The Most Scenic Drives in Tuscany: Explore The Best Road Trip In Italy

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Most Scenic Drives in Tuscany

Driving in scenic Tuscany is one of those must do Italy bucket list items!
During my second trip to Italy with my mom, we had the chance to drive the beautiful Tucan countryside. We found the most scenic drives in Tuscany and I’m going to share my stops and everything with you! So let’s get right into it.

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The Most Scenic Drives in Tuscany

The Most Beautiful Road Trip In Tuscany

It has been a bucket list item for me to drive by the rolling hills and scenic roads in Tuscany. I finally had a chance to experience driving through Tuscany on my last trip to Italy with my mom! We had a day and a half (36 hours in Tuscany) and I had to make the most of our short time in Tuscany.

Related Article: What You Need To Know Driving In Italy Rules & Laws

After researching a few popular drives in Tuscany, I decided to plan our Tuscany road trip/drive to the famous Cypress lined road in the UNESCO World Heritage Val d’Orcia and visit some of its picturesque villages: Pienza & Siena, take a dip in some of Italy’s best thermal baths at Bagni San Filippo and spend some time relaxing in a luxury hotel in the Siena town of Greve in Chianti.

We picked up our rental car in Florence and drove towards Siena toward our Tuscan villa hotel to unwind in the Tuscan countryside. Here I’ll share my experience and the most beautiful and scenic drives in Tuscany!

Rent A Car In Advance: Check Prices & Availability

Since I can only drive an automatic vehicle, I made sure to reserve the car in advance (3 months). I found that Picking the rental car up at an airport was the most economical and saved the most money. I used the company below and had a great experience. They had the best prices and a flexible cancelation policy.

The first half of the trip and drive in Tuscany was to arrive and enjoy our hotel which was located in the cute town of Greve in Chianti. Just an hour’s drive from Florence. We enjoyed the rest of the day there, and early the next morning we headed on our scenic road trip. Details below.

Want to be driven? Take a tour that handles all the logistics for you, all you have to do is enjoy the ride, and cheese and wine tasting included!

Check Pricing & Availability for Day tour from Florence to Tuscany.


Most Scenic Drives in Tuscany

Which Towns In Tuscany To Visit

Where to Drive To In Tuscany

Which towns in Tuscany should you visit? Well, since my goal was to see the most scenic drive in Tuscany (see below!) from Florence, I had to narrow it down based on my #1 location which was in the Val’Dosay region by the town of Asciono. When I was researching towns in Tuscany to see, there are so many to choose from, here are the top towns in Tuscany to consider seeing along the way:

  • Lucca: The Walled City. Lucca is a charming walled city that is known for its well-preserved Renaissance architecture. The town’s historic center is pedestrianized and is a joy to explore on foot or by bike. you can walk along the city walls and enjoy stunning views of the surrounding countryside. Lucca is also known for its delicious food and is home to some of the best restaurants in Tuscany! I really was considering visiting but unfortunately, we did not make it this time.
  • Siena: Siena is a charming medieval town that has preserved much of its historic architecture and art. The town’s centerpiece is its stunning cathedral, the cathedral is a must see! You can explore the town’s winding streets and admire its beautiful architecture, including the Palazzo Pubblico and the Torre del Mangia.
  • San Gimignano: San Gimignano is a beautiful medieval town and it’s interesting because nowhere else in Italy has as many towers.
  • Montepulciano: Home of the famous red wines of Italy, Vino Nobile di Montepulciano. The town’s historic center is filled with beautiful palaces and churches, including the Palazzo Comunale and the Cathedral of Santa Maria Assunta. It’s a beautiful town that is perched up high on a hill, allowing you to see breathtaking views of the Val D’orcia region.
  • Pienza: Pienza is like picture perfect postcard. Pienza is a small town that was built in the 15th century as a Renaissance utopia. The town’s historic center is a UNESCO World Heritage Site and is known for its stunning architecture and beautiful views of the surrounding countryside
  • Montalcino: If you’re a vino, and red wine is your go-to, then Montalcino is not to be missed! It is a charming hilltop town that is known for its production of the famous Brunello di Montalcino wine.
  • Asianco: A Hidden Gem in Southern Tuscany. Located in the southern part of Tuscany, Asciano is a small and charming town that is often overlooked by many. However, in my opinion, it has one of the most scenic drives in Tuscany, with beautiful views of the surrounding countryside and Cyper lines trees with a small medieval town in the background (the photo above!). The town is home to several excellent restaurants that serve local specialties such as pici (thick, hand-rolled pasta) and wild boar stew. Additionally, Asciano is known for its olive oil production, a great gift to bring back for friends and family.

TIP: A lot of these towns are small and can be seen in less than an hour. Parking is very limited in these small Tuscan towns. As most of them, you cannot drive through the town, and depending on the day and time of year, your time gets eaten up searching for parking.

Because I had limited time in Tuscany, I had to narrow the list down to 4 towns on the way to Asciano. So the route I decided on was to the famous region of Val D’orcia in Siena, Pienza, Asciano, and Bagni San Filippo and give each at least a little of the time they deserve and then back to Florence to return the car. I could have driven the car to Rome but decided it was faster to take the train from Florence and less traffic to deal with in Rome.

 When is the best time to drive in Tuscany? I went in May during spring in Italy. It’s one of the most beautiful times to drive through Tuscany because of the beautiful green colors at this time of year – which most would prefer to the sunburned yellows in summer.

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town of Siena

Driving From Siena To Asciano

The Most Beautiful Tuscany Scenic Drive

Via Strada Provincia 438 Driving Distance: 31.3km Driving Time: About 40 minutes

From Siena, take SS73 to SP438 and drive to Asciano. This is the most beautiful drive. It is South-east of Siena, is called Le Crete, or the Crete Senesi. There are so many stops, to get out of the car and take photos and admire the view. This is why I wanted to drive in Tuscany. Truly the most picturesque and most scenic drive in Italy. Make sure to stop at this viewpoint.The cypress lined road is so pretty! This viewpoint is the most iconic in Tuscany. Get my driving directions on google maps here (edit your starting point from Siena, we started from our hotel)

tuscany most scenic drives
Ascianco famous cypress lined road

We went into the town of Asciano to view the Basilica di Sant’Agata. Then went into Bar Herve di Manieri for coffee and lastly picked up some olive oil. Then off to PIenza we went!

Asciano to Pienza Drive

most scenic roads in tuscany

via SP 14/60/71 driving time: 39 min distance: (31.4 km)

On the way to Pienza, there are a few iconic and must see stops. The first one is the famous The Cypresses of San Quirico d’ Orcia. Here is the exact google maps location.

next is the most photographed Capella della Madonna di Vitaleta, a UNESCO World Heritage Site. It is a picturesque little chapel set in the midst of the Tuscan hills. The exact google maps location.

Once in Pienza, we parked and went into the town to explore for a bit. Pienza is famous for its pecorino cheese so of course we had to do a quick tasting! Before heading to the next stop we stopped at the famous Hollywood movie shooting spot of “Gladiator”. You can find the location here.


Tuscany best kept secret natural hot spring

This hidden gem is a natural hot spring not yet known to the masses on social media (although I’m sure that will be changing!) The entrance to the hot springs is free of charge, there is a small fee for parking. Read more about this hidden gem here. After a quick soak, we made our way to Siena.


Scenic Roads in Tuscany

take SR 2 all the way to Siena Driving Time: 1:08 hr Driving Distance 66km

It was time to head back and see the town of Siena. Our last stop before heading back to Florence to return our rental car and take the train to Rome. It was a total of 4 hr and 30 mins driving time. Since it was broken down into smaller segments the drive didn’t feel too long. But it’s one of the most scenic drives in Tuscany!

Siena is such a cute town, we parked outside of town and spent about an hour walking around and seeing the cathedral in Siena.


Driving to Siena from Florence

total driving time 1:04 min total distance 77km

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Cathedral in Siena

Lastly, back to Florence. If you don’t want to hassle with driving and want to be driven, you can book this tour that will take care of all the driving for you and includes a wine and cheese tasting!

Or elect to drive a vintage fiat from Florence to Tuscany !


Italy Travel | Planning Guide

Where To Visit in Italy:

NORTH VS SOUTH ITALY (COMPARISON): Which region to visit?

LAKE COMO: Villa Del Balbianello (Como’s most beautiful Garden)

Things To Do in Italy:

LAKE COMO: Visiting Villa Del Balbianello

LAKE COMO: Best Bout Tours In Lake Como

Italy Tips:

DRIVING TIPS : All you need to know (rules and requirements)

Italy Itinerary:

TUSCANY: Most Scenic Drive in Tuscany


CAR RENTAL: Car Rental in Italy



The most beautiful drive is from Siena, take SS73 to SP438 and drive to Asciano. You’ll find the famous Cypress lined trees town here.

Driving around Tuscany can be challenging, especially in the more densely populated areas or during peak travel times. Tuscany has narrow and winding roads, and some of the smaller villages and towns can have limited parking options. Additionally, many of the roads can be quite steep and hilly, which can be daunting for some drivers.

That being said, if you are an experienced driver and feel comfortable navigating unfamiliar roads, driving around Tuscany can be a great way to explore the region. Just be sure to take your time and pay attention to road signs and local driving customs. It’s also a good idea to familiarize yourself with Italian driving laws and regulations before setting off.

San Gimignano (Italian pronunciation: [san dʒimiɲˈɲaːno]) is a small walled medieval hill town in the province of Siena, Tuscany, north-central Italy known as the “walled city”.

Yes if you want to explore smaller towns, no if you want to just see main towns such as Florence, Siena.

The easiest and best way to get around Tuscany is by a car or a tour.

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  1. This is a road trip that I would love to do, and maybe stay a night or two in some of the towns you mention along the way. Such beautiful countryside to drive through.

  2. I would love to go on this road trip to Tuscany, especially the cypress-lined road to Ascianco. It looks stunning.

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