An epic Italian adventure
Ultimate 5-day Tuscany Road Trip Itinerary
Planning a trip through Tuscany? This 5-day route covers the best villages, landscapes, and local gems. It's perfect if it’s your first time in Italy or you’re craving Renaissance towns, thermal springs, and cypress-lined roads.
We’ll stop in icons like Florence, Siena, and Pisa… but also dreamy hill towns like Montepulciano, Saturnia, and San Gimignano. I’ve included tips for parking, budget hotels, photo spots, and the best times to visit each place.
I remember vividly how in awe I was when i first looked at the Tuscan valleys lined with trees and the Italian sun turning everything to gold.
ON THIS PAGE:
The Ultimate 5-Day Tuscany Road Trip Itinerary
Tuscany Road Trip FAQ: What to Know Before You Go
Watch the Journey: My Tuscany Road Trip in Motion
Day 0: Arrive in Rome → Drive to Saturnia
Day 1: Hot Springs, Val d’Orcia Views & Montepulciano
Day 2: Pienza, Montalcino & Arezzo’s Hilltop Magic
Day 3: Siena, Volterra & Crystal Glass Secrets
Day 4: Towers, Leaning Icons & Hidden Towns
Day 5: Florence – Tuscany’s Crown Jewel
🎥 Watch the Journey: My Tuscany Road Trip in Motion
Want a real glimpse of what it’s like to road trip through Tuscany? Here are 4 videos with detailed views for each day of this road trip. From magical sunrises to medieval hill towns and dreamy hot springs.
Tuscany road trip Itinerary videos
Tuscany road trip Day 1
Tuscany road trip Day 2
Tuscany road trip Day 3
Tuscany road trip Day 4
Some facts about Tuscany
Tuscany 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.
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.
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.
Take a train to Milan and spend a bonus 1-2 days there to discover this beautiful city.
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, the train or a bus/shuttle service.
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
Saturnia to Val d'Orcia: 1.5 hours
Val d'Orcia to Montelpuciano: 25 min
Motalcino to Arezzo: 1.15 hour
Siena to Volterra: 1 hour
Volterra to San Gimignano: 38 min
Cetaldo to Pisa: 1 hour
Train from Florence to Milan: 2-3 hours depending on the train
Train from Rome to Florence : 1.5 hours (if non-stop)
Train cost from Florence to Milan: 38-50 euros
Day 0: Arrive in Rome → Drive to Saturnia
Your adventure begins in Rome. I landed at Fiumicino Airport because flights were cheaper and more frequent than Florence or Pisa. Depending on your arrival time, you can either:
Spend a few hours sightseeing in Rome
Or grab your rental car and head straight to Tuscany
🚗 Drive to Saturnia: about 2.5 hours
This is where I spent the first night and honestly, you’ll be so glad to do this as well. Saturnia is the gateway to one of Tuscany’s most magical spots: its natural hot springs.
🛌 Where I Stayed (Budget-Friendly Options Near Saturnia):
1. Quercia Rossa Agroturismo : Average rate is $150-$190 per night.
2. Sweet Hills Hotel. Via Cavallini 55, Manciano
3. Agriturismo Le Cascatelle: Average rate is $160-$200 per night. Right next to Cascate del Mulino.
Day 1: Hot Springs, Val d’Orcia Views & Montepulciano
Start your day soaking in the warm turquoise pools of Cascate del Mulino. The mineral-rich waters flow down travertine terraces surrounded by countryside.
It’s free to visit, but come early. It gets busy, fast. I arrived at approximately 7:30a.m. and parking was almost full to capacity and it was impossible to take pictures without people on them.
👉 Note: Don’t confuse Cascate del Mulino with Terme di Saturnia, a private hotel/spa nearby.
If you’re up for one more thermal experience, consider Bagni San Filippo, a lesser-known, forest-hidden hot spring with white calcium formations that look like frozen waterfalls.
If you decide to visit only one of these hot springs, I highly recommend Cascate del Mulino , just by its mere charm.
🗺️ Route to Val d’Orcia:
The rest of day 1 is dedicated to the Val d'Orcia region, a UNESCO World Heritage site.
Drive north into the postcard region of Val d’Orcia. This is where Tuscany’s most iconic views are born. Rolling hills, winding roads lined with cypress trees, medieval towers in the distance.
But on your way there make a quick stop scenic stop:
🔹 Pitigliano – An epic medieval, cliff-top town that looks like it’s carved from the stone itself.
🛌 Top 3 Budget Hotels Around Montepulciano:
1. Agriturismo Sanguineto: Average rate is $120-$150 per night.
2. Agriturismo La Sovana: Average rate is $230-$250 per night.
3. Agriturismo Nobile: Average rate is $125-$155 per night.
Tuscany Top sites to visit Day 1:
Cascate del Mulino (Saturnia’s hot spring)
Bagni San Filippo (optional second spring)
Pitigliano (medieval town stop)
Monticchiello – The Church of Saints Leonard and Cristopher + scenic viewpoint
Montepulciano – Visit:
Piazza Grande
Palazzo Tarugi
Church of San Biagio
Historic wine cellar at Cantina Contucci
📸 Photography Tips
Frame Val d’Orcia’s hills with cypress rows at golden hour
Catch rising morning mist from hilltops for dreamy shots
If you’re at Cascate del Mulino early, shoot from above or behind the flow
Day 2: Pienza, Montalcino & Arezzo’s Hilltop Magic
Kick off Day 2 in Pienza. Honestly one of the prettiest towns I visited in Tuscany. I made sure to arrive early to skip the tour groups and enjoy those quiet cobblestone streets with just the smell of fresh bread and views of Val d’Orcia all to ourselves.
I spent 3-4 hours exploring all the viewpoints searching for all the instagram's iconic pictures of the Tuscan landscape, we tried Pecorino di Pienza cheese and some local pastries.
Don’t miss:
Walking the Passeggiata Panoramica
Sampling Pecorino di Pienza (grab it from a street deli)
Piazza Pio II and the Cathedral
🛑 Hidden Gems Along the Route:
Bagno Vignoni – A traffic-free town with ancient hot spring pools in the main square
San Quirico d’Orcia – Charming lanes + Chapel of Madonna di Vitaleta nearby
Cypress-lined roads – Pull over often, trust me
Wrap up the afternoon in Montalcino, home of Brunello wine. Visit a cantina, sip with a view, and if you love music, try to time it with the monks’ Gregorian chants at Sant’Antimo Abbey. It’s haunting in the best way.
🛌 Where to Stay (Between Arezzo & Siena):
1. Castello di Gargonza: Average rate is $160-$190 per night.
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.
Tuscany Top Sites to Visit Day 2:
Pienza: Cathedral, Piazza Pio II, viewpoint walk
Bagno Vignoni: Thermal pool square, Piscina Termale
San Quirico: Santa Maria Assunta, Madonna Vitaleta Chapel, Cypress of San Quirico
Montalcino: Fortress, Banfi Castle & winery, Sant’Antimo Abbey
Arezzo (if time allows): Piazza Grande, Cathedral of San Donato, Medici Fortress
📸 Photography Tips:
Pienza is perfect at golden hour—especially from the panoramic walkway
In Montalcino, shoot vineyards from above
Use arches and windows to frame landscape shots
Day 3: Siena, Volterra & Crystal Glass Secrets
Start early in Siena. This city gets packed by mid-morning. I arrived just after sunrise, and the silence in Piazza del Campo was everything. It felt like stepping into a painting.
See:
Siena Cathedral (Duomo) – the facade alone is a masterpiece
Piccolomini Library – Look up, the ceilings are unreal
Torre del Mangia – Climb for views, if you’re up for it
Scenic Drive Through the Region:
After Siena, drive to Monteriggioni. A tiny walled village that looks like a medieval movie set. Walk the ramparts, snap photos, grab a coffee. Then continue on to:
Colle di Val d’Elsa – 95% of Italy’s crystal glass is made here.
My favorite stop? The Crystal Glass Museum. Super underrated.
Finish the day in Volterra, one of Tuscany’s most underrated historic towns. It’s got Etruscan walls, Roman ruins, alabaster art studios, and views for days.
➡️ Don’t miss: Climbing Torre del Maschio. It’s only €5 and gives you a jaw-dropping panorama of the valley.
🛌 Top 3 budget hotels (Around Castagno Val d’Elsa):
1. Fattoria La Striscia: Gambassi Terme
2. Tenuta Quadrifoglio: Via Camporbiano
3. Agriturismo Casa al Povero: Volterra area
Tuscany Top sites to visit Day 3:
Siena: Cathedral, Piazza del Campo, Torre del Mangia, Piccolomini Library
Monteriggioni: Castle walls, Church of Santa Maria
Colle di Val d’Elsa: Crystal Museum, Porta Volterrana
Volterra: Etruscan walls, Roman Theater, Alabaster Museum, Torre del Maschio
📸 Photography Tips
Siena Cathedral: Zoom in on the facade for textures + lines
Volterra: Best shots are from Torre del Maschio at golden hour
Monteriggioni: Great drone or flatlay views from above the ramparts
More Tuscany hidden gems !
Day 4: Tuscan Towers, Leaning Icons & Hidden Towns
Day 4 of this Tuscany road trip starts in San Gimignano, famous for its medieval towers and dreamy skyline.
I loved walking through the narrow streets early in the morning before the day trippers arrived. It really felt like stepping into another century.
Must-see spots:
Torre Grossa – Climb for panoramic views
Piazza della Cisterna – One of the prettiest main squares
San Gimignano 1300 Museum – A 3D mini replica of the town’s past
Then it’s a full loop through some of Tuscany’s most famous and underrated towns:
🛑 Quick Stops to Include:
Certaldo – Small and colorful with a local vibe
Pisa – Go ahead, take the classic Leaning Tower photo. No shame
Lucca – Bike the city walls, explore the oval-shaped Piazza dell’Anfiteatro
Pistoia – Totally underrated! No crowds, great architecture, local energy
End your night by either staying near Pistoia or pushing on to Florence (like I did) so you can explore it fresh in the morning.
🛌 Top Hotels Near Pistoia (If Stopping Overnight):
1. Hotel Patria: Average rate is $140-$170 per night.
2. M2 Hotel: Average rate is $95-$130 per night.
3. Ibis Firenze Prato Est: Average rate is $65-$95 per night.
Tuscany Top Sites to Visit Day 4:
San Gimignano: Torre Grossa, Piazza della Cisterna
Certaldo: Old town and cable car up
Pisa: Leaning Tower, Pisa Cathedral, Piazza dei Miracoli
Lucca: City walls, Lucca Cathedral, Piazza dell’Anfiteatro
Pistoia: Cathedral of San Zeno, San Giovanni Fuoricivitas, medieval churches
📸 Photography Tips:
In San Gimignano, shoot the tower skyline from just outside town
In Pisa, go early or late to avoid crowds in photos
Lucca’s walls offer top-down views of hidden courtyards
Day 5: Florence – Tuscany’s Crown Jewel
Start your final day in Florence, and make it count. The art, the gelato, the views. It’s overwhelming in the best way.
I stayed overnight nearby so I could see Florence from morning to night.
🖼️ Morning Stops:
Uffizi Gallery – Home to Botticelli’s Birth of Venus and so much more
Florence Cathedral (Duomo) – Climb the dome if you can, but just standing outside is epic
Baptistry – Look up at the golden mosaics inside
🏛️ Afternoon Ideas:
Ponte Vecchio – Iconic bridge with shops and Arno views
Piazza della Signoria – Open-air art museum and a replica of David
La Accademia – To meet the real Michelangelo’s David (optional but worth it)
🍝 Evening in Florence:
Grab gelato from a tiny alley gelateria
Have dinner at a no-frills trattoria with red wine and gnocchi
End with sunset at Piazzale Michelangelo. The views of Florence glowing at golden hour? Unforgettable.
👉 Need ideas on what to wear to Tuscany? Here are some looks i usually wear for my travels — comfy, photo-friendly, and perfect for road days.
🛌 Top Hotels to Stay in Florence (Budget Options):
1. Hotel Patria: Average rate is $140-$170 per night.
2. Campi Bisenzio Hotel: Average rate is $95-$130 per night.
3. Ibis Firenze Prato Est: Average rate is $65-$95 per night.
Tuscany Top sites to visit Day 5:
Uffizi Gallery
Florence Cathedral + Dome
Baptistry
Ponte Vecchio
Piazza della Signoria
Piazzale Michelangelo
📸 Photography Tips
Shoot golden hour from Piazzale Michelangelo
Inside Uffizi, use the arched windows for framing Florence views
Capture Florence Cathedral’s details with a wide lens early in the day
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.
Rome to Florence via Tuscany
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Do you like road trips?
If you love road trips with a mix of adventure, local culture, and epic views, check out my El Salvador road trip itinerary for another unforgettable experience.
And if going on hikes while traveling to a new destination inteterests you, make sure you check my El Caminito del Rey hike post in Malaga, Spain. or my bucket list visit to Mount Rainier National Park.
Need help deciding your travel style? Don't worry, I got you!
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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.
Also check my FREE Resources here
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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: Bucket list Destinations, Adventure travel, Road trips, Hidden Gems, Outdoors, Group travel
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