Day Twelve - Sunday, November 1, 2026 San Gimignano to Colle Di Val d’Elsa

Weather-sunny & cold (7°F below normal) with clouds covering 90% of the sky and strong winds - High 55, Low 41, On Route 9.14 miles, Total Distance 11.89 miles, 28,812 steps

Cold, Blustery and Busy Day

It was hard to leave our cozy nest of an apartment this morning. The heat came on during the night, keeping it nice and warm as we showered, dressed, scrambled eggs and packed up to go. Yet, we arose at 6:30 and were out the door at 8:00 on the nose. 

     What a contrast to yesterday afternoon. The crowds of tourists were nowhere to be seen. In Gambassi at 8:00 the piazza was full of locals grabbing a breakfast at the cafe and visiting in the square. Here a few tourist cafes were open to feed the locals as they came to work, but there was no clusters of people chatting. 

    We walked the main street to the southern portal and exited this amazing city, the buildings perfectly preserved, spotlessly clean overlooked by its columns of stone towers. 

     Right away we had two ladies from France pass us. Within a mile a group of twenty, each with a dog passed us. As the morning progressed and the miles passed under our feet we had people catch and pass us, perhaps 40 in all? Two German women, a couple from the Czech Republic, a man from London, three groups of Italian men, and others we didn’t get a chance to talk with. We saw more pilgrims today than we have seen in all the other days combined. Most were finishing their walk in Siena. We suspect it is the weekend that is the cause of the crowds. People out for a three or four day hike between towns. 

    Our route was downhill the first 2.5 miles as we left San Gimignano perched on its hill. We started on busy city streets and then ducked onto country roads, some rutted from erosion and only passable with an off road vehicle. After the long descent we climbed past extensive vineyards, topped out on a ridge and the descended only to repeat the process. It was again stunningly beautiful in spite of the cold wind and threatening skies. 

     At about the halfway point for the day, as we descended a rugged dirt road, we came upon a bright yellow house on the left. As we approached a man climbing up to the house from below with his dog turned into the entrance, set out an aperto sign and set some menu boards up. I asked if he had Coca Cola. He replied with a strong “Si!” I dropped my pack on the bench out front and entered his cluttered outdoor dining area. Sally was only a few steps behind and we sat at a table and asked for two Cokes. 

    The proprietor was a happy man in his early sixties, humming and singing as he passed behind a curtain of stringed beads and returned with our drinks, glasses, and two small bowls, one with four dates and one with four cookies. Sally paid the €6. He busied himself feeding his dog and working behind the curtain, turning on opera music on his speaker system and singing along. Soon he was cutting blazing white slices off a ball of something about the diameter of a football. “What is that”, we asked. In broken English but mostly Italian we told us it was a fungi he finds in the surrounding forest. There was another on the table, the size of a soccer ball. He described finding them up to 25 kilos in size. He quickly surmised our interest and brought out a platter of open face sandwiches, bread with a grilled slice of this mushroom on top drizzled with olive oil and lemon. He plated two for us and refused our offer to pay. I was carrying food for lunch, but this offering made them dead weight in my pack as we completed our fair. 

    We would have loved to stay longer, but we had to keep walking. We thanked him for the lessons and the food and were on our way. Another climb of 300-400 feet brought us to a plateau with a paved road and houses spaced as if on 20 acre lots. Soon we were dodging traffic in the city of our destination, Colle de Valle d’Elsa. We stopped for a potty break at a cafe, buying a acqua frizzante for its use. We walked into the beautifully preserved old town on the hill. It was devoid of people on this Sunday afternoon and we walked the length of it before descending a steep bricked road at the far end into the more modern lower town. The wind had made its presence a nuisance and it was really quite cold. We wove through the town and navigated via gps to our Osteria for the night. It was locked up. We tried a weathered wood door and found it barred, but suddenly it opened from the inside and a young heavyset woman let us in.  There was no one else inside this large, 50 bed hostel. A phone call to the manager steered us to room five. We had to use our headlamps to find it because the power appeared to be shut off. The lights worked on room five. We picked two beds to use from the eight in the room. We made ourselves at home although without heat we left our jackets on. At least there was no wind in here. After half an hour the manager came to collect our €42 for our night’s stay. We got the code for the door from him, then locked up our stuff in a cabinet and headed for a Donar Kabab place just a five minute walk away. We hoped it was heated so we could sit and plan the next day’s route while we ate. It was. Hal an hour later we took a quick walk 4 minutes further to a grocery store for yogurt to fill out our menu for the coming days and we scurried back to the hostel as the wind blew and light rain began to fall. We were surprised to find another occupant, a woman from France. We got the tea pot working and chatted with her in the dining area, keeping our hands warm wrapped around our cups. I nuked a full Platypus water bottle for Sally to use as a hot water bottle and tucked it inside her coat. 

We climbed into our beds about 6:30, happy to have a fluffy quilt on top to keep us warm. What a luxury to be able to hike all day and then have no responsibilities in the evening.  We laid in our separate twin beds and read and planned and both were asleep by 7:30.

    The weather looking forward shows no rain for another week and the temperatures are coming up again. Another great day complete, with many more in front of us. Life is good (even if a little chilly).

San Gimignano before the tourist buses arrive

What a gorgeous town in a gorgeous setting

People with pooches walking the Via Fracigena

Beautiful fall forests to walk through

A stream crossing at a low point before climbing to the next ridge top

Signs mark the way

Halfway up a ridge with the previous one behind us

Salvatore’s “cafe”

Cokes and Fungi

Fungi and Eggplant

Walking into Colle di Valle d’Elsa

In the old part of town

Looking down on the new part of town from the old hill town

Day Eleven - Saturday, October 31, 2026, Zero Day at San Gimignano

Weather-sunny & a little cooler with a cool wind, High 63, Low 49, On Route 0 miles, Total Distance 3.80 miles, 9,304 steps

A Series of Unfortunate Decisions-Continued

I slept well last night in spite of my misgivings about our lodgings. I put two heavy woolen blankets over my sheet and bedspread and was toasty and comfortable in spite of the electric heater failing sometime shortly after midnight. Sally was awake when I woke and was scouring the Internet for a better place to spend our day off.  

    It took us 25 minutes to find what sounded like a sweet AirB&B just off the tourist bustle on the main road, close to downtown, with kitchen, heat, WiFi, hair dryer, TV, living room with couch, bedroom and bath for $20 more than we had paid for our spartan cell in the monastery. We hummed and hawed for only a minute before requesting the apartment. We have paid for two places in one night before. Expensive, but this place we are in really stinks. 

    We decided we would backtrack to the laundromat we had spotted yesterday coming into town, wash our now 10 day old stinky clothes, walk another block to a grocery we had seen and buy food for the next three meals, then hang out in the piazzas until our new room was ready. We had asked for early check in and the host said he would do what he could to get us in by 1:00. 

     The laundromat was down below street level on the back side of some buildings. It was secluded so we showed no shame in stripping all our clothes off in the laundromat and slipping into sleeping clothes so we could wash everything. We plunked €7.00 euro into an automatic washer, then read the instructions again and realized we had frozen the machine. We moved our clothes to a different washer, followed the instructions carefully, added another €7 and got the wash cycle started.      

     While Sally watched our belongings, I walked the 100 yards down the street to the grocery store we noticed yesterday and pieced together food for the next 36 hours. Here is where bad decision number three for the 24 hour period occurred.  Because I wasn’t sure of what our living situation was and how far to the Coop brand discount grocery store from our new apartment was I ignored the high prices in this quaint little store and just filled my shopping bag with the things on my list. It came to €37. I bought veggies for a large salad, eggs and yogurt for breakfast and more. I didn’t buy meat and cheese for sandwiches cause the price seemed really high. Later in the day after we were in our new place I walked the ten minutes to the Coop store and found the prices 1/3 the price I paid here. Example?  A can of corn for our salad was €3.95 at the little store, €1.26 at the Coop store. Comparable prices occurred for all the items I had bought. Oh well. I feel good we helped the small time merchant support his family through our donations. Plus, the shop was frequented by a steady stream of older women buying a few items from the man behind the counter. It was cute and quaint. 

    Back at the laundry our clothes were just finishing the wash cycle when I returned with my expensive groceries. One euro worth of drying in the dryer and we changed again into our now clean clothes and headed into town again. 

     We hung out in the piazzas for an hour waiting for our room to be ready. We got a note on WhatsApp that it was available about 1:00 and were soon inside. What a palace, especially in comparison to the cell in the monastery!! Heat. WiFi. Kitchen. Couch. Bedroom. Tea kettle. And More!  Except for my run to the Coop grocery store we both spent the afternoon and evening resting, writing and sleeping. We made a huge salad for dinner along with Top Ramen, watched a movie and researched our route for the coming days, making reservations for the next four nights, through to Siena. 

    Three sketchy choices. The monastery room, the washing machine and the grocery store made this a very expensive day. Or, we considered we made some nice donations today, supporting the local church and merchants. Life is good. 

Sally finishing up at the laundromat

Piazza de Duomo in San Gimignano on Saturday with vendors under their canopies

Tempting goat cheeses at €45/kg

Walking the backstreets to our B&B

Cool arches and grinding stones

Too Ramen and salad dinner

Our apartment

Bedroom

Bath

Bathroom

Tourists in square with Gelato

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 Jimmy yawn-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. 

Gambassi piazza for breakfast

Descending from town toward San Gimignano

Tuscan countryside

Winery along the way

Climbing a hill with Gambassi on the hill behind

Gambassi in the distance behind us

Tree lined road

Church across the road

Breast feeding Madonna

Gimignano looking like the Emerald City from the Wizard of Oz

The main street of San Gimignano

Us with Ken in front of the duomo in San Gimignano

Day Nine - Thursday, October 29, 2026

Midpoint of Day 3 stage to Gambassi - Weather-sunny & warm, High 69, Low 49, Clear blue skies all day. On Route 7.38 miles, Total Distance 9.78 miles, 22,927 steps

Our taxi was 40 minutes earlier today than yesterday. He arrived promptly at 7:50. This time it was the boss, Ernesto. He drove us to the same point as yesterday, but went around the east side to get there rather than the west side. New territory to see. He was very good with his English and we conversed the whole way. 

This section is supposed to be the quintessential Tuscany landscape. Vineyards, olive trees, wineries, sweeping view. It did not disappoint. After a long descent from our drop off point we started to contour around rolling green hills on the ridge tops with orchards and vineyards stretching into the distance under clear blue skies. It was magnificent. This went on for a few hours as the miles clicked by, yet we never tired of the view. 

    I couldn’t help myself. Periodically I would hoot and holler, leap into the air and sprint up the nearest hill, pack bouncing on my back. It may be just stents they put in, but I feel like I am in a new body. At Camp Sheppard we always had fun “stress testing” everything. If a Saxon cross belay can stop a sliding person easily, how will it do with 8 people and 20 feet of slack in the rope (I got a sprained ankle from that one).  If the tents can hold up in a sixty mile per hour wind, what if we move them to where the funneled wind is blowing 80. How do they do now? I feel that way with this “new” body I have. How much can it take?  How fast can I hike up hill? Run uphill with pack on? How hard can I push until I feel familiar pains? (The answer so far is, I haven’t found that limit yet. Needs more stress testing.). If you were a Star Trek the Next Generation fan you might remember an episode where the Doctor falls in love with a being that is really two beings, a body and a symbiant that lives inside the body. I feel like I just got a new body. Looks the same, but man, does it feel different. 

    Eventually we started dropping to our low point for the day. Along the way we found a grassy spot in the sun with a nice view to sit and eat our lunch of focaccia bread, meat and cheese, banana, almonds and a Coke to share. Sally pointed to a town up on the hill and guessed it was our destination, Gambassi Terme. I disabused her of the idea as it was at a right angle to our last direction of travel. She insisted. Out came the map (on my phone). Oops. She was right. We make a hard right just a half a mile ahead and then climb for the next 2.8 miles to reach the town. 

    The day has become warm. Not hot like our friends Susan, Tom, Jonathan and Franny had experienced, for us a mere 69°. But with the sun beating down on us and a long climb underway, it began to wear on Sally. We kept to the shade where possible. With the sun low in the sky as winter approaches long shadows off the trees provided shade that would not have been available a month ago. Still, she grew uncomfortably warm. Combine four elements, lack of sleep the night before, uphill climb, hot sun and end of the day mileage and the result is fatigue. About a third of the way up, after a short but steep section we came upon a young woman sitting at a picnic table. Any place to sit is a welcome sight so we joined her. As the conversation progressed we learned she was originally from Russia, moved to London, married, divorced, moved to Florence, married the Italian National race car driver and now lives out here on a high end tourist facility with villas and rooms to rent. She was a beautiful woman, but the vibe we got was she new it and used it to get what she wanted in life. How judgmental of us. She offered to let us use the pool while we washed our clothes. Surprisingly, we turned her down. It just didn’t feel right. We started up the hill again and soon she passed us in her car, heading to town to pick up her four year old. If she had stopped to offer Sally a ride that is one offer we would not have turned down. 

    Our route hit the main road to town. Soon we were passing bus stops. The conversation turned to riding the bus to the town, a little less than two miles further up the hill. We passed two more stops, then hit a particularly steep section that sealed the deal. We had passed a bus stop at the bottom of it and she toyed with the idea of walking back down to it to catch the bus. I was sure there was a bus stop just ahead. The scheduled bus would be here in less than 20 minutes so time was of the essence.  Rather than backtrack, I dropped my pack and ran ahead. Sure enough, 200 yards ahead, on gently ascending ground was another bus stop. We made it to it with a few minutes to spare. I scanned the QR code on the bus stop sign to download their app, but didn’t finish reading how to ride the bus before the bus arrived. 

     We were only about 0.2 miles from the hostel we were supposed to be staying at (we had made reservations last night and could see it from the bus stop) but it was 3/4 of a mile below the town. We thought we would ride the bus to town, enjoy our afternoon there and then walk down. Good plan, don’t you think?

    Unlike our experiences last year, this bus driver actually wanted us to pay the bus fare. I had €4.80 in change in my hand. I was sure that would be enough. Not quite. It was €2.50 each. He let us on with the €4.80, somewhat exasperated with our ineptitude at riding his bus. A mile later and 300 vertical feet we were in town. It was about 2:00, meaning everything was closed. We walked around the corner to a gorgeous green park with its bordering piazza, found an open cafe, got Cokes and rested at a table. 

. .  . hmmmm

    This town is lively and cute. Why do we want to walk 3/4 of a mile down to a hostel and miss the evening in town. A quick search of the guidebook and booking.com revealed the Gambassi Hotel offered a room for €60, the same price as the hostel, actually cheaper because we would have had to eat the dinner they served at the hostel for €15 each. I called the hotel. She said she would meet us in 10 minutes. It was 100ft from the table we were sitting at, just around the corner. I called and cancelled at the hostel. Good decisions!!

   We moved into our room about 2:15, relaxed for a few, then went in search of the thermal bath here in town, just two blocks away. We found it, but at only 93°F it was too cold for my liking, plus the €35 price was too steep. We returned to our room, plotted tomorrow’s adventures and then headed to the grocery about 3/4 mile away for makings of a cold dinner. We settled on scissor salad with added tuna and corn. We ate it in the same park outside, now dark and filled with town folk. Must have been 60 people there. Maybe 15 kids. We struck up a conversation with a woman. Turns out the town is here every night until 7:00, then everyone goes home to cook dinner, to be served about 8:00. Little kids in bed by 8:30, adults in bed about 10:00. She was very sweet and generous with her time. 

    With salad complete, we headed up to our room for the night. We left the town square knowing we were “in” Italy, not viewing it from outside. As far as we could tell, we were the only “non-locals” in the piazza that night. We are so blessed to have the health to be able to do this. 

Inside our hostel of two nights

Green is the taxi route this second time, light blue is today’s route

Heading down hill from drop off point

Rolling hills

Sunny, no wind, gorgeous Tuscan scenery

Beautiful

Sally rounds another rolling hill

Can’t remember feeling this good!!

Amazing

Scissor salad in the piazza with the locals