My 21-Day Solo Road Trip

I'm writing this from the driver's seat of Gypsy Rose, my trusty travel companion, as I’m embarking on what might be the most ambitious solo adventure I've ever planned. For 21 days, I'll be weaving through Montana, Oregon, Washington, and Canada, chasing sunsets, mountain vistas, and that unmistakable feeling of freedom that only comes from hitting the road for my 60th birthday gift to myself.

But here's the thing – I don't want to do this journey alone. Not entirely.

I'm inviting you to join me virtually on this grand adventure! Every single day, I'll be sharing my experiences, discoveries, and yes, probably a few mishaps through Instagram Stories. Think of it as your front-row seat to a real-time travel documentary, complete with behind-the-scenes moments, spontaneous detours, and those magical encounters that only happen when you're brave enough to venture out solo.

Feel free to slide into my DMs with questions, suggestions for hidden gems along my route, or simply to cheer me on when the road gets challenging. There's something beautiful about carrying a community of adventurous spirits with you, even when you're miles from home

Here’s my general route…

I'm kicking off the adventure in Sunriver, just outside Bend, Oregon, where I’m celebrating the 4th of July weekend with my family. It's particularly special because my parents met on the 4th of July 62 years ago, and my sister and her husband chose July 6th for their wedding. July is truly our family's month of love, and what better way to start an adventure than surrounded by the people who shaped your heart?

From Oregon, Gypsy Rose and I will make our way north through Washington to Crescent Beach in Surrey, British Columbia – a place that holds the promise of ocean breezes and new perspectives. Then we'll head east to Kamloops before reaching the crown jewels of this trip: Jasper and Banff National Parks.

I'll admit, I'm typically the type to avoid tourist traps, but I've made an exception for the Hop-On Bus in Banff. Sometimes the most efficient way to see everything is to surrender to the process, take in all the key sites in one day, and then follow your instincts about which places deserve deeper exploration the next day.

I’ll drop back down into Montana, through the Flathead Valley, with a stop at Swan Lake before returning home to Bozeman. I’m excited that the whole route will take me from ocean horizons to mountain peaks and prairie skies.

While I've secured some campsite reservations, I'm intentionally keeping my itinerary flexible. I’m a big believer that some of the best adventures happen when you're willing to change course, to follow that dirt road that caught your eye, or to stay an extra day in a place that unexpectedly captures your heart.

I'll be camping under the stars when I'm not staying with friends, and I'm honestly excited to test both myself and Gypsy Rose. I prepped a lot before leaving, having my van’s engine checked and serviced, and then getting intimately familiar with its water system. I cleaned out the 35 gallon tank and the lines to the sink with a bleach solution and then ran fresh water through it a couple times to flush it all out before filling the tank with filtered water for the trip. I now have a system for refilling with filtered water while on the road that makes sense to me. I also got my compostable toilet ready, which isn’t my favorite task, but makes mornings on the road easier and safer for me, especially when I’m on my own in unfamiliar territory. I definitely feel more confident than ever in my van!

For my Dare Guides members, I've included my complete 21-day itinerary with all the details you need to recreate this journey yourself. When I return, I'll be hosting a live Zoom Coffee Chat where we can dive deeper into the stories, the surprises, and the insights that only come from saying yes to the unknown. I'll also be sharing my curated collection of road trip essentials – those tried-and-true items that make van life smoother, cozier, and infinitely more fun.

The road ahead is uncertain, and that's exactly what makes it beautiful. Every month brings new destinations, new possibilities, and new invitations to dare greatly.