She was a corporate high-flyer who traded boardrooms for backcountry trails. After joining Jackie on the O Circuit in Patagonia—celebrating a sobriety milestone and conquering suspension bridges—Ginger Cooper came home and sold her house, quit her job, and built a life on her own terms. From solo camper van trips above the Arctic Circle to kayaking with beluga whales, her story is a joyful reminder of what’s possible when you say yes to what calls you.

Caution: may inspire spontaneous ticket purchases.

Resources:

• Follow Ginger on Instagram at @gspiceadventures
• Please follow the show, leave a 5-star review if you love it, and share with your travel buddies
• Don’t miss Jackie’s behind-the-scenes communications - hop on our email list at TravelingJackie.com
• Massive thanks to Osprey.com and ObozFootwear.com for sponsoring and supporting our show!

Produced by NOVA

She grew up watching her dad walk across the country—literally—from capital to capital. Decades later, Sherry Ott is finishing what he started… by bike. In this episode, Jackie sits down with the travel veteran (and six-time guest!) to talk about her latest quest: a cross-country cycling journey that’s equal parts tribute, personal challenge, and epic adventure.

What began in the 80s with paper maps and pushpins has become “Capital to Capital,” Sherry’s self-filmed docuseries chronicling her ride through rural America. Along the way, she’s faced down busy highways, wild dogs, flat tires, and self-doubt—but also discovered unexpected connection, confidence, and joy in the process.

It’s a story about legacy, learning as you go, and saying yes to something big before you’re ready.

Resources:

• Find and follow Sherry on Instagram at @Ottsworld
• Read about Sherry's quest: ottsworld.com/blogs/capitol-to-capitol-quest-walking-and-cycling-to-the-united-states-capitols
• Watch Sherry's docuseries: https://youtu.be/tzbofptX92I
• Please follow the show, leave a 5-star review if you love it, and share with your travel buddies
• Don’t miss Jackie’s behind-the-scenes communications - hop on our email list at TravelingJackie.com
• Massive thanks to Osprey.com and ObozFootwear.com for sponsoring and supporting our show!

Produced by NOVA

He was a small-town guy from Montana, she was living the big city life in New York. They met on a trip to Morocco and got engaged four years later in Antarctica, and they had an adventure date on every continent in between. Listen in as Jackie gets the whole story from guests Andy Austin and Chelsea Anderson, two globe-trotting professionals who fell in love as they journeyed to the ends of the earth, together.

Pairs well with pajamas and champagne.

- The sweetest thing you will watch today: Andy & Chelsea's sweet 7 for 7 love story on TikTok

- Find and follow Andy at @AndyAustinPhoto and Chelsea at @Chesea_ea

- Please follow the show, leave a 5-star review if you love it, and share with your travel buddies

- Don’t miss Jackie’s behind-the-scenes communications - hop on our email list at TravelingJackie.com

Massive thanks to Osprey.com and ObozFootwear.com for sponsoring and supporting our show!

Produced by NOVA