4-day Tuscany road trip itinerary
Last updated on February 10th, 2026.
A Tuscany road trip is one of the most memorable travel experiences you can have in Italy.
How do I know? Because I say this as someone who’s a local and who’s also traveled much of the country by car.
And if you’re looking for an easy and realistic 4-day Tuscany road trip itinerary you're in the right spot.
I've designed this guide for anyone looking to experience the best of Tuscany by car — without visiting the larger cities.
It’s the perfect road trip for Tuscany if you want to:
- Explore the Tuscany countryside
- Avoid large tourist crowds
- Discover the best scenic drives in Tuscany
- Stay in, or close to, lesser-known hilltop towns
- Travel at a relaxed pace
This Tuscany itinerary covers UNESCO-protected landscapes, ancient hot springs and photogenic roads like the cypress road in Val d'Orcia.
It'll also cover popular topics such as:
- What are the best places to visit in Tuscany?
- What to see in Tuscany
- Is Tuscany good for a road trip?
- Is it hard to drive in Tuscany by car?
Whether you're a first-time, or seasoned Italy, traveler, use this guide to travel Tuscany and to plan your Italy trip.
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Why choose a road trip through Tuscany?
Tuscany is a region that was made for road trips.
Winding roads lined with cypress trees make you feel like you’re driving through a real-life painting.
Add to this the romantic hilltop towns and medieval villages that have retained much of their original features.
While trains and buses work well for visiting larger cities, seeing the smaller towns by car is more convenient.
Renting a car gives you the freedom to take spontaneous detours to little hamlets, vineyards or viewpoints. Most notably, hiring a car is a big timesaver if only visiting Tuscany for 4 days.
4 things you need before embarking on a Tuscany road trip
1. A valid driver’s license and international driving permit
2. A GPS or international cellphone plan (cell coverage is good but it can be intermittent, not just on quiet country roads).
3. Patience for narrow roads and
4. A small rental car is more practical.
What makes this itinerary special?
Unlike other Tuscany road trip itineraries that squeeze in cities like Florence and Siena, this route focuses on smaller Tuscan towns.
You’ll get to see plenty of postcard-worthy landscapes — without the tour groups.
Each day balances sightseeing with spontaneous exploration. And I'll be adding my two cents as a local to bring you real local insight.
This itinerary may not be the best route for a Tuscany road trip but the truth is, no route is. My intention is that you use this as a loose guide to plan your perfect itinerary for Tuscany.
What you’ll find in this road trip itinerary for Tuscany
- Day-by-day breakdown of a 4-day Tuscany road trip
- Recommended hotels and agriturismos (farm stay)
- Restaurant tips for regional specialties
- Directions for scenic driving routes
- Travel tips for driving in Tuscany
- Extra stops if you want to expand your road trip
What you won’t find in this Tuscany road trip itinerary
I won’t be covering Florence, or other cities in Tuscany, in this itinerary.
Florence warrants its own itinerary (see 2 days in Florence) especially if it’s your first time visiting. What's more, a car isn’t necessary to visit the city.
Much of the center is accessible by foot and public transport will take you to other parts around Florence.
🎥 Watch: Tuscany road trip you have to do once in your life
How many days do you need in Tuscany?
How long do you need in Tuscany depends on the type of trip you plan to take.
Vacations can range from a Tuscany city break to a 7-day trip including a mix of countryside, cities and towns.
While a full week lets you dive deeper, 4 days is enough to get a satisfying taste of Tuscany’s highlights.
Why 4 days in Tuscany?
Four days is the sweet spot to embark on a road trip in Tuscany.
Three days could feel like a bit of a squeeze while 6 days on the road might lead to burnout. Instead, a 4-day trip is a good amount of time to see a mix of places in the region.
- Tuscany road trip 3 days: focus on a specific area, for example, Val d'Orcia.
- Tuscany road trip 4 days: do this itinerary as outlined.
- Tuscany road trip 5 to 7 days: add a larger city like Siena or Pisa and/or explore southernmost towns like Pitigliano.
Can you do this Tuscany road trip itinerary without a car?
As this itinerary is specifically for a road trip the straightforward answer is no.
Some of the places in this itinerary are reachable by train or bus. However, traveling by car is more practical, and time saving, to fully enjoy areas like the Crete Senesi.
The best alternative to driving in Tuscany is to book day tours. Florence is the best option as a base for choice and availability.
When is a good time to visit Tuscany?
Tuscany is a year-round destination, but good weather makes the biggest difference for the perfect road trip.
For reference, we visited in early June. We were blessed with excellent weather, blue skies and higher temperatures than usual for this time of year.
June has always been one of the best times to visit Italy and it didn’t let us down on this trip.
What to expect each season in Tuscany
Spring (April to June): wildflowers, full vineyards and sunshine (towards late May and June). Temperatures are warm and pleasant. There are fewer crowds than summer.
Autumn (late September to October): one of the best times for a Tuscany road trip. The harvest season has sunshine, mild weather and a soft, golden light you find in autumn.
Summer (July to August): very hot, busy and expensive. Best avoided unless you love heat and plenty of crowds.
Winter (November to February): quiet with fewer crowds, but colder, more rainfall and limited daylight.
How I planned this Tuscany road trip
Every great itinerary needs some planning especially when planning a road trip in the fifth largest area in Italy.
When designing this Tuscany road trip itinerary, I wanted to ensure that it was:
- Relaxed, not rushed
- Located around central and southern Tuscany
- Flexible
- Centered around towns in Tuscany.
Direction of travel
This itinerary follows a north to south direction, starting from our home in Veneto, northeastern Italy going south towards Tuscany.
For many of you reading this, your trip will likely start in Florence or maybe even Rome.
Personally, I’d recommend Florence as a base given the 4-day timeframe. For one, you’re already in Tuscany and two, the journey times to the destinations mentioned throughout this itinerary are shorter.
Daily driving time breakdown
The beautiful thing about driving through Tuscany is that it’s not about speed but enjoying the journey.
On most days, we drove around 90 minutes, give or take, and made impromptu stops whenever we wanted.
| Day | Route | Approximate drive time |
| 1 | Barberino di Mugello to Barberino Val d'Elsa. Barberino Val d'Elsa to Certaldo | 45 mins (39mi/62km)/21 mins (10mi/16.3km) |
| 2 | Barberino Val d'Elsa to San Gimignano. San Gimignano to Monteriggioni. Monteriggioni to San Quirico d'Orcia. San Quirico d'Orcia to Pienza | 24mins (10mi/15.9km) / 36mins (16.2mi/26km) / 1hr 6mins (40mi/64km)/ 12mins (6mi/9.6km) |
| 3 | San Quirico d'Orcia to Asciano and to Crete Senesi. Crete Senesi to San Quirico d'Orcia | 35mins (19mi/30km) / 38mins (22mi/36km) |
| 4 | San Quirico d'Orcia to Bagno Vignoni. Bagno Vignoni to Cappella della Madonna di Vitaleta. Cappella della Madonna di Vitaleta to Montalcino. Montalcino to Volterra | 8mins (3.3mi/5.3km) / 19mins (5mi/8km) / 30mins (13mi/21km) / 1hr 46mins (62mi/100km) |
Map: 4-day Tuscany road trip itinerary
Tuscany road trip itinerary – day 1, 2, 3 & 4
Day 1 – Barberino di Mugello, Barberino Val d’Elsa and Certaldo
I won’t go into detail of the first part of our road trip journey from Veneto to Tuscany. It bears little relevance to this Tuscany road trip itinerary and much of it took place on the highway.
In brief, the drive from our home in Veneto to the periphery with Tuscany took around 2hrs 40mins. This included one stop at the Autogrill service station for coffee and brioche.
Barberino di Mugello
Our first, and unplanned, stop of day 1 was at the small, and very residential, town of Barberino di Mugello.
The town technically sits within the Metropolitan City of Florence, but it feels like a world apart from the capital.
We'd no valid reason for choosing to stop at Barberino di Mugello. It was simply on route to our first destination in Tuscany plus it was almost lunchtime.
Our then 11-month-old daughter was due for her lunch and my husband and I wanted somewhere with few tourists.
And we got our wish with Barberino di Mugello.
The small Tuscan town has several attractions to its name, the most notable being the Barberino Outlet.
Located just outside the town, the outdoor mall has a mix of high-end Italian and international stores at discounted prices.
As we’d no intention of going shopping we focused our attention on the town center. Local, residential and not a tourist in sight — apart from us — we set our sights on the main piazza.
Lunch in the piazza
The public square is filled with a variety of shops, bars and restaurants. With not a ton of choice (and an increasingly agitated and hungry baby) we chose L’Oste in Piazza.
Situated beneath the portico of Piazza Cavour, the rustic osteria serves a range of traditional Tuscan dishes.
I chose paccheri with leeks and sausage while my husband opted for the tagliatelle with cinghiale (wild boar). Paying less than 30 for two people (with drinks) we ate well and enjoyed our time there.
Would I recommend Barberino di Mugello as a standalone destination in Tuscany? Probably not. It’s a nice, little town if you prefer to avoid the crowds of Florence but there’s little to see.
Recommended time: 1 hour (not including shopping)
L’Oste in Piazza – Piazza Cavour, 10
Barberino Outlet – Via Meucci
Barberino Val d’Elsa
Our next destination, and the first real stop of our Tuscany road trip, was to another Barberino, Barberino Val d’Elsa.
The tiny village is also part of the Metropolitan City of Florence despite being around 24mi (38km) away.
Why Barberino Val d’Elsa?
Our main intention wasn’t to visit Barberino Val d’Elsa but to explore the surrounding area. It’s why we chose to stay at a nearby agriturismo called Borgo Poneta.
An agriturismo is accommodation (typically apartments) set on a working farm. Some agriturisimi have a restaurant, sometimes a shop, on site where they serve produce made on their land.
Many agriturismi tend to be more affordable and convenient especially if visiting Italy with a baby or young children.
An affordable agriturismo that oozes charm and has extraordinary views, Borgo Poneta is an excellent accommodation choice for this area.
For reference, our journey from Barberino di Mugello to Borgo Poneta took around 1 hour.
Certaldo Alto
After a short rest and shower break, we traveled to the last stop of day 1: Certaldo Alto.
The medieval town is divided into two parts. Certaldo basso (lower) is the modern and the largely residential part while Certaldo Alto (higher) is the medieval part.
You can reach Certaldo Alto by cable car (Funicolare di Certaldo) or car and the views are impressive from either.
Another advantage of adding Certaldo Alto to your Tuscany road trip itinerary is that it’s reachable by public transport. Trains run frequently between Firenze Santa Maria Novella train station and Certaldo making the town an ideal Florence day trip.
Step back in time
Suffice it to say, Certaldo Alto is where you’ll want to explore. Red brick palaces, panoramic towers and impressive views characterize the medieval town.
We spent our time in Certaldo Alto exploring attractions like the home of renowned author, Giovanni Bocaccio, and Palazzo Pretorio. The 12th-century palace at the top of Via Giovanni boasts historical frescoes and a peaceful courtyard.
Two highlights that stood out for us were the views from Via Rivellino and the medieval dinner. It just so happened that the town was a hosting a dinner the same evening of our visit.
The long dining tables covered in red fabric and laden with medieval-style tableware fit in perfectly with the town.
It was an unexpected and unique way to end our visit in Certaldo Alto.
Recommended time: 2 hours
Bistecca alla Fiorentina for dinner
We ended our first evening with a dinner of the classic bistecca alla Fiorentina. A must-try when in Tuscany (for meat eaters), it’s a delicious cut of steak that’s juicy, moist and packed with flavor.
A word of warning: the bistecca alla Fiorentina is always served on the rarer side. While asking for a more 'well done' steak is one of the things not to do in Italy restaurants will accommodate your request.
Our restaurant for the evening was Osteria Enoteca i Vignaioli. A 20-minute drive from Certaldo, the rustic-style restaurant was the ideal setting for our Tuscan steak.
Osteria Enoteca i Vignaioli, Via Michelangelo, 1, Barberino Tavarnelle
Day 2 – San Gimignano, Monteriggioni, San Quirico d’Orcia, Pienza
Breakfast in Barberino Val d’Elsa
Day 2 of our Tuscany road trip itinerary began with breakfast in Barberino Val d’Elsa.
A historic center consisting of a principal street with medieval houses and modern restaurants, the village is tiny.
Unfortunately, the only place open at the time was a local bar (outside the center). With friendly staff and decent choices, we had a quick breakfast outdoors.
The views are beautiful from the village and it's worth stopping by if in the area.
Recommended time: less than 1 hour.
San Gimignano
Our first ‘proper’ stop of the day was the hilltop town of San Gimignano.
The UNESCO World Heritage Site wasn’t originally on our Tuscany road trip itinerary. However, we knew we had to visit when we realized how close the town was from where we were.
San Gimignano draws you in long before you arrive. Its iconic medieval towers and surrounding walls are a majestic sight from a distance.
The ‘Manhattan of the medieval ages’ 14 of the original 72 towers remain. One of the towers, Torre Grossa, is open to the public to see the views from the top.
While we didn’t get to climb the tower (a little difficult with a stroller) we explored the others in town.
Exploring every corner
We spent much of our time in San Gimignano walking through the town, piazza and enjoying the impressive views.
Via San Matteo is a main street lined with a mix of artisan shops, eateries and vendors selling wine.
Speaking of wine, you can’t visit the town without trying the local Vernaccia di San Gimignano. The white wine was the first to be awarded DOCG status — the highest classification for Italian wines.
Prices are reasonable and it’s the perfect souvenir (for wine enthusiasts) to remind you of your time in San Gimignano.
Other highlights in San Gimignano
The end of Via San Matteo leads to two main landmarks in San Gimignano.
The first is Piazza delle Erbe, which is where you’ll find the town’s cathedral. If a visit to the Duomo interests you, consider buying tickets in advance to avoid waiting in any long lines.
A little further ahead is Piazza della Cisterna. The large, photogenic square is filled with more restaurants, hotels and plenty of tourists.
While there are many different shops and services in the piazza, there’s one place that steals the show.
Gelateria Dondoli is an award-winning gelateria best known for using local ingredients and influences from San Gimignano.
It won’t be surprising to read that lines for Gelateria Dondoli were long, and that was before 11am.
Unfortunately, we didn’t get to try the gelato so I can’t tell you if it was any good. But going by the reviews and impressive accolades it might be worth lining up for. I’ll leave it for you to decide.
Things to know before visiting San Gimignano
San Gimignano was one of the more touristy towns that we visited on this Tuscany road trip. Parking fills up quickly as do the historic streets in town. That said, come earlier to beat the crowds or later in the afternoon.
There's an elevator available for visitors with mobility issues or with a stroller (like us). We parked at a public parking lot on Via Bagnaia and it was a 1-minute walk to the elevator.
Visit Parco della Rocca. The ruin of a medieval fortress has a peaceful park and panoramic views.
If you really want to visit San Gimignano but don’t plan to hire a car, consider joining a tour.
The following tours make perfect Florence day trips.
- Pisa, Siena and San Gimignano day trip with lunch - from Florence (11 hours)
- Pisa, Siena, San Gimignano and Chianti experience – from Florence (12 hours)
- Florence day trip with free time in San Gimignano and Siena (9 hours)
- Pisa, Siena, San Gimignano and Chianti day trip – from Florence (12 hours)
- San Gimignano, Siena, Chianti and wine tasting lunch – from Florence (11 hours)
Recommended time: 3 to 4 hours
🎥 Watch: jaw-dropping towns in Tuscany, Italy
Lunch in Monteriggioni
From San Gimignano we continued our Tuscany road trip towards the southern part of the region.
Like Barberino di Mugello the day before, we wanted to factor in a lunch stop for my baby, and for us.
Unlike Barberino di Mugello, the next stop on our trip was to a place we’d already been before.
It was approximately a 35-minute drive from San Gimignano to the medieval fortress village of Monteriggioni.
Consisting of one piazza and an intact circular wall, Monteriggioni looks almost exactly as it did in the 13th century.
On this road trip however, we’d no intention of entering, or eating anywhere, inside the fortress walls. Instead, our eyes were set on a cozy, low-key restaurant that confusingly has ‘bar’ in its title.
A simple and aromatic lunch
Bar dell’Orso is one of my favorite places to eat rustic, traditional Tuscan meals. They serve simple, yet flavorsome, dishes, big portions and reasonable prices.
I ordered a simple spaghetti with a tomato and aglione (mild garlic) sauce. Aromatic, saucy and perfectly covering every strand of spaghetti I was in foodie heaven.
Bar dell’Orso, Via Cassia Nord, 23, Monteriggioni
Onto San Quirico d’Orcia
The next leg of our journey was the longest of day 2 with a drive time of around 1 hour.
From Monteriggioni, we departed for the town of San Quirico d’Orcia, located in the picturesque Val d’Orcia.
Like day 1, our destination wasn’t San Quirico d’Orcia but our accommodation for the next two nights, Agriturismo il Poderuccio.
Located down a long and dusty road, the agriturismo is an ideal spot if looking for a quiet Tuscan retreat. The views from the property are pretty spectacular too.
Last stop: Pienza
We made a late call to the last place of day 2 on our Tuscany road trip itinerary at Pienza.
After a short 20-minute drive we arrived in the medieval town. The sun was still out, the temperature was perfect and the day crowds had long departed.
One of the most enchanting small towns in Tuscany I dare you not to be instantly enamored. Commissioned by Pope Pius II, Pienza is architecturally perfect and truly charming.
What we enjoyed most about Pienza was finding surprising viewpoints that led to the most spectacular views.
Two that particularly stood out were the viewpoints by the Duomo (cathedral) and Palazzo Piccolomini (museum).
As you continue walking towards the Tuscan landscape behind the Duomo, you’ll find the restaurant Idyllium. They have outdoor dining with unbeatable views, but we couldn’t experience this as we didn’t have a booking.
Instead, we sat down to a sublime dinner at Ristorante il Rossellino. I had the guancia brasata (braised beef cheek) with potato puree that melted in the mouth. Great service, food and atmosphere and I would eat here again without hesitation.
Ristorante il Rossellino, Piazza di Spagna, 4, Pienza
Recommended time: 2 to 3 hours
Day 3 – Asciano, Crete Senesi, Agriturismo Baccoleno, San Quirico d’Orcia
Day 3 of our Tuscany road trip took us to the town, and surrounding lands, of Asciano.
If I’m being completely honest, we didn’t make the journey to Asciano to see the actual town.
Instead, I’d my eyes, and heart, set on seeing the famous curved roads of Tuscany lined with superior cypress trees.
They weren’t easy to find, and it took a bit of research, and driving, before we finally saw a glimpse.
Asciano historic center
There's a noticeable difference the second you start walking around Asciano’s historic center: there are few to no tourists.
Maybe it was the day we visited (Monday) and the time of day (12:15pm) that explained the few people around.
Though we saw some attractions like Cassioli Museum and Basilica di Sant’Agata, there’s not much to do in Asciano.
Personally, it also lacked the ‘wow’ factor that we found in San Gimignano and Pienza.
Asciano is a town for its locals and rightly so. If you want to see towns more like Pienza and Certaldo, Asciano may not be the right choice.
Recommended time: 1 hour
Driving around the Crete Senesi
After a quick lunch in Asciano we began our afternoon drive to see the iconic winding cypress-lined roads.
The area known as Crete Senesi refers to the landscape in this part of Tuscany. One of the best places to visit in Tuscany by car, it can be best described as cinematic and surreal.
Two main roads that take you through the Crete Senesi are the SP60 and the SP438.
A very helpful lady at Asciano’s Tourist Information Center armed us with maps and tips to seeing the best spots.
Beautiful points in the Crete Senesi
Famous curved road lined with cypress trees
From Asciano, type in Agriturismo Baccoleno to your GPS (a tip from the lady at the tourist office). It’s a short drive from Asciano and straightforward too.
However, one important thing she forgot to mention is that the road leading to Agristurismo Baccoleno isn’t open to the public.
Guests, and of course workers, have access to enter the famous curved road. For the rest of us mere mortals we can only admire it from afar.
Luckily, there’s a panoramic point where it’s safe for cars to stop and take photos/videos. Type in ‘punto panoramico Asciano’ and it should take you to the right spot.
Alternatively, consider booking a night or two at the gorgeous 4-star Agriturismo Baccoleno.
Apartments embrace a classic Tuscan style with beamed ceilings, wrought iron beds and views overlooking the Crete Senesi hills.
Beautiful cypress tree-lined road
Another scenic and peaceful place close to Asciano is the road leading to the 4-star Borgo Beccanella.
It doesn’t have the dramatic curve like Agriturismo Bacccoleno but the road is accessible to everyone.
Other highlights of the Crete Senesi
I lost count, and location, of the number of unbelievably beautiful scenes we saw on our drive.
As my photos show, the whole area is photogenic and it was near impossible to take a bad picture.
Our journey back to San Quirico d’Orcia included a short visit to the Abbazia di Monte Oliveto Maggiore. A monastery dating to the 12th century, we spent a short time admiring the historic paintings, frescoes and the garden.
Abbazia di Monte Oliveto Maggiore, Monte Oliveto Maggiore, Asciano
We also passed by the small towns of Chiusure, San Giovanni d’Asso, Montisi and Castelmuzio. While I’d like to write that we stopped to see them all, the truth was we were tired.
Recommended time: 1 to 2 hours
Best scenic drives in Tuscany in the Crete Senesi
SP60
The route from Asciano to San Giovanni d’Asso passes by rolling green and while hills, sun-bleached ridges and tiny villages.
SP438
The SP438 leads to Siena as well as Via Lauretana Antica, one of the most legendary roads in Tuscany.
Tips for driving Crete Senesi
- Drive slowly and look out for panoramic points where you can safely stop and park.
- Consider downloading a paid-for app like Waze (see ‘Best Italy apps’) before embarking on your Tuscany road trip. We relied on the popular, and free, maps app (starts with a ‘G’) and it failed us umpteen times. It also didn’t show us the routes between towns that the locals advised us to take. For reference, these roads were all accessible.
- Avoid visiting when it’s raining. It might sound obvious, but sunshine makes a huge difference to seeing the Crete Senesi.
Dinner in San Quirico d’Orcia
After a much-needed shower and rest we stayed local for our last night in San Quirico d’Orcia.
It was our first chance to explore the town’s historic center, and we were not disappointed.
There’s a stark contrast between the modern San Quirico d’Orcia and the medieval center. What this means is that it's impossible to miss the archway entrance.
Via Dante Alighieri is the principal street that runs throughout the center. It's lined with beautiful Tuscan-style houses, shops, bars and restaurants.
It's a small, but pretty, town center with several attractions to its name. They include:
- Collegiata di San Quirico d’Orcia – a striking Romanesque church with three different portals.
- Horti Leonini – 16th-century Renaissance gardens in the center of the town
For dinner, we sat down to a traditional Tuscan meal at the superb La Bottega di Ines. Bearing the same name as our daughter it was a no-brainer that we had to eat there.
With delicious food, drinks and service it was the perfect ending to our time in San Quirico d’Orcia.
Recommended time: less than 2 hours
Day 4 – Bagno Vignoni, Cappella della Madonna di Vitaleta, Montalcino, Volterra
The last day of our Tuscany road trip itinerary included a spa town, hilltop wine capital and the beautiful Volterra.
After bidding addio to Agriturismo il Poderuccio and San Quirico d’Orcia, we made the short 8-minute drive to Bagno Vignoni.
One of the best Tuscany thermal towns, Bagno Vignoni has a massive ancient thermal pool at its center.
The peaceful, car-free village makes a beautiful short stop or an ideal spa getaway.
Want to make it a spa weekend? Check into nearby hotels like Albergo Le Terme and ADLER Spa Resort Thermae.
During summer, the public springs at Parco dei Mulini and at Antiche Terme Romane Libere make the perfect cooling spots. Open to the public, don’t follow our lead by not bringing your swimming costumes.
Recommended time (without bathing or dining): Less than 1 hour
The most beautiful chapel
Our next stop was at one of the most beautiful chapels in Tuscany, Cappella della Madonna di Vitaleta.
Around a 20-minute drive from Bagno Vignoni, the tiny, secluded chapel is a striking sight in the Tuscany countryside.
The parking lot fills up quickly so either come early or in the late afternoon before sunset. Another point worth mentioning is that it’s around a 10-minute walk from the parking to the chapel.
Closed at the time
To our dismay, we found that that chapel, and the Vitaleta Gourmet cafe, were both closed despite it being June.
Despite this, we’re glad we visited. We enjoyed seeing the chapel up close and the scenery was out of this world.
Recommended time: 30 minutes or less (if the chapel and cafe are closed)
Montalcino
Our penultimate stop of our Tuscany road trip itinerary was the hilltop wine capital of Montalcino.
A straightforward 25-minute drive later from the chapel and we arrived mid-morning.
The town is best known for its namesake Montalcino wine, Brunello di Montalcino — one of Italy’s finest (and priciest) wines.
With noticeably more tourists and foreign accents around, Montalcino had a similar vibe to San Gimignano.
Of all the towns we visited on our Tuscany road trip, Montalcino was the most challenging with a stroller.
We tackled several sloped, and cobblestone, streets that gave my husband and I a good workout — without wanting one.
We didn’t get to try some of the best things in Montalcino, like climbing the impressive fortress (Fortezza di Montalcino). Nor did we get to try a Brunello vineyard tour and wine tasting.
Instead, we settled on admiring the fortress from afar and explored the town as much as we could.
Lunch in Montalcino, but not the center
For lunch, I found a beautiful restaurant that also doubles as a cooking school. Locanda Demetra & Montalcino Cooking School is a short drive from the center and perfect for an outdoor lunch.
The restaurant has an impressive garden on which it grows much of its produce. We feasted on delicious homemade ravioli and hummus with roasted vegetables and freshly baked bread.
We were very lucky to get a table despite not having a booking. If you plan on visiting Montalcino I promise you won’t be disappointed dining here.
Locanda Demetra & Montalcino Cooking School, Podere La Buca, 221, Montalcino
Recommended time: 2 hours
Final stop: Volterra
The last, and longest leg of our Tuscany road trip itinerary was to the hauntingly beautiful town of Volterra.
Our baby took advantage of the 1hr 45min drive from Montalcino to Volterra by sleeping for most of the journey.
Hands down one of the most beautiful places in Tuscany, Volterra will instantly put a smile on your face.
The Etruscan town perched above the Cecina Valley is striking at first glance. Volterra is known for several attractions which include:
- The Roman Theatre – one of the best-preserved in Italy
- Palazzo dei Priori – the oldest town hall in Tuscany
- The Etruscan Gate (Porta all’Arco) – an archway dating to the 4th century BC
Dinner and a dreamy sunset
After a brief shower and refresh we began our exploration of Volterra Tuscany.
The warmer than usual early June temperatures were ideal for our evening walk. From our hotel near the center of Volterra, Hotel San Lino, we strolled slowly through the town.
We paused to admire the architecture and to soak up the ambience in Piazza dei Priori before moving on.
Though Volterra was noticeably busy it never felt like it. Its historic center is large and filled with many spaces to explore away from the crowds.
Our ‘dinner’ that evening was more of an apricena at a grocery store called Podere al Centro. We shared a charcuterie board of various hams with a side order of pecorino and two glasses of red wine.
Podere al Centro, Via Antonio Gramsci, 5, Volterra
We ended our Tuscany road trip in Volterra in the best way possible, with a fantastical Tuscan sunset.
A short walk from the center is the viewpoint from Viale dei Ponti. It's the perfect spot to perch on the brick wall and to admire the Volterra views and sunset.
If you’re wondering ‘is Volterra worth visiting’ the answer is a resounding yes. The history, the town, the food and the views all live up to the hype.
Recommended time: 2 to 3 hours
Other destinations to add to your Tuscany road trip itinerary
The beauty of this Tuscany itinerary is that you can customize it as you like.
As I said at the beginning, we purposefully avoided larger cities like Florence, Siena and Pisa. Should you prefer to swap Volterra or Asciano for one of these feel free to do so.
From Volterra, there’s also the option to discover more of western Tuscany like Livorno and Lucca further north.
If an island in Tuscany sounds appealing, you may want to add Elba Island to your itinerary. It’ll involve some extra planning but will make for a memorable vacation.
Other alternative places in Tuscany that might interest you are:
- Chiantigiana Road (Via Chiantigiana) – road that travels around the Chianti area from Florence to Siena.
- Cortona – the town that featured in the film ‘Under the Tuscan Sun’
- Montepulciano – a town famous for its namesake wine
Tuscany driving tips
Compared to other regions in Italy, it’s not hard to drive in Tuscany by car. However, there are some things to be aware of before departing on your road trip.
Smaller cars are more practical
While much of the region can cater to larger vehicles, smaller cars are superior in many ways. Parking and maneuvering are much easier as is driving through narrow roads in Tuscan towns.
Avoid ZTL zones
‘Zona Traffico Limitato’ areas are in nearly every historic center in Tuscany and the rest of Italy. Drive into one, even accidentally, and you risk getting a steep fine.
Have an international driving permit
Make sure to get an international driving permit alongside your regular license. Rental agencies won't likely ask to see it, but the police might. Without one you risk incurring a fine.
Grab one from your country’s automobile association (AAA in the USA) before flying to Italy.
Check your tires
Something rarely mentioned when discussing a Tuscany road trip is the potential damage to tires.
Stones can puncture tires if driving too fast along the dusty country roads in Tuscany. It happened to us on our trip, and we spent an hour getting it fixed at a local tire shop.
Prepare for toll roads
Tuscany isn’t full of highways compared to other Italian regions. However, it’s worth being prepared once you exit the highway (autostrada) with your payment (coins or a contactless card).
There are two types of lanes, Telepass and cash, of which you can go to either. As locals, we’ve a paid Telepass that means we drive straight through the toll barriers.
Tuscany travel tips (straight from a local)
Travel essentials
Have a SIM card, or purchase an eSIM, that allows you to use GPS on your mobile. It’s essential to navigating the roads in the countryside in Tuscany.
Have cash on hand. It's helpful for paying for smaller items like a coffee as well as for paying for toll roads.
Comfortable shoes. Ladies, leave the high heels to the local women and wear suitable walking shoes. Medieval Tuscan towns have sloped roads and cobblestone streets.
What to pack. Pack according to the season of when you plan to visit. What to wear in Italy as a local outlines clothing and useful items to pack month by month.
Beware of limited traffic zones (ZTLs)
As already mentioned, be on the lookout for ZTLs.
You’ll typically see signs before entering a town center.
When the ZTL is activated, you’ll notice that few cars will enter these areas. These will likely be residents and have permits.
ZTL areas are enforced with cameras and will capture any cars without a permit. If you think nothing will happen, think again. Your rental company will bill you weeks later for any violations.
FAQs
What is the best time of year to go to Tuscany?
September to early October for fewer tourists, cooler temperatures and the wine harvest.
How do I plan a Tuscany road trip?
Choose a region (like Val d’Orcia) for 4 days, book accommodations and rent a smaller car.
Where should I stay when visiting Tuscany?
Pienza, Montalcino or San Gimignano have scenic views and easy day trip access.
Is driving in Tuscany difficult?
It’s not difficult but there are some challenges. Use a GPS, avoid ZTLs and park outside historical centers.
What is the best way to get around Tuscany?
Driving is the best mode of transport. A car is more practical for visiting smaller towns and lesser-known spots. Public transport is limited in this regard.
What are the best scenic drives in Tuscany?"
The SP146 between Pienza and San Quirico d’Orcia, Via Chiantigiana in the Chianti region and the Crete Senesi south of Asciano are beautiful drives.
What thermal towns are worth visiting in Tuscany?
Bagno Vignoni is a unique town with an antique thermal bath.
Where is the chapel everyone photographs in Tuscany?
Cappella della Madonna di Vitaleta, near San Quirico d’Orcia.
What is Montalcino famous for?
Montalcino Brunello wine and its medieval fortress.
What are your thoughts on this 4-day Tuscany road trip itinerary? If you have any questions, leave me a comment or send me a DM on Instagram.
Disclosure: This post may contain affiliate links, which means I may receive a commission if you click a link and purchase something that I’ve recommended. Thank you for your support.
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Hello!
Its a wery intrestedt blog you have. So nice to Reed.
I’vant to give may son a Tripp like this in June. He have his 40 yer celebration. He loves Italy and talks a lot of going to see this area again. We have Ben in San Quirico d’Orcia and Randicofani, ther before. He liks vine. Can you recommend som other place in stedt of thes to a mention for you! We like to stay at the farm. 4 star maby.
im sorry about may english.
thank you.
best regards Anita
Hello Anita, thank you so much for your comment. I will send you some recommendations on email 🙂
Thank you for sharing a Tuscany road trip that goes to some of the smaller, less touristy towns! It's neat to get to explore some places that are off the beaten track.
It's my pleasure! It's a beautiful region to explore by car
This Tuscany road trip itinerary is so helpful! I really liked the mix of towns, food, and views, so would love to explore Tuscany someday.
I hope you do, it's such a beautiful part of Italy
I've never been to Italy before but it's on my holiday list. This place looks amazing. I need to go here
Come and visit us one day!
I absolutely love Tuscany and have done several road trips through the region—it's truly a dream to drive those winding roads lined with cypress trees. This 4-day itinerary is full of helpful tips, especially for avoiding the big city crowds and focusing on charming hilltop villages. Val d’Orcia and the scenic drives in that area are some of my favorite spots in Italy. I completely agree—Tuscany is made for slow, scenic travel and spontaneous vineyard stops!
Thank you Agnes! I'm glad you've already experienced this, Tuscany is a living dream!
I enjoyed reading through your blog post especially because of fond memories of Tuscany from over 20 years ago! We drove a tiny Fiat Punto (2 door) over the rolling hills of Tuscany and enjoyed San Gimignano and Siena too along with lots of Chianti. We did a totally impromptu trip without any prior bookings ( I cannot do that now) and enjoyed Tuscany with our two daughters. We loved this place and thanks for your tips. 🙂
Aw I'm glad this brought back fond memories! It's so beautiful to see as a family
Roadtrips are always a great idea! Happy to know that Tuscany is a year-round destination, but I just like you -- I think May or June is going to be the best. Thank you for sharing this detailed itinerary. I am keen to explore the medieval town and just step back in time.
Glad you enjoyed it!
Hiring a car and driving yourself around a country is the best way to discover hidden gems and to get to places less frequented by tourists. I don't have an international driving permit so that would be the first step for me.
It's important to get one so you can do this incredible road trip!
I'm such a nervous driver. I'm not sure I could do it, but I'd love to be a passenger on this kind of road trip. 🙂
I understand that, there are tricky parts but it's manageable!
Thanks so much for this very comprehensive and informative guide to traveling in Tuscany. I will definitely put it on my bucket list, although I will probably go with a friend because I am scared of driving on narrow windy little roads in a tiny car.
You're very welcome! I totally understand how you feel I am the same 😀
I can't thank you enough for the amazing guide. I go to Tuscany every few years, I love it...Your guide is very thorough and very very helpful. Thank you so much.
It's my pleasure! I'm glad that you love Tuscany as much as we do
My cousin and I love road trips so much. I hope we can explore Tuscany someday all together
I really hope so too!
Tuscany has always appealed to me. The scenery in particular looks stunning especially with those beautiful cypress trees!
It really is like that! You will love this itinerary
Thanks for putting this 4-day Tuscany road trip itinerary together. Will be super helpful for me in the future.
It's my pleasure, I hope you visit Tuscany one day
What a lovely itinerary for a trip to Tuscany you certainly had a great trip. I am saving this for when I am feeling confident about travelling again
Thank you, it was a wonderful trip! I hope you feel confident soon x
That’s it. I’m sending this to my husband right this second. This will be our next family road trip, no questions asked!
I'm happy to read that!