Tuscany Road Trip: Florence, Siena, Montepulciano, San Gimignano

    Tuscany Road Trip: Florence, Siena, Montepulciano, San Gimignano

    Italy is filled with a lot of stunning locations. Tuscany is one of the most beautiful regions & has a lot of popular hotspots such as Florence to more, small places such as Montepulciano and San Gimignano. Nonetheless, they are still worth a visit. Check out this blog post on how to plan the best Tuscany Road Trip to Florence, Siena, Montepulciano and San Gimignano.

    Hello everyone & welcome back to my little corner on the internet! In today’s post, I am going to be talking about my Tuscan adventure. In my Rome post, I mentioned that I won a scholarship to study for free in Italy for six months. Naturally, I did more travelling than actual studying, however, I still aced all my classes!

    For many people, when they think of Italy, the first image that comes to mind is Rome or Florence, Pisa or Verona. While all of these cities and other major landmarks are beautiful, Italy has a lot more to offer.

    Tuscany is by far my favourite region. After that is the Emilia-Romagna region which is where my apartment was located! As you’ll see later on this post, going to the rural side of Tuscany is like stepping into a whole new world away from busy streets and big monuments. It is like you stepped back in time to more quieter and simpler days.

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    My Tuscan adventure started out when my friend, who was studying in the Netherlands at the time, came to my apartment to go to an Enrique Iglesias concert in Bologna. Seeing him in person was a dream come true! That’s a story for another time though. 

    The next morning, we woke up super early and got on the train to Florence.

    Getting around in Italy:

    Trains in Italy are by far the easiest I have ever used anywhere in Europe. Towns and cities are very well connected and the prices are relatively affordable. The official website is Trenitalia. Unfortunately, they don’t have an app like DB in Germany but the website is very easy to use and you can buy tickets from other websites and apps such as, (formerly known as GoEuro), Rome2Rio and Trainline. Another (and sometimes cheaper option) is FlixBus. They’re all over Italy and sometimes you can cross the entire peninsula for less than €10! You can also buy tickets from the train stations. This is not my favourite option as 1) lines can be pretty long and 2) pickpocketing is fairly common there.

    All in all, I recommend purchasing your tickets online!

    Another thing to keep in mind is that sometimes, each city and/or town has more than one train station. If you want to stop by the city centre, always look for the Name of City + Centrale. For example, if you want to go to the heart of Bologna, stop at Bologna Centrale. 

    Choosing the best Tuscany tour:

    I have been to Florence a couple of times before with my family. However, I never went on a tour around Tuscany. Both me and my friend wanted to see the rural side so the tour was perfect for us!

    As soon as we got off the Maria Novella train station, which is the main train station in Florence, we spotted a couple of stands offering tours of Tuscany. We stopped at one of them and decided to reserve a spot for the next day. I can’t remember exactly which one we opted for, but this website has a number of different tours you can look at. There are also stands all over the train station. You can’t miss them!

    Our tour was around €45 and it included air-conditioned transport, English speaking guide, 3 cities, wine tasting, free water and WiFi.



    If you’re looking for a super cheap place to rest your head at night and meet people from all over the world, WOW Hostel is the place for you. We met people from all over the world: from Sicily to India, to America and the UK.

    There are a number of hostels dotted all over Florence, as well as Airbnb’s. As usual, I always recommend staying out of the city centre to save some money!

    At the end of this post, there is a map with all the places I mentioned!

    What to do and see in Tuscany:

    ▷ Ponte Vecchio in Florence:

    The Ponte Vecchio, literal translation being ‘the Old Bridge’, dates back to medieval times. I did some research prior to visiting and what I found is that this bridge was built in 1218 and rebuilt to its current state in 1345. According to Visit Florence, this was the only bridge the Germans during WW2 didn’t burn down. Read more about it here!

    ▷ Ponte Santa Trinita:

    A few metres down from the Old Bridge, there is another one called Ponte Santa Trinita.


    This is another popular tourist hot spot and it is located on the Arno River, the same as the above bridge I just mentioned. Here you can see me striking a pose for the Gram! Speaking of which, I post about ALL my adventures on Instagram so if you’d like to keep yourself updated, you can follow me here!

    ▷ Pitti Palace:

    A short distance away from the Ponte Vecchio, you can find the Pitti Palace. It is a stunning piece of Renaissance architecture.

    As you can see from the picture, you can sit down and bask in the Tuscan sun outside this palace which is what many people do. Opposite of the palace, there are some couple ice-cream shops. We couldn’t say no to ice-cream in Italy and we were not disappointed!

    The Medici family were the most powerful family in Florence and they ruled over Florence for many years. This palace was commissioned by Anna Maria Luisa de Medici who was a patron of the art. The castle is open to the public but you’d have to purchase tickets beforehand. Unfortunately, when we went it was closed but you can find more information here if you’re interested in visiting!

    ▷ The Duomo: 

    You can’t go to Florence and not stop by one it’s most famous landmarks. I’ve been here several times before and it’s still as grand and as beautiful as the first time I saw it.

    Also known as the Cattedrale di Santa Maria, this is one of Florence’s most famous landmarks. It was built way back in the 1400s. You can go inside but I recommend purchasing tickets beforehand. We tried buying ours right there but they were sold out.

    We instead decided to grab a bite to eat from one of the restaurants located close by. Surprisingly, it wasn’t too expensive so that was a plus! You can learn more about the Duomo here.

    Galleria dell’ Accademia:

    The ‘Gallery of the Academy of Florence’ houses the infamous David sculpture by Michelangelo.

    You’re a fan of the arts, this is the place for you. You’d need to buy your tickets beforehand and you can also book your own private tour! More information here.

    ▷ Monument of Cosimo I:

    I am a huge history buff (I studied it in college) and the history of the Medici family has always been an interest of mine. I remember watching a mini TV Series called ‘Medici: Masters of Florence’ and I was fascinated! While we were walking, we stumbled upon this monument of Cosimo.

    Cosimo was the second Duke of Florence, subsequently becoming the Grand Duke of Tuscany. The Medici family were a successful family who first started out in banking. They also contributed greatly to the art scene of Florence. The majority of the popular landmarks in Florence were commissioned by them. Lorenzo de Medici commissioned and supported the work of Renaissance artists and sculptures such as Leonardo da Vinci and Michelangelo.

    This is what we managed to see in a day. The next day, we woke up super early, made it back to the train station and met with our tour guide and fellow tour group to start our rural Tuscan adventure!

    After the tour guide introduced himself, we got on the bus and our first destination was


    Siena is a BEAUTIFUL medieval city in central Italy’s Tuscan region. I remember Siena being a fortified city and we had to walk in through majestic gates, sort of like in Mdina, Malta before going into the actual city centre.

    We met with our tour guide in Siena and we went to ..

    ▷ Piazza Del Campo: 

    Fun fact about Piazza Del Campo is that there is a horse race held twice a year! This race goes by the name Palio Di Siena. The horses run around the square three times. There are a total of 10 drivers and horses each representing a city ward. They all wear different colours. Dating back to medieval times, the piazza was always a public place where a number of games were held.

    You can go up the tower, Torre del Mangia, and you’ll get a stunning 360-degree view of Siena! It is worth the 400+ steps. I wish we had time to go up there!

    One of my favourite parts about our trip to Siena was the narrow, medieval streets. I loved walking down them. It felt like I was in a different world and a different time.

    ▷ Piazza Del Duomo:

    Just like in Florence, you cannot miss the Duomo.

    The ticket to go inside was included in the tour package that we purchased from Florence. If you’re interested in going inside the Cathedral, you can get more information about purchasing tickets here.

    The cathedral was PACKED but our tour guide was great and she gave us a detailed account of all the paintings in there. It reminded me so much of the Cathedral that we have back at home!

    We had some free time after we left the Cathedral. Me and my friend bought some souvenirs and roamed around the city. We found this unfinished piece of architecture. It turns out that this is the unfinished part of the Cathedral. Construction stopped after the black death in the 1300s which drastically reduced Siena’s population. Had the construction been completed, Siena’s Duomo would have been Italy’s finest and biggest Duomo, surpassing the Duomo in Florence and Milan!

    Unfortunately, our time in Siena came to an end and we had to go to our bus to go to our next destination.


    San Gimignano:

    San Gimignano is a small, medieval village in the heart of Tuscany. I have been here a couple of years ago with my family and I remember falling in love with it! My favourite part is the stunning views you get from every corner of the village. I mean .. look at all that greenery!

    ▷ Admire the skyline:

    If you go to San Gimignano, keep your eyes peeled for the stunning skyline where you can see the 13th-century medieval towers.

    It is the perfect location to walk around and admire the buildings. It can get a little bit crowded but San Gimignano’s charm will for sure steal your heart, as it did with mine.

    Other recommendations on what to see:

    1. Piazza del Duomo
    2. Collegiate Church
    3. Torre Grossa
    4. Piazza Della Cisterna
    5. Sant’ Agostino Church
    6. Collegiate Church of San Gimignano


    Montepulciano is a hilltop town in Southern Tuscany. It is surrounded by a vast array of vineyards. This is where we had our wine tasting and I realised why so many people like Tuscan wine.

    The bus dropped us off at the foot of the gill and we had to walk up to go into the actual city. It wasn’t fun walking up a hill in the scorching Tuscan sun but the views made it all worthwhile. As soon as you enter this small Tuscan fortified city, it is like you’re stepping into a huge courtyard.

    below images are in slider mode. click on arrows and hover over images:

    We then walked around and took a ton of pictures. From the get-go, it may seem like these places all look the same. That might be true, but if you look closely and observe well, each city/village/town has its own uniqueness and charm. And that is what I love about Tuscany. Each place in this region is unique and has a unique history behind it.

    Other recommendations if you have more time in this city:

    1. Piazza Grande (where walked around)
    2. Church of San Biago

    Wine Tasting:

    And now comes one of the most exciting, and the final, part of our tour! We went to Contucci to taste some amazing Tuscan wine.

    We were first given a tour of the place and then we were led to a table where we all sat down and talked to each other. We sat next to the sweetest American couple from California! They were travelling in Europe for the whole Summer and they also happened to be visiting Malta after Italy.

    The wine was delicious and it was such an experience. This has been my first ever wine tasting experience and I’m so glad I got to do it in one of my favourite countries and one of my favourite regions.

    And with that alcoholic ending, I bring this post to an end! I really hope you enjoyed this rather long post and feel free to look around my blog and read about my other adventures. I have SO much more coming! In the meantime, follow me on my social media. All of them are linked in my sidebar!

    I hope you find this useful! I mentioned some places that I know but I’ve never visited before 🙂






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