Here’s my ultimate 3-day Tuscany itinerary that let me fully experience this romantic Italian region – brimming with rolling fields, hilltop villages, charming towns, and mouthwatering local food and wine.

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What to see in Tuscany in 3 days

What makes Tuscany special?

Tuscany is one of Italy’s most breathtaking regions, frequently topping European bucket lists alongside Cinque Terre, Rome, and the Italian lakes. Renowned for its picturesque countryside, enchanting small towns, and exceptional cuisine – including celebrated wines like Brunello di Montalcino and Chianti Classico – Tuscany captivates all who visit. The region has also served as the backdrop for many iconic films by directors like Bertolucci and Fellini. With its undeniable romantic charm, Tuscany remains a beloved destination for honeymooners and travelers alike.

How to get Tuscany?

The most convenient way to reach Tuscany is by flying into either Pisa International Airport or Florence’s Peretola Airport. Pisa is generally preferred due to its better connectivity with several major airlines and direct train links to Florence every two hours, with a journey time of about 57 minutes. Florence’s airport, while closer to the city, has limited international flights and tends to be more expensive, especially since low-cost carriers often avoid it.

Based on previous experience with public transport challenges in nearby regions like Cinque Terre, we decided to rent a car at Pisa airport (as it offers the advantage of flexibility and ease of access to various Tuscan attractions without being bound by train or bus schedules.)

Where to stay in Tuscany?

One of the highlights of our 3-day Tuscany itinerary was staying at La Canonica Di San Michele, a charming family-owned villa nestled near Monteriggioni and Siena. After multiple trips to Italy, I’ve realized that traditional hotels often fall short for me – they tend to disappoint when it comes to value, quality, and overall experience. In contrast, local accommodations like this villa offer an authentic touch that truly elevates the trip. From the warm hospitality to the delicious homemade breakfasts, these stays create memorable moments that make the entire journey feel worthwhile.”

Best time to visit Tuscany

Although we visited Tuscany in July – well into the high season – staying outside of Pisa and Florence felt surprisingly peaceful, with far fewer crowds and a more relaxed atmosphere. It wasn’t until we arrived in Pisa that we truly noticed the tourist influx, with thousands of visitors gathering to snap the classic Leaning Tower photos.

That said, the ideal time to explore Tuscany is typically in spring (April to June) or fall (September to October), when the crowds are even thinner and the weather is comfortably mild.

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 stunning town and the perfect starting point for any Tuscany itinerary. Be sure not to miss the iconic Piazza del Campo, the soaring Torre del Mangia, and the magnificent Siena Cathedral – one of Italy’s most renowned landmarks. While in Siena, we enjoyed a memorable lunch at Osteria da Divo, a cozy, cave-like restaurant warmly illuminated by candlelight.

Unique Siena experiences and day trips:

Visiting San Gimignano

After lunch, we made our way to San Gimignano, one of Europe’s most enchanting medieval towns and a UNESCO World Heritage Site since 1990. We loved wandering through its historic center, soaking in the sight of towering medieval structures, winding cobblestone streets, quaint cafés, and savoring local flavors. Key highlights not to miss include Torre e Casa Campatelli, the Bell Tower, and the stunning Duomo di San Gimignano. For dinner, we indulged in a delectable truffle pasta at the charming 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 exploring the Val d’Orcia region, which ended up being my favorite part of the trip. It perfectly embodied everything you expect from Tuscany – stunning landscapes, charming atmosphere, and delicious food. While visiting three small towns in a single day felt a bit rushed, experiencing Pienza, Montalcino, and Montepulciano was truly amazing.

Although I was especially excited to stroll through Montepulciano’s streets, partly because of its appearance in The Twilight Saga, Pienza ended up being my favorite town. Unfortunately, Montepulciano’s central square was closed for renovations during our visit, which was a bit disappointing in terms of 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

Early in the morning, we left our cozy villa, La Canonica di San Michele near Monteriggioni, and set off toward Pisa, making a brief stop in Volterra along the way. Known as the Etruscan city, Volterra is a fantastic destination for history enthusiasts and lovers of archaeology. While the Roman Theatre didn’t impress me quite as much as the one in Mérida, Spain, it remains a noteworthy site in Tuscany.

Be sure to visit Piazza dei Priori, Palazzo dei Priori, the Cathedral of Santa Maria Assunta, and Porta all’Arco. Although we didn’t have time to explore the Volterra Museum of Torture or the Etruscan Museum Mario Guarnacci, both are popular attractions worth considering.

Leaning Tower of Pisa Italy

Visiting Pisa

After exploring Volterra and enjoying lunch there, we continued on to Pisa and spent the evening in the city. I don’t regret not dedicating a full day to Pisa – this visit felt like the natural conclusion to our Tuscan adventure. While the famous Leaning Tower is undoubtedly a must-see and one of those iconic sights you can’t leave Italy without checking off, the city itself was overwhelmingly crowded with tourists, which made it feel less charming than the rest of our trip.

Unique experiences to book in Pisa:

Is Tuscany worth visiting?

Tuscany is without a doubt worth visiting – one of Italy’s most beloved regions, it’s renowned for its stunning landscapes, rich history, and exceptional food culture. Unlike some other popular Italian destinations that didn’t quite live up to my expectations, Tuscany was love at first sight. If you’re drawn to rolling hills, charming villages, and authentic Italian cuisine, it truly lives up to the hype.

I loved wandering through medieval towns that felt frozen in time and indulging in the region’s rich culinary traditions. While Italy is known worldwide for its cuisine, Tuscany also stands out as a top-tier wine destination – which was a delightful bonus. Even in summer, staying in the countryside offered a peaceful, romantic escape that felt increasingly rare in other parts of the country.

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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