Tuscany Road Trip: The Perfect 5 Day Itinerary
A road trip through Tuscany is something you have to do once in your lifetime. You will be truly taken away by the beautiful scenery, from the rolling vineyards and cypress-lined lanes to medieval hilltop towns. There are so many beautiful hidden gems to discover away from all the tourists. The countryside in Tuscany is just unreal especially if you have the chance to watch the sunset in incredible places like Agriturismo Baccoleno or Chapel Vitaleta. Read on for the perfect 5-day itinerary for your Tuscany road trip.
Just a heads up! This post may contain affiliate links, meaning I get a commission if you decide to purchase something through the links, at no additional cost to you. Your support helps me continue doing what I love ♡. Thank you! Read our Affiliate Disclosure here.
Day 1: Arrive in Florence or Rome
On day 1 of your Tuscany road trip, you’ll want to fly into Florence or Rome. Both airports are close to what we cover in this itinerary!
I’d suggest you pick up the car straight away and head to the first town on your Tuscany itinerary.
I personally flew into the Rome Airport and drove straight to Saturnia which is the town that has the most unique hot springs in the world!
On day 1, I’d recommend you stay close to the hot springs so you can properly see them and also have a hotel nearby to be able to shower there after, as there are few facilities open to the public nearby.
Hotel recommendations near Saturnia Hot Springs:
8380 Il Tiglio Verde is where I stayed. It is a family-run stay only a 10-minute drive from the hot springs. This cozy apartment is tucked away in the countryside so you’ll definitely need a car if you stay here. I loved the charming place and the fact that I was greeted daily by so many adorable cats and kittens.
B&B Villa Giulia in Saturnia looks absolutely stunning and the prices are fair at under €100 a night.
Casa Caracciolo is located in Pitigliano which is only around 30 minutes from Saturnia Hot Springs and it’s a really cute village to explore and a great base for your Tuscany road trip.
Day 2: Tuscany Road Trip
Morning: Cascate del Mulino
Cascate del Mulino aka Saturnia Hot Springs is a unique thermal bath in Tuscany near the town of Saturnia.
Although unknown to many non-Europeans it still is a busy place so you’ll want to start your day here early. I arrived for the sunrise and it was purely magical. Not only were there few people, but the sky was lit up with the orangey red hues.
Just be aware that the water smells like sulfur and it can leave a smell on you and your swimsuit. There are also tiny red worms in the water but they are harmless.
The hot springs are therapeutic to soak in and the temperature is around 37.5 C (F).
⏱️ how long to spend here: 3 hours
🚗 where to park: there’s a lot right before the entrance to Cascate del Mulino
Afternoon: Montemerano
After showering in your hotel, head to the nearby charming town, Montemerano.
I truly loved visiting here because the town was full of hearts! And I flew up my drone and saw that the town was even shaped like an actual heart!
It’s also considered one of the most beautiful villages in Italy. You can easily see why when you walk the cute picturesque streets all adorned with hearts!
The views are super unreal with rolling Tuscan hills and vineyards all around.
Don’t miss lunch at Osteria Passaparola Nell’Antico Frantoio where you can find a view of the countryside. I very much enjoyed my aubergine and sun-dried tomato pasta! It was actually so delicious.
⏱️ how long to spend here: 3-4 hours including lunch
🚗 where to park: There’s a free parking lot at the start of the town (Google Maps Location)
Day 3: head to Pienza or your second base
On day 3, you’ll want to start early and head to your second base of Pienza, Montalcino, or Montepulciano. This is a 2.5 hour drive. Along the way, you can stop by 2 amazing towns, Pitigliano and Sorano.
I found Pienza to be a great base for the second part of my as it was close to all the places I wanted to see on my Tuscany road trip.
Hotel recommendations for your second base:
Millefiori is located in the heart of Pienza. It was a charming place with a balcony and a small kitchen area. If you walked out, you’d be moments away from all the main attractions in Pienza. I loved my stay here and it was central to all the places I visited on my Tuscany road trip.
Precise Tale Poggio Alla Sala in Montepulciano is an absolutely beautiful hotel worth a splurge on! For around €400 a night depending on the season, this 5 star hotel offers countryside views and a pool. It really looks like a dream stay!
Guesthouse da Idolina dal 1946 is right in the center of Montalcino. For around €100 a night, it’s an affordable base for your exploration of the Tuscany countryside.
Morning: Pitigliano
Before you head to your second base of the trip, Pitigliano is definitely worth a visit.
It’s known as “Little Jerusalem” due to its once-thriving Jewish community. The streets are full of potted plants and flowers, brown brick buildings, and narrow cobblestone pathways.
I’ve been eating so well on this Tuscany road trip. I had the most amazing pizza at Locanda del Pozzo Antico. I highly recommend it. I mean it was one of the best pizzas I’ve had in a while! They also had a few tables outside and it was a perfect break in the shade from my walk around the town.
⏱️ how long to spend here: 3-4 hours including lunch
Afternoon: Explore Sorano
Take a quick look at Sorano before your drive to Pienza or wherever you choose for your second base.
Sorano is famous for its medieval architecture including fortified walls, towers, and historic buildings. Have a visit to the Orsini Fortress which offers amazing views of the area. If you have more time, visit Vie Cave, an ancient Etruscan pathway carved into a tuff rock. San Niccolò Church is also a notable church to visit.
⏱️ how long to spend here: 1-2 hours
🚗 where to park: As soon as you enter the town you will find many options to park. (Google Maps Location)
Day 4: Hot Springs & Villages
Morning: Bagni San Filippo
Same concept as Cascate del Mulino but is a little less popular and known is Bagni San Filippo.
These hot springs are also super cool! They are tucked away in a forest and there are so many cozy nooks to relax in warm water. There are a few pools to choose from and you can even cover yourself in the mud from the pool grounds and leave with really soft skin!
⏱️ how long to spend here: 4 hours
🚗 where to park: Right before the entrance you will find parking lined to the right of the street. It is €1.50 per hour to park.
Montepulciano
Montepulciano is another beautiful medieval town in Tuscany worth a stop. Here I had the most incredible panini of life. It was at La Schiaccia dell’Opio and was heavenly. I took it to eat in the main square of the town, Piazza Grande. This lovely square is home to the Cathedral of Santa Maria Assunta.
If you continue your walk through Montepulciano from here, you will hit the famous viewpoint (Google Maps Location) which shows the brown-washed buildings in front of the Tuscan hills and vineyards.
Pienza
After Montepulciano, head back to Pienza your home base, and explore the town. Enjoy dinner before heading out to an incredible sunset spot nearby, that of Chapel Vitaleta.
Worth seeing in Pienza is first and foremost, the Cattedrale dell’Assunta which is front and center of the town. Alongside it, you will find many nice views of the rolling hills in Tuscany near to the city walls.
Walk through the maze of streets including Via del Bacio (Street of the Kiss) and Via dell’Amore (Street of Love). Both named this due to the charming romantic feel.
Try Pecorino Cheese, which is famous in Pienza. You’ll find it in many of the shops.
⏱️ how long to spend here: 2 hours or 4 hours including dinner
🚗 where to park: The white spots in the parking lot I’ve linked here are free to park in. Blue lined spots are paid.
Sunset: Chapel Vitaleta
The Chapel of the Madonna di Vitaleta is a tiny church located in the hills of the Val d’Orcia. It only takes 15 minutes to drive there from Pienza and is on the way towards San Quirico. It’s really great to see at sunset and is possibly the most photographed church in Tuscany.
Day 5: Explore the true Tuscan countryside
On day 5, you’ll want to experience the true Tuscany countryside.
Luckily most of these spots are all within 30 minutes of each other. Plus, anywhere you drive around Tuscany is stunning so be sure to make tons of stops along the way as you see beautiful places on your drive.
Tuscany Countryside Spots:
- Podere Belvedere: This zigzag road is lined with stunning cypress trees (Google Maps Location).
- Gladiator Shooting Spot: Gladiator had a scene in Tuscany shot in San Quirico d’Orcia (Google Maps Location).
- Cipressi Ring & Cipressi di San Quirico d’Orcia: These trees form a circle which is really unique to see (Google Maps Location).
Afternoon: Montalcino
Really near to the Cipressi Ring is the town of Montalcino. This cute picturesque town is worth a stop during your 5 day itinerary to Tuscany. You can enjoy lunch here at Taverna del Grappolo Blu which is a Michelin recommended restaurant. There is also a really nice view outside at this point.
Sunset: Agriturismo Baccoleno
Sunset: don’t miss the incredible sunset at Agriturismo Baccoleno (Crete Senesi vista – location on google maps). This is one of the most iconic places in Tuscany and this famous photo point is also what drew me to visit Tuscany.
I thought sunset would be a bad time to visit due to more crowds but I visited in June and it wasn’t that bad at all. Plus, you have ample photo opportunities without people in the shot as the area is quite large.
Just note that the actual tree lined street is private property and only hotel guests are allowed to drive or walk through.
You may also like these posts:
Tuscany’s Hidden Hot Springs: Bagni San Filippo
💗 Visiting Montemerano, the Heart Town in Tuscany
👩 Solo Female Travel Guide to Italy
For more Italy travel, visit my Italy Section!
