A One Day Road trip Itinerary

through Val d’Orcia

During our honeymoon in Italy, we spent an entire week drinking wine, exploring medieval towns, and eating the most incredible food in Tuscany. My favorite day during the trip was our Tuscany road trip from Montalcino to Montepulciano, with stops in between along the Val d’Orcia region. We rented a car, packed our favorite local snacks, and spent the entire day driving the windy vineyard roads. In this post, I share how to spend the perfect day in Tuscany with this road trip itinerary.

The total drive takes just about 3 hours so when you add in the expected time you’ll spend in each location, you should plan for a full day trip (~8+ hours). I recommend getting an early start and leaving around 9:30AM. Have breakfast in Montalcino and then hit the road!

xxA

Quick Links

Road Trip Overview
Detailed Road Trip Itinerary
Map & Directions
How to Get to Montalcino
Where to Stay
TBP Insider Tips

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Road Trip Overview

Start & End: Montalcino
Stop 1: Abbey of Sant'Antimo
Stop 2: Castiglione d’Orcia
Stop 3: Bagno Vignoni Hot Springs
Stop 4: Montepulciano
Stop 6: Cugusi Pecorino di Pienza
Stop 6: Pienza

Total driving time: ~3 hours
Including stops: ~8 hours

Detailed Road Trip Itinerary

Abbey of Sant’Antimo

The Abbey of Sant’Antimo was built in the 12th century and still stands in near perfect condition. It’s about a 20 minute drive South from Montalcino and is the perfect place to start your day. On weekdays, it is open from 10AM-12:30 and 3:30-5:30 daily and on Sundays and holidays it is open 9AM-10:30Am and 3:30PM-6PM. The monks that occupy the abbey still practice the art of Gregorian chants during services. Plan to spend about a half an hour walking through the grounds, listening to a chant and stopping by the gift shop.

Castiglione d’Orcia

Castiglione d’Orcia was not originally on our list of stops, but we made the decision that we’d pull over for any little town that caught our eye. Castiglione d’Orcia was one of those towns. As we were driving to the hot springs (stop #3), we looked up to see rolling Tuscan hills that lead to what appeared to be the ruins of a castle. The main attraction here is Rocca (castle) di Tentennano which is now converted into a museum. You can enter the castle and climb to the top of the keep to get some of the best views of Val D’Orcia.

Bagno Vignoni Hot Springs

I discovered that there were natural hot springs in Tuscany during my research and knew we had to make a trip. While Bagno Vignoni are smaller than the more popular Saturnia Thermal Baths, we chose them because of their proximity to Montalcino. While the town is called Bagno Vignoni, the actual hot springs are located in Parco dei Mulini which is just a quick walk from the parking main parking lot. Don’t forget your bathing suit and a towel! After you swim, feel free to explore the town for a bit. If you’ve worked up an appetite up to this point, there are a number of restaurants and an amazing gelato shop in the town square.

Montepulciano

Before you loop back toward Montalcino, it’s time to visit Montepulciano. Montepulciano is a medieval town that may have been a settlement as early as the 4th-3rd centuries BC. The town is built on top of a limestone ridge and has gorgeous views of Tuscan vineyards. Montepulciano is famous for its food and wine. You’ll need to park at the bottom of the hill below town since many of the streets do not allow cars. Spend an hour or so strolling through the town and exploring the wine and cheese shops.

Cugusi Pecorino di Pienza

Your final stop on the road trip is Cugusi Pecorino di Pienza, the most magical location overlooking Tuscany’s gorgeous landscape. Pienza is famous for its pecorino cheese, and this place is where you want to try it. After driving down a very long driveway, there is a parking lot and a tiny shop called Cugusi. Stop in and for just about 17 USD, you can purchase a picnic basket with bread, cheese, prosciutto (or your sliced meat of choice) and a small bottle of wine. Take that outside to the picnic tables and enjoy.

Pienza

Next is the town of Pienza. We made only a quick ~20 minute stop here for a shot of espresso and to see the beautiful Duomo, which is one of the earliest cathedrals designed in the Renaissance style. The main highlight of our stop was meeting the mayor of Pienza. We were sipping our espresso and started to chat with a man sitting at the bar with us. He asked how we liked our visit to Pienza and we complimented the gorgeous buildings. He was an incredibly friendly guy and after he walked out, the café owner said, “You just met the mayor of Pienza, Fabrizio Fè.”

Road Trip Map & Directions

How to Get to Montalcino

Montalcino is located south of Florence and Siena, two of the main cities in Tuscany. It is just under a 2 hour drive from Florence and about an hour drive from Siena. We highly recommend renting a car for your Tuscany trip. Tuscany is fairly spread out and there is not a lot of public transportation.

We chose to take a train from Bologna to Florence (here’s our Bologna Blog post) and then rent a car to explore Tuscany. We booked the train through Trenitalia and it only cost 29 euros total for my husband and I! Once we arrived to the Florence train station, we had to transfer to the Florence airport to pick up our rental car (we used Avis to rent and had a great experience with them). Public transportation by metro is located just outside the train station and it should take less than a half hour to get to the airport. We simply asked a policeman how to get to the airport and he pointed us to the metro, which cost only a few euros per person. It’s important to remember to plan for travel time when you return so you don’t miss your departing train.

The day after our road trip, we had a pool day at our accommodation, Antica Grancia Di Quercecchio.

Where to Stay

We chose to stay in Montalcino for four days and Chianti for three. A week in Tuscany was incredibly relaxing, but Daniel and I are adventurous travelers so we could have probably done 4-5 days total instead of a full week. My two favorite days in Tuscany were this road trip as well as a truffle hunting Airbnb Experience in Chianti.

We chose to stay in Montalcino for the first half of our Tuscany trip because it is known for producing the most delicious wine in Italy (in my opinion), Brunello. Brunello is a bold red wine that is made using 100% Sangiovese grapes. We also had multiple friends who recommended this quaint town as our home base.

We chose Chianti because it is closer to Florence for our departure, and I found the incredible truffle hunting Airbnb Experience that I knew we had to take. In addition, Chianti has its own special wine called Chianti Classico. While I preferred Brunello, Chianti Classico is incredible in it’s own right.

Here are some of the small town options for your stay in Tuscany:

Chianti
- Known for Chianti Classico wine
- Close to the famous restaurant from Chef’s Table, Darrio the Butcher; Make a reservation here
- Only an hour drive from Florence
- We stayed in this Airbnb
Montalcino
- Known from Brunello wine
- Situated in Val d’Orca, the most picturesque area of Tuscany
- Delicious food and the perfect starting point for this road trip
- We stayed at Antica Grancia Di Quercecchio
Montepulciano
- Staying here is similar to staying in Montalcino
- Known for vino noble red wine
- Montepulciano is the farthest stop on this road trip, so you could simply take it backwards

Lavender bushes outside of Abbey of Sant’Antimo

TBP Insider Tips

> We recommend taking a train to Florence and renting a car to get around Tuscany. We booked a train through Trenitalia and used Avis to rent our car. More info above in our “How to Get to Montalcino” section.

>You’ll need an International driver’s permit to drive legally in Italy. Before Daniel and I came on the trip we thought this was a scam, but when we got pulled over for speeding (I’m looking at you, Daniel), the policeman asked to see this and let us go with a warning.

>In Europe, you’ll need euros. You can bring cash and exchange money at the airport or get a no-fee debit card like the one I have from Fidelity. It’s super easy and free to get, and will allow you to take out money from international ATMs with no fees. You just load it up in advance.

>Make advanced reservations for restaurants in Tuscany. In Montalcino, we recommend Osteria Osticcio. Don’t miss out on the pici al burro. It was the best pasta I have ever tasted in my entire life.