This week, Tim Regan and Katie Umland take a lighter approach on the Retirement Readiness Podcast as they explore the ins and outs of road trips in retirement. With summer on the horizon, Tim and Katie discuss why the freedom that comes with retirement is the perfect opportunity to rediscover the classic American road trip—whether it’s a weekend getaway, a cross-country adventure, or something in between.

Drawing from their own experiences and stories from clients, they cover how travel styles shift in retirement, options for planning road trips (from fully spontaneous to professionally arranged), and the unique memories created by embracing both the expected and the unexpected. “You never talk about the trip that went perfectly. You always talk about the trip fondly... those kinds of things,” Tim shares.

The conversation also touches on RV living, group travel, train journeys, and how travel can evolve into a meaningful way to connect with family and create new traditions during the retirement years.

Tune in for practical advice, personal anecdotes, and inspiration for making the most of your post-career freedom—on the road and beyond.

3 Key Takeaways

• Retirement opens up a new world of travel possibilities, from impromptu weekend outings to month-long adventures you may never have considered before.
• There’s no single “right” way to plan a road trip: some prefer the flexibility of no reservations, and others feel more comfortable with a detailed itinerary or hiring a travel planner.
• Road trips can create lasting memories and become vehicles (literally and figuratively) for family bonding and expanding your horizons in retirement.

Give this episode a listen and discover how to craft your perfect road trip in retirement—whether you’re seeking adventure, connection, or just a change of scenery.