Landing Lightly: The End of the Road, For Now
From Santiago to South Carolina to Portland — the final stretch of a soul-led journey
#14
It was time to disembark.
This cruise has been good to us. We stayed healthy, rested, and I had the highlight day of the entire trip here. During one port with decent Wi-Fi, I booked us a hotel for four nights in Santiago, about an hour and a half from the port city of San Antonio where we got off the ship. Normally I’d have arranged our transfer in advance, but Tim assured me we could just figure it out when we got there. Unusual for me, and a good practice in letting go.
Sure enough, it was a little chaotic. We used up all our remaining cash but found a van headed into town with a few other travelers. They were coughing, the windows didn’t roll down… not ideal. But as the countryside rolled past, I reminded myself: Where do I want to put my energy? I chose the view out the window.
The hotel turned out to be a win! Reasonable price (thank you, exchange rate), a great breakfast, a pool, gym, and a peaceful outdoor courtyard. It was in a nice part of town with blue skies and warm weather to greet us. We were still in a smaller room, but I had no bandwidth left to hunt for an apartment. In hindsight, I stuck to my usual booking sites out of habit — and didn’t pause to look for other options.
We didn’t rent a car as Santiago is very walkable, and we spent the next few days exploring. Tim was road-weary and ready to head home. I, on the other hand, was still happy to be on the road. The grey, wet weather in the Pacific Northwest wasn’t exactly calling me back. We’ve done remarkably well as a couple, but by now, we both needed a little space.
I found Santiago to be quite charming. I had no expectations of being here as it was literally where the boat docked, but I found it to be clean, felt relatively safe and full of walkable neighborhoods. One sunny afternoon, we joined a vineyard tour just outside the city. Gorgeous views, delicious tasting, and a highlight moment of our stay.
From Santiago, we had flights booked through Dallas to return to the States. But we had a few wild-card connections to follow first. During this trip, we’d met a couple and a solo traveler who both lived in Greenville, South Carolina — one on a beach walk in Eleuthera, the other in the lobby of a hotel in Rio. Different people, different moments, same destination. Was Spirit nudging me? I wanted to find out.
Tim and I agreed it made more sense for him to return home from Dallas while I continued on solo. That decision brought up mixed emotions: We’ve been together every day for six months… and now we won’t be. But also: I need to be in my own energy. It felt both necessary and strange. Maybe you’ve felt that too — when the next right step is clear, but still carries some discomfort.
So I changed Tim’s flight back to Portland and continued on to Greenville alone.
Re-entry to the States was surreal. More adjustments, more pivots. But I loved the little airport and already was charmed. I rented a car, and the next morning connected with Jim — the kind and hilarious man we met in Rio — who picked me up and gave me a tour of the city. Greenville was everything I hoped it might be: charming, friendly, full of Southern hospitality, lush parks, and great food. Jim took me to a classic Southern lunch spot where I ate fried chicken, grits, greens, and biscuits. So. Darn. Good. We ended the day with a drink near the park, and I was so grateful for his warmth and welcome.
The next day, I drove 45 minutes to see the couple from Eleuthera. They lived on a beautiful lake and welcomed me with such generosity with a boat tour, local dinner, and a slow morning before I headed out on a three-hour drive to Charleston. It was a magical 48 hours made possible by people we met on the road and chose to stay connected with. That’s the power of travel — if you stay open, the world will surprise you with its kindness.
As a woman traveling solo again, I was mindful. I paid attention to energy and surroundings, and trusted my intuition completely. But I was in full alignment with this chapter and incredibly grateful for both connections.
I returned the car at the Charleston airport and Ubered into the city to avoid parking and more car rental fees. I splurged on a charming hotel in the heart of town knowing this might be a once-in-a-lifetime visit and let myself soak in every bit of it. I walked for miles, admired the stunning architecture, toured a historic mansion, and even did a boat ride around the harbor. On my final day, I treated myself to shrimp and grits with a biscuit at a local spot. Worth every bite.
Charleston was lovely. I’m so glad I went. But for me? A one-and-done kind of place. It didn’t hold the energy I was seeking. Greenville, though… that one got my attention. Still, after more thought, I realized it wasn’t quite right either. Too far from family. Too much to rebuild. It ticked many boxes, but it won’t be my next home base.
Before heading back to Portland, I used a standby pass (thanks to my brother, a United pilot) to visit him and my sister-in-law in Houston. They’d just finished some home renovations I wanted to see, and it filled me up to connect with them — and my niece! — even for a short overnight visit.
And then… home. Portland.
The amount of gratitude I have to have been able to experience this type of slow travel is immeasurable. One of my dearest friends Nina asked me recently if I had ever planned on doing something like this, and it was never really in my awareness that I could indeed do this type of experience until I met Tim. I was always under the concept of a vacation here and there, for a week or two at most, and I had never even gone on a three week vacation before this time. It was always limited due to kids and work. But as an empty nester and wanting to be in sunshine and warm, and now having a travel partner to do this with, my world has opened up in ways I never could have expected.
One of my favorite phrases is “highest and best,” because we are often limited in our minds around what we can co-create with life. But asking the question of Life, staying open to the answers, and then trusting the unfolding will allow all of us to truly live the highest and best version of ourselves full of joy, wonder, adventure and whatever else we want to experience. We only have a limited amount of time here on Earth, and while I have my health, I want to experience as much as I can.
And so, as the plane touches down in Portland, I rent a car for the first month as I figure out my life, the next steps, and I have a beautiful home to rent with furnishings from my beloved friend Nina while I do all of this. I’ll see Tim again soon, and we miss seeing each other and have enjoyed the space apart. We consciously choose the upward spiral and focus on that.
I’ll be sharing more around my biggest lessons and what this adventure taught me in future blogs, and also how I am preparing for the next travel adventure starting in Europe! But this time, I’ll be writing in real time.
Thank you, thank you for being a part of this journey with me. I have put all of this out there in hopes you have taken some gems with you to incorporate in your own world - whether it be inspiration for your own version of a travel adventure, but more importantly, growth for your soul and all you’re here to be.
There’s no time like now. Go live it.
To your highest and best,
Dianna
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