Itinerary : 5-day road trip in Tuscany
Tuscany is world-famous for its wine, but you should know that there are many other things to see and do in Tuscany… I love Italy, and this trip had clearly been on my list for a long time. It’s time for a road trip in Tuscany.
So we’re going to help you plan your 5-day Tuscany itinerary with some must-see places.
- Arrival in Pisa (Day 1)
- Village of San Gimignano and Siena (Day 2)
- Chianti region and Florence (Day 3)
- Visit to Lucca (Day 4)
- Return to Pisa (Day 5)
Tuscany in 5 days
How do I get to Tuscany ?
If you choose to fly, you can arrive in Pisa or Florence. You can compare and book your flights on Ulysse. Take advantage of a €10 discount through our referral link with the code PVWYP4ESA.
You can also travel by train or car, depending on your point of departure.
When to take a road trip in Tuscany ?
May/June or September/October are the best months. Whether you do the Vespa Trip or not, the temperatures will be more pleasant than in midsummer, when it can be VERY hot. I personally did it at the end of August, and it’s true that the heat was sometimes overwhelming.
Getting around in Tuscany
Since I travelled with the Vespa Trip and loved the experience, I can only advise you to hire a 2-wheeler ! The main advantage is that you don’t have to worry about parking in the towns. But if you’re not comfortable with that, you can of course choose to hire a car for this week’s itinerary in Tuscany.
Alternatively, if you only want to visit the main towns in Tuscany, you can use the Italian rail network, which is pretty well served and cheap !
🛵 Vespa Trip in Tuscany
If you’d like to do exactly the same trip as I did, I’d recommend The Vespa Trip – which I’d already mentioned in our Amalfi Coast road trip itinerary. They organise the same type of holiday in Tuscany. The principle is simple : everything is turnkey !
For 5 days, you’ll have your Vespa at your disposal and they’ll take care of everything : hotel bookings (2/3* range), transport of your luggage during the day… You’ll change hotels every day and all you have to do is enjoy the Tuscan countryside, eat Italian food and let themselves be guided by their recommendations. As usual, the Vespa Trip is great value for money.
>> All the information about the Vespa Trip in Tuscany can be found by clicking here.
If you don’t want to go on The Vespa Trip, I’ll give you my advice on where to stay in Tuscany at each stage of the itinerary.
Tuscany road trip itinerary : 5-day trip
I’m going to take you step by step through the stages of my road trip in Tuscany.
Day 1 : Arrival in Pisa
Pisa is world-famous for its Leaning Tower, a UNESCO World Heritage Site, but that’s not all ! It’s a colourful little town that’s great for strolling around.
For those travelling with the Vespa Trip, this will be your point of departure with the Vespa and your point of return. You’ll arrive in Pisa and have time to enjoy the city on your first day, before setting off on your next adventure.
What to do in Pisa during your road trip in Tuscany ?
The Tower of Pisa and Piazza Duomo
If there’s one must-see in Tuscany, it’s the famous Leaning Tower of Pisa ! As well as having a goofy photo session in front of the tower, you can visit it and climb its 297 steps. From the top, you can enjoy a unique view of the city.
I recommend that you book your entry ticket to this site in advance, with the ticket-cutting option to avoid long waits. Your reservation will also allow you to enter the Notre-Dame de l’Assomption cathedral.
Why is the Leaning Tower of Pisa tilted ?
You might think that the leaning of the Leaning Tower of Pisa is due to the will of a mad architect, but no ! In fact, very soon after it was built, it began to tilt, due to the unstable ground caused by the presence of water deep below the surface. The more the years went by, the more the Tower of Pisa tilted, so numerous attempts were made to solidify it so that it wouldn’t collapse.
In the end, it’s a blessing in disguise, as this tilt has made it famous and attracts tourists from all over the world.
🏘️ Visiting Pisa city centre
From now on, I advise you to head south on foot, where you can visit the pretty centre of Pisa. Among the places to see are the botanical gardens (entrance fee payable), the Piazza del Cavalieri and the quays with their pretty, colourful buildings. In reality, I wandered through the streets at random, without a precise itinerary.
🍴 My good addresses in Pisa :
- Have a drink : During the walk, I came across a small bar where I drank the best Aperol Spritz of my trip to Tuscany. This is a rare commodity as most places I’ve been to cut the Aperol with low-end white wine instead of Prosseco (the ultimate SACRILEGE). What’s more, they have the nerve to sell it at prices equivalent to those in France.
In short, if you want to drink a good cocktail at reasonable prices (€4) in Pisa, go to the bar The Parisian.
- Eating in Pisa : Two tried and tested addresses : Pizzeria il Borgo 21 and Ristorante Santa Maria.
- Evening in Pisa : if you want to extend your evening and go for a drink, head to Piazza della Vettovaglie, which is surrounded by bars, or to the Arno Vivo terrace on the quayside.
🛌 Where to stay in Pisa ?
Here are two establishments I recommend :
B&B Di Camilla, which is beautiful with a garden and well located, or La Torre Garbata, which has a crazy charm !
Day 2 : San Gimignano and Siena to start your Tuscany tour
Vespa and Road Trippers, let the adventure begin !
Road trip in Tuscany : itinerary
Click here to book your Vespa road trip (limited availability)
What to do in Tuscany ?
The road between the two towns is magnificent, and you’ll be amazed at almost every bend in the road.
♥️ Visit the village of San Gimignano
I particularly enjoyed the medieval village of San Gimignano. The centre is surrounded by charming walls and high towers. You’ll have a lot of fun wandering around. Once again, there’s no specific programme, just walk around it. For a good ice cream, head for Gelateria Don Dondolio, which has won the title of world champion several times. My verdict : I found it a little too sweet, but maybe that’s because I’m not a fan of desserts. You’ll tell me !
For a tasty Italian sandwich : go without hesitation to Vinaio di San Gimignano. Seating is limited, but I’d advise you to take away and picnic in the shade of the olive trees in the Parco Rocca di Montestaffoli, a 5-minute walk away.
🏊♀️ River swimming in Tuscany
I was really hot after visiting San Gimignano, so I went looking for a place to take a cool break. I wasn’t disappointed when I discovered this little paradise! I wasn’t expecting this kind of place in Tuscany at all.
To get there, head for Colle di Val of Elsa. The access on foot is located on this GPS point.
It’s an easy 5/10 minute walk downhill. You can continue along the river until you find a quiet spot to rest. The water is an incredible turquoise blue… The temperature is cool but it feels good !
Arrival in Siena
Siena is a city worthy of a film set. Its historic centre is also a UNESCO World Heritage Site. It’s a must-see place to visit in Tuscany !
What to do in Siena during your road trip in Tuscany ?
Here again, I wandered around at random, but here are the names of the places to see in Siena :
- Piazza del Campo, which is the main point of the city. It is laid out in the shape of a snail and is lined with tourist bars and restaurants. I wouldn’t necessarily recommend them, as the prices are high.
- The Basilica of San Domenico, located high up so you can admire the view over Siena
- The Duomo di Siena (cathedral) for fans of the Gothic period
- The historic centre and its narrow streets.
If you want to make sure you don’t miss anything and get to know the history of Siena inside out, I recommend this 2-hour guided tour of the city : click here to book.
🍴 Where to eat in Siena ?
I had dinner at Osteria Permalico Siena and it was delicious! The terrace is very pleasant. A second address I’d recommend with a traditional decor : the Grotta Santa Caterina da Bagoga restaurant.
🛌 Where to stay in Siena ?
To stay close to the centre of Siena, you have two options : the Santa Caterina Hotel, built within an 18th-century villa, or the Hotel Alma Domus, just a 2-minute walk from the Basilica of San Domenico.
If you want to stay in the heart of nature, with a swimming pool, and not too far from Siena, I’ve found 2 wonderful establishments for you : the Gli Archi di Corsanello, or the Borgo La Torre alle Tolfe.
Day 3 : The Chianti Valley, on the road to Florence
The Tuscany region is famous for its vineyards. Chianti is one of the most famous appellations. So we’re going to take advantage of this road trip in Tuscany to marvel at the typical stretches of vineyards.
The villages of Radda in Chianti and Greve in Chianti
Along the way, don’t hesitate to stop and admire any viewpoints you like. That’s another advantage of the 2-wheeler : you can stop anywhere.
You’ll pass through Radda in Chianti, a tiny village where it’s nice to stop for a cappuccino (or a glass of wine if you’re not too early in the morning 😂).
After a few stops, I had lunch at the Bottega del Moro restaurant in Greve in Chianti’s main square. The prices were a little higher than the average in Tuscany, but it was absolutely delicious. I would definitely recommend this restaurant !
What to do in Florence during your road trip in Tuscany ?
After a day in the vineyards, it’s time to head to the beautiful city of Florence. If you’d like to explore the city with a guide, you can book a free guided tour on this website.
Here are the must-see places in Florence :
Piazzale Michelangelo
Piazzale Michelangelo is located a little outside the city on a hill. Here you’ll have the best view of Florence, with the mountains behind. It’s simply breathtaking.
Piazza del Duomo
This square is home to 4 splendid monuments : Florence Cathedral, St John’s Baptistery, a museum and Giotto’s campanile. The square. I recommend going there very early in the morning to be able to admire it without tourists.
> Florence Cathedral
You can visit Florence’s Duomo and climb to the dome by taking just over 400 steps. From here, you’ll have a view of the whole city.
Click here to book your ticket to the Cathedral, the Dome and the Opera Museum
Ponte Vecchio
A beautiful spot for sunset or any time of day, the Ponte Vecchio is the city’s most famous bridge. It is the only bridge to have survived the bombardments of the Second World War. Don’t hesitate to go over the bridge, but also to walk away from it along the quays to admire it from the outside.
Piazza della Signoria
Another superb square to see during your stay in Florence. You’ll see, it’s well worth the diversions.
There are many other places of interest to see in Florence that I didn’t have time to do: the Pitti Palace and its garden, the Santa Croce basilica, countless museums, Florence’s central market… If you’re passionate about art, history and architecture, I recommend allowing 3 days to enjoy it.
🍴 Where to eat in Florence ?
The city has no shortage of Italian restaurants or even restaurants of other nationalities. You’re in for a treat ! I particularly recommend Trattoria Zà Zà, an institution. Alternatively, for a more intimate and traditional setting, you can head to La Fettunta, a restaurant serving Tuscan dishes.
🛌 Where to stay in Florence ?
You’ll find a wide selection of accommodation in Florence, to suit all budgets, on Booking.com
Day 4 : From Florence to Lucca… for your road trip in Tuscany
Let’s continue our Tuscany road trip itinerary, heading for the last stop on the trip.
I stopped off in the village of Vinci, which owes its name to the famous Leonardo da Vinci, since that’s where he came from. To be honest, I didn’t see much of interest there… There’s nothing exceptional about the village, but there is a museum dedicated to the painter, so you’re free to go there if you’re interested.
What to do in Lucca ?
Lucca is a pretty town surrounded by ramparts built in the 16th century. This gives it a very special charm ! In the old town, within the ramparts, you can wander through the narrow streets and even walk on the walls on the paths that have been laid out. The Piazza dell’Anfiteatro is remarkable and highly original, being built in the shape of a Roman amphitheatre.
The top of the Torre Guinigi (the one with the trees) also offers a splendid view of the surrounding area. Access costs €5, but beware of closing times!
Where to eat in Lucca ?
Even if they are tempting, avoid the restaurants in the Piazza Dell’Anfiteatro because of the high prices. I had a delicious pizza at Pizzeria SUD, with great ingredients and reasonable prices.
Where to stay in Lucca ?
I stayed in a hotel outside the city centre with a swimming pool which was great. Click here to book.
Day 5 : Return to Pisa
It’s already the end of this road trip itinerary in Tuscany with the Vespa Trip ! I hope I’ve shed some light on what to do in Tuscany during your trip.
Don’t hesitate to ask your questions in the comments section. For other travel guides to Italy, visit this page of the blog… This article contains affiliate links. If we’ve helped you organise your trip or if you’d just like to support us, think about booking your activities and hotels in Tuscany by clicking on our links. We’ll earn a small commission and the price stays the same for you of course. 🤍
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