7 Dates on 7 Continents - a Travel Love Story (JUMP 189)

What if the biggest party on two wheels was happening in the middle of Iowa every summer—and you were invited? Cyclist Eric Whalen joins Jackie to share the magic of RAGBRAI, the week-long ride across the state that’s equal parts endurance, community, and carnival. From pies and slip-n-slides to costumes and late-night music, Eric reveals how this ride became a father-son tradition and why it’s one of the most joyful cycling adventures in the country.Resources:Learn more about RAGBRAI: Register’s Annual Great Bicycle Ride Across IowaCheck out Pork Belly Ventures for charter services and added comfort on the rideJoin the conversation on the RAGBRAI SubredditFollow Eric on Instagram: @whaylenPlease follow the show, leave a 5-star review if you love it, and share with your travel buddiesDon’t miss Jackie’s behind-the-scenes communications - hop on our email list at TravelingJackie.comBe part of the conversation! Watch the video version by subscribing to our YouTube channel todayMassive thanks to Osprey.com and ObozFootwear.com for sponsoring and supporting our show!Produced by NOVA Take a leap with Jackie IRL - join us in Greece and Norway in 2025 at JUMPadventures.comAdvertising Inquiries: https://redcircle.com/brands

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 @gspiceadventuresPlease follow the show, leave a 5-star review if you love it, and share with your travel buddiesDon’t miss Jackie’s behind-the-scenes communications - hop on our email list at TravelingJackie.comMassive thanks to Osprey.com and ObozFootwear.com for sponsoring and supporting our show!Produced by NOVA Take a leap with Jackie IRL - join us in Greece and Norway in 2025 at JUMPadventures.comAdvertising Inquiries: https://redcircle.com/brands

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 @OttsworldRead about Sherry's quest: ottsworld.com/blogs/capitol-to-capitol-quest-walking-and-cycling-to-the-united-states-capitolsWatch Sherry's docuseries: https://youtu.be/tzbofptX92IPlease follow the show, leave a 5-star review if you love it, and share with your travel buddiesDon’t miss Jackie’s behind-the-scenes communications - hop on our email list at TravelingJackie.comMassive thanks to Osprey.com and ObozFootwear.com for sponsoring and supporting our show!Produced by NOVA Take a leap with Jackie IRL - join us in Greece and Norway in 2025 at JUMPadventures.comAdvertising Inquiries: https://redcircle.com/brands

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 NOVATake a leap with Jackie IRL - join us in Greece and Norway in 2025 at JUMPadventures.comAdvertising Inquiries: https://redcircle.com/brands

Dr. Chelsea Anderson never imagined that becoming a veterinarian would allow her to travel the world and work and live in places like Sri Lanka, Uganda, Papua New Guinea, Australia, and beyond. But early on in her career, she figured out how to combine her two passions of traveling and working with animals. Today she shares with us her stories from volunteering her veterinary services all across the globe. Tune in to this inspiring story to find out how she does it, where she’s been, and the things she’s learned abroad that she applies every day to her veterinary work at home. - If you’d like to reach out to Chelsea for travel veterinary purposes, you can find her at [email protected] Find and follow Chelsea’s vet adventures at @EatSpayLove - 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 NOVATake a leap with Jackie IRL - join us in Greece and Norway in 2025 at JUMPadventures.comAdvertising Inquiries: https://redcircle.com/brands

Join Jackie and Jason Moore from Zero to Travel Podcast today as they unpack a recent experience in Norway, including first impressions, cultural differences and adaptation in expat life, what makes up the “real" Norway, and a via ferrata on “the highest sea cliff in Europe” that catapulted Jackie straight out of her comfort zone. Takeaways- Only WE have the power to get ourselves through hard situations- Everybody needs a little help sometimes- Hold on to your curiosity - it has the power to take you FAR beyond what you thought you were capable of - Find and follow Jason at ZeroToTravel.com and @zerototravel - 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 Take a leap with Jackie IRL - join us in Greece and Norway in 2025 at JUMPadventures.comAdvertising Inquiries: https://redcircle.com/brands

Join Jackie for this solo episode on a balcony overlooking the sea in Albania as she recaps a week-long road trip full of adventures across Southern Albania. Alongside details that will help you plan a future trip to Albania, she shares her experiences and stories, which include delicious food, wild landscapes, the kindness of strangers, and how she and her friend got through a rather scary mishap on a steep mountain pass. Plus, she shares about what she believes is a currency stronger than money in this corner of the planet. Bring a snack or drink and pull up a chair, take notes for your own future adventure to this beautiful country!- If you liked this episode, let Jackie know! @travelingjackie- 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 Take a leap with Jackie IRL - join us in Greece and Norway in 2025 at JUMPadventures.comAdvertising Inquiries: https://redcircle.com/brands

Jackie sits down with the one and only Samantha Brown as she shares her journey from being an aspiring musical theater actress to becoming a star TV host on the Travel Channel and ultimately going on to create her own show, 'Places to Love,' on PBS. She discusses the importance of grit, persistence and resilience in achieving dreams, recounts a wild story about a pivotal audition experience, and emphasizes the impact of kindness and support from others. Samantha also reflects on her purpose in travel and authentic storytelling through her TV show, focusing on celebrating the stories of people and communities and highlighting the significance and power of connecting with individuals rather than just visiting iconic sites.Takeaways- Samantha's audition story illustrates the importance of seizing opportunities and going to great lengths to act on them.- Travel can be a tool for celebrating the stories of people and communities.- Samantha believes in the power of travelers to make a positive impact through their choices.- Authenticity is about being true to oneself, both on and off camera.- Traveling is not just about the destination, but the experiences and stories we gather along the way.- Travelers are moving away from superficial experiences.- Samantha's show focuses on uncovering places through their people.- Travel can be meaningful without going far from home.- Your own curiosity is enough to determine the path you take and the stories that await you.- Find and follow Samantha Brown at Samantha-Brown.com and @samanthabrowntravels - 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 Take a leap with Jackie IRL - join us in Greece and Norway in 2025 at JUMPadventures.comAdvertising Inquiries: https://redcircle.com/brands

Rachel Rudwall (aka RachelRoams) shares her story of growing up in the Midwest to becoming a successful travel TV producer and host and adventuring across the globe. Today we explore her journey, including the exact steps she took to create the career in media that would enable her to pursue her dream of exploring the world. In this conversation, Jackie and Rachel discuss navigating career choices, learning from mentors, embracing your authentic self, chasing what scares you, and aligning with your unique dreams and purpose. Rachel’s story is an inspiring example of doing the hard work and taking risks to break the glass ceiling, building the travel career of her dreams and living a wildly full life during this beautiful existence.Takeaways- Self-selection can limit potential; it's important to take risks.- Mentorship plays a crucial role in personal and professional growth.- Hard work and curiosity are essential for success in any field.- Investing in yourself is crucial for growth.- Only you can be the unique version of yourself.- Every detour teaches valuable lessons.- Asking questions opens doors to opportunities.- Aligning with your purpose leads to fulfillment.- Embrace what scares you as a path to growth. - Find and follow Rachel at RachelRoams.com and @rachelroams- 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.comBig thanks to Osprey.com and ObozFootwear.com for sponsoring and supporting our show!Produced by NOVA Take a leap with Jackie IRL - join us in Greece and Norway in 2025 at JUMPadventures.comAdvertising Inquiries: https://redcircle.com/brands

Chris and Sara bought a 1988 Land Cruiser Camper and set out just over a year ago with plans to drive it from the US all the way down to Argentina, with their dog Kramer in tow. Today they tell all as we find out what kinds of adventures and major misadventures they got into throughout Central America, and why they now have their sights set in an entirely new direction. Our conversation flows from traveling with a dog, to balancing home life and camper travel, to the chaos and beauty of life on the road, vehicle issues, interacting with locals, the importance of slow travel, and how travel affects us all individually and uniquely through different times of our lives. Chris and Sara are podcast hosts of What No One Tells You and YouTubers who share their travel experiences—the beautiful, the not so great, and even the near death—and how they get through the hard things and keep going with smiles on their faces.Pro tip: today’s episode pairs well with fish tacos- Find and follow Chris & Sara at ChrisandSara.com and @chrisandsara_- 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.comMassive thanks to Osprey.com and ObozFootwear.com for sponsoring and supporting our show!Produced by NOVA Take a leap with Jackie IRL - join us in Greece and Norway in 2025 at JUMPadventures.comAdvertising Inquiries: https://redcircle.com/brands