Two days on the road in Tuscany, Italy

italy tuscany map

Tuscany is a place many know from books by authors like Frances Mayes, seen in the movie Under the Tuscan Sun or read about in travel guides and magazines. Toscana (in Italian) is a fascinating and picturesque region in Italy and two days is not even enough to see just a few cities and other places. You need at least a week to relax a little and get a good experience of what this region is about. But two days was all I had and you have to make a choice of a few places. There really is no use in trying to see everything because most often the more you drive, the less you experience.

My trip started in Milano where I rented a Volkswagen Polo for my travels through Italia. I wished my rental car was a Alfa Romeo or even more expensive Italian bolide but your expectations can’t be too high at the Avis rental desk when you reserved a compact car. But this is not about the car, even though it was just perfect for what I needed for my journey through this beautiful country. The trip started with a stay in the Maranello region and a visit to the Ferrari museum but it went quickly south from there. Literally speaking of course.

This road trip was in January of 2010, not exactly high season for tourists and other travellers. This can be good for quiet towns and great hotel rates. But it also is a time when the weather may not be exactly what you expect after seeing most images of the Toscana region. Yes, there is winter here and the weather can have quite a bite as I found out.

Gaiole in Chianti

A few major travel websites provided quite a few deals on accommodation in the Chianti area. The pictures, reviews and website of the Albergo La Fonte del Cieco in the little town of Gaiole in Chianti (Siena) looked quite nice and something very different from the usual hotel chains. Smaller towns are always quiet and it often isn’t difficult to find a place to park. I arrived early in the evening and the town was pretty much deserted. The Albergo was dark and there was a note taped to the front door with a phone number and some writing in Italian. My best guess was “if you want a room for the night, you better call this number”. I didn’t have a mobile phone that worked in Italy or couldn’t find a pay phone anywhere in town. Fortunately, I found a very small bar with a welcoming glow through the windows. I stumbled in and the locals curiously checked out the stranger.

01 Gaiole In Chianti Siena Italy Tuscany 2010

My Italian is limited to a few words so I made the international phone gesture of my hand with a pinky and thumb pressed to the side of my head. The kind bar man read the note with the phone number and name of the albergo and he quickly understood the reason of my visit. He made a quick call to the proprietor (who he probably knew) that sounded like “there is a dude here who wants you to come open the door’ in Italian and discussed what happened in town this evening. Almost needless to say, it was a short call because not much happens in this town after dark.

My duffelbag was still waiting for me when I got back to the albergo and the proprietor arrived a few minutes later. Check-in was quick and the exchange of a few smiles and a room key completed my interaction with the friendly lady. She didn’t speak much English but you don’t need many words most of the time. There was one other guest at La Fonte del Cieco but he checked out the next day. It was wonderfully quiet. My single room was about € 40,00 and included breakfast. Rates are higher in high season but it still is an excellent value.

05 Gaiole In Chianti town centre with Italian flag Italy Tuscany

The entrance to the hotel was a bit difficult to find at first and you have to park a few hundred metres in a public parking lot. The town and this hotel were designed when cars weren’t even invented yet. Keep in mind climbing some stairs is part of the charm of these old buildings and towns. The town centre was quaint and pretty much what you expect of an old Italian town.

02 Stairs To Albergo La Fonte Del Cieco Italy Tuscany 2010

The albergo is small and cozy. I imagine it to be a wonderful start of the day when you can have breakfast outside on the patio. But this was January so breakfast was served in a room next to the entrance. Friendly lady asked when I wished to have my breakfast in the morning and 8:00 seemed like a reasonable time. As I was the only guest, it was great that she came in every morning at 7:30 and set up breakfast just for me.

I quickly learned a regular cup of coffee is called a Caffè Americano which basically is a few shots of espresso and hot water. Fortunately, it was not the same as American coffee which is comparable to warm water with a slight coffee flavor. The Americano is similar to drip coffee in strength but taste is different. And of course a cappuccino is another favorite which goes great with breakfast. I decided to splurge and tried both. Delicious. Italian breakfast is pretty light (continental) and usually offers bread, butter, jelly and of course biscotti. Meats and cheeses can often be found at the breakfast buffet as well.

08 Albergo La Fonte Del Cieco breakfast room Italy Tuscany 06 Historical pictures Of Gaiole In Chianti Italy Tuscany

San Gimignano and Pisa – Day 1

I was going to be in the region for two full days. As always, much too short and I knew I was only going to experience a sampling of this wonderful place.  The forecast for the first day was going to be great with a reasonable temperature and sunny skies.  The other…  well, that wasn’t going to be too great.

The sunny day was going to be perfect for motoring through the Tuscan countryside, visiting a few small towns and then on to Pisa.  I am sure all of this can be done with public transportation but having a car makes life so much easier.   Tuscany is a wonderful place for touring by car, motorcycle or even bicycle.

Pictures and movies of the rolling countryside doesn’t do it justice.  You have to be emerged in the entire landscape to truly experience its beauty and grandeur.  As a motorcyclist, I can only imagine what it would be like to ride through Tuscany on a Ducati or Moto Guzzi on a nice summer day.  All the more reason to go back some day but the Polo was just fine for now.

20 Tuscany houses on The hillside Italy Tuscany

Many may dream of buying an old building like this and transform it into a rustic summer home or Bed and Breakfast.  For many, it will always be a dream but this one has potential and could be your Bramasole.  Well, if your dream is really big and your pockets are filed with lire.  Oh wait, Italia is part of the euro zone these days so the lira is a thing of the past.  Too bad really because I always felt like a rich man with a pocket full of lire with many zeroes in the denomination.  I do not miss having to change money for each country while travelling through Europe though.

27 Old house And fixer upper In Tuscany Italy

The road was quiet on this sunny January 4th because there were hardly any tourists around.  My travels took me to the small historic town of San Gimignano.  It is a walled medieval town and is also know as the Town of Fine Towers.  The hilltop setting truly provides a unique skyline of this UNESCO world heritage site.  I can only image this place packed with tour buses in summer but it wasn’t too difficult to find a parking close to the centre of town on a chilly day.   Strolling through town and enjoying the impressive architecture was very enjoyable.  It was lunch time and a small restaurant was a good place to enjoy a sandwich while overlooking the main square and watch people.  I don’t need much to be content in a beautiful foreign place.

16 San Gimignano architecture Italy Tuscany 15 San Gimignano stairs In Old building Italy Tuscany

The day trip continued and it was onwards to Pisa, occasionally dodging slow three-wheelers also known als Piaggo Ape (Ah-pay) on the curvy country roads.  It was early afternoon by now and the wide-open views were waiting after each corner and made me mumble “Wow” each and every time.   The cypress trees in Tuscany can be seen everywhere and it is hard to imagine the landscape without them.  It is often referred to as the Tuscan cypress tree, even though its origins are in Persia or Syria.  They can reach up to 20 -25 meters in height and are useful for protection against wind, wood for furniture and decoration.  And they look fantastic in pictures.

30 The road And wide open views In Toscana Italy 31 Piaggio Ape On The road In Tuscany Italy

I am not big on touristy places and I imagined Pisa could be a nightmare.  It is one of those places you have to see once in your life though and it didn’t disappoint.  I had the urge to slap the occasional tourist wanting to make that extremely unique picture of them holding up the leaning tower but behaved myself and just smiled.  There is just so much history and beautiful architecture.  The Piazza dei Miracoli is breathtakingly beautiful. I just sat on a bench for a while thinking “Am I really here?” and absorbed the grandness of it all.  There was a huge line to get into the leaning tower so I left that for a future visit.  It was already close to sunset and the fading sunlight casted a warm yellow glow on the buildings. Perfect for taking some pictures.

32 The Duomo And Leaning Tower Of Pisa Italy


The following morning, the friendly lady at the albergo arrived at the hotel shivering and mumbles Freddo!  This translates to cold!  So it looked like winter returned to Tuscany.  The plan was to head towards Florence and taking somewhat of a scenic route through the mountains.  Looking back, this was not such a good idea but I figured I was used to driving in snow so how bad could it be?

Winter Tuscan roads and Florence

The snow wasn’t really that bad but my rental car was fitted with summer tires. There were a few times when going down a hill , I wasn’t sure the car would stop before the corner or not. I had visions of being the news story of the next day proclaiming a tourist was found in a VW Polo wrapped around a tree after a drop of a few 100 metres. There was hardly any traction and it sometimes felt the car didn’t have any brakes at all.

I have never been so scared in a car and promised myself I will never drive a car with summer tires in winter ever again. Luck was on my side though and there were no horrific accidents that day. Even though it was a grey and dark day, the snow was quite nice and showed a side of Tuscany the average tourist probably never sees. But to be honest, the sun and blue skies of the day before was quite a bit nicer.

39 Roofs covered with snow In Gaiole In Chianti Italy Tuscany

40 Snow In Tuscany Italy

The snow turned to rain when coming down the mountains. Florence looked like a wet piece of art from the distance. It was still a spectacular sight and the gloomy skies could not spoil the experience. Firenze (as Florence is known in Italy) is the capital of Tuscany and is the largest city in the region. There are 370,000 people living in the city itself and more than 2.5 million in the metropolitan area. That’s a lot of people. It doesn’t come to a surprise the historic centre is a UNESCO world heritage site as well.

42 Ponte Vecchio In Florence Italy 41 Florence city view Italy Tuscany

There is so much to see and so many places and museums to visit, it is impossible to do everything in one afternoon. The rain wasn’t actually too bad and it was just nice to stroll through the centre of town, watch the people and absorb the history of the place. Ponte Vecchio was always on my list of things to see because it is so well-known and shows up in so many pictures. The picture above is the street on the bridge and is lined with all kinds of small shops.

48-Ponte-Vecchio-Italy-Tuscany 46 Ponte Vecchio street Italy Tuscany

The Basilica di Santa Maria del Fiore is the name of the huge cathedral in the centre of town. Its Duomo can be seen in almost every picture of the Florence skyline. It was nice there were no lines to see the inside and there wasn’t an entrance fee either. Pictures can hardly show the amazing inside and feel of the main space.


The rain was coming down again after I left the cathedral so it was time to head back to my comfy albergo. Pretty much the only way back to Gaiole was through the mountains again but fortunately most of the snow on the road melted away. While still a bit slow at times, it wasn’t the horrifying experience I had earlier that day. I usually don’t eat dinner in restaurants when I am on the road by myself. It often is much nicer just to shop at a local supermarket and get some basic things. Prosciutto, salami, bread and bottle of local wine are perfect for dinner after a long day on the road. And it also can save quite some money that can be spent on more travel. Wine and good quality meats and cheese are very affordable in Europe so this is dinner for a few Euros.


Weather hadn’t improved much the following day. The friendly lady served breakfast for the last time and I knew I was going to miss her. She knew me so well by now that she served a Caffè Americano first and a cappuccino when I was done with breakfast while plotting my route and plan for the day. Grazie mille! It was sad to leave this wonderful region behind because there was still so much left to explore and see. The plan was to go south towards Napoli and the Amalfi coast. This is where the sunny, wet and snowy Tuscan adventure ends but more about about the rest of the trip later. Arrivederci…!

Further reading: Check out this well-written blog post from a local Tuscan describing what Tuscany is like in winter. Tuscany in January Her blog At Home in Tuscany has a lot more good information about the region so make sure to check it out. The trip continued to Napoli, Pompeii and the Amalfi coast but that will be covered in a future topic soon.



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