas every day? Do those things."

Go to a yoga studio. Find a café you like. If you work out, find a gym. The first visit, no one notices. The second, they register you. By the third, the conversation starts: "Why are you still here?" And then: "You want to grab a coffee?"

It's a deceptively simple idea—and the panelists proved it works. Julie became a familiar face at the restaurants near her apartment in Florence, communicating across a language gap through repetition and goodwill. Steven got tickets to the opera and to two Valencia soccer matches—neither easy to procure without local knowledge. Cynthia knew the bartender at a rooftop bar well enough that when Andrew visited her in Porto, she marched him straight over to introduce them.

Bob added a particularly charming story from Amsterdam. His group went to a small restaurant, and the server—noticing they were American—asked if they'd like ketchup with their fries. "No," the whole table said in unison. "Mayonnaise." The server laughed. "You're locals."

On the Role of Community Managers

If there was one topic that generated the most enthusiasm across all five panelists, it was the Community Manager.

Julie described arriving in Valencia late, exhausted, soaking wet from the rain—and finding Community Manager Suzie waiting at the door with a big grin, ready to show her up to her apartment, open the blinds to reveal the cityscape, and walk her through everything she needed to know. There was a welcome basket: toiletries, food, wine, coffee. "She had coffee," Julie said. "It was just so welcoming."

Beyond the arrival experience, Community Managers were consistently described as the difference between a good trip and a great one. Steven needed tickets to a soccer match in Valencia—not easy to get, since games are announced informally and last-minute. His Community Manager figured it out. She also found them a gay bar showing the Eurovision final. Bob's Community Manager in Amsterdam helped them plan day trips that eventually covered two countries and several hundred miles. Cynthia's Community Managers in both Lisbon and Porto helped her explore different areas of Portugal every weekend, taking the train to different coastal towns as she tried to figure out where she might actually want to live.

As Andrew put it: "They love their cities. They want to make sure you have a good time. They are facilitators."

On Apartments and Logistics

Cynthia, with her background in the travel industry, came in with high standards for accommodation. She left impressed. The apartments, she said, were vetted—not the "Instagram vs. reality" problem you get with booking platforms. They're close to everything: restaurants, markets, pharmacies. And there's always a welcome sheet that covers everything you might need, including which hospital to call if something goes wrong.

Steven, who was in the very first Valencia cohort, had the experience of working through a few early kinks—including a washing machine with only Spanish-language buttons. Andrew acknowledged those early programs involved trial and error, but described the evolution: gathering feedback, upgrading apartments, eventually finding buildings where the team could establish a longer-term presence. In Paris, The Good Life Abroad has now taken out a multi-year lease on a building they love.

On Two Weeks vs. Thirty Days

For those wondering whether a month is too long—the consensus was unanimous: it's not long enough.

"The two-week trip was really short," Julie said. "The 30 days goes really quickly. It's surprising." Steven found that, rather than wanting to take side trips out of Valencia, he kept discovering new neighborhoods he hadn't explored yet. Flea markets. Hidden piazzas. More things to see.

Cynthia—now planning to spend 183 days a year in Europe—acknowledged the practical concerns people have: pets, medications, mail, phone service. Her answer was that The Good Life Abroad has thought through most of it, and the support before and during the program helps people prepare. "They really have thought of everything."

What Happened After

At the end of the webinar, Paul asked each panelist a simple question: would you do it again?

Barry had already started a spreadsheet for a Paris trip in fall 2027. Cynthia is planning to do a two-week Short Stay in Italy once she gets settled in Lisbon. Julie is booked for London in the fall, has her eye on Crete, and has already started traveling with people she met on previous programs. Bob and Mary signed up for Barcelona the week they got back from Amsterdam—and two people from their Amsterdam group are meeting them there. Steven and his husband are headed to Madrid in September, and have already registered for a Pride-focused program in Amsterdam in 2027.

Interested in Experiencing It for Yourself?

Whether you're drawn to the idea of slow travel, living like a local in Europe, or simply want to take the leap without doing it all alone—The Good Life Abroad's Month-Long Signature Programs are designed for adults 55+ who are ready to go deeper.

Explore destinations → Watch the full webinar → Request a free catalog →

Have questions? Email us at info@thegoodlifeabroad.com or schedule a one-on-one consultation with a member of our team.