Tuscany is one of the most beautiful and popular destinations in Italy. Despite being Italian, neither me nor my mum had ever been, so we felt it was time to change this.
We spent four days in Tuscany, 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, including useful information like where to stay, key highlights to see and how to travel between cities.
So what are you waiting for? Let’s dive in and start planning your own trip to Tuscany!
Before you read on, have you got everything you need for your Italy trip? Check out my Italy packing list to make sure you do!
How to travel to & around Tuscany
All the main cities in Tuscany have airports. You can fly internationally to Florence and Pisa, and from there get a train or bus to other cities in Tuscany.
For this Tuscany 4-day itinerary we did all transfers by train. Italy has a very efficient, if occasionally delayed, train system.
If you’re planning to spend longer in Tuscany and want to travel to the countryside or smaller towns you will be better off renting a car and doing a road trip.
That way you will have more flexibility and will be able to explore places that trains might not go to.
Tuscany 4-day itinerary: Day 1 – Pisa
We started our Tuscany trip in Pisa, and went straight 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) that 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 you can visit also the interior. You can climb to the top of the Leaning Tower of Pisa and enjoy the view over the rooftops of Pisa.
After Piazza dei Miracoli we wandered around the streets of Pisa, exploring the cute cobbled streets, doing a bit of shopping and walking along the River Arno.
No Italy trip would be complete without a culinary experience, so make sure to try some traditional Tuscan food for your first night in Pisa.
Where to stay in Pisa
Budget: Safestay Pisa – This hostel has spacious dorms, big communal areas and a fun social atmosphere. What else can you ask for from a hostel?
Mid-range: La Terrazza Sui Miracoli – Central location, spacious rooms and a beautiful terrace with view over the roofs of Pisa without breaking the bank. Ticks all the boxes if you ask me!
Luxury: Palazzo Cini Luxury Rooms in Pisa – If you’re looking to treat yourself, this is the place for you. With a lovely garden and romantic rooms, it’s the perfect place for a luxury stay in Pisa.
Tuscany 4-day itinerary: Day 2 – Siena
Siena is a beautiful city, with a wonderful old city centre. The historic city centre has remained pretty much intact from the medieval times, 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.
As soon as we arrived in Siena we went straight to the central Piazza del Campo di Siena. This is where in summer they hold the famous Palio di Siena, the horse racing competition.
We also visited 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.
We finished the day with an Italian aperitivo on the terrace of our hotel. It had a gorgeous view over the Tuscany countryside, and was a perfect end to the second day of our Tuscan itinerary.
Where to stay in Siena
Budget: Al Mercato B&B – This cute bed & breakfast is a great option for those who don’t want to break the bank. It has spacious rooms and is very centrally located.
Mid-range: Hotel Athena – We stayed here and I loved it. They have spacious rooms, are located inside the old town walls and have epic views over the Tuscan countryside.
Luxury: Grand Hotel Continental Siena – Starhotel Collezione – If you’re looking to spoil yourself, look no further. This luxurious property has everything you need.
Tuscany 4-day itinerary: Days 3&4 – Florence
Firenze is the main city in Tuscany and deserves two full days out of your Tuscany itinerary.
The first thing to do once you arrive in Florence, is to wander around the streets of the city centre. Walk around the main streets and side streets, soaking in the Tuscan atmosphere.
The main spots you absolutely have to visit include the Duomo, Ponte Vecchio, Palazzo Pitti, Piazza della Signoria and Palazzo Vecchio. Just admiring these beauties from the outside will easily take up your first full day in Florence.
In Italian we would say Florence is a “Museo a cielo aperto”; a museum under the open sky. Everything in this city is beautiful, and you can enjoy incredible artworks and historical statues dotted everywhere around the city.
Make sure to end the day at Piazzale Michelangelo, a gorgeous park from which you can enjoy the best sunset in Florence.
From here you can watch the sun go down, lighting up the sky and rooftops of Florence with a soft golden light.
As simple as it may seem, watching the sunset over Florence from Piazzale Michelangelo is considered by many to be one of the best things to do in Italy.
If you can’t get enough of these killer views, make sure to check out the 11 best viewpoints in Florence.
We then had dinner at a lovely Osteria just next to our hotel. As we walked past we saw them making fresh pasta, it was hard to say no!
In case you didn’t know already, we care very much about our food in Italy, if you want to learn to cook like an Italian make sure to check out this guide on how to choose the best cooking class in Florence.
On our second day in Florence we tried going to the museum of the Uffizi Gallery.
We didn’t get in as the queue for walk in entry was several hours long. So learn from my mistakes and make sure to book your ticket to Uffizi Gallery online beforehand!
We then had lunch at the Mercato Centrale of Florence. Here you will find loads of different food stalls, with a big central dining area. You can grab food from any stall and then eat at any of the tables.
It’s perfect if you’re travelling with friends and you can’t decide what you want to eat, as you can all get different stuff but still eat together.
If you want more details check out this Florence two-day itinerary to find out more things do in Tuscany’s capital.
Where to stay in Florence
Budget: Plus Florence – This hostel is perfect for those on a budget. The dorms have single beds instead of bunk beds, and it has a gorgeous rooftop terrace with view of the Duomo.
Mid-range: Palazzo Riblet – We stayed at this historical hotel and loved it, it even had affresco paintings on the ceiling dating to the Napoleonic era!
Final thoughts on my Tuscany 4-day itinerary
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.
I loved my time in Tuscany, and I hope you find this Tuscany itinerary useful in planning your own trip!
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