Siena to St. Gimignano

Between Siena and San Gimignano

The cities in this post—Siena, San Gimignano, Monterrigioni and Colle di Val d’Elsa—are within a relatively short distance of each other; e. g. 47 km from Siena to San Gimignano.  If you’re staying in the Tuscan countryside, as we usually do, (Hotel Belvedere di San Leonino), you can drive south to Siena for a day trip, possibly adding Monteriggioni on the way back or northwest to Colle di Val d’Elsa and San Gimignano.  But as noted in my Finding Italy post, I can turn any driving in Italy into an adventure or disaster. 

I’ve been visiting these cities since my first bike trip in the early 1990’s up through 2021.  I’ve divided this post first by individual towns, then brief observations from each visit, followed by discussions of the major sights.  I’ve also included some restaurants.


Bike Trips


I saw Siena for the first time on a bike trip in Italy.  We stayed on the edge of Siena and did loops to the towns in Chianti such as Castellina and Radda.  But we also spent some time wandering around Siena, particularly the Campo and its environs.  Unfortunately the only photo I can find is one of the Campo, although I’m sure I must have been in awe of the Duomo.


I came back in 2000 on my second bike trip. We were staying in a little village called Murlo and rode from there to Siena.  I have a hilarious picture of myself, helmet askew, grinding up the hills to the southeast entrance. (I think.)


Based on my pictures from that trip, I think we spent several hours walking  the winding streets from the Campo to the Duomo.  I wrote in my photo album next to the picture of me in Siena that I hoped I didn’t look this bad all the time.


Based on those two visits, I knew when my sister and I  started planning our 2010 trip, that I wanted to come back to Siena, especially since it was my sister’s first trip to Italy.   That was the first time I drove in Italy and it was quite the learning experience, especially trying to get from Montalcino where we stayed for 2 days to Siena.  I first drove us to Monte Oliveto, a beautiful monastery and then to Siena.

 Here’s an excerpt from my 2010 journal and photos from that trip.

From there (Monte Oliveto Maggiore) we went back through Buonconvento and on to Siena.  Luckily Roberto gave us good directions ‘cause the roads that look major on the map—like the SR2-are super winding and scary, albeit beautiful.

We followed Roberto’s directions to the Campo parking, which turned out to be where we came in to Siena on my last bike trip, and it was a short walk to the Campo and then to the Duomo.  Sue said seeing the Duomo alone made the trip worthwhile. 

Normally the Duomo is the Centerpiece of any article on Siena but I’ve written about it extensively in my  Cathedrals and Abbeys  post, plus added more information and photos below from later trips.

Siena duomo
Siena Duomo

We strolled the streets back to the campo on our way to the car,  going into the courtyard of the Palazzo Pubblico and walking around admiring the interesting statues and architecture.


Probably the most memorable visit to Siena was in 2014.  My niece asked me to organize a guided tour of Siena so I contacted our hotel (Belvedere di San Leonino) and they booked us with a phenomenal guide.  The five of us–my sister, niece, her two friends and I– had a private three hour tour where I learned more about Siena than I had in my previous visits combined.

Our hotel gave us directions to the parking area closest to where we would meet our guide but it was still insane trying to get through the roundabouts and headed the right direction.  Then came finding a parking space and orienting ourselves to where we needed to be which made everyone pretty cranky.

We found a space near a really pretty park with statues of horses. While I didn’t recognize the area at the time, I’m fairly certain it was near Porta Camollia based on our 2018 visit.

A park in Siena


San Domenico

We finally succeeded in finding  our way to San Domenico where we were to meet our guide.  Since we were a bit early, we walked a couple of blocks to a gelato shop and treated ourselves.

We located our guide in front of the Basilica and she took us through the interior giving us a history of St. Catherine whose head is kept there.  I declined to look at the head but found the history very interesting especially how St. Catherine convinced the popes to return to Rome from Avignon.

The Streets of the Centro

From the Basilica we took a narrow street to via Sopra di Banchi stopping in Piazza Salimbeni where our guide told us about the bank facing the piazza, Paschi di Siena, and its history with Siena and its recent financial difficulties.   Either there or later on our way towards the campo, she talked about the many statues throughout the city of the She Wolf  suckling Romulus and Remus and the myths about Senius son of Remus being the founder.  We also asked her about what appeared to be family crests on the palazzos around the piazza and the iron rings which she said were for horses.

The Duomo

From the area around Piazza Salimbeni we walked to the Duomo.  I’ve included our guide’s fascinating discussion of the inlaid floors, a sculpture by Michelangelo and the library in my Cathedrals and Abbeys post.  But  I’ll  include a gallery here of the interior.

I’m sure we spent at least an hour there and everyone in our group was enthralled with the beauty and history.

The Palio Neighborhoods

As a little background, the Palio horse race is run every year in  July and August, pitting the different neighborhoods or contrade against each other.  (For a detailed explanation, read this article in Discover Tuscany,

From the Duomo we walked to the Civetta Contrada or Owl neighborhood which had won the Palio that year.  The neighborhood is close to Piazza Tolomei and our guide gave us detailed information on everything from the symbols and flags of the neighborhood to how the horses are chosen and where they keep the horse prior to the race.  It was my favorite part of the tour, although the entire tour was captivating.


We, then, strolled to the Campo where our tour ended with the guide showing us how the Palio is staged.  We asked her for advice on dinner and she recommended a nice and untouristy trattoria nearby.  I wrote that it was ‘hellish’ getting out of Siena in the dark but it was totally worth it.


In 2016 we stayed three nights in Siena with our walking tour with GoAhead Tours, see Thoughts on choosing a tour group, airline or place to stay post.  We were dumped off at our hotel (the hideous NH Siena) in the rain with vague directions as to how to find restaurants.  Our hotel was on the northwest edge of Siena near the stadium and after looking at the map, I realized it was a fairly short walk to San Domenico and from there I was sure I could get us to the Campo and then to the little trattoria we ate at in 2014.  Not!  I’d like to blame it on the rain but I don’t think I can.

Here’s what I said in my journal of that episode: [My sister] and I showered in our miniscule bathroom, dressed and headed out a little after 7:00 pm intending to try to find the restaurant we ate @ 2 years ago.  Our hotel is just a couple of blocks away from St. Catherine’s [make that San Domenico’] where our tour started in 2014 so we headed there then down the same street getting to the Campo fairly easily.  But from there I had us hopelessly lost.  We circled the Duomo several times running into the couple from Boston.  We ended up near Rocca [dei Salimbeni]  and with the help of some locals got back to the piazza we’d walked through earlier.  We went into a little trattoria where I ordered ribollita (not good) and Sue ordered pizza (very good) and a liter of OK table wine.

The next day we did a hike from Monteriggioni (more on that below) then met up with the group midafternoon for a guided tour of Siena.  That tour couldn’t remotely compare to the one in 2014 but was still interesting.  We started at the campo and then walked to the Duomo but didn’t receive much information on the neighborhoods or palazzos. 

That evening we had a group dinner at a restaurant which was memorable only because I’ve never been thrown out of an Italian restaurant before.  Post dinner was great though and here’s what I wrote: And we were literally thrown out @ 8:30 pm infuriating most of us.  The couple from Texas organized a group for after dinner drinks in the campo which was a blast.  The wife is hilarious and will say anything.  So the conversation was heavily laden with sexual innuendo.  We left w/ the couple from Boston and damned if I didn’t get us turned around again.  I finally saw the sign for San Domenico and got us back to NH.

The next day I skipped the group trip to San Gimignano because of a cold and just walked the city myself, writing: Around 12:45 pm I tried the route we took to the campo yesterday finding it easy peasy; walked around the campo, then returned the exact same way.  Still baffled as to why I couldn’t find it last night or Wednesday night. 


Whenever I travel to Italy, I try to see at least one new city or region plus at least one or two old favorites and Siena will always be on my favorites list.  In 2018 after a crazy trip that went from Istanbul to Bologna to Montecatini Terme, Chianti, Perugia and finally Firenze, we did a day trip to Siena from Firenze.  Unfortunately it was pouring and about all we saw was the Duomo, along with a small trattoria near Piazza del Duomo. 


1992 Bike Trip

Monteriggioni is a very small, but lovely hill town just a few kilometers from Siena.  On our way from Siena to San Gimignano in 1993, we stopped here for a picnic.  I didn’t know the name of the town until our walking tour in 2016 when I realized it was Monteriggioni.  I couldn’t find my journal from that trip; however I did find the pictures which are hilarious.


2016 Walking Tour with GoAhead Tours

We did a day trip to Monteriggioni with our walking tour, after which we did a fairly long walk from the town along the via Francigena. 

Here’s what I wrote in my 2016 journal: We left @ 9:15 am for Monteriggioni where I think my first bike group had lunch.  After telling us there was nothing to do there, our guide dumped us for an hour.  But it was a beautiful day and I enjoyed strolling around the piazza.  

When I compared the pictures from that trip to those from 1993 I realized Monteriggioni was our picnic spot in 1993. So here are some lovely pictures.  It’s definitely worth a visit.

Colle di Val d’Elsa


In 2014 as I was working on itineraries for our October trip, I came across this article, ‘A Day in Colle di Val d’Elsa,’ at  and tried to get the rest of our group interested in visiting but we ended up going to Montalcino instead.  So in 2016 when my niece asked me to put together a day trip in or near San Gimignano, I suggested going to Colle di Val d’Elsa on the way.  She was agreeable and it was one of the nicest days of that trip–although that may have had more to do with all the wine we consumed at Tenuta Torciano. (See Vineyards, wineries and enotecas post.)

The town was an easy stop between our hotel (Belvedere di San Leonino) and  Poggibonsi where we got off the highway to go to Tenuta Torciano and San Gimignano.  I should have read the referenced article more carefully because I parked in the first place I could find then realized after walking around that there was parking closer to the street that leads to Piazza Arnolfo de Cambio. 

We walked up and down that street for a while looking for the lift, then finally decided to walk up to the old city along the road. We strolled the streets of the old town, going into a church and a couple of stores, eventually finding the lift, right next to a school.   I wrote in my journal: I’m not sure Sue and R enjoyed Colle di Val d’Elsa that much, partly because it was a tough, hot climb to the old city.  But I enjoyed the narrow streets and the panoramic view near the lift. We sat in the main piazza for a while cooling off after taking the lift down.

San Gimignano

I’ve visited San Gimignano  four times over the years and always enjoy it.

1992 Bike Trip

My first bike group rode to San Gimignano from Siena where we’d been staying and doing loops into the countryside, stopping in Monteriggioni for lunch.  We spent 2 nights in San Gimignano before finishing our trip in Firenze.

As I look at my pictures of that trip I must have been daunted seeing the town rising above the fairly flat lands below.

The view of San Gimignano

I don’t recall where we stayed but given the layout of the centro storico and the fact that cars are not allowed inside the walls, we must have ridden to one of the parking areas, left our bikes with the van and walked to our hotel.  We took the opportunity to get our pictures taken with the towers in the background and even did a full group photo in Piazza della Cisterna.



In 2014 my sister asked to do something different during our second week in Italy so after my niece and her friends left and my daughter arrived, we headed to San Gimignano for two nights.  We had been staying in Montalcino and our terrific host in Montalcino gave us good directions on how to go through Poggibonsi and get on the road to San Gimignano.

Still I was nervous about getting into San Gimignano because our hotel, Antico Pozzo, was in the centro storico. One of the many good things about the hotel is that they not only had a map on their website but a video which I watched multiple times.  

As we started up the road to the town, I handed the map to my daughter who looked at me like I had two heads.  But almost immediately I started seeing the landmarks described in the video and was able to get us to the hotel, unload suitcases, then drive back to the parking lot without too much trauma. It cost us about 30 € to park for two days but I’m not aware of any other option.

It was late October by then and we had one cool windy day while we were there but San Gimignano was blessedly quiet and less crowded than normal.  After getting settled in our room, we wandered the town for a while then my daughter suggested the terrace of a small restaurant where we quickly discovered the joys of Moretti rossa.

Laura and I in San Gimignano
A refreshing Moretti

I think both nights we had pre and post dinner wine in the small bar at Antico Pozzo where the pleasant desk clerk gently corrected our pronunciation of ‘grazie.’

Our full day in San Gimignano was everything my sister wanted for her birthday celebration.  I think I was the only one to get up in time for breakfast and I enjoyed the time alone sipping my cappuccino.  When my sister and daughter got up, we settled on a plan for the day.

Things to See and Do

After wandering a bit and taking photos of the towers against the brilliant blue sky, we went to the archaeological museum.  I found it fascinating especially its collection of centuries old pharmacy articles. The museum also has a lovely garden and a nice shop where we bought some mementos.

As I recall, our museum ticket could be used at one other museum in San Gimignano so we wandered back to Piazza della Cisterna and decided to walk up the Torre Grossa.  There was also a special exhibit of 15th century art in the Torre or more accurately in the Pinacoteca that looked similar to Byzantine religious art.  Unfortunately I didn’t write down the name of the artists at the time.   We only made it about half way up the Torre before vertigo set in but we did get some great photos.

We went back to the room for a while, then had lunch in a little pizzeria.  My sister and I went into the church in the Piazza (the Duomo of San Gimignano) while my daughter set up shop in the outdoor seating at one of the restaurants.  We joined her there for our afternoon Moretti,  watching the world go by (and a bizarre puppet show). We did lots of shopping too, especially my daughter.

Where to eat

The highlight of our visit was a birthday dinner for my sister at a restaurant recommended by our hotel.  The name of the restaurant is La Mangiatoia and I’ve written about it in my post on ‘Places to eat.’  We still talk about what a fun time we had there and I think it may be my sister’s favorite birthday  dinner.

Dinner at La Mangiatoia


As I mentioned above, when we returned to this area in 2016 we planned out a day where we started in Colle di Val d’Elsa, then did a lunch and wine tasting in Ulignano at Tenuta Torciano, then went to San Gimignano.  We had so much to drink at lunch that we had to spend some time in the garden of the winery sobering up before heading to San Gimignano.  (Tenuta Torciano is gorgeous and you can read about it in my Vineyards, wineries and enotecas post.) We stopped along the way and my sister got several good pictures of San Gimignano across the valley. 


I wrote in my journal: We found parking without too much trouble which led us to a different entrance from 2 years ago.  When we got to the top of the street, we walked to Piazza della Cisterna and sat on the steps of the Duomo  relaxing for a while and people watching.

We strolled around the town but didn’t go in the torre, then stopped again for photos as we came out the porta, getting some pretty shots of the countryside.  All in all it was a very pleasant afternoon.  

Unfortunately I was sick when our walking tour came back about a week later (and wanted to make sure I could go to a dinner and wine tasting that evening) so I skipped that part of the itinerary but my sister did get some great photos.


 I revisited San Gimignano in October 2021 with my sister.  I’ve written extensively about it  in my Five Days in Southern Tuscany  post, but will give a brief summary here. 

We were staying in Ulignano, at Hotel Vecchio Asilo, which is a short drive from San Gimignano. We walked around Piazza del Duomo and up a couple of side streets taking pictures.  Then we walked down to Piazza della Cisterna, taking more photos.  From there we took a fairly steep street almost to the edge of the centro.  There were lots of interesting shops, and we stopped in two that had beautiful ceramics. As we walked back to Piazza della Cisterna we noticed a small walkway along the wall where there were spectacular views over the valley.

We headed back to Piazza del Duomo and wandered around a bit before we could find the ticket office for the tower.  We bought tickets to walk up Torre Rognosa (I think) and made it about 2/3 of the way before the open stairs freaked us out.  We stopped on the way down and went through several rooms of religious art.

Then it was a very enjoyable lunch at Bar le Torri in one of the main piazzas.



I always come away from a trip in Tuscany wanting to go back to all these towns.  The most difficult decision is  how to see something new but go back to our favorites at the same time.




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3 thoughts on “Siena to St. Gimignano

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  2. Grazie per il tuo commento. Viaggio in Croazia e Slovenia quest’autunno, e intendo di scrivere un post su quei paesi quando torno. Ti chiedo gentilmente di farmi sapere se ti piacerebbe scrivere un post su Maramures per il mio blog nel futuro.”

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