Tuscany is one of the most beautiful regions and popular destinations in Italy. Despite being Italian, neither me or my mum had ever been, so we felt it was time to change this. We spent four days exploring the main points of interest of the region, travelling from Pisa to Siena and then Florence. We visited some of the main landmarks such as the Leaning Tower of Pisa and the Piazza del Campo di Siena, but also the less known one such as the Contrada della Lupa, winner of the 2016 Palio di Siena. In this post I will share with you our exact 4-day Tuscany itinerary, that you can also follow on your next trip to Tuscany to ensure you check out all the best places to see and things to do.
About Tuscany + how to get there
Tuscany is a region in Italy famous for its green rolling hills, the medieval towns, wineries and good food. It’s located in the north of Italy, close to Liguria and Lombardy. There are airports in Tuscany that you can fly to, such as Siena, Pisa, Florence and other smaller ones. However these smaller airports can at times be more expensive to fly to. Given how short the distances are in Italy (relatively) you can also fly to a bigger airport like Milan and then go to Florence or other cities in Tuscany by train. We travelled between all cities by train, one of the best transport modes in Italy.
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Tuscany 4-day itinerary
Day 1 – Pisa & Siena:
We started our trip by arriving in Pisa very early in the morning, around 9am. We parked as close to the centre as we could, and walked to the Leaning Tower of Pisa. It might be a touristy spot but you can’t go to Pisa and not see the Leaning Tower. There are also other things to see in Piazza Dei Miracoli (the square where the Leaning Tower is) which people don’t talk about as much. We spent a bit of time wandering around the Piazza, admiring the beauty of the Pisa Cathedral, Pisa Baptistry, and Camposanto Monumentale. The buildings are all open to the public, and if we had more time we would have visited the museums inside. However we had a train to catch around lunch time headed to Siena, so we slowly made our way to the train station, exploring the side streets and shops of Pisa.
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After a brief train journey we arrived to Siena in the early afternoon. After checking in to our hotel, a lovely hotel within the walls of the medieval city centre, we headed out to explore Siena. The historic city centre has remained pretty much intact, and is distinguished by its typical medieval brick buildings. It is also recognised by the UNESCO as World Heritage. Needless to say, with few cars allowed within the city walls, walking around the medieval streets is pretty magical. We went to the central Piazza del Campo di Siena, which is where in summer they hold the famous Palio di Siena, the horse racing competition. We closed the day with a typical Italian dinner in a local restaurant, and then off to bed early to get ready for Day 2!
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Day 2 – Siena & Florence
On the morning of the second day we went to visit the Contrada della Lupa. This is the part of town that won the Palio di Siena both times in the summer of 2016, which apparently in the whole history of the horse racing competition, has only happened a couple of times. Visiting their local church and museum, where all the trophies and medieval relics are held was an extremely interesting experience. Especially when accompanied by a member of the Contrada della Lupa, who was telling us all about the competition and their history, her enthusiasm and passion were contagious. By early afternoon it was time to get moving again and we jumped on a train headed to Florence. We arrived in Florence in the late afternoon, just in time to walk up Piazzale Michelangelo to watch the sunset.
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Day 3 & 4 – Florence:
In Florence we had the pleasure to stay in a historical hotel, it even had affresco paintings on the ceiling dating to the Napoleonic era! We spent Day 3 visiting the main landmarks in Florence, including the Duomo, Ponte Vecchio, Palazzo Pitti, Piazza della Signoria and Palazzo Vecchio. We tried going to the museum of the Uffizi Gallery, but we didn’t book tickets before hand and the queue for walk in entry was several hours long. To be honest, neither me or my mum are museum people, and Florence is basically a “Museo a cielo aperto” how we call it in Italian; a museum under the open sky, with beautiful historical statues dotted everywhere around the city. We had dinner at a lovely Osteria just next to our hotel, where they were also making fresh pasta! On Day 4 we spent the morning wandering through the markets and Florence, ticking off any landmarks we hand’t seen the previous day. Around lunch it was time for us to say goodbye and each head back our own ways, back to London for me and Milan for my mum.
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All in all, it was a fantastic trip, check the video for the full footage of these beautiful cities! Have you been to Tuscany before? How did you find it? Let me know in the comments below! This 4-day itinerary covers only the main cities and sights in Tuscany, however if you’re visiting Tuscany for longer I highly recommend doing a trip to smaller towns and the Tuscany countryside, or you can even go off the beaten track to explore the beautiful Giglio island.
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