Tuscany: birthplace of the Italian Renaissance and home to beautiful rolling hills, hidden vineyards, ancient hilltop villages, and mouthwatering food. Spend days of an Italy itinerary winding your way through the Tuscan countryside, strolling the cobbled streets with a gelato in hand, and stocking up on local wine and pecorino cheese. Discover all the hidden gems this stunning corner of Italy offers with our ultimate 5-day Tuscany road trip itinerary.
Our Must-do Tuscany Itinerary
We think the easiest way to see this incredible region is by renting a car, giving you total freedom to change your trip as you go. Nothing beats a road trip through Tuscany with the windows down and the sun on your face, discovering new and unexpected delights around every corner.
We’ve crafted this Tuscany itinerary to give a good mix of cities, nature, and unique experiences — all doable in five days!
Tip: If you have more time, discover the underrated neighboring region of Umbria (just as impressive but with fewer crowds!).
We recommend to rent a car in Italy through Sunny Cars with free cancellation and insurance included. Book your rental car here.
Florence
You can pack a lot into one day in this relatively small but beautiful city, famed for its incredible architecture, delicious food and wine, and fascinating art culture.
You can’t visit Florence on your Tuscany road trip without seeing the iconic Cattedrale di Santa Maria del Fiore, one of the world’s biggest cathedrals, with a stunning white, pink, and green marble exterior.
The Cathedral also has one of the world’s largest domes, which you can access for an incredible city view. See tickets and availability here
From here, head to the Arno River to cross Florence’s oldest bridge, the Ponte Vecchio. This bridge is famous for being lined with jewelry shops, so it’s a shopper’s heaven! If you have time, allocate a few hours to also explore the quieter neighborhoods on the other side.
Now it’s time for food! You can spend days discovering all the city’s foodie spots but start with the famous panini from All’Antico Vinaio. Afterward, grab a creamy gelato from Gelateria La Carraia, with their unusual flavors (see all options here). There’s even ricotta cheese and pear!
End your day with a delicious plate of fresh pasta at Trattoria San Pierino, which was one of our favorites on the trip! We’re vegetarian, but if you’re a meat eater, look out for ‘Pappardelle al cinghiale’, a typical Florence pasta dish with wild boar ragu. Check out all the must-try traditional foods in Florence here.
Where to Stay in Florence
Florence in Tuscany has plenty of accommodation options depending on your budget and style. We’d recommend hotels in the Santa Croce neighborhood, as it’s close to the center and has a lively cafe and bar culture.
Pisa
Pisa is another small but mighty city that makes for a relaxed day of wandering. Don’t miss the famous Leaning Tower of Pisa for your iconic photo as a memory of your road trip through Tuscany. However, don’t miss out on exploring the other beautiful buildings in the same square.
For example, the Camposanto, the Baptisterium, and the intricately designed Romanesque Cathedral. The pedestrianized space is a lovely spot to rest your feet for a while. We also found it the perfect spot to sunbathe on the grass and take in the stunning architecture.
Book a guided tour that includes entrance to the Baptistery, Cathedral, and Leaning Tower.
Next, head to the ancient street Borgo Stretto for the best shopping in Pisa! This beautiful street is lined with beautiful colored townhouses, making for a picture-perfect shopping experience.
From here, get lost amongst tiny alleyways and pretty squares as you search for a delicious spot for lunch or dinner. Pisa often has excellent evening events, so check out this handy event calendar before you go.
Where to Stay in Pisa
If you don’t have much time, we recommend staying in the Santa Maria area, which is very central. However, Pisa is small enough that most places are within a reasonable walking distance. Choose accommodation in the San Giusto neighborhood if you’re on a budget.
Tip: We stayed right next to the Leaning Tower of Pisa, which was such a unique experience. See availability for our hotel here.
Day 2 – Siena, Tuscany
This charming and atmospheric city, with its steep, winding, cobbled streets and dusty-colored houses, is a must-see on your Tuscany itinerary!
Start your day in the Piazza del Campo, a lovely shell-shaped square, before a short walk to the Duomo di Siena. This stunning cathedral was uniquely built using black and white striped marble and has beautiful frescoes inside.
From here, get lost in the winding streets, explore the grand Palazzo Pubblico, and discover beautiful hidden corners. We recommend finishing off the day with a delicious dinner at Osteria Permalicoa. (Here are some typical dishes from Siena you should try!)
The Elsa Trail: Highlight of your Tuscany Itinerary
If you have more time on your Tuscany itinerary, escape the bustle of Siena by taking a hike along the peaceful Elsa Trail. Conveniently, it’s located just a 30-minute drive from the city.
Hike this picturesque trail that takes you through verdant greenery to some of the bluest water we’ve ever seen! At the end of the path, you’ll be rewarded by the beautiful Diborrato Waterfall, where you can cool off after your walk.
San Gimignano, Tuscany
We combined our visit to the Elsa Trail with a trip to nearby San Gimignano, a small medieval village known as the ‘Manhattan of the Middle Ages’ for its unusually tall towers. If you have time on your Tuscany itinerary, we recommend spending an afternoon exploring the historic town with its pretty streets and squares.
Additionally, don’t miss out on trying ‘The World’s Best Gelato’ at Gelateria Dondoli — this totally lived up to the hype!
How to get from Florence / Pisa to Siena
It is two hours from Pisa and one hour from Florence to reach Siena by car. However, we recommend selecting the option ‘avoid highways’ on Google Maps, which will direct you along the longer, windier routes. Taking these smaller roads allows you to see all the incredible natural beauty of Tuscany.
There are fairly frequent trains and buses from both cities if you don’t have a car on your Tuscany itinerary.
Where to Stay in Siena
If you’re only staying for one night in Siena, stick to the city center (around the Torre del Mangia), so you are close to all the historic landmarks, bars, and restaurants. This was our hotel
Alternatively, if you want to get back on the road early the next day, book countryside accommodation within easy driving distance of the city.
Day 3 – Pienza or Montepulciano
Both these beautiful hilltop towns are good options to add to your Tuscany itinerary, particularly as they’re only 20 minutes apart. Montepulciano is slightly bigger and offers more options in terms of places to eat and wine tours. Alternatively, for a more relaxed destination, choose the more peaceful Renaissance town of Pienza.
Also check out our 7-day Italy itinerary
Pienza: Must-see on a Tuscany road trip
Unusually, this small village perched on a hill is famed for its pecorino cheese. As big cheese lovers, we couldn’t miss this town, and it absolutely lives up to expectations. In fact, if you’re following your Tuscany itinerary in September, there’s even a cheese rolling competition named Fiera del Cacio!
Located in the Val d’Orcia, the hilltop village has spectacular views of the rolling Tuscan hills surrounding it. It’s renowned for its stunning Renaissance architecture, which has led to its UNESCO World Heritage Site status.
Spend an afternoon wandering Pienza’s tiny streets and alleyways, exploring piazzas and palazzos, and admiring the views from the ancient city walls.
Tip: Pienza is also a lovely place to shop for souvenirs like cured meats, pecorino cheese, and local artwork.
Montepulciano
Known for its delicious wine, this medieval hilltop village just 20 minutes from Pienza is full of charm and history; it’s a great place to slow down on your Tuscany itinerary and enjoy all the delights this region has to offer.
Start in the Piazza Grande and climb to the top of the clock tower to get panoramic views of the village and surrounding Val d’Orcia. From here, wander through the pretty streets and browse the shops and gelaterias before heading to Veduta Panoramica or Palazzo Comunale for another spectacular viewpoint.
If you’ve got time on your 5-day Tuscany itinerary, spend the afternoon sipping wine on an underground cellar tour (book your tour here) or visit a nearby vineyard.
Alternatively, take a cooking class to learn something new and fill your belly with delicious Tuscan cuisine. This is always one of our favorite ways to meet new people and learn about the country we’re visiting from knowledgeable locals.
Extra: Food Tour at Fattoria La Vialla
Just an hour’s drive from Montepulciano, discover the ultimate food tour at Fattoria La Vialla, an eco-farm set amongst the rolling Tuscan hills. This was one of the most memorable experiences we’ve had in Italy!
You’ll dine at a long picnic table with other families and friends, enjoying up to 6 courses of delicious homemade pasta, bread, and salads. Everything is made from fresh organic ingredients and grown right there on the farm. You can even tour the estate to see how they cultivate ingredients among the verdant fields, vineyards, and beautiful cypress trees.
Send them a message to reserve your spot or to see availability for a beautiful overnight stay.
How to get from Siena to Pienza / Montepulciano
From Siena to Pienza/Montepulciano, it takes roughly an hour to drive, depending on your route. However, we recommend staying off the highway as much as possible to see the most beautiful scenery.
There are some fantastic wineries in this area, so if you’re lucky enough not to be the designated driver (usually Hannah!), take the opportunity to sample some local wines in a stunning vineyard setting.
Tip: We noticed that it’s much cheaper to buy wine directly from the winery, which is worth considering if you want to take some home with you. They will also be able to give you great local recommendations.
Where to Stay in Pienza / Montepulciano
Stay in the historic centers of Pienza or Montepulciano to be close to shops, bars, and restaurants. Alternatively, opt for a more rural setting and book an incredible agriturismo property in Tuscany. These farmhouses normally have pools and beautiful gardens, so enjoy relaxing after your road trip with a glass of wine while you take in beautiful views of the rolling Tuscan hills.
Day 4 – Saturnia and Montemerano
Spend day 4 at the wonderful hot springs of Saturnia before spending the night in one of the most beautiful villages in all of Italy: Montemerano.
Saturnia in Tuscany
Saturnia is an ancient spa town famous all over the world for its beautiful blue hot springs. The springs cascade over several levels into a series of pools, all looking out over the stunning Tuscan countryside. Our B&B was just a 5-minute walk from the baths!
Known by the Italians as Cascate del Mulino, the thermal springs are a great place to soak for a couple of hours in healing volcanic water, which is 37°C (98.6°F) all year round. It is especially lovely at sunrise or sunset when the light is beautiful and there are fewer people.
Tip: Bring shoes you can wear in the water, as the bottom of the pools can be a bit rough.
Opening Times: The hot springs are open 24 hours a day, seven days a week. If you can get here before 7 AM, you will skip most of the crowds. The best thing about Saturnia Hot Springs is that it is completely free! Find out all you need to know about visiting Saturnia here.
Montemerano
After some time enjoying the hot springs, head to the small and charming town of Montemerano for the evening (just 15 minutes from Saturnia). Spend an hour or two exploring one of the most beautiful villages in Italy; stroll along quiet streets lined with ancient stone buildings and balconies filled with pots of flowers before tucking into traditional Tuscan dishes at a local trattoria.
Our Top Tip: There are loads of great restaurant choices in Montemerano. One that looks particularly special is Dal Moro, which has stunning countryside views from its terrace.
How to get from Pienza / Montepulciano to Saturnia
Pienza and Montepulciano are located close to each other, so both have a similar driving time to Saturnia. Pienza to Saturnia is just over an hour and a half. Alternatively, if you’re leaving from Montepulciano, it is just under two hours.
It is difficult to make these routes by bus, as it requires many connections. Because of this, if you don’t have your own transport, your quickest option would be to take a taxi.
Where to Stay in Montemerano on this Tuscany Itinerary
There are a few cozy inns and apartments in the villages of Saturnia and Montemerano. However, you’ll find a wider variety of accommodation options further out, with big rustic farmhouses, vineyard hotels, and beautiful villas dotting the countryside.
Orvieto: Must see on your Tuscany Itinerary
The ancient hill town Orvieto is packed with beautiful churches and fascinating museums and temples. Plus, you’ll find a variety of cute ceramic shops (our favorite!) and a fascinating network of underground tunnels and caves.
Alternatively, if you want a more relaxing activity, just wander the pretty streets and have a few glasses of Orvieto Classico Wine over a long lunch. In many places in the city, you’ll be able to take in the beautiful hilltop views of the surrounding countryside.
Restaurant Tip: Although we sadly didn’t get a chance to visit, there’s a stunning restaurant named Ristorante Locando Orvieto (situated within an Agriturismo on the city’s outskirts). It showcases the best of Italian produce freshly grown on the farm. The views look exceptional! Book your table here.
Rome
When in Rome (!), spend the last part of your Tuscany itinerary visiting a few of the city’s most iconic sights, like the Colosseum or the Pantheon. Don’t forget to make a wish at the famous Trevi fountain!
Squeeze in a final plate of fresh Roman pasta in the picturesque Trastevere neighborhood before heading to the airport. If you have more time on your Tuscany road trip, we recommend spending 2-3 days here, enjoying all the top things to do in Rome.
How to get from Saturnia to Rome
It is a 3-hour drive from Saturnia to Rome if you go via Orvieto. This route means you can experience a taste of Umbria, the region to the east of Tuscany; we think this area is just as beautiful, and there are definitely fewer crowds. If you can, spend a few nights here, too!
If you are traveling by public transport on your Tuscany itinerary, there is even a train to Rome from the nearby coastal town of Albania. The journey takes approximately two hours.
Where to Stay in Rome
We recommend staying a few nights in Rome to fully explore this incredible city. Accommodation in Piazza Navona and San Lorenzo is ideal, as the central areas are within walking distance of many top attractions. However, hotels in San Lorenzo are slightly cheaper if you’re traveling on a budget.
Tip: We also really liked the look of hotels in Trastevere, a more authentic ‘Roman’ neighborhood by the river, with many cute shops, restaurants, and bars to explore.
How to Visit Tuscany in 5 Days
Both Pisa and Florence have international airports with frequent daily flights available to many destinations worldwide.
If you are traveling overland, the train is a great option, as the Italian railway connects with many other European cities. The good news is that night train routes are becoming increasingly available, too.
An even cheaper alternative is the bus, although this will take a lot longer and take time away from your Tuscany itinerary!
Getting Around Tuscany
By Car
The best way to see the region is by renting a car, so you have complete flexibility. A Tuscany road trip means you can stop whenever the mood strikes and visit the smaller villages that are less accessible by public transport.
Travel distances vary, with the longest stretch on our Tuscany itinerary being around three hours. However, we recommend stopping off for pasta and cappuccino breaks as often as possible! You can rent a car in Pisa or Florence and drop it back in Rome to see more of the region.
We recommend to rent a car in Italy through Sunny Cars with free cancellation and insurance included. Book your rental car here.
By Public Transport
Another option is taking buses and trains on your Tuscany itinerary, which can work out cheaper. It’s also incredibly convenient when traveling between cities as you don’t need to worry about navigating busy roads and parking. However, you may have to take taxis from bigger towns to the more remote places, which can be expensive.
By Tour
If you are basing yourself in one city and want to explore the surrounding countryside, the best option is to take day tours. Many tours leave from the bigger cities like Florence, Siena, and Pisa and take you out into the Tuscan countryside to explore the wineries and hilltop towns.
Our Favorite Accommodations in Tuscany
The Tuscany region offers some fantastic accommodation options, whether it’s rustic farmhouses, luxurious country villas, cozy city apartments, or budget hostels. Here are some of our favorites from each destination on the Tuscany itinerary:
- Florence: Velona’s Jungle Luxury Suites, Santa Croce 14, Casa Botticelli
- Pisa: Rinascimento Bed & Breakfast, La Torre Garbata, The Rif Boutique Hotel
- Siena: Ca’ Bianca Tuscany Relais, Residenza d’Epoca Le Aquile, B&B Alle Due Porte
- Pienza: Castello di Spedaletto da Laura, La Chiocarella, Il Mastio di Spedaletto
- Montepulciano: Il Tosco, Lupaia, Agriturismo San Gallo
- Montemerano: The Nest in Maremma, Acquaviva Wine Resort, La Casa di Nonna Libia
- Rome: Colosseum Palace Star, Casa Modelli, Sentho Roma
How Much does a 5-Day Tuscany Itinerary Cost?
Tuscany is one of the more expensive regions in Italy to visit as it is a popular tourist destination. Remember that prices will increase even more during the summer, and Florence, in particular, can be costly.
If you are on a tighter budget, stay in hostels instead of hotels where available, eat in small local trattorias or make picnic lunches, and avoid pricier tourist attractions.
Best Time to Travel to Tuscany
The best time to complete your Tuscany itinerary is from April to October, when it is sunny and warm, and all the tourist attractions are open.
Try to avoid peak tourist season in July and August when it can get crowded, and the heat is intense, which can make sightseeing more uncomfortable. For this reason, we always choose to travel to Italy in the shoulder seasons of April/May and September/October.
October is also a great time to visit for foodies as it is harvest time, with fresh truffles, newly-pressed olive oil, young wines to try, and lots of local food festivals.
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Hi, which airport did you drop off your car at in Rome from sunny cars?
Hey! At Fiumicino, but Sunny Cars provide both options!