Imagine a picture-book perfect countryside with cypress avenues, olive trees, and vineyards wherever you look. While you cruise around, you let down the window and feel the warm wind dancing up your nose, carrying a scent of orange blossom. On your Tuscany road trip you dive into the sweet Italian life. As the sun slowly lowers, those soft-colored hills, dotted with old villas and medieval towns, gleam as pretty as postcard motives. Time for a glass of wine!
Table of contents
Which places to visit on your Tuscany road trip?
Northern Tuscany
Firenze (Florence)
Firenze
To do in Florence:
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Walk across Ponte Vecchio – the iconic bridge with houses on it
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Walk up to or take an e-bike tour to Piazzale di Michelangelo for the best view across the city, especially for sunset when it’s tinted in orange light
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Join a free walking tour – to learn more about the historic place
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Visit the cathedral Santa Maria del Fiore – one of the most beautiful cathedrals in Italy
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Visit the Uffizi – the famous gallery showing many of Da Vinci’s stunning pieces of art
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Join a Chianti wine tour and tasting – to try some of the best Italian wines in the gorgeous Chianti hills
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Learn how to make Pizza and Gelato – a unique experience at a farmhouse outside of Florence
Lucca
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Visit Torre Guinigi – this tower gives you the perfect panoramic view across Lucca with several old oak trees on top
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Walk across the ancient city walls “Mura di Lucca” – You don’t have to do the entire 4 km. And you don’t even have to walk. You can rent bikes or just take a seat close to one of the gates.
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Stroll through the old, cobblestoned alleys to Piazza dell’Anfiteatro – as you enter the oval-shaped piazza you get a hint of the feeling it must have been entering the Roman theater
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Acquedotto del Nottolini – Take a short walk outside of town and admire this old aqueduct that used to carry water to the town. The perfect photo spot!
Lucca
Vinci
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Take a stroll – Explore the steep alleys by strolling around
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Walk up to the castle Castello dei Conti Guidi – to enjoy the view on the stunning countryside
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Visit the Leonardo da Vinci Museum – What would be a visit to da Vinci’s birthplace without learning something about him?
Pisa
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The Tower – Make sure to get a Skip-The-Line ticket for the Leaning Tower
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The historic center – Don’t miss lingering through the winding alleys of the historic center
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The river – Take a walk along the river Arno
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Outside of Pisa – Stop by the Via del Gombo in Parco San Rossore, a beautiful cypress avenue
Pisa
Central & southern Tuscany
San Gimignano
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Climb up Torre Grosso – A true highlight is the view across the town and its surrounding landscape from this tower.
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Take the effort to queue at Gelateria Dondoli – to try the world-famous and awarded ice cream
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Vino – Try the Tuscan white wine Vernaccia di San Gimignano & stop by the closeby Vineyard Teruzzi & Puthod.
San Gimignano
Siena
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Climb up the 400 stairs of Torre del Mangia – for a panoramic view across the city
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Allow yourself to get lost – to take some time to look at the small details on the historic monuments, such as the animals marking which district you’re in
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Take the marvelous “Porta di Cielo” tour of the dome’s roof
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Visit the Piazza del Campo – a busy fan-shaped square where both locals and tourists like to spend time
Montepulciano
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Visit the underground city – to see its caves and tunnels
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Stop by the lovely Piazza Grande – the town’s main square
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Join a Vino Nobile wine tasting – such as the free tour and tasting by Azienda Agricola Ercolani
Val d’Orcia & Asciano
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Drive around – It’s all about the landscape over here, so take some time to drive from one cute village to another and stop on the side of the road whenever you catch a special view.
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Montalcino – Visit the cute hilltop town
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Try the delicious Brunello di Montalcino wine – to get a true taste of the area
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Visit the Cipressi di San Quirico – where the traditional cypress trees are planted in a circle
Saturnia
Beach time
Tuscan beach time
Hidden gems in Tuscany
Hidden gems in northern Tuscany
Pistoia
Pistoia
Poppi
Greve in Chianti
Time for wine tastings
Hidden gems in central & southern Tuscany
Bolgheri
Volterra
Arezzo
Monteriggioni
Colle Di Val D’Elsa
Tuscany itineraries
Enjoy the road
Enjoying the landscape in Tuscany
Tuscany Itinerary 7 days
7 days round trip starting and ending in Florence (suggestion 1):
Florence (2 nights) ⇨ Vinci ⇨ Lucca (1 night) ⇨ Pisa ⇨ Montepulciano (1 night) ⇨ Val d’Orcia / Asciano ⇨ Siena (2 nights) ⇨ San Gimignano ⇨ back to Florence
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Florence: The capital of Tuscany is a great start for your trip, especially if you arrive by plane. After 2 days in Florence, you can pick up your rental car.
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Florence ⇨ VinciStart your Tuscany road trip with a short distance and a day trip to Vinci.
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Vinci ⇨ LuccaAfter a morning/afternoon in Vinci, head on to Lucca where you can enjoy dinner, spend the night, and use the next morning to explore.
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Lucca ⇨ PisaIn case you feel like seeing this tourist magnet, you can stop in Pisa, as it’s quite close to Lucca.
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Lucca/Pisa ⇨ BolgheriAfter spending your morning in Pisa, be ready for a longer drive down the E80 along the coast. Feel free to spontaneously stop wherever you feel like. A great stop is Bolgheri. Don’t take the highway, because the idyllic E80 is so much more fun.
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Bolgheri ⇨ MontepulcianoOnce you turn inland after your stop in Bolgheri, it’s time for the typical Tuscan countryside. This route is one of the most beautiful parts of your Tuscany itinerary.
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Montepulciano ⇨ SienaSpend the night and a relaxed day in Montepulciano, before driving to Siena. I’d suggest driving through Val d’Orcia, Val d’Asso or Asciano, as this area is extremely beautiful. Then, spend two nights in Siena, as there’s so much to see.
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Siena ⇨ San GimignanoOn your way back north, San Gimignano is the perfect stop, as it’s a small town.
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San Gimignano ⇨ back to FlorenceIn case you fly back home from Florence, the last part of your road trip takes you back to where you can return your rental car. You could add a stop in Greve in Chianti, if you’d like to.If you came all the way with your own car, why not add another few stops such as Volterra or Arezzo on your way back north?
7 days round trip starting and ending in Florence (suggestion 2):
Florence (2 nights) ⇨ Greve in Chianti ⇨ Arezzo (1 night) ⇨ Montepulciano ⇨ Val d’Orcia (1 night) ⇨ Montalcino ⇨ Siena (2 nights) ⇨ Colle di Val d’Elsa ⇨ San Gimignano (1 night) ⇨ back to Florence
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Florence: Just as in the first suggestion, start your Tuscany itinerary with two days in beautiful Florence.
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Florence ⇨ Greve in ChiantiPick up your rental car and drive down 45 minutes to the wine region Greve in Chianti.
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Greve in Chianti ⇨ ArezzoAfter spending your morning or afternoon in Greve, head on to Arezzo where you can enjoy dinner, spend the night, and use the next morning to explore.
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Arezzo ⇨ MontepulcianoNow, it’s time to head further south with a stop in Montepulciano.
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Montepulciano ⇨ Val d’OrciaAfter a morning or afternoon in Montepulciano, dive deep into the Tuscan landscape around Val d’Orcia where you spend another night with stunning surroundings.
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Val d’Orcia ⇨ MontalcinoBeautiful Montalcino is the perfect stop-over to spend a few hours before driving to Siena.
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Montepulciano ⇨ SienaSpend two nights in gorgeous Siena, and soak up this beautiful gem.
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Siena ⇨ San GimignanoOn your way back north, the small town San Gimignano is the perfect stop.
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San Gimignano ⇨ back to FlorenceIn case you fly back home from Florence, the last part of your road trip takes you back to where you can return your rental car.If you came all the way with your own car, you could add another stop such as Volterra or even Lucca on your way back north.
Tuscany Itinerary 10 days
10 days round trip starting and ending in Florence:
Florence (2 nights) ⇨ Vinci ⇨ Lucca (1 night) ⇨ Pisa ⇨ add Bolgheri & a beach stop (1 night) ⇨ Montepulciano (1 night) ⇨ add Val d’Orcia (1 night) ⇨ Siena (2 nights) ⇨ add Monteriggioni or Colle di Val’dElsa ⇨ San Gimignano (1 night) ⇨ back to Florence
Florence (2 nights) ⇨ Greve in Chianti ⇨ Arezzo (1 night) ⇨ Montepulciano ⇨ Val d’Orcia (1 night) ⇨ Montalcino ⇨ Siena (2 nights) ⇨ Colle di Val d’Elsa ⇨ San Gimignano (1 night) ⇨ add Bolgheri (1 night) ⇨ add Pisa ⇨ Lucca (1 night) ⇨ add Vinci or Pistoia ⇨ back to Florence
Florence (2 nights) ⇨ Poppi ⇨ Arezzo (1 night) ⇨ Montepulciano (1 night) ⇨ Val d’Orcia/Asciano (1 night) ⇨ Siena (2 nights) ⇨ Monteriggioni ⇨ San Gimignano (1 night) ⇨ Volterra ⇨ Lucca (1 night) ⇨ back to Florence
Tuscany itinerary with one base
Good to know
What’s the best time to visit Tuscany?
How to get around Tuscany?
How much time do you need for a Tuscany road trip?
Where to start your Tuscany road trip?
Where to stay in Tuscany
What to be aware of?
Sustainable travel in Tuscany
That brings us to the next part. When you eat out or buy products at a local market, and cook yourself, you support the locals. That’s awesome because your money goes right to the Tuscans instead of international companies.
Also, try to avoid unnecessary waste by bringing your own tote bag for shopping and a food container, and your own cutlery for your snacks. In case you buy something that causes litter, make sure to take it with you when you leave and properly ditch it into bins where you can separate the trash. This way, you can make sure that it gets properly recycled. Many parking areas along the beaches in Tuscany have trash bins with waste separation.
One of the largest polluters is bottled water. So avoid buying plastic bottles. Instead, bring your own water bottle. There are many public water refill stations in Tuscany. Just search for “Casa Dell’Acqua” or “drinking water fountain” in Google Maps. Those are stations where you get free filtered water or sometimes for 5 cent/liter.
Besides, you can also bring your own water purifier, such as a Grayl water bottle. This way, you can take water from any tap and filter it yourself.
Great guide with lots of details! It made me want to visit Tuscany! Saving it for when I will plan my own road trip in the region!
Hi Elina,
I’m so glad to hear that my post made you want to visit Tuscany. Thanks so much for your kind words!
Tuscany is a region I am dying to explore. You’ve convinced me to book a trip next summer. I also love your itinerary suggestions. I will need to do more research to choose which one to copy. In the meantime, I will dream of being there through your photos. Thanks for sharing the great post.
Thanks for your lovely comment, Mayi.
All the itineraries include amazing places, so the choice is hard, I know. But one thing is for sure: You will fall in love with Tuscany, no matter where you go!
[…] While many of the windows were no longer used in the following years, and some even got bricked off, the wine windows celebrated a revival in recent history. They’ve become such an important part of Tuscan culture and travelers love to try the experience of ordering a glass of wine from a window when they’re on a Tuscany road trip. […]