The Perfect Day Trip to Tuscany From Florence
Spending a few days in Florence after our nine-day cruise with Holland America, I knew I couldn’t leave Italy without seeing the rolling hills and picturesque villages of Tuscany. I’d spent way too much time ogling Tuscan agriturismos on Instagram to let this opportunity pass. So, my husband and I decided to take a day trip to Tuscany from Florence.
If you’re in Florence and wondering whether a road trip to Tuscany is doable, the answer is a resounding yes. It’s an easy drive, stunningly scenic, and completely worth your time.
Here’s how we spent our day exploring Montalcino, Montepulciano, and Pienza—and how you can do the same.
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The Best Tuscany Itinerary
- Drive from Florence to Montalcino (1 hr 45 min)
- Explore Montalcino – wine tasting at Tenuta Poggio Il Castellare, historic sites, bike rentals
- Visit the Gladiator Fields & Madonna di Vitaleta Chapel
- Drive to Montepulciano – wine tasting at Talosa, explore the medieval town, film locations
- Visit Pienza – stunning Renaissance architecture, views of Val d’Orcia, lunch with pecorino cheese
- Return to Florence (1 hr 30 min)
Val d’Orcia Region
After traveling by high speed train from Rome to Florence, we spent a day exploring Tuscany and the scenic Val d’Orcia region.
When you only have 1 day in Tuscany, I urge you to visit the Val d’Orcia region too. As one of a few UNESCO World Heritage sites in Tuscany, you will be in awe as you travel this area.
Located in the central region of Italy in the Province of Siena, the region is the quintessential image of Tuscany—rolling golden fields, winding cypress-lined roads, and hilltop villages that feel like they belong in a painting.
If you’ve ever seen a postcard of Tuscany, chances are it was taken in the Val d’Orcia.
The area is stunning and is also a haven for food and wine lovers.
This day trip to Tuscany explores the beautiful landscape and the prominent products of this area, including olive oils, pecorino cheese, and world-renowned wines like Brunello di Montalcino and Vino Nobile di Montepulciano.
Montalcino: A Wine Lover’s Paradise
We left our Florence hotel, Room Mate Luca, early in the morning, coffee in hand, ready for the adventure.
The drive to Montalcino was about an hour and 45 minutes, but it felt much shorter with the scenery. Rolling hills, olive groves, and vineyards stretched as far as the eye could see.
Montalcino, perched on a hilltop, is famous for Brunello di Montalcino, one of Italy’s most prized red wines.
We kicked off our morning with a visit to Tenuta Poggio Il Castellare, a 500-year-old winery and agriturismo where we tasted some incredible Brunello wines.
Agriturismo, a term that combines agriculture and tourism, are villas or farmhouses on an estate which offer charming accommodations, dining, wine, and even cooking classes.
After sipping our way through Brunello history, we drove a short distance into town.
There are over two hundred wineries in this area and Montalcino is loaded with local winery tasting rooms and wine bars with extensive wine lists. This is absolutely the best place to buy wine, especially if you want to ship it home.
Of course, you could spend a day here wandering through the different tasting rooms, along the cobblestone streets, and browsing the shops.
However, Montalcino is also the perfect spot to rent bikes and explore the many scenic trails. Rent bicycles from Bike Point Terra Eroica and ride one of five routes all of which begin in Montalcino.
The historic sites in Montalcino are also worth a stop, including the Church of Sant’Agostino and the Tempio del Brunello, where you can learn about the wine’s production process.
Montalcino is truly a wine lover’s paradise.
Gladiator Fields & Madonna di Vitaleta Chapel
Leaving Montalcino, we took a short detour to visit the famous Gladiator fields, where Russell Crowe’s character walks through golden wheat fields in the opening scene of Gladiator.
Seeing those rolling fields in real life is absolutely surreal.
Nearby, we spotted the Madonna di Vitaleta Chapel, a tiny, postcard-perfect stone chapel nestled among cypress trees.
This charming 16th-century chapel is said to be the site of an apparition of the Virgin Mary to a shepherd, making it a place of both beauty and legend.
Though you can’t enter the chapel, the surrounding scenery—rolling Tuscan hills, golden wheat fields, and that classic cypress-lined path—makes it worth the visit.
It’s a photographer’s dream and one of the most iconic spots in the Val d’Orcia region.
Montepulciano: More Wine and Movie Sites
From there, we made our way to Montepulciano, a gorgeous medieval town famous for its Vino Nobile di Montepulciano, another top-tier Tuscan wine.
We parked outside the historic center. After wandering through charming cobblestone streets lined with wine cellars, artisan shops, and Renaissance buildings we made it to our first stop, the Talosa Winery.
This historic winery set behind huge wrought iron gates has quite the surprise upon entering – its underground aging cellar dating back to the 16th century.
The Talosa wines are incredible, and the underground setting makes the experience even more special. We ventured down dark stairways and through tunnels into ancient wine cellars beneath two Renaissance palaces.
These tunnels date back to the 1500s, and the massive wooden barrels store some of Italy’s finest wines.
After learning about the wine aging process and discovering the wine is aged in uncovered Etruscan tombs, we were led back to the incredible tasting room.
We opted for the Taste of Talosa experience, a light lunch paired with four wine tastings, including three DOCG wines.
DOCG is Italy’s highest wine classification, ensuring strict regulations on production, aging, and authenticity. Wines with this label undergo rigorous testing and must carry a government-issued numbered seal on the bottle’s neck.
Talosa’s selection was exceptional. We also sampled olive oil from Talosa’s groves and Pienza’s famous pecorino cheese.
After lunch, we wandered Montepulciano’s steep streets—let me tell you, the hills are no joke. Consider this your cardio for the day.
We made it to Piazza Grande, the main square where movies like Under the Tuscan Sun and Twilight: New Moon were filmed. Even if you’re not into movies, the square’s Renaissance architecture and sweeping views make it worth the climb.
Pienza: The Renaissance Ideal
Our last stop was Pienza, a small but stunning town designed by Pope Pius II in the 15th century as the “ideal Renaissance city.”
Pienza is small but packed with history and charm. You can rent an e-bike here if you want to explore the countryside, but we opted for a leisurely stroll.
One of the highlights was the Palazzo Piccolomini, where you can either roam around and take photos or join a 30-minute guided tour.
The Pozzo dei Cani (Dog’s Well) in the main square is another fun sight, along with the Duomo of Pienza, which offers breathtaking views of the Val d’Orcia, a UNESCO World Heritage site.
For lunch, we found a cozy café, Speroni Nudo, where I had an unforgettable Caesar salad loaded with pecorino cheese. A simple dish, but somehow, it was the best salad I’ve ever had.
Maybe it was the setting, or maybe it was just that good. Either way, if you love cheese, Pienza is the place to indulge.
Driving and Parking in Tuscany
Driving through Tuscany is an experience in itself with winding roads, postcard-perfect scenery, and the freedom to explore at your own pace. But there are a few things to keep in mind.
ZTL Zones
Many historic towns in Italy, including Montalcino, Montepulciano, and Pienza, have Zona a Traffico Limitato (ZTL) areas, which are restricted zones where non-resident vehicles aren’t allowed. If you enter one by mistake, you’ll likely get a fine in the mail. Always park outside the ZTL and walk into town.
Parking in Montalcino
Parking in Montalcino is relatively easy, but it can get busy during peak hours.
There are several paid parking lots just outside the historic center, such as Parcheggio Via Aldo Moro and Parcheggio Viale Strozzi. From there, it’s a short walk to the main attractions.
Parking in Montepulciano
Montepulciano is built on a steep hill, so no matter where you park, you can expect a hike.
Look for Parcheggio P8 or Parcheggio P7, which are well-located and have a reasonable number of spaces. Parcheggio P6 takes you closer to the historic center, but the drive is tight.
Parking in Pienza
Pienza is smaller and has free and paid parking lots just outside the town walls. Parcheggio Via Mario Mencattelli is a good option, as it’s a short walk to the main square. Just be mindful of parking signs to avoid fines.
Gas Stations & Toll Roads
If you’re renting a car, keep in mind that gas stations are not always open late, especially in rural areas. Also, major highways have tolls, so carry a credit card or some euros.
Top Tours for a Day Trip to Tuscany From Florence
I would love to tell you that we did this day trip to Tuscany on our own. While it is totally possible, we opted to leave the driving and parking to someone else, because let’s be honest, that meant more wine tasting!
There are plenty of fantastic day tours from Florence to Tuscany, however we booked the Tuscany Hills Postcard View: Val d’orcia Scenery with Wine Tasting through Viator.
Our small group tour left promptly at 8:00 AM from Florence and returned around 6:00 PM. It was the perfect day with the exact itinerary I wrote about in this blog post.
So, if you want to see the best of Tuscany and don’t want the hassle of an international license, renting a car, parking in the correct lots, and following an Italian map, then I highly suggest this tour.
Other Day Trips From Florence to Consider
Some other top-rated Tuscany tours include:
- Tuscany Day Trip from Florence – A full-day experience with lunch that takes you to on a guided tour through Siena, San Gimignano and Pisa.
- Half-Day Wine Tasting Tour in the Chianti Region – This tour includes stops in the Chianti Classico wine region for wine, olive oil, and cheese tastings.
- Tuscany Vespa Driving Tour – Enjoy a full-day Vespa tour. Explore vineyards, San Gimignano, a light lunch with a wine pairing, and several photo stops along the way.
Final Thoughts for Taking a Day Trip to Tuscany from Florence
Our one day trip from Florence to Tuscany was the perfect ending to our nineteen night European vacation, beginning with a layover in Paris, a stay in Murano, a nine-night Holland America Adriatic cruise, and an adventure in Rome.
If you love wine, history, and incredible views, you won’t regret taking a day trip to Tuscany from Florence.
The drive is easy, the towns are magical, and the food and wine? Absolutely worth every calorie.
Would I do it again? In a heartbeat.
