How A Two-Week Solo Trip Sparked A Lifelong Mission To Help Women Heal

What if your next trip wasn’t about seeing more, but about feeling better? We open the year with a clear pivot: moving beyond packing lists and must-see cities toward purposeful, healing-centered travel. Cheryl shares how a lifetime of journeys—from a childhood RV trek to a two-week solo reset after divorce—shaped a coaching approach that helps women 50+ navigate grief, trauma, and reinvention with travel as a supportive tool.

You’ll hear the story of Jamaica after her mother’s passing and why unexpected moments can spark hope when words fall short. We also unpack a candid Camino de Santiago experience on the Portuguese route: the training, the high expectations, the loneliness, and the physical strain that refused to fit a neat healing arc. The lesson is honest and freeing—travel rarely transforms on command, but it does create space for patience, perspective, and small, steady shifts that last.

If you’ve felt overwhelmed by life and underwhelmed by your options, this conversation offers practical guidance for designing why-cations with intention. Think slower itineraries, nature-forward routes, reflection rituals, and gentle support that pairs well with therapy. We talk about building confidence on the road, learning to be still, and choosing trips that restore rather than deplete. Ready to start a season of renewal? Book a discovery call at Cherylbeckesh.com, subscribe for future episodes, and share this with a friend who needs a hopeful nudge toward her next chapter.

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Chapters

• 0:00 New Year And Podcast Pivot
• 0:33 Why-Cations And Purposeful Travel
• 1:50 Early Travel Roots And Perspective Shifts
• 2:37 Divorce, Solo Trips, And Restoration
• 4:28 Jamaica After Loss And Renewed Hope
• 5:15 Coaching Women Through Grief With Travel
• 6:26 Walking The Camino For A New Start
• 7:47 When Travel Doesn’t Go As Planned
• 9:10 Patience, Healing, And Making Space
• 11:12 Learning To Be Still On The Road
• 12:08 Invitation To Begin Your Healing Journey

Transcript

SPEAKER_00: 0:00

Happy New Year, everybody. Well, welcome back to Solo Travel Adventures. I'm Cheryl Esh, your travel coach and solo travel advocate. I'm so happy you're here and ready for a fresh start as I am, I'm sure. Well, if you've been following me for a while, you'll probably notice there's been a slight shift in my focus of my podcast. And I wanted to share a bit of my story today, but also give you a little hint as to the new direction the podcast may be going as you start to listen more and more. Now, I will still offer you tips and tricks and packing stuff and different highlighted places, places like cities and countries that you should probably try to get to. Absolutely, because I love doing that. And that's the whole thing I love about travel, as I'm sure you do. And I want to provide these resources for you, but I also have focused more on the aspect of healing and travel. I have a travel coaching program called Healing Through Travel specifically for women 50 and above, Christian women, that I guide through and help get through some hard times, such as grieving or uh traumas, and provide transformation. And this could happen for anybody. So it's not just a vacation, although it can be, but there is more to travel than just that. And data even says that this year, 2026, will be the year of what they call why cation. What does that mean? Well, there's gonna be more of a purpose or a why behind your travel. So it's not just let's go and see something, check something off a bucket list. It's gonna be more meaningful than that. And I think that's where my story comes in today. And I've had the travel bug for a long time, and actually since probably about age nine, our family went on a five-week RV trip across the US, and I think that is where that seed was planted. And I do love the national parks, I think, because of this, but I also love being outdoors as well. At age 23, I also went on a five-week backpacking trip to Europe. Now, this was my first international trip, and that was so life-changing, and it changed my whole perspective on travel in general. And it transformed how I saw travel. But later in life, my travel became more focused on solo and finding those times alone, especially after my divorce. And I realized how restorative it was for me personally. And I know there are other women out there, like yourself, maybe, that are hurting or going through a hard time grieving, or especially if you had a trauma happen, and I've grieved a lot in my life, so I certainly can help guide women through that process. And I feel travel can be a vehicle to help with that. And that's why I've developed a travel coaching program. And my program is called Healing Through Travel that I offer. But my story has many layers as to how travel has helped heal me in the process of going through some very trying times, some grieving times, some traumas as well. And sometimes these trips were intentionally planned for times of healing or restoration. And sometimes it sort of showed up spontaneously, and I was not anticipating that happening. For example, a trip to Jamaica almost immediately after my mother passed away showed me that it is possible, even without knowing it, that time in Jamaica, which you can I recount the whole thing in episode 147. I encourage you to go back and listen to that of how I found myself really at the depths of my sorrow, but how that trip really gave me a sense of hope for my future. And there have been other trips that I have made that have also provided some restoration to me. And the most infamous one that I've I know I've shared before, and I think this was the catalyst to really show me that there is potential in helping other women going through issues of trauma, grief, or loss, that this travel can really be that extra tool or resource. And I'm not saying it's the only thing you should do, but it can be coupled with some other things such as therapy. And it was, I don't know, just so liberating. There was such a sense of freedom um having coming out from under a marriage that was not great. I didn't feel I could be myself or or bloom in that relationship, and so I felt very stifled. So having that opportunity to adventure out and take this two-week trip on my own, which I had done a little bit of solo travel prior to that, but this was a whole other level because it was longer, I think, than I've ever done a solo trip by myself up until that point. I've done longer solo trips since, and it was just a way for me to recapture and rediscover the things that I love, things that make me me. And I came back from that trip more confident because I was starting to understand who I was again, and that trip really set the groundwork for what I do now in my healing through travel program. And I did another trip just to recap another opportunity where I took a solo trip, and this was actually I walked the Camino. This was intentionally supposed to, you know, help me heal from a uh trauma that happened about the year before. Yes, so it happened about the year before, and I was really hoping that that time away walking the Camino would provide me with sort of a new start. I wanted it to signify a new start and this journey of this pilgrimage. I would did the Portugal route. I started on the coast and then went up through the central part of Portugal and ended up in Santiago, Spain, and at the cathedral. And there's a couple episodes that I did from 2024 actually, and they highlight sort of what I learned on the Camino, but I'll give you a little snippet here. There's more details in those. Uh there were two episodes that I did um after I came back, and I think there was one before. But it didn't turn out as I had planned. And so big learning experience for me was that travel never turns out as you plan. I I kind of knew that, but I think because I had set such a hard intention, like I really was putting such high expectations on this trip that it would transform me and you know, take away the the pain of the trauma that I had and in 2023, and you know, wipe my slate clean and make everything seem like I was starting afresh and new, but it did not feel that way. There were definitely some challenges along the way on the Camino walking. I did it solo, and so that was there were times when I was alone, but also times when I felt lonely. And there was some physical challenges as well on that trip that I had not anticipated since I thought I was in good shape, and I had really worked on walking with a heavy pack um prior to doing the Camino. But what I did learn and what uh I think what just uh being patient in that healing process was really kind of what it showed me, and that it wasn't just gonna be like this magic eight ball and just go away, and that it was healing in itself is a process. And so I want to encourage you, if maybe that's where you are today, and you're thinking travel's gonna cure it all, it's not a quick fix pill, but it certainly gives you skills and a mindset that can change your perspective and attitude on the situation that you're facing. It may also provide actual physical restoration that maybe you need or mental reprieve that you need. It can give you the space to grieve, which I know is often really hard in our busy lives and in our work life, family life situation, to carve away some time to actually just let it go and and cry it out. And we often have to, as women, hold it together. We have to keep our family together, we have to look like we're put together, and so getting away on a solo trip, even just to do that, you get away and you just spend some days crying and journaling and restoring your physical and mental body with some peace and quiet, then that is all worth it. And so, yes, there's intentional planning that is good to have, and that is sort of what I guide my clients through, and I can guide you through. If that is something you are looking to move forward with in your life, I like to say, because as I mentioned, it is definitely a tool or a resource, but it's not that magic pill, and but it's definitely it could show you so much about yourself, your situation, and give you that space to process grieve and just be, just be. That's such a hard thing for us to do, to just sit and be. I mean, I struggled with that, just an example. I was somewhere and they had a pool, I was dog sitting, and I had decided that I would just go out and lay in the pool, like on the raft, and just relax, and even just spend some time outside without my phone. And you know, those first 10 minutes were, I'll be honest, agonizing. And then it sunk in. Okay, I can relax. But then you get I have such a mindset, we all do that. We have to be doing, doing, doing that just to be, just to relax and just be and not worry about what's coming next or what we have to do, what's on our to-do list, is so hard. And solo travel can even provide that if that's simply all you need. And I want this year for you, especially if that's you and you are struggling to get past a certain thing, and you really want to travel, but you have some hesitations, or maybe you're overwhelmed with the whole process. That is what I help you do in the coaching program. And so I would love for you to book a discovery call and see if you are a good match for to do the program. And if so, I would love to get you started and get you on a healing journey through your next travels. You can find me at Cherylbeckesh.com. And I'll also put a link below where you could actually, for my calendarly, you could actually schedule that discovery call for yourself and get that started. Don't waste time. Let's make 2026 a year of healing, a year of these great expectations being fulfilled, a year of transformation for you, so that you can go on and enjoy life, enjoy your travels, and feel more of a of a full person, a real person. We're all real people, but I mean, like just feeling more like yourself and having that experience. I want to guide you through that. So I hope you will book that call.