Tuscany: birthplace of the Italian Renaissance and home to rolling hills, hidden vineyards, ancient hilltop villages, and delicious food. We spent 5 days of our Italy itinerary exploring the Tuscan countryside, strolling the cobbled streets with a gelato in hand, and stocking up on local wine and pecorino cheese. In this ultimate Tuscany road trip itinerary, we’re sharing all our favorite places in the region, including where we stayed and how we got around.
Our Must-do Tuscany Itinerary
After seeing nearly all regions in Italy, Tuscany remains our favorite! There’s something about the architecture, nature, and food that keeps us coming back. We explored it for five days by renting a car, which is the easiest way to see this incredible region and gives you total freedom to change your trip as you go.
We recommend to rent a car in Italy through Sunny Cars with free cancellation and insurance included. Book your rental car here.
Day 1 – Florence or Pisa
It’s the first day of our 5-day Tuscany itinerary; welcome to Italy! We began the trip in the beautiful city of Florence (Pisa is also an option), so spend at least a day exploring before heading off to Siena.
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.
- A must-see on your Tuscany road trip is the iconic Cattedrale di Santa Maria del Fiore with its white, pink, and green marble exterior. You can visit one of the world’s largest domes here, too. (Browse tickets here).
- We then headed to the Arno River to cross Florence’s oldest bridge, the Ponte Vecchio.
- Explore the quieter neighborhoods on the other side of the bridge for a few hours – highly recommend!
Read on: Best things to do in Florence
For food, you can easily spend days discovering all the city’s best spots. We really liked:
- The sandwiches from Panetteria e Stuzzicheria de Neri.
- Creamy gelatos at Gelateria La Carraia (see all unique flavors here).
- ‘Pappardelle al cinghiale’ (Florence pasta) at Trattoria San Pierino. Our favorite!
Where to stay? There are so many options depending on your budget and style. We stayed in a hotel in the Santa Croce neighborhood, which is 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 an iconic photo to remember your road trip through Tuscany. However, there are many other beautiful buildings in the same square.
We really enjoyed visiting:
- The Camposanto, the Baptisterium, and the intricately designed Romanesque Cathedral. We loved sunbathing in the pedestrianized space between the stunning architecture. You can book a guided tour that includes entrance to many buildings!
- Borgo Stretto for the best shopping in Pisa! This street is lined with beautiful, colored townhouses.
- The tiny alleyways and pretty squares while searching for a delicious lunch or dinner spot. Pisa often has amazing evening events, so check out this event calendar before you go.
Read more: Best things to do in Pisa
Where to stay? We recommend staying in the Santa Maria area, which is very central. Choose accommodation in the San Giusto neighborhood if you’re on a budget. We stayed right next to the Leaning Tower of Pisa, which was such a unique experience. This is the hotel.
Day 2 – Siena, Tuscany
This charming and atmospheric city, with its steep, winding, cobbled streets and dusty-colored houses, is one of our favorites on this Tuscany itinerary! Driving time: Two hours from Pisa and one hour from Florence by car.
Tip: Select the ‘avoid highways’ option on Google Maps. That way, you get to see all the incredible natural beauty of Tuscany. Alternatively, there are trains and buses from both cities. (book your tickets here)
Start your day in the beautiful Piazza del Campo, before walking to the Duomo di Siena. This stunning cathedral was uniquely built from black-and-white striped marble and features beautiful frescoes inside. From here:
- Get lost in the winding streets;
- Explore the grand Palazzo Pubblico;
- We had dinner with our friends at Ristorante Fonte Gaia on Piazza del Campo, with stunning pink skies – so memorable!
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. Driving time: 30 minutes from the city.
This picturesque trail 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.
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. We parked here (or here as an alternative) and spent an afternoon exploring the historic town with its pretty streets and squares.
Tip: Don’t miss out on trying ‘The World’s Best Gelato’ at Gelateria Dondoli. We had to wait 20 minutes in line but it’s so worth it!
Where to stay in Siena? If you’re only staying one night, stick to the city center (around Torre del Mangia). This was our hotel. Alternatively, if you want to get back on the road early the next day, book a countryside accommodation.
Day 3 – Pienza or Montepulciano
Both these beautiful hilltop towns were favorites on our Tuscany itinerary, particularly as they’re only 20 minutes apart. Montepulciano is slightly larger and offers more restaurants and wine tours.
Alternatively, for a more relaxed destination, choose the Renaissance town of Pienza. Driving time: Both towns are about an hour away from Siena.
Also check out our 7-day Italy itinerary
Pienza: Must-see on a Tuscany road trip
This small village is famed for its pecorino cheese. As big cheese lovers, we couldn’t miss it. In fact, if you’re following this Tuscany itinerary in September, there’s even a cheese rolling competition named Fiera del Cacio! We parked here (1,70 EUR per hour) as the free parking lot was full.
Located in the Val d’Orcia, you have incredible views of the surrounding rolling Tuscan hills from here. It’s also full of UNESCO-listed Renaissance architecture, so we loved getting lost in the little streets.
Tip: Pienza is small, so we saw the whole town in about 3,5 hours. If you want quieter times, visit before 10 AM or after 5 PM. We did some great souvenir shopping for cured meats, pecorino cheese, and local artwork.
Montepulciano
Known for its delicious wine, this charming medieval hilltop village is a great place to slow down. However, we found there wasn’t much to see, so we spent only an hour here. Driving time: 20 minutes from Pienza.
Start in the Piazza Grande and climb to the top of the clock tower to get panoramic views of the village and the surrounding Val d’Orcia. Then, from here:
- Wander the pretty streets and browse the shops and gelaterias;
- Head to Veduta Panoramica or Palazzo Comunale for another viewpoint.
- And 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 try delicious Tuscan cuisine. We didn’t do it here, but it’s one of our favorite ways to meet new people and learn about the country we’re visiting.
Read more: Best things to do in Montepulciano, Italy
Extra: Farm-to-Table Tour at Fattoria La Vialla
Just an hour’s drive from Montepulciano, discover the ultimate farm-to-table 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 from the farm.
- You can tour the estate to see how they grow their ingredients in the verdant fields, vineyards, and among the beautiful cypress trees.
Send them a message to reserve your spot or to see availability for a beautiful overnight stay.
There are also 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 great to know if you want to take some home. We also got many great local recommendations!
Where to stay? The historic centers of Pienza and Montepulciano are both close to shops, bars, and restaurants. Alternatively, opt for an incredible agriturismo property in Tuscany. These farmhouses normally have pools and beautiful gardens!
Day 4 – Saturnia and Montemerano
On day 4, we went to the wonderful hot springs of Saturnia before spending the night in one of the most beautiful villages in all of Italy: Montemerano. Driving time to Saturnia: Just under 2 hours. Don’t have a car? A taxi is then the quickest option.
Saturnia in Tuscany
Saturnia is a world-famous ancient spa town because of its beautiful blue hot springs. The springs cascade over several levels into a series of pools, all overlooking the stunning Tuscan countryside. Our B&B was just a 5-minute walk from the baths!
These thermal springs are a great place to soak for a couple of hours in healing volcanic water that is 37°C (98.6°F) year-round. Opening times: 24/7, but we recommend arriving before 7 AM to avoid the crowds. It’s also free entry!
Tip: Bring shoes you can wear in the water, as the bottom of the pools can be a bit rough.
Montemerano
After some time enjoying the hot springs, head to the small and charming town of Montemerano for the evening. Driving time: Just 15 minutes from Saturnia.
Spend an hour or two exploring; stroll along quiet streets lined with ancient stone buildings before tucking into traditional Tuscan dishes at a local trattoria.
Our Top Tip: One restaurant here that looks particularly special is Dal Moro, which has stunning countryside views from its terrace.
Where to stay? There are a few cozy inns and apartments in the villages of Saturnia and Montemerano. However, there’s more further out, like rustic farmhouses, vineyard hotels, and beautiful villas.
Day 5 of the Tuscany Itinerary – Finish in Rome via Orvieto
It’s time to head to our final stop on this Tuscany itinerary: Rome! Take your time getting there; we recommend stopping in the beautiful, historic town of Orvieto in the Umbrian hills.
How to get there: It is a 3-hour drive from Saturnia to Rome via Orvieto. This route lets you experience a taste of Umbria, the region 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!
Orvieto: Must see on your Tuscany Itinerary
The ancient hill town of Orvieto is packed with beautiful churches, fascinating museums, and temples. Plus, we found so many cute ceramic shops and a fascinating network of underground tunnels and caves.
We also saw this e-bike tour of Orvieto, which includes entrance to the underground city.
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 with beautiful views of the surrounding countryside.
Restaurant Tip: Although we sadly didn’t get a chance to visit, there’s a stunning restaurant called Ristorante Locando Orvieto (situated within an Agriturismo on the city’s outskirts). The views look exceptional!
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.
Where to stay? We’ve stayed in an accommodation in Piazza Navona and a hotel in San Lorenzo (a bit cheaper), as they’re really central. But 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, you can:
- Travel by train, as the Italian railway connects with many other European cities. Night train routes are becoming increasingly available, too. (Check tickets here)
- Come by bus, although it takes much longer and takes time away from your Tuscany itinerary.
Getting Around Tuscany
Once you get to Tuscany, you can explore the region in a few ways:
By car: Our favorite (and the best) way to see Tuscany is by renting a car. This means you can stop wherever you want and can visit less accessible locations.
The longest time we’ve been in the car in one stretch on this itinerary was 3 hours! However, we recommend stopping for pasta and cappuccino breaks as often as possible. 😉
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: A cheaper alternative, and great between cities as you don’t need to navigate 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: Best option if you base yourself in one city and explore by taking day tours. Many tours depart from larger cities like Florence, Siena, and Pisa and take you into the Tuscan countryside to explore wineries and hilltop towns.
Our Favorite Accommodations in Tuscany
The Tuscany region has such amazing accommodation options, whether it’s rustic farmhouses, luxurious country villas, cozy city apartments, or budget hostels. Our favorites from each destination on this Tuscany itinerary are:
- 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?
We found Tuscany to be one of the more expensive regions in Italy, as it is a popular tourist destination. Prices will increase even more during the summer, especially in Florence.
If you are on a tighter budget, stay in hostels instead of hotels if possible, eat in small local trattorias or make picnic lunches, and avoid pricier tourist attractions.
Best Time to Travel to Tuscany
We visited at the end of September and loved it! It was warm enough to jump in the pool on sunny afternoons, yet cozy in the evenings (light jacket needed). Plus, there were much smaller crowds compared to the summer months.
- Peak season: June-August, when it’s busy and the weather is hot.
- October: Great month to visit for foodies, as it’s harvest time, with fresh truffles, newly pressed olive oil, young wines to try, and lots of local food festivals.
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Hi! Where was that rooftop photo overlooking the Duomo in Florence taken? I am looking for a hotel/BnB option to stay at that has a terrace with a view like that. Thanks! Also, loved this guide!
Hi Lindsey, thank you! This is that place you’re looking for! Enjoy!