Day 1: From Siena to San Quirico d’Orcia

Map and Elevation Profile

Our day started relatively early for my standards, but late for every other pilgrim’s standards. We woke up at 7am and headed downstairs for breakfast, where we ate as much as we could to prepare for the long trip ahead. According to the guide we had to ride 55km before reaching the town of San Quirico d’Orcia, our first stop along the way back to Rome. Our hostel was outside of town though, so we actually had over 60km ahead of us!

Ready to go!

We make it back to Siena, and we tried reaching Piazza del Campo – the starting point of our adventure. Our plans were once again foiled by the Palio and it took us a little longer than expected to actually cross the city and leave through its southern gates, what with having to let horses pass ahead of us and everything. We finally left the city at around 9am, and our adventure officially began.

Just outside of the city we stopped to take a few pictures of the breathtaking landscape, and we met the first of many friends we’d have the pleasure to interact with during our trip. We didn’t quite catch his name, but he was an Australian man who moved in the area over 30 years before with his late wife. He was kind enough to take this picture of us:



After saying our goodbyes, and after shaking our hands on knowing we were headed all the way to Rome, we parted ways with him and went on our way.

Our first planned stop was in Monteroni d’Arbia, a little town less than 20km outside of Siena. We were in good spirits, and despite it being Ferragosto (an Italian holiday) we managed to find two little bars for our second breakfast. After a short break we set off again, with another planned break in the city of Buonconvento. This is where things started to get a little challenging.

We went through some stretches of gravel road, that followed the curve of the Tuscan hills. There was a lot of climbing and descending, and most of the time we had to get off our bikes and push to avoid losing traction on the treacherous terrain. We made it to Buonconvento without incident though, where we had an excellent lunch and a little rest. We were in great spirits, and eager to get back on the road again.


Lunch in Buonconvento

Soon after leaving Buonconvento I realized how deceiving distances can be. I’m a fairly strong rider, and I was expecting to cover the distance between Siena and San Quirico in less than 5 hours, breaks included. I was so wrong! The road after Buonconvento became even harder, with more hills and more gravel. Luckily the landscape was indescribably beautiful, so taking it slow isn’t too much of a chore when you’re surrounded by such amazing views.

We were running out of water though, so things started becoming a little heavy after a while. It took us a long time to reach Torrenieri, a small city with an amazing history just a handful of km away from San Quirico d’Orcia. We stopped at a little fountain where a local hung up stone slabs with stories from the place, and a nearby sign informed us of the story of the city: there used to be a fort nearby, and once it was attacked and destroyed the locals moved back in the area and founded what then became Torrenieri.

We were so glad to find a fountain that we stopped there for a few minutes, knowing that our destination was really close. After a short rest we set off again, and attacked the steep hill that separated us from San Quirico d’Orcia. And this is when the unthinkable happened.
As we were trudging up the hill, I reach down to grab one of my water bottle but my hand only seizes empty air – I look down, and realize in horror that my water bottles were missing. So we stopped, I quickly unloaded the bike and left Anna (who promptly fell in a ditch) and our begs by the side of the road, and flew down the hill to retrieve my bottles. I was lucky enough to find them there, and then I was free to start climbing the hill for the second time.

Hey water bottles, I’ve missed you!

After a gruelling climb we finally reach the entrance of San Quirico d’Orcia, a good 8 and a half hours after leaving Siena. We make it to the convent where we were supposed to stay for the night, but once we get there a lady tells us that the place is fully booked and that we were being relocated elsewhere. A nice nun from the Philippines joined us to bring us to this other place, where we find out that our beds had been given away! There was some misunderstanding with the bookings apparently, but we still managed to sleep on a bed that night while some other people had to sleep on the floor. They didn’t mind it too much though, it seemed. So there was a happy resolution for all.

Entering San Quirico

That day we met a nice couple from Brescia, another cyclist from Milan, and a young guy who shared the room with us. This was my first taste of the pilgrim life, and I instantly became hooked. I loved being able to share stories from the road, rumors heard by other pilgrims, or tips about the city we were in or the ones we were to visit. The road brought us all together in a way I could have never imagined.

After a quick shower we went on to explore the town. We visited its rose garden with its creepy statues, we walked around the walls, and we just enjoyed the simple fact of having completed the first leg of our trip.

Creepy much?

San Quirico square

We had dinner in the lovely piazza of the city that turned out to be quite pricey. We didn’t particularly mind, as we brought all of our leftovers with us (along with some bread we took from the little basket). We were absolutely spent, so we turned in quite early. After chatting some more with our new friends from Brescia, specifically about the route we had to tackle the following day (it was the same distance for walkers and for cyclists – which is strange, considering we cover twice as much distance in a day as the walkers) we headed to our room. I was hoping to fall asleep soon, but a band was playing in the city’s piazza and we could hear everything! I think they stopped playing some time after midnight, and that is when I finally fell asleep. I envied Anna a little, because judging from her vigorous snoring I gathered that she had been asleep for quite some time.

I have learned two important lessons on our first day of the trip. The first one being that on a bike tour, when gravel is involved, it is quite hard to judge how long it will take to get from point A to point B. It wasn’t a race though, and we always left early in the morning, so that was never much of a problem. The second lesson, maybe the most important of the two, is NEVER say no to sunscreen. Ever. The skin on my shoulder is still all flaky, since I was so arrogant to believe my complexion was dark enough to protect me from the sun. But the sun is relentless, kids! I had a hard time sleeping the first day because my shoulders were so burnt!