Wheels Up, Windows Down

A travel podcast

The best travel stories rarely go according to plan.

Airports, road trips, wrong turns, questionable hotels, and the stories worth telling afterward.

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Season 01 · Episode 02

When the Road Trip Fights Back

49 minutes

What starts as a family road trip to Ohio turns into storms, potholes, car trouble in Chicago, five people crammed into one Camry, a 2:30 a.m. tire change, and an invasion of Arkansas mosquitoes. Ric tells the story of a trip where almost nothing went according to plan—and how a return run to Chicago finally gave him the chance to finish Route 66.

The premise

Part travel show. Part cautionary tale.

Two hosts swap the funny, surprising, maddening, and occasionally wonderful stories that happen between leaving home and finally getting back.

Meet the hosts

Host

Ric Wayland

Ric Wayland is a lifelong traveler, meticulous planner, and collector of stories born from wrong turns, strange hotels, and questionable decisions.

On Wheels Up, Windows Down, he brings a practical traveler’s eye, dry humor, and a belief that the best trips rarely go according to plan. Ric also runs Fork in the Road Trip and is a managing partner at the Open Road Archive.

Stylish blonde woman in an airport lounge at sunset, holding a champagne flute while seated beside a passport, travel bag, and books, with airplanes visible outside the window.

Host

Jennifer Do

Jennifer Do is a lifelong traveler and enthusiastic jetsetter who has explored more than 50 countries across five continents. On Wheels Up, Windows Down, she brings an international perspective, destination inspiration, practical travel hacks, and a willingness to go far out of her way for something extraordinary.

Jennifer is also a travel advisor and the creator of Jennifer’s Path, where she shares travel stories, destination guides, and ideas for seeing more of the world.