Chuck's News: Day Ten - Friday, October 30, 2026 Gambassi to San Gimignano

Weather-sunny & a little cooler with clouds blocking the sun all afternoon, High 63, Low 49, On Route 8.75 miles, Total Distance 10.64 miles, 26,059 steps

The first in a Series of Unfortunate Decisions

Gambassi really sits high on a hill. If yesterday was a 2.38 mile continuous climb to get to town, this morning was 2.38 miles of continuous descent to leave it behind. And so, that is how the day began. Cup of tea in the piazza with a pastry, then down the hill for an hour until we bottomed out. Then up and down all day, more than yesterday. Yesterday, all the climbing was saved until the final assault on the town. Today’s is spread out over the whole distance.

Leaving town we could see our destination in the distance, San Gimignano. (we pronounce it “San gym-ing-Nah-No”) It has a very distinct skyline, still sporting 14 stone towers emerging high above the town’s surrounding walls. It is reminiscent of pins sticking out of a pin cushion from our 8 mile distance.

If I describe the scenery as more of the same from yesterday it might sound like we were tiring of it or taking it for granted. No such thing is possible in the midst of this grandeur. We passed each vineyard, olive grove, winery and green field with appreciation and amazement. What a honor and joy to be able to walk through this beautiful land.

For most of the morning San Gimignano remained hidden by hills. But, every once in a while we would come upon a tract of high ground and find it looming in the distance.

At one low point we came upon an ancient church that happened to be right where they wanted to build the highway. They tunneled under the church rather than try to build around it on this steep hillside. The church boasts two features, a sculpture and painting of the Virgin Mary breast feeding baby Jesus and a life size nativity scene under the church in a grotto. We used its outside short walls to eat lunch upon, then visited its sights. While eating, Helen with her cart caught up with us, as did Ken with a group of men pilgrims.

With chatted with them a few minutes, then went down to see the nativity while they departed.

The route climbed up a fair amount after the church and then traversed a hillside for more than a mile, San Gimignano visible in the distance. With its position on the horizon and its towers rising above the walls it reminded Sally and I of the Emerald City from the Wizard of Oz. If only the road we were walking on was yellow . . . Still we sang the song as we strolled along . . . Even tried skipping for a while.

The final approach to the city was up a busy road with sidewalks. We took note of a laundromat and a grocery store on our way up the hill. We had met Ken at the bottom at the roundabout and had been walking with him as we approached town. We crossed through the wall at the north portal and strolled up the trinket shop lined main street to the duomo’s piazza. We took a seat at an outdoor cafe with Ken, had a Coke and waited for our room to become available at Monastero di San Girolamo, the monastery in town. At a little after three we began navigating to it and found it was a bit of a walk out of the way, still inside the walls of the city, but out on the very edge. We rang the video buzzer and a voice answered about a minute later “stop light”. We looked down the street and saw a stop light and walked to it. There were a couple of doors down there. We tried them all but they were locked. About two minutes later a severe looking woman in religious clothing in her 70’s opened the door and admitted us. Ken registered first, paid his €25 and left with his room key to find his room. We had requested two nights over the phone yesterday. Today she told us the first night would be at pilgrim rate, the second night at tourist rate. The total came to €146. Sally and I were staggered. Why so much. Should have been about €100. It appears the tourist rate is €45 a night per person plus €6 city tax. We looked at each other. That seemed like a lot for a room in a monastery. But, we didn’t have any options up our sleeve so we agreed and handed over €146 in cash. She quite sternly told us that if we visit Italy we should learn Italian before coming. If she went to America, she would have learned English before she came. This in mostly Italian with a few English words mixed in and with a scowling countenance.

She led us up the elevator to our room. It was pretty big with a bathroom. There were plenty of blankets and towels, but as she told us “no heat”. She then asked our religion. When we said nada the scowl deepened on her round severe face and she exited the room.

We surveyed our new territory. No soap. No hair dryer. No heat. No Wifi. Beds looked okay. Both of had a bad feeling about two nights here. But, first we needed to do something about dinner and we had a meeting with Heidi of Lift Up Toledo to electronically check into. We wandered back up to town and found a casual restaurant that served pizza and had good WiFi. We got our food and found a table out of the way and then called Heidi. We spent maybe 15 minutes on the phone ironing out the particulars of a donation while poor Heidi watched us down pizza. Meeting and dinner done we headed back up to the Duomo piazza to check it out after dark. We didn’t find it remarkable. Back at our room we checked AirB&B, Expedia and booking.com for available rooms in town for tomorrow night. While doing so we heard a knock on our door. One of the sisters was delivering an electric plug in heater. We thanked her, plugged it in and enjoyed the heat from it as we crawled into bed. The room was never cold, but it wasn’t warm either. The heater made a small difference. We each snuggled under blankets in our separate twin beds and called it a night.

With no Wifi we were left with slow or nonexistent cellular communication and little ability to plot the course of our days ahead. No cooking facilities left us at the mercy of expensive tourist restaurants. No heat left us in jackets and fleece. Taking a shower to clean up meant a chilly drying off period with wet hair. Staying here two nights, especially the second at €90 was a bad decision brought on by inadequate research on both our parts. Learn from the experience and move forward.