Here’s my ultimate 3-day itinerary for Tuscany that helped me enjoy this romantic Italian region, full of charming fields, hilltop hamlets, quaint little towns, and delicious local food and wine.

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What to see in Tuscany in 3 days

What makes Tuscany special?

Tuscany is one of the most beautiful regions in Italy, often topping all the European bucket lists together with Cinque Terre, Rome, and the Italian lakes. Tuscany is known for its charming countryside, beautiful small towns, and delicious food, including wines , like Brunello di Montalcino and Chianti Classico. The region has been a filming location for many iconic movies, including the classics of Bertolucci and Fellini. It is a popular honeymoon destination, as Tuscany’s romantic feel is quite undeniable.

How to get Tuscany?

The best way to reach Tuscany is to fly to Pisa or Florence. Rome could also work, but you’d need to drive a few extra hours. Since my previous experience with public transport in Cinque Terre was not very good, for this trip I rented a car in Pisa to move around the region freely.

Where to stay in Tuscany?

One of the best parts of this 3 days in Tuscany itinerary was our stay at a very local family-owned villa called La Canonica Di San Michele, near Monteriggioni and Siena. After traveling to Italy several times, I’ve recently come to the conclusion that, for some reason, hotels there have rarely worked for me. They almost always end up being a disappointment in terms of price, quality, and expectations. Unlike local stays, where even a delicious homemade breakfast feels worth the whole trip.

Best time to visit Tuscany

Even though we traveled to Tuscany in July, which was not during the offseason, staying outside of Pisa or Florence felt quite relaxed in terms of tourists and overcrowded places. We only realized it was a popular destination when we got to Pisa and saw thousands of people gathered for that famous picture of holding up, pushing, or whatever else they were doing with the Leaning Tower of Pisa. However, the best time to visit Tuscany is usually in spring (April to June) or fall (September to October), as there are fewer visitors and the temperatures are more pleasant.

3 days in Tuscany itinerary Italy
3 days in Tuscany
3 days in Tuscany itinerary
The cute place where we lived during our holidays in Tuscany

3 Days Itinerary for Tuscany

Day 1: Siena and San Gimignano

Visiting Siena

Siena is a beautiful town to start any Tuscany itinerary. Don’t miss Piazza del Campo, Torre del Mangia, and the Siena Cathedral, one of the most famous landmarks in Italy. In Siena, we also had a nice lunch at Osteria da Divo, a cave-like restaurant lit up with candles.

Unique Siena experiences and day trips:

Visiting San Gimignano

After lunch, we headed to San Gimignano, one of the most charming medieval towns in all of Europe. San Gimignano has been a UNESCO World Heritage Site since 1990. We mostly enjoyed a simple stroll through the historic center, with its tall towers, cobbled streets, tiny cafes, and tasty dishes. Don’t miss Torre e Casa Campatelli, the Bell Tower, and the Duomo di San Gimignano. For dinner, we shared a delicious pasta with truffles at Perucà restaurant.

Unique San Gimignano experiences and day trips:

walking the streets of San Gimignano
San Gimignano – one of the most beautiful towns in Tuscany
San Gimignano Tuscany Italy
The secret streets of San Gimignano

Day 2: Pienza, Montalcino, and Montepulciano

Visiting Val d´Orcia

We dedicated our second day in Tuscany to the region of Val d’Orcia, which ended up being my favorite part of the trip. It’s everything you expect to see when traveling to Tuscany in terms of landscapes, atmosphere, and food. While visiting three small towns in one day felt a bit brief, exploring all of them was amazing: Pienza, Montalcino, and Montepulciano. Although I was mostly excited to walk the streets of Montepulciano, especially since seeing it in The Twilight Saga, Pienza was probably the town I liked the most. In Montepulciano, the central square was closed for renovations during our visit, so it honestly disappointed us a bit with the views.

Unique experiences to book:

Montepulciano Italy Itinerary Toscana
Montepulciano
3 days in Toscana itinerary Italy
On the road during our 3-day Itinerary in Tuscany
Pienza Tuscany in 3 days
Pienza
houses and flowers of Pienza tuscany Italy
Pienza

Day 3: Volterra and Pisa

A stop in Volterra

First thing in the morning, we left our cozy La Canonica di San Michele near Monteriggioni and headed toward Pisa, making a brief stop in Volterra. Volterra is often called the Etruscan city, and if you’re interested in history and archaeological sites, it’s a great place to visit. While the Roman Theatre impressed me less than the one in the Spanish city of Merida, it is still a must-see in Tuscany. Don’t miss Piazza dei Priori, Palazzo dei Priori, the Cathedral of Santa Maria Assunta, and Porta all’Arco. We didn’t visit the Volterra Museum of Torture or the Etruscan Museum Mario Guarnacci, but these are also popular stops in Volterra.

Leaning Tower of Pisa Italy

Visiting Pisa

After visiting Volterra and having lunch there, we drove to Pisa and spent the evening in the city. I don’t regret not leaving a full day for Pisa because this was when our romance with Tuscany actually came to an end. While you can’t leave Italy without checking the Leaning Tower of Pisa off your bucket list, the city was packed with tourists.

Unique experiences to book in Pisa:

Is Tuscany worth visiting?

Tuscany is definitely worth visiting! It is one of Italy’s most beloved regions, known for its stunning landscapes, rich history, and delicious food scene. Unlike many other popular Italian destinations that did not live up to my expectations, Tuscany truly deserves its international fame. I enjoyed exploring the numerous medieval towns that seem to have remained untouched for centuries, as well as the local gastronomy. While Italy is globally renowned for its delicious food, Tuscany is also a great wine-tasting destination (which was a nice bonus). Additionally, I loved that despite visiting in June, staying in the local countryside offered a quiet and romantic getaway, which later felt impossible to find in other parts of Italy.

Romantic Holidays in Tuscany Pinterest

For more ideas to plan your epic Italian vacation check my Pinterest board – Italy Travel Tips and Destinations.

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