A Tuscany Road Trip Itinerary; Pisa to Florence

Last week I embarked upon a road trip adventure through the rolling hills of Tuscany. With multiple stops, hotels and towns to visit, it’s a trip I had been planning for quite some time. This time I was very lucky to be able to bring my boyfriend along, who didn’t take much convincing to be my plus 1! Thankfully he also doubled up as great travel buddy, driver and photographer. Here is part 1 of my Tuscany road trip…


The trip first came about as I was invited to go and experience a stay at the Castello di Casole, a beautiful 5 star property in the Tuscan countryside. Being equal in distance from both Pisa and Florence, it provided a luxurious base for exploring the surrounding area.


Because of Castello di Casole’s amazing location, I decided to turn it in to an opportunity to visit as many Tuscan towns as possible in a little 5-day adventure. In order to optimise our time, we strategically booked flights into Pisa and out from Florence. We also collected our hire car in Pisa and dropped it off in Florence. This way we could plan an A to B route without having to retrace any ground. Perfect! Our route for the trip was as follows;

Day 1 – Pisa
Day 2 – Casole d’Elsa and San Gimignano
Day 3 – Siena
Day 4 – Florence
Day 5 – Florence 

Here’s Part 1 of what I got up to on my Tuscany road trip.

Day 1: Pisa

Our British Airways flight from Gatwick landed into Pisa at about 1.30pm. The flight only took 1hour 30 minutes and after taking a few long haul flights recently, it felt as if we were in the sky for no time at all. As soon as we landed we jumped on a transfer bus to the car hire terminal and went to collect our hire car. After a bit of tedious admin and grown-up insurance talks, the keys were handed over and freedom was ours!


We had originally booked a new Fiat 500 but we ended up with a Silver Corsa, perfectly zippy for getting around the winding country roads. We took the car for its first test drive into the centre of Pisa, our first stop of the trip. Being only 25 minutes from the airport and with fairly simple roads, it was an easy drive for Scott to get to grips with driving on the right hand side of the road (his first time driving in Europe).


Of course landing in Pisa it would have been rude not to make the Leaning Tower our first stop of the trip, so off we went into the centre of town to see one of the 7 Wonders of the World. The Tower is located in the Piazza dei Miracoli along with the cathedral, baptistery and cemetery, which together make up one of the finest architectural complexes in the world. Before visiting Pisa I had no idea that the leaning tower is just one of the many stunning buildings in the complex and because of it’s fame it outshines the spectacular cathedral, which is also well worth a visit. One thing I didn’t realise about the tower before visiting is that you can actually still climb up it to the top!


We had just enough time to stroll around the walled piazza, take our obligatory photos and stop for our first gelato before heading back to the car for our 2 hour drive to Castello di Casole (keep an eye out for a full hotel review on the blog soon)

Day 2 Morning: Casole d’Elsa

After a delicious breakfast of omelette and an Italian cappuccino, we were up and raring to go on our first full day of the road trip. Casole d’Elsa is the closest town to the Castello di Casole and was the smallest of the towns we visited.


Located on the top of a hill and surrounded by green countryside, Casole d’Elsa is a sleepy little Italian town with picturesque streets, historical buildings and not a single tourist in sight! There are only a handful of restaurants and you wouldn’t need more than 1/2 a day to explore the whole town, so we arrived mid morning and stayed ’til lunch.


The concierge at Castello di Casole kindly recommended a nice restaurant for us to have lunch in, which we stumbled across before we even went looking for it. The restaurant was called Caffe Casolani and was a few minutes walk from the main piazza of the town.


Tables stretched along the street and beautiful vines grew up the sides of the wall. I had the feeling this place hadn’t changed a bit since it opened. When the waiter brought out our menus we were presented with a piece of paper with Italian scribbled all over it, so it had to be authentic! Asking for an English menu probably would have been out of the question (let alone very uncool) so we did our best to translate and took a gamble on what we ordered!


My dish turned out to be a simple pasta dish with the most delicious and fresh pesto. With a glass of red wine on the side, it was absolutely perfect.



Day 2 Afternoon: San Gimignano

After lunch we found a beautiful panoramic spot at the end of the town before jumping back into our car to continue our Tuscany road trip in San Gimignano. This town had been recommended to me by a contact who had also visited Castello di Casole and it turned out to be my favourite stop of the whole trip.


San Gimignano is much larger than the sleepy town of Casole d’Elsa, but still much smaller than the likes of Pisa, Siena and Florence. The walled medieval hillside town is brimming with history and famous for having the best gelatos in Tuscany. San Gimignano is home to a total of 14 medieval towers which have been amazingly preserved and make for a beautiful terracotta sky line when approaching the city.


The sun was out and there was a real buzz in the air as we walked through one of the walled gateways of San Gimignano. It immediately felt much more touristy than Casole d’Elsa with lots of people wandering around. We made our way through a winding street lined with ceramic shops and arrived at the central Piazza del Duomo in search of Gelato.


Whilst we had been told that San Gimignano was the place to get THE best gelato, we didn’t know exactly which gelataria to head to. So we took our chances on one of the two establishments in the central piazza called Gelateria Dondoli. Both had huge queues outside them, but when we saw that this place was named ‘Gelato World Champion’, we decided to hedge our bets and give it a go.


As with most of the gelaterias in Italy, there were endless choices in terms of flavours but I went for a hazelnut and nutella combo. Was it the best gelato I have ever had? Absolutely, without a doubt, 100% yes!


Gelatos in hand we found a sunny spot in the piazza to sit and soak in the atmosphere. Musicians filled the square with music and we stopped to watch a traditional Punch and Judy puppet show which had a crowd of kids engrossed. Top things to do in San Gimignano include climbing the Torre Grossa (the town’s tallest tower with breathtaking countryside views), the selection of Town Museums and the slightly dark but ever so fascinating Museum of Torture.


What did you think of part one of my Tuscany road trip? Have you visited any of the towns mentioned or are you planning a similar trip? I’d love you to leave a comment for me in the box below if you enjoyed this post x


Jessica Ruth Gibson is the Founder and Editor of Travelista and an award-winning travel content creator of 10 years. She lives in York, UK with her son and has travelled to over 50 countries; her favourites being Italy, Canada and Vietnam.


  • What a nice read! I think you had a great fascinating trip. Tuscany can offere several locations, landmarks and places to see, and there are some of them considered as a “must to see”. Like San Gimignano, for example, but I can suggest the close village of Volterra, a stunning beautiful place.
    I will also suggest, Pistoia, Lucca, Montefioralle and Monteriggioni. and if you have enough time a charming day in the countryside area between Montaione and Castelfalfi.

  • Ian Carrick

    We stayed a week nearby in Castel San Gimignano last year and went back time and time again to San Gimignano it is absolutely gorgeous. To be honest the whole area around there is – Volterra, Colle di Val d’Elsa, Monteriggione, Pienza, Siena, Lucca & the thermal baths at Montecatini Terme (a little difficult to find in the town but truly worth the search).
    We flew back out of Pisa & having been told it’s a one trick pony and not to expect too much of it, ended up truly amazed and fell in love with the Piazza Dei Miracoli. Campo Santo there was an absolute delight as was the Duomo but it has to said no matter what images you have seen of the tower… in the flesh it seems to defy gravity. There is no way that thing should still stand; the lean is incredible. It, and in fact the whole square put the widest of smiles on my face the whole time I was there. I’ll be back!
    I’m interested to hear what you have to say about Florence… to see how it compares with my impressions…

  • What a great trip! Italy by road sounds like the way to do it – you can at your own pace, pack up and leave when you want. The buildings are so beautiful!

  • Travelera

    I went to Pisa years ago and coming back later this summer, I have a wedding in Italy so I will be also doing a road trip in this area 🙂
    It looks lovely, your post makes me even more excited! xx

  • I’m sure one day building a great roaming

  • We loved reading this, and will be mentioning it on our facebook page. Just to let you know, your dessert was in fact Vin Santo (literally blessed wine) and is a fortified local wine (you are right, very similar in colour to Cointreau, but far less sweet), plus our biscotti made with a special secret ingredient (honey!) which makes then softer and smoother than they are traditionally. We look forward to reading part 3!

    Caterina – L’Osteria di Giovanni

  • It seems like you had a wonderful time exploring. I love how you ordered directly off the Italian menu – the pasta looks like it was delicious! Thanks for sharing the photos.

    • Thanks for your lovely comment Lauren! That pasta was one of the best things I ate on the whole trip, it’s just tastes BETTER in Italy! Stop by the blog again soon for Part 2 🙂 x

  • I’ve spent a few weeks in Tuscany with family when I was younger we stayed really close to San Gimigiano and Siena and it was perfect! We used to spend afternoons tasting olive oil and parmesan!

    I love the smaller Tuscan towns with their cobbled streets and hills. So pretty!

    • How amazing is it Hannah? Such a gorgeous place you should definitely try and re visit again now as an adult and do it with a hire car. So lovely to have so much freedom especially living in London and relying on public transport all the time. Olive oil and parmesan tasting sounds divine ! xx

  • It looks lush, I’m going to Pisa, Florence and Rome in 3 weeks. Do you have any restaurant recommendations in Pisa? X

    • Hi Amy, thanks for your comment! I don’t have a recommendation for Pisa as we didn’t stop and eat there but when you’re in Florence you must visit this place —> http://www.osteriadigiovanni.com for dinner. It’s an amazing authentic restaurant down a quiet back street but once you’re inside the restaurant is buzzing and has amazing atmosphere. The waiters give you free prosecco on arrival, delicious breads and free biscotti and cointreau for dessert. The mains are also delicious and very reasonably priced. I will be blogging about Florence in part 3 so stay tuned 🙂 x

  • Ooh Jess it looks dreamy! I’ve only been to Pisa very briefly and I was about 14 so I’d love to go back and appreciate it properly. I can’t wait to see what you got up to in Florence, I love it there!
    Lots of love,

  • Lovely photos! Looks like you had a ball x

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