An epic Italian adventure
Ultimate Tuscany 5 day Road Trip Itineray
Planning a trip to Tuscany? Here's a 5-day itinerary that will help you see the best of this beautiful region. We will explore all the iconic cities in Tuscany like : Florence, Siena, Chianti, Val d'Orcia, Saturnia, San Gimignano, San Quirico d'Orcia , Volterra
But before we dive into my full itinerary , lets try to answer the most asked questions when you start thinking about your plans for a Tuscany trip.
Where is Tuscany?
Tuscany, known as the cradle of the Renaissance, is a region in central Italy. It has Florence as its capital and is home to some of the world’s most recognizable Renaissance art and architecture. It's in Florence where lives the famous sculpture of David done by Michelangelo, but also Botticelli’s works in the Duomo di Firenze.
Also known for its beautiful countryside, including rolling hills, charming villages, olive groves, vineyards and extensive roads lined up by cypresses.
Tuscany’s region is made up of ten provinces located about 185 miles south of Milan and 175 miles north of Rome.
The closest international airports are Aeroporto di Firenze in Florence and Galileo Galilei Airport in Pisa.
I started this roadtrip arriving in Rome’s Fiumicino Airport because it offered more affordable flights and more available flights in general.
For the purpose of this blog, the roadtrip ended in Florence. If your time is limited you can choose Florence as your departure city. But if you have more time you can save a bit of money on that flight by leaving from Milan, which like Rome, offers more flight options and connections to the rest of the world. Use that bit of extra money and take a train to Milan and spend a bonus 1-2 days there to discover this beautiful city. After all, you are still in Italy, right?
Even though Florence and Pisa airports are International, there are little to no options to non European countries. The way to connect these airports to other major hubs is by taking a domestic flight with a regional airline, the train as I’m suggesting or a bus/shuttle service.
Tuscany Road trip Day 0:
Arrival in Rome and Saturnia's Warm Welcome
Upon arrival at Rome International Airport, your road trip officially starts. Collect your rental car and depending on how much time you have available and the time of your arrival , you can choose to roam around Rome for a few hours to visit the main sites. After all, you are already there. Right? You can also make it an overnight stay and leave for Tuscany early in the morning. Saturnia, our first stop in Tuscany, is only 2.5 hours away.
After leaving Rome, drive towards the picturesque town of Saturnia, located near the stunning Tuscan coast. If after the 2.5 hour drive you are feeling tired or jetlagged , don't worry. Once you arrive at the first stop, I’ll guarantee you will forget about it. You will arrive in Saturnia, the gate to visiting the hot springs in the area. This is where I spent the first night to be able to visit the springs first thing in the morning.
These are my Top 3 Budget friendly hotel recommendations around Saturnia
1. Quercia Rossa Agroturismo : Average rate is $150-$190 per night. Address: Fraction Montemerano, Santarello, 89, Manciano, GR, 58014
2. Sweet Hills Hotel. Via Cavallini 55, Manciano
3. Agriturismo Le Cascatelle: Average rate is $160-$200 per night. This is located right at the site of Cascate del Mulino
Some approximate driving times to consider :
Rome to Saturnia: 2.5 hours
Rome to Florence: 3.5 hours
Florence to Pisa: 1.5 hours
Florence to Milan: 4 hours
Train from Florence to Milan: 2-3 hours depending on the train
Train from Rome to Florence : 1.5 hours (if non-stop)
Saturnia to Val d'Orcia: 1.5 hours
Val d'Orcia to Montelpuciano: 25 min
Pienza to San Quirico d'Orcia: 15 min
Motalcino to Arezzo: 1.15 hour
Arezzo to Siena: 1 hour
Siena to Volterra: 1 hour
Volterra to San Gimignano: 38 min
Cetaldo to Pisa: 1 hour
Pisa to Lucca: 26 min
Average cost of train from Florence to Milan: 38-50 euros
Tuscany road trip Day 1:
Saturnia, Val d'Orcia Allure and Montepulciano's Elegance
You wake up in Saturnia.Here, your tiredness will melt away as you soak in the soothing thermal waters of Cascate del Mulino ,a perfect prelude to the delights that await. The thermal springs are not to be confused with Terme di Saturnia which is a private Hotel & Spa .
Cascate del Mulino access is free, but beware. It is a very popular spot and it gets very crowded. Nonetheless, the place is magical and it deserves a visit, even if you decide not to get in the water.
Another popular hot spring to visit is Bagni San Filippo. A more off the beaten path kind of gem. If you decide to visit only one of these hot springs, I highly recommend Cascate del Mulino , just by its mere charm.
The rest of day 1 is dedicated to the Val d'Orcia region, a UNESCO World Heritage site known for its rolling hills, picturesque villages, and stunning landscapes. There are many panoramic viewpoints .
Most of Tuscany’s iconic pictures you’ve seen online and in social media were taken in this region. I suggest spending 3-4 hours driving around and stopping at some of these viewpoints. But on your way there make a quick stop at Pitigliano for epic views of this medieval town built on top of a rock cliff. It is breathtaking!
These are my Top 3 Budget friendly hotel recommendations around Montelpuciano:
1. Agriturismo Sanguineto: Average rate is $120-$150 per night. Address: Via Sanguineto 1, Montepulciano, SI, 53045
2. Agriturismo La Sovana: Average rate is $230-$250 per night. Address: Via di Chiusi 37, Sarteano, SI, 53047
3. Agriturismo Nobile: Average rate is $125-$155 per night. Address: S.S. 146 Km 24-100, Montepulciano, 53045
Tuscany Top sites to visit Day 1:
1. Cascate del Mulino
2. Bagni San Filippo
3. Saturnia: Explore the charming village, its historic center, and the ancient Roman baths.
4. The Church of Saints Leonard and Cristopher: A church from the 12th century that is the most remarkable monument in Monticchiello.
5. The panoramic terrace in Monticchiello.
6. Sanctuary of the Madonna di San Biagio, Palazzo Tarugi and Piazza Grande in Montepulciano
7. Historic Cantina Contucci
📸 Photography Tips
Capture the sweeping vistas of Val d'Orcia by framing the rolling hills with cypress trees and charming villages.
Capture the ethereal mist rising from the ground at sunrise or sunset for dreamlike photos.
Tuscany road trip Day 2:
Montalcino's Splendor and Arezzo's Riches
Day 2 promises more wonders. Begin in Pienza, without a doubt, one of the most beautiful towns in Tuscany. I choose to explore it in the morning to avoid the crowds and navigate it with ease. Here, you can walk the city walls, explore all the viewpoints for iconic picture of the Tuscan landscape, try Pecorino di Pienza cheese and pair it with a regional wine. You can easily spend 3-4 hours in Pienza.
Next stops in Day 2 are Bagno Vignoni (a car-free town), San Quirico d'Orcia and Montalcino, home to one of Italy's most famous wines, Brunello di Montalcino. Sip the exquisite wine while soaking in the panoramic views.
These are my Top 3 Budget friendly hotel recommendations between Arezzo & Siena:
1. Castello di Gargonza: Average rate is $160-$190 per night. Address: Loc. Gargonza 3, Monte San Savino, 52048
2. Castello di Leonina Relais: Average rate is $230-$250 per night. Address: Strada Di Leonina 5, Asciano, SI, 53041
3. Podere La Chiusella: Average rate is $120-$155 per night. Address: Loc. Armaiolo, 64, Rapolano Terme, SI, 53040
Tuscany Top Sites to Visit Day 2:
1.Terme Bagno Vignoni and Piscina Termale both in Bagno Vignoni.
2. Piazza Pio II, Pienza Cathedral and Passeggiata Panoramica in Pienza
3. Collegiatta di San Quirico, Santa Maria de Asunta church, Chapel of Madona Vitaleta and Cypress of San Quirico.
4.Fortezza di Montalcino, Banfi Castle and Winery, Sant 'Antimo Abbey, renowned for its Gregorian chants.
5. Piazza Grande,Donato e Prieto Cathedral and the Medicci Fortress all in Arezzo
📸 Photography Tips:
Capture the golden hues of the vineyards during sunset and seek out unique angles close to cypress for atmospheric shots.
Tuscany road trip Day 3:
Siena's Grandeur and Volterra's Mystique
Day three starts in Siena, a city of remarkable grandeur and history. A lot of people swing by Siena for a quick day trip from Florence, and that usually means it gets pretty crowded smack in the middle of the day.
If you want to experience the city when it's chill and serene, try going early in the morning, which is the reason why I choose Siena first thing in the day. You'll get to savor the place without the crowds.
After spending a few hours of the early morning in Siena we continue our day visiting Monteriggioni, Colle di Val d'Elsa, Volterra and Castagno de Val. d'Elsa
These are my Top 3 Budget friendly hotel recommendations around Castagno val d'Elsa:
1. Fattoria La Striscia: Loc. Castagno Val d'ElsaStrada Prov. Volterrana, 5450050 Gambassi Terme
2. Tenuta Quadrifoglio: Via Camporbiano 20, Loc. Il Castagno, Gambassi Terme
3. Agriturismo Casa al Povero: Volterra, Tuscany
Tuscany Top sites to visit Day 3:
1. Siena: Siena Cathedral (Duomo), Piccolomini Library, Palazzo Pubblico/Museo Civico, Torre del Mangia, Piazza del Campo
2. Monteriggioni Castle, Church of Santa Maria Assunta, Historic center of Monteriggioni and Walking the medieval walls
3. Colle di Val d'Elsa Cathedral, Crystal Glass Museum was my favorite stop here. Colle di Val d’Elsa accounts for 95 % of Italian crystal glass production . Other spots are Porta Volterrana and the Archeological Museum
4. In Volterra: Piazza,and Torre del Maschio, the Roman Theater, Etruscan walls, a visit to ECOMUSEO DELLa ALABASTRO and the Panoramic viewpoint
📸 Photography Tips
Capture the intricate details of Siena Cathedral's facade and explore angles that showcase the magnificence of the Piazza del Campo.
In Volterra make sure to go to the top of Torre del Maschio to get the epic view of the whole town and valley, It cost 5 euros to go up.
More Tuscany hidden gems !
Download My Tuscany Digital Maps
You’ll get immediate access to a beautiful PDF map that serves as a guideline for each day and you will also receive immediate access to My Tuscany Google map. Which includes detailed stops.
Layered in colors and filters for easy access. More than 100 spots of the most iconic pictures you can take, some hotels in each of the areas I recommend to spend the night and a couple of suggestions for experiences I had.
★★★★★
WITH THIS MAP YOU JUST HAVE TO SET YOUR GOOGLE MAPS APP AND GO! NO OVERTHINKING ON STOPS OR ROUTES. THE JOB IS DONE FOR YOU. IT COMES WITH EASY TO FOLLOW INSTRUCTIONS.
Tuscany road trip Day 4:
A Journey Through Tuscan Treasures
Day four of this roadtrip opened with the captivating San Gimignano, a medieval town famed for its towers that pierce the sky. Meander through the cobbled streets and absorb the medieval atmosphere.
Then, we ventured through Certaldo, Pisa, Lucca, Pistoia.
No trip to Tuscany is complete without a visit to Pisa and its iconic Leaning Tower. Marvel at the architectural wonder of the Piazza dei Miracoli, snap the quintessential tourist photo, and explore the city's rich history. Our journey continued to Lucca followed by the often-overlooked gem of Pistoia. Stroll through the charming town center, visit the exquisite Pistoia Cathedral, and soak in the local culture.
And… ultimately headed to Florence.
I opted to head straight to Florence later in the evening to be able to enjoy the next day from dusk til dawn in Florence. If your itinerary allows you more time, then you can choose to stay close to Pistoia. I'm offering 3 top options for hotels near Pistoia.
These are my Top 3 Budget friendly hotel recommendations around Pistoia:
1. Hotel Patria: Average rate is $140-$170 per night. Address: Via Crispi, 8/12, Pistoia, PT, 51100
2. M2 Hotel: Average rate is $95-$130 per night. Address: Via dei Confini 217, 217, Campi Bisenzio, FI, 50013
3. Ibis Firenze Prato Est: Average rate is $65-$95 per night. Address: Via Fratelli Cervi, Località Capalle, Campi Bisenzio, FI, 50013
Top Sites to Visit Day 4:
1. San Gimignano: Torre Grossa and the Towers of San Gimignano, Piazza della Cisterna, San Gimignano 1300 Museum
2. Pisa: Leaning Tower of Pisa, Pisa Cathedral, Baptistery of San Giovanni, Piazza dei Miracoli
3. Lucca: Lucca City Walls, Lucca Cathedral (Duomo di San Martino), Piazza dell'Anfiteatro
4. Pistoia: San Zeno Cathedral ,San Giovanni Fuoricivitas, Chiesa di San Bartolomeo in Pantano
📸 Photography Tips:
San Gimignano offers excellent opportunities for capturing the unique skyline and historic streets.
In Pisa, experiment with creative angles to capture the Leaning Tower's iconic tilt. Dont overthink it, fall for the touristy picture.
Lucca's well-preserved city walls provide a fantastic vantage point for panoramic shots of the city.
Tuscany road trip Day 5:
Florence: The Queen of Tuscany
The final day of your journey leads you to Florence, a city synonymous with art, culture, and beauty. Begin with the Florence Cathedral, an architectural masterpiece that dominates the skyline.
Florence: Artistic Marvels Await
Begin your day with a visit to Florence's crown jewel, the Uffizi Gallery. Home to some of the world's most renowned artworks, including pieces by Michelangelo, Botticelli, and Leonardo da Vinci, this gallery is a testament to human creativity.
Florence Cathedral and Baptistry: Architectural Wonders
Next, explore the Florence Cathedral (Duomo) and the Baptistry. Admire the awe-inspiring architecture of the cathedral and the stunning mosaics that adorn the Baptistry's interior.
Ponte Vecchio: Iconic Bridge
Cross the iconic Ponte Vecchio, a historic bridge lined with jewelry shops. Take in the picturesque views of the Arno River and enjoy the unique charm of this medieval bridge.
Piazza della Signoria: Outdoor Museum
Stroll through Piazza della Signoria, an open-air museum filled with sculptures, including a replica of Michelangelo's David. Absorb the vibrant atmosphere of this historic square.
Gelato and Tuscan Cuisine: Culinary Delights
Indulge in delicious gelato from one of Florence's artisanal gelaterias and savor Tuscan cuisine at a local trattoria. Tuscan flavors will delight your taste buds.
Florence at Night: A Magical Experience
As the sun sets, experience the magic of Florence at night. Visit Piazzale Michelangelo for panoramic views of the city illuminated under the night sky. It's the perfect ending to a day filled with art and culture.
These are my Top 3 Budget friendly hotel recommendations around Florence:
1. Hotel Patria: Average rate is $140-$170 per night. Address: Via Crispi, 8/12, Pistoia, PT, 51100
2. M2 Hotel: Average rate is $95-$130 per night. Address: Via dei Confini 217, 217, Campi Bisenzio, FI, 50013
3. Ibis Firenze Prato Est: Average rate is $65-$95 per night. Address: Via Fratelli Cervi, Località Capalle, Campi Bisenzio, FI, 50013
Top sites to visit Day 5:
1. Uffizi Gallery: Explore the world of Renaissance art with masterpieces by iconic artists.
2. Florence Cathedral (Duomo): Marvel at the stunning architecture and climb the dome for panoramic views.
3. Ponte Vecchio: Discover the history and craftsmanship of this iconic bridge.
4. La Accademia to have a first encounter with David.
📸 Photography Tips
Experiment with night photography at Piazzale Michelangelo to capture the city's enchanting lights
Love, ❦ Karen Lee
Looking for a day trip alternative from Florence?
Ok, Florence is fun and magnificent, but it can get very crowded with tourists during high season
While majority of tourists flocks to Florence, everyone else has fun in Perugia
Perugia is a charming city where you can get a more local Italian experience. It sits on a large hilltop and that is teeming with life, thanks to its famous university, which was founded in 1308.
Check out Perugia, an underrated city to visit along 9 other underrated cities to visit around the world from the OFF THE BEATEN TRAVEL creators.
MEET Sasha and Megnote. They've traveled to 50 countries, 48 states, & have been full-time travelers for the past 2 years with their now 5-year-old son.
They are a great resource for off the beaten path places and hidden gems.
Top things in Florence
Rome to Florence via Tuscany
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5 day road trip in tuscany italy
ABOUT THE AUTHOR
I'm Karen Lee, a world traveler turned travel blogger & content creator who wants to inspire you to explore the world no matter what your budget or circumstances are, whether you're a seasoned traveler or just getting started. I work full time and my free time is dedicated to wandering new destinations, taking photos, creating memorable travel stories that I share with my travel community daily.
TRAVEL EXPERTISE: Bucketlist Destinations, Adventure travel, Roadtrips, Hidden Gems, Outdoors, Group travel
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