Tuscany Road Trip: The Ultimate 5-Day Itinerary Tuscany Road Trip: The Ultimate 5-Day Itinerary

Tuscany Road Trip: The Ultimate 5-Day Itinerary

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.

A Tuscany Road Trip Itinerary

The easiest way to see this incredible region is by renting a car. This gives 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. Here’s how to spend five days on a Tuscany road trip.

Tip: If you have more time, discover the underrated neighboring region of Umbria (just as impressive but with fewer crowds!).

road trip tuscany landscape

Day 1 – Florence or Pisa

It’s the first day of your 5-day Tuscany itinerary; welcome to Italy! You’ve likely begun your trip in the beautiful cities of Florence or Pisa, so spend at least a day exploring before heading off to Siena

Tuscany road trip florence italy


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.

Tuscany road trip florence Cathedral Santa Maria del Fiore

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.

Tuscany road trip florence Ponte Vecchio

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 and end your day with a delicious plate of fresh pasta at Trattoria San Pierino.

Where to Stay in Florence

Florence in Tuscany has plenty of accommodation options depending on your budget and style. We’d recommend the Santa Croce neighborhood, as it’s close to the center and has a lively cafe and bar culture. 

Tuscany italy road trip Palazzo Vecchio


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.

Tuscany road trip pisa italy

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. Plus, it’s the perfect spot to sunbathe on the grass while you take in the stunning architecture. 

pisa Piazza dei Miracoli

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.

best restaurants pisa italy
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.

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 road trip!

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.

No time to read now?
No worries! Save on Pinterest to read it later.
Save to Pinterest
Tuscany Road Trip: The Ultimate 5-Day Itinerary

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.

things to do tuscany siena

The Elsa Trail: Highlight of your Tuscany road trip

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. The trail leads to the Diborrato Waterfall, where you can cool off in the bright blue water surrounded by greenery.

Elsa Trail waterfall tuscany italy

San Gimignano, Tuscany

You could also combine 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. Spend 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 — a must-do on your Tuscany road trip!

san gimignano italy things to do

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.

hills Tuscany italy road trip
Here’s the location of the photo.

Where to Stay in Siena

If you’re only staying for one night in Siena, stick to the hotels in the city center (around the Torre del Mangia), so you are close to all the historic landmarks, bars, and restaurants. Alternatively, opt for accommodation within easy driving distance of the city.

things to do siena day trip San Gimignano

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.

Pienza: Must-see on a Tuscany road trip

Unusually, this small village perched on a hill is famed for its pecorino cheese! However, it’s more importantly known for its stunning Renaissance architecture, which has led to its UNESCO World Heritage Site status. Located in the Val d’Orcia, the hilltop village has spectacular views of the rolling Tuscan hills surrounding it. It is also a lovely place to shop for souvenirs like cured meats, pecorino cheese, and local artwork.

Spend an afternoon wandering Pienza’s tiny streets and alleyways, exploring piazzas and palazzos, and admiring the views from the ancient city walls. 

Tip: If you’re doing your Tuscany road trip in September, don’t miss out on the Fiera del Cacio. This annual festival is dedicated solely to pecorino, complete with a cheese rolling competition and lots of tasting opportunities!

pienza italy hills tuscany


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 road trip and enjoy all the delights that Tuscany has to offer. 

things to do Montepulciano italy

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.

Montepulciano italy things to do

If you’ve got time on your 5-day Tuscany itinerary, spend the afternoon sipping wine on an underground cellar tour or visit a nearby vineyard. Alternatively, take a cooking class to learn something new and fill your belly with delicious Tuscan cuisine. There are plenty of options in Montepulciano!

Montepulciano restaurants

How to get from Siena to Pienza / Montepulciano

From Siena to Pienza/Montepulciano is roughly an hour of driving, depending on your route. However, we recommend staying off the highway as much as possible to see some beautiful scenery. There are some fantastic wineries in this area, so if you’re lucky enough not to be the designated driver, take the opportunity to taste some local wines in a stunning vineyard setting. 

Tip: If you are looking to buy wine to take home with you, it is much cheaper to buy directly from a winery. They will also be able to give you great recommendations.

tuscany italy fiat 500

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 in any of the incredible ‘agriturismo’ properties. 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 hills of Tuscany.

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. 

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.

Saturnia Tuscany road trip


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.

road trip tuscany Montemerano

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 do these routes by bus, as it requires so many connections. Because of this, if you don’t have your own transport, your quickest option will be taking a taxi.

view montepulciano

Where to Stay in Montemerano on this Tuscany road trip

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. 

Day 5 of the Tuscany Road Trip – Finish in Rome via Orvieto

It’s time to head to your final stop on your Tuscany road trip: Rome! Take your time getting there; we recommend stopping at the beautiful and historic town of Orvieto in the Umbrian hills.

Orvieto: Must see on your Tuscany road trip

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 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.

best things to do orvieto italy duomo


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!

things to do rome italy pantheon

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.

things to do in rome italy colosseum

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, which is just as beautiful but with fewer crowds. If you can, spend a few nights here, too! 

If you are traveling by public transport on your Tuscany itinerary, there is a train to Rome from the nearby coastal town of Albinia. The journey takes approximately two hours.

things to do umbria italy perugia

Where to Stay in Rome

We recommend staying a few nights in Rome to fully explore this incredible city. Piazza Navona and San Lorenzo are central areas within walking distance of many of the top attractions. However, San Lorenzo is slightly cheaper if you’re traveling on a budget. Trastevere is another great neighborhood by the river, which has a more authentic ‘Roman’ feel and loads of cute shops, restaurants, and bars to explore.

Tuscany road trip rome bakery

How to Visit Tuscany in 5 Days

Both Pisa and Florence have international airports with frequent daily flights available to many destinations worldwide. 

Find flights to Tuscany ✈️

If you are traveling overland, the train is a great option, as the Italian railway connects with many other cities in Europe. 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 road trip!

winery tuscany

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.

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.

Tours & Tickets 🥾View all
Tuscany road trip colosseum rome

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:

pienza italy tuscany

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.

Costs of Traveling in Tuscany

Travel on a budget in Tuscany, from $480 − $360 USD weekly per person, mid-range $1210 − $2670 USD, and high-end from $2600 − $3770 USD. However, costs depend on factors like accommodation, transportation, and activities. We did not include flights. Check flight prices here

* Average daily costs
Budget tip!
Traveling to a country with a different currency? Avoid ATM transaction fees and pay in local currency with a Wise Card. Having used it for over 5 years, we've saved loads on fees.
Get a Wise Card

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 do a Tuscany Road Trip

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, the shoulder seasons of April/May and September/October are ideal.


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.

24/02/2024 https://www.saltinourhair.com/italy/tuscany/
Blog comments (11)

Looking for more travel information? Plan a chat with us for personalised travel advice or get an answer from the Salt in our Hair Travel Community on Facebook.

  • Thanks very much for these very helpful itinerary suggestions. One recommendation—please change out the photos of Cascate del Mulino! They are not crystal blue and untouched, as in the photos. They are greenish and full of people.

    • Salt in our Hair

      Hi MP, we visited the place a long time ago and this truly was what it looked like. We are aware it’s now extremely crowded, and the green color must be because of that reason.

Your email address will not be published. Required fields are marked *


This article was about:
Last updated: