What were we thinking?  I repeat – analyze a destination before deciding to go with young children, particularly two young children in strollers.  I knew we were visiting hilly places, but somehow, it did not sink in that we would have to get two sets of strollers up and down these hills and stairs.  The next stop on our tour of Italy’s hilliest towns was San Gimignano in Tuscany. But first, an afternoon in Pisa, which is flat!!!

This trip marked my fourth time in Italy and Rob’s second time, yet neither of us had ever seen The Leaning Tower of Pisa.  It was more or less on the way to San Gimignano, so clearly we had to stop. I had always heard it was a little underwhelming, but how could I pass up the chance for a cheesy photo of me holding up the tower?!?  It had to be done.

From what I could tell, Pisa is just worth a stop en route to somewhere else.  The area surrounding the tower was there simply to support the hordes of tourists constantly arriving via tour buses.  As you approach the tower, you are overwhelmed with the number of souvenir stands lining the roads. How many tourists there must be in high season to support the sheer number of trinkets being offered to us as we passed?  We avoided eye contact and made our way to the tower. Knowing that climbing the tower with the boys was off the table, we quickly toured the Pisa Cathedral then let the boys blow off some steam running aimlessly around the pathways surrounding the cathedral and tower.  

The dark grey clouds loomed overhead as we captured our required photos, but somehow we avoided rain once again.  

By this point in our trip, we had developed a steadfast rule to eat lunch on the go and to allow ourselves a sit-down dinner.  Lucky for us, the #1 restaurant on TripAdvisor for all of Pisa is a panini shop called “I Porci Comodi”. We were unfamiliar with most of the deli meats displayed, so I am not really sure what we ended up eating, but it was good.  There were only three small tables inside, so we took our chances with the rain and walked back towards the tower. It was starting to sprinkle ever so slightly, so we ducked into a doorway of the cathedral facing The Leaning Tower of Pisa and scored the best lunch spot in town.  

As we left and tried to make our way quickly through the souvenir stalls, a child-sized bright blue shirt caught my eye.  Displayed proudly on the front was none other than Lightning Mcqueen and Mater directly in front of The Leaning Tower of Pisa and the word “Italia”.   It was so tacky and perfect at the same time. Right then and there, I had an epiphany – all of the tacky souvenirs I would never buy for myself could now be purchased for my children.  After haggling with two different souvenir vendors, I had my two Lightning McQueen & Mater Pisa shirts for just 15 euros. Trust me, we definitely got our money’s worth, yet I can only find this one photo of my kids in their favorite shirt.  Here it is in all of its tacky souvenir shirt glory!

After acquiring our treasures, we were soon on our way to San Gimignano – a well preserved medieval town perched atop the hills of Tuscany.  You would think it would be easy to spot a hilltop town, but alas, this was not the case. Apparently, everyone arrives in San Gimignano from Florence, but we were coming from Pisa which is apparently off the beaten path.  We roamed the Tuscan countryside, sometimes in the wrong direction. There were no signs to San Gimignano until we were a couple of miles away. International mobile plans were not in our budget back in 2015 and the google maps turn-by-directions I had printed on multiple pieces of paper were not cutting it.  We ended up stopping every so often, trying to find somebody who could give us directions in broken English or in arrows scribbled on a piece of scrap paper. After much trial and tribulation, we finally made it to the town which is not meant for cars.

We had directions to get to our accommodations, Hotel Leon Bianco, directly on the central piazza, but we could not for the life of us, figure out the maze of one-way streets that surrounded the piazza, so we eventually decided to park where we could, despite it not being a legal parking spot, because we could tell from the map that we were close to the hotel even if we were not directly in front of it.  We unloaded all of our stuff and made the steep walk to the hotel. After checking in, Rob was directed where to park our car permanently. The parking lot was at the bottom of the hill that the town is perched atop and then a bit further. I had no concept for how far it was away, so as I waited for him in our hotel room with the boys, I wondered if he had taken this opportunity for some alone time at a bar.  Apparently, that was not the case, it really was that far. I just hoped we had not forgotten anything in the car!

We chose Hotel Leon Bianco for its Tuscan feel and central location.  The location ended up being extremely important on our first night as shortly after Rob returned from the car, it began to rain.  We tried to wait it out but eventually decided to eat a quick meal at Bar Le Torri which was more or less attached to our hotel. It was not bad, but I would not recommend it unless you were staying at Hotel Leon Bianco and were trying to avoid a rainstorm.  But why worry about a mediocre meal when you are staying across the piazza from the gelato world champion and the rain ends right as you are finishing your dinner? In a matter of seconds, we were staring at the endless array of flavors at Gelateria Dondoli unable to decide which one to choose.  One of the things I love about gelato is the smaller scoops that allow you to try multiple flavors without consuming too much.  I am a taster, I love to try as much as possible and apparently when it comes to gelato, as often as possible. We enjoyed at least one gelato stop each day we were in Italy but nowhere did we enjoy gelato more than at Gelateria Dondoli.  The flavors here were so unique, and we did not taste any that we did not enjoy!  

Overnight, the rain clouds passed, and we were blessed with a perfect spring day.  We took advantage of the weather by spending the entire morning and early afternoon walking the town.  San Gimignano is a walled medieval town, and most of the walls are still intact. I had read that when visiting San Gimignano, one must walk the path along the medieval walls.  It is the only way to truly appreciate the rolling hills of Tuscany dotted with iconic Tuscan cypress trees as far as the eye could see. We were prepared for an initial struggle to get atop the walls, but we were not prepared for the endless cycle of up and down that walking the walls entails.  

While we did not make it the entire route along the walls, we explored enough to appreciate the beauty of the surrounding countryside.  

We reached a commerce area along the route where one of the restaurants I had read about on TripAdvisor was located.  Caffe Giardino offered the view we were seeking of the Tuscan countryside without walking up and down the town’s medieval walls.  It also allowed us to grab a quick bite without a long, involved sit-down meal. We ordered at a counter and soon had our meal.  Unfortunately, the boys were not cooperating with sitting down for this meal so we stepped outside and sat on a bench where we were afforded the same view.  The silver lining is that this area also happened to be near where our car was parked, so we were able to get a few items that were of course forgotten in our rush to find our hotel the day before.

After finishing our lunch, we were at an entrance to the town along the wall, so we chose to walk the far less steep route through the town along the shopping streets.  I can not stress enough how important it is to bring umbrella strollers when traveling with young children in foreign lands.  In America, everything is ADA compliant, but that is impossible in places as antique as San Gimignano or in other places without funding for these types of endeavors.  Although it would have been nice to have the sturdiness and comfort of our double stroller, there is no way we would have been able to get through the doorways of many of the stores we popped into that afternoon.  

Every so often, we would let the boys out of their strollers to run throughout piazzas and climb the steps leading to the many historic buildings and cathedrals.  

Throughout the afternoon, we acquired wine, bread, cheeses, as well as a couple of trinkets for the boys. Shopping in San Gimignano proved to be quite entertaining, even if we did have to carefully navigate the shops with two strollers!

By the end of the day, my feet were begging me for a break.  What better place to take that break than the jacuzzi on the hotel rooftop.  Not only did we book Hotel Leon Bianco for its central location, but for the fact that our room had a separate living area that housed the boys baby cots – the jacuzzi was the icing on the cake.  The boys needed a proper nap, so Rob stayed with them while I enjoyed the rooftop jacuzzi, a rare moment alone. At this phase in the twins’ lives, I would rarely spend time alone because of “mom guilt”.  Rob and I did things together while somebody watched them for a quick date or I would leave them with Rob so I could do something with others. However, I never allowed for “me time”, I would use that time to do something that needed to be done in the house.  I am convinced that I would not have enjoyed these memorable, relaxing moments if we were not in a distant land where I wanted to take full advantage of every opportunity presented to me, and this is one of the reasons I encourage you to travel with children.  

We were all rested and relaxed as we made our way to dinner at Il Trovatore, a short walk to the outskirts of town.  After a few wrong turns, we finally made our way.  It was too cool to sit outside, so we were not really able to appreciate the view from the restaurant but definitely appreciated it before we entered.  

It had a very family friendly vibe, and the staff was very sweet to our boys and entertained us as we watched them cook our meals on their open fire indoor grill.  Rob opted for one of their big steaks that you could choose from a case, while I had pasta and ordered lasagna for the boys. It was hands down the best lasagna we had in Italy, so we ended up eating most of theirs!  See my TripAdvisor review here:


We did not dare try dessert at Il Trovatore, as we had a date with the gelato at Gelateria Dondoli, and we do not cheat on those we love. Eating our gelato in the middle of the central piazza while the night was winding down was the perfect ending to our stay.  Some people complain that San Gimignano is too crowded and touristy, but for us, the hordes of tourists making day trips from Florence allowed us to better appreciate the evenings when we had the town to ourselves and could enjoy the calm after the storm.  If you worry about the crowds here, my sister and brother in law enjoyed their visit to Volterra, a less touristy version of San Gimignano nearby. I can personally recommend Siena and Pienza as other Tuscan towns that can be used as a base to explore the area, although I have never visited these places with my children.  There is a good chance that I take them there one day though, and I will definitely let my readers know how it goes! In spite of our literal ups and downs along the wall and some initial issues finding our hotel by automobile, San Gimignano was a perfectly paced visit to Tuscany for The Explore More Family!