The Freedom of Retirement: Time to Reimagine the Road Trips

In this episode of The Retirement Readiness Podcast, hosts Katie Umland and Tim Regan steer the conversation away from the usual financial insights and dive into something that’s close to many retirees’ hearts: travel, specifically the classic American road trip.

Reflecting on their own family experiences and client stories, Katie and Tim highlight a simple but powerful realization—retirement offers you time and flexibility in ways that the working years rarely do. Many retirees, they observe, don’t initially realize the extent of their newfound freedom: gone are the days of cramming adventures into a two-week vacation window. Now, you can chart your own course, linger in places that call to you, and design trips—short or long—around your interests, not your work schedule.

The Many Flavors of Road Tripping in Retirement

Katie and Tim break down just how diverse road trips can be for retirees. While it’s easy to picture a grand month-long trek across America, the reality is often a combination of big and small journeys. Sometimes it means driving instead of flying to see family, making the most of relaxing drives and spontaneous stops. As the hosts note, flying can seem less appealing as you get older due to the stress of airports, security lines, and tight schedules. Driving, by contrast, puts you in control—set your own pace, pull over wherever you like, and relive the joy of winding down the windows on the first fresh days of summer.

Tim shares that his family has enjoyed both meticulously unplanned adventures—where the route is open and accommodations are decided on the fly—and more structured trips that minimize surprises, each type offering its own rewards. One of Katie’s most memorable stories involves a last-minute hotel search during a drive through the Dakotas: what started as a regrettably rundown motel stay quickly became the kind of laugh-filled story that families treasure for years.

Beyond the Car: RVing, Train Routes, Group Excursions, and More

The episode also shines a light on how retirees can tailor travel to fit their sense of adventure—and comfort. Tim recalls clients who embraced RV living, one couple going so far as to sell their home and tour the country for three years, stopping to work as camp hosts and living in the heart of nature. Others have explored iconic drives like Route 30 (the Lincoln Highway), followed the twists of the Mississippi, or even put their RVs on trains for unique cross-border journeys like Mexico’s Copper Canyon.

Travel planning doesn’t stop at solo or couples’ travel, either. The hosts discuss group travel options—from fossil-hunting or photography-themed caravans to intergenerational grandparent–grandchild adventures where young ones help choose each stop from a travel “catalog.” There’s even room for curated experiences through travel agents who specialize in bespoke road trips, taking the pressure off those who find planning overwhelming.

And for those put off by long stretches behind the wheel, Katie and Tim suggest considering train travel—offering retirees the chance to watch the world roll by through the Canadian Rockies or Alaska, all while everyone can relax and take in the views together.

Road Trip Tips and Takeaways from the Podcast Hosts

Drawing from their personal travels, the hosts offer practical wisdom for retirees setting out on the road. Tim recommends scheduling natural breaks about every four hours—a rhythm that makes longer drives more pleasant and allows for quirky, unexpected discoveries (like the “largest waterfall in Missouri” that became a family joke). Both agree that the charm of the road trip is often found in its mishaps and surprises rather than perfect execution.

Katie notes that every trip adds new tricks to your repertoire, whether it’s finding the best routes or learning to weigh structure versus spontaneity. Their key advice for retirees: let go of the idea of a “perfect trip.” The best stories come from rolling with the punches and savoring those one-of-a-kind experiences along the way.

Final Thoughts: Your Retirement, Your Road

As the conversation makes clear, retirement is the perfect time to embrace the road trip spirit! Whether you’re navigating new family dynamics (like Katie preparing for twins), reconnecting with grown children, or seeking solo adventures, the possibilities are endless.

Ready for your own adventure? Katie and Tim invite listeners to connect, share travel dreams, or seek road trip advice—the journey begins with a single, open-ended route. 

For more details and practical tips, check out the full episode or reach out to our team!