A Happy Siena Ending

I’ve started and stopped writing this post twice already. This will likely be the third time because I probably won’t have time to finish before I get back on my bike in 45 minutes or so. As I sit here in my cozy room, with a view out to a small piazza in the hilltown of Pienza, it’s raining. I just finished the breakfast provided to me by the host of the B&B – me along with an older Italian couple who didn’t speak English – and now I’m checking the radar. It looks like, best case scenario, the rain may stop by 9:30 and I could have a mostly sunny window of good weather until about 1:00. If that holds, that might be just enough time to reach Siena before the thunderstorms that are forecast for this afternoon set in. Crossing my fingers.

This latest post has been difficult to write because when I write I like to capture the mood of the moment. How I’m feeling. How things are going. My reflections on the trip so far. But the problem is, one day I’ll sit down to write and my mood will be up. Positive. Optimistic. Joyful. Then the next day when I sit down to review what I’ve written and add to it, I’m feeling uncertain and low. Such has been the case with my bike ride through Italy.

I talked to a friend recently about my writing, and we talked about how it’s important for me, when I write, to be honest and truthful. That’s the reason I write. If I’m not going to be honest, then I question the point. But, at the same time, when I’m on a vacation, and doing something like this, something I’ve talked about and promoted with others for some time now, I feel this sort of strange pressure to frame my trip as a wholly positive thing, to write only about all the amazing times I’m having, all the beautiful memories I’m creating, all the wonderful people I’m meeting. I feel a reluctance to write about the challenges, especially those of the mental or emotional variety.

You might be laughing right now because, it might seem from your perspective, I do often write about the challenges I’m facing in life. Haha. Yes, that is the case. Sometimes I am like an open book. But, it’s still hard for me. And, during experiences like this, I somehow just want you, and everyone, to think I’m having this amazing, incredible, life-changing experience. I don’t want to focus on the bad. Not during times like this. I want to paint a picture of beauty and wonder and joy. Maybe I want to do this for my readers. Maybe, in some way, I want to do this for myself.

It’s especially hard to write when I’m having such a mix of experiences. Like I mentioned, some days when I sit down to write I’m in seventh heaven, reflecting on the awesome time I’ve had that day. But other days I’m feeling depressed and frustrated and wishing the trip was soon ending. The feelings, my mood, have been quite inconsistent on this trip.

This trip has been quite incredible, I must say. It’s not exactly what I thought it would be, and it’s not been that nonstop, fluid joy-ride I suppose I was hoping for. But it’s been incredible, nonetheless. The expression, “You can’t see the forest for the trees,” comes to mind. I have no doubt in a month or a year or in 10, I’ll look back at this trip as a very consequential and wonderful experience in my life. And I’ll be extremely proud of myself for doing it. I already find myself doing that for the first week or two of the trip, even though I know at the time I was hating certain parts of those first days. But, there have been moments, lots of them to be honest, in which my depression has kicked in, or I’ve wished I was home, or I’ve been lonely, or I’ve felt like I’ve failed for some silly reason. Pushing my bike up endless hills and losing confidence as a cyclist. Feeling depressed on a rest day, in a beautiful setting and asking myself, “What can’t you just be happy?!” The anxiety of continually having to modify plans, change routes, book hotels, schedule train connections, figure out where to get food. Blah, blah, blah. It’s been a lot, and I’ve been doing it all alone, of course. I can’t tell you how many times I’ve wished I had someone here with me, someone to bounce ideas off of, someone to share the load of the decision making and route planning. It’s often been hard to make all those arrangements, and all those decisions, completely by myself.

Okay, here’s the moment of my third writing pause. The rain is letting up so it’s time for me to set off. I’m heading to Siena where, hopefully, I’ll pick this back up again. 

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Siena came and went, and no, I did not pick up my writing from there. I’m actually in Bologna as I write this, at a train station cafe, waiting for a connecting train to take me to the Austrian border later this afternoon. It’s Friday, and it’s the first day of my journey home.

Yes, home. Siena was always meant to be a milestone in my journey. A place to celebrate how far I’d come and a place to rest and take time to figure out what would come next. It wasn’t meant to be an ending, but that’s what it became.

My ride into Siena on Tuesday was about as joyful as any ride I’d experienced on this trip. Much of it was downhill out of Pienza, and there were long stretches of twists and turns when all I had to do was keep my hands on the brakes and my eyes on the incredible scenes of Tuscany passing by all around me. It was good roads, little traffic, only medium (and manageable) climbs, and one last stop at a quintessential Italian neighborhood bar for an espresso and some time to charge my phone. It was the kind of ride I’d dreamed about when planning this trip.

Arriving into Siena was even more joyful than the ride getting there. As I approached the city center I kept looking for a glimpse of the mammoth Torre del Mangia tower that looks down on the city. When I finally spotted it, then used it to guide me into Piazza del Campo, I felt a jubilation as strong as any I’ve experienced during my ride. I captured a bunch of photos, including some taken by a kind, Romanian young man, of me with arms extended in a victory pose, the city hall tower in the background.

Siena was a place I’d been before. In 1998, with Tricia, her mom, Donna, my brother, Nathan, and my dad, Bill. We were a ragtag bunch of misfits, traveling together through Europe. And Siena, for Tricia and me, became a highlight of the three-week trip. So much so that we gave our daughter, Sammie, the middle name, Siena. So, being back in this special place, after a great day of cycling, felt perfect. And memorable. And a real highlight of my trip so far. I grabbed  table at a pizzeria in the piazza, asked for a beer, told the young waiter I’d want a second in short order, then in a few minutes was absolutely in heaven, with a big pie, a second cold beer, and nothing but time and peace to enjoy where I was.

Such was the context by which I made my decision the following day. I had thoughts of taking a train back to the Adriatic coast, or across the mountains to Bologna, and continuing to ride four to six more days to Venice. I actually spent hours that day planning it all out. My route options, hotel possibilities, train connections. Everything. But in the midst of it all, an overwhelming, immediately satisfying, thought popped into my head. “Maybe I should end my trip here. In Siena.”

It felt right. Afterall, my ride into Siena had been one of the best of the trip. Getting there had felt like a milestone. And I was so exhausted. Physically and mentally.

At the same time, I was extremely happy. I had achieved so much. I’d had so many challenges, and so many spectacular moments. What did I have left to prove? Nothing, really. And I’d dodged any real danger, or injury, or bike breakdowns. I could end on a high note. End in this perfect place, with this perfect feeling, and be completely satisfied and happy with everything my trip had been. This felt like a good ending. A happy, Siena, ending.

I let these feelings sit for the remainder of the day, and I slept on them. For a passing, groggy moment as I was waking up the next morning, I had thoughts of pushing on. But those thoughts didn’t last. By 8:00 a.m. I was booking trains and a flight to take me back to Minnesota. It all, still, felt right. I was completely at peace with the decision.

That meant yesterday could be a care-free one. My last in Siena. I had a nice hotel breakfast, being invited to join a couple of American flight attendants from Washington state at their table. We exchanged stories of our experiences in Tuscany. I later napped, watched some tennis from Rome on my computer, organized my stuff, and did an afternoon Rick Steves audio walking tour of the city. More pizza and more gelato were consumed. I also breathed a sigh of relief and felt a huge smile overcome me every time I walked past a cyclist in the city, especially those loaded down with pannier bags and gear like the kind I’d been loaded down with these past four weeks. I didn’t envy them. I felt happy my cycling tour was complete.

Last night was magical. I think it was the relief of having made a decision, the feeling of being content with the success of my ride, and the wonder of nighttime in Siena. I grabbed a great meal of pici pasta and veal with a half liter of red wine while watching the new American Pope give his first address to the public from the Vatican on the restaurant TV. An after-dinner espresso with sugar – which I’ve grown quite fond of by the way – gave way to my exit and some completely random city strolling. I went to neighborhoods I’d never been to before, then ended with one last gelato and time to gaze across the gorgeous, lit-up Il Campo piazza. I didn’t want the moment to end, but of course it had to. I said my goodbyes, wandered back to the hotel, crashed immediately, got up very early, and now, here I am.

My decision to end things in Siena means I didn’t reach the “30 Days” I’d set as a goal for myself. But that fact had very little bearing on my decision. Almost none at all. My ride, and route, shifted quite early on this trip, so the original thought of this as an adventure to get from Point A to Point B became irrelevant. And when it did, the ride became much more about the journey than about a quest to a destination. I came close to 30 days, close enough that cycling a few more days to reach that milestone seemed silly as a reason unto itself. There were just far too many better reasons to call Siena the end.

I’ll continue to post the remainder of the “30 Days, 30 Stories” stories. There are some really good ones yet to come! It’s been such a pleasure sharing these stories, and it was such an honor to have so many friends step up and contribute. This trip was never just about the cycling. It was about my own personal journey, raising money for mental health, and sharing all these wonderful stories with all of you. I hope you’ve enjoyed the experience of reading them as much as I have.

Back to how I began this post… I wrote that sitting down now is the third or fourth time I’ve sat down to write this post. I have a lot more to share. A lot more I’ve already written, about the specific experiences I’ve had over the last 10 days or so. I think I’ll share some of that in a future post because I made a ton of wonderful memories during those days. But for now, this is it.

It’s been a blast. A crazy, sometimes stressful, often physically punishing, wonderful, blast. I can’t wait for some time to pass and for me to be able to take the chance to reflect back on everything that transpired. The miles, the pizzas, the coffees, the climbs, the Peronis, the people. So many highpoints. So many hilltowns! My train will take me today to Brenero and a part of the country much more culturally similar to Austria than to Italy. Tomorrow is a short train to Munich where I’ll return to where this all got started. It’s been a wild ride.