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JUMP with Traveling Jackie

Join me behind the scenes for podcast news, group adventure opportunities, and personal journey updates.

Featured Post

And the WINNER of Best Travel Podcast is... 🏆🥹!!!

Hello from Austin! I'm here for the iHeartPodcast Awards, which they call "the Oscars of podcasting" because (in case you missed the memo a few weeks ago) we were nominated for BEST TRAVEL PODCAST (🤯). You know, it honestly hadn't even occurred to me to attend this event until some of YOU started asking me if I was going to go. To say that I am SO grateful I decided to show up is an understatement, because... WE. WON. iHeartPodcast Awards Best Travel Podcast: JUMP with Traveling Jackie The...

Greece Bike Boat Tour 2025

"I can do hard things. If I just put myself out there, I can do hard things. Being in a group dynamic, going on a guided tour, which is not usually how I travel, and doing this bike adventure... makes me want to go do this again. I just want to go do this again, because I can. I believe in myself so much more than I did... I can do things that I didn't believe I could." - C.K. THAT right there is what we are ALL about around here. That is a real life quote from a real life person just like...

Jackie Osprey Oboz

Hello from Montana, where the sun is FINALLY starting to shine again, snow is melting, and I'm counting down the days until my trails are dry once more. (Wishful thinking, winter doesn't end in Montana until June...) In the meantime, I have some fun news for you! In case you missed it, last week we opened our Peru trip for booking. We still have space, AND (as if we didn't already have you at Peru)... we have BONUS GEAR for all participants! Check this out: For ALL JUMP Peru 2025...

Peru Trip 2025

Story time: Once upon a November 5, 2011 at sunrise, I was the very first person to enter Machu Picchu through the visitor gates. Once through, I didn't even wait for my travel buddies. I ran down the path until I could see the ruins before me and was met with silence, a misty morning fog, and a wild thrill of being alone in the Lost City of the Incas. I may have happy-hollered and took a bad, sweaty selfie. I turned and went up a short trail that brought me to an overlook, where my people...

I have some happy news today - especially if YOU have ever listened to my podcast JUMP with Traveling Jackie: We’ve been nominated for Best Travel Podcast at the iHeartPodcast Awards 2025!! This nomination is a HUGE honor, as there are only five travel podcasts in the running, and we’re in some pretty esteemed company. Not to mention that it’s iHeartRadio and will be announced live at SXSW in Austin, TX! I’m grateful to YOU for sticking with me and listening to my voice for nearly 11 years...

Hi, This email is personal. It’s not about the trips we have coming up. It’s not about the latest episode of the podcast. It is simply a message from me to you, and an invitation. Most of last year was a b*tch. Despite making some well-intended changes to my life and business, I had a really tough year. This year I'm on a new track (largely thanks to taking a sabbatical last summer). Whether you know me in person or through the podcast or IG, or even if you don't know me very well, I invite...

Happy New Year! It's going to be a good one, because we're heading to three NEW countries in 2025 🤩 But before we spill the beans on our next new destination, let's take a moment to celebrate our sweet 2024 adventures. Together, we: Went to 4 countries on 4 continents, including Mexico, Switzerland, Chile, and New Zealand (3 of those were new to JUMP!) Hiked, biked, kayaked, snorkeled with sea lions, paddle boarded, danced, sang, hot tubbed, star gazed, bird watched, whale watched, trekked...