7-day (one week) Tuscany itinerary

Imagine strolling through the vineyards with a glass of Chianti in hand, savoring the rich flavors and soaking up the timeless beauty of Tuscany. It's not just a vacation - it's an immersion in centuries-old traditions, world-class wines and unforgettable cuisine. Tuscany is a region where every hill, every village and every vineyard has a story to tell. Here’s our guide to crafting the perfect Tuscany itinerary.

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Why visit Tuscany?

Tuscany draws travelers with its perfect mix of history, natural beauty, and culinary delights.

From the charm of medieval hilltop villages to the artistic treasures of Florence, it’s easy to see why this region is so beloved. Tuscany is a paradise for wine lovers, offering vineyard tours and tastings of world-famous wines like Chianti and Brunello di Montalcino, set against stunning landscapes of rolling hills and cypress trees.

Any Tuscany promises a heady blend of culture, breathtaking scenery, and unforgettable flavors—making it a destination that lives up to its reputation.

Best places to see in Tuscany

In Tuscany, every town and city offers something unique and unforgettable. Whether you’re marveling at Renaissance art in Florence or tasting world-class wine in Chianti, Tuscany is a region filled with beauty and history at every turn.

Florence

The capital of Tuscany, Florence is a must for art and history lovers. Highlights include the Florence Cathedral (Duomo), the Uffizi Gallery, the Accademia Gallery (home to Michelangelo's David), and the iconic Ponte Vecchio bridge.

San Gimignano

Known as “medieval Manhattan” for its striking towers, San Gimignano is a well-preserved city where you can be transported back in time. Wander its cobbled streets, sample award-winning gelato and admire the breathtaking view of the surrounding countryside from one of the towers.

Pienza

A UNESCO World Heritage site, Pienza is celebrated for its Renaissance architecture and harmonious urban design. Visit the beautiful Piazza Pio II, explore the cathedral, and sample the town’s famous pecorino cheese. Pienza is a gem in the Val d’Orcia valley with a distinctive charm.

Chianti Region

For wine lovers, the Chianti region is paradise. Famous for its Chianti Classico wines, this area is dotted with vineyards, wineries, and rustic villages. Take a leisurely wine tour to savor the region’s finest wines and soak in the breathtaking countryside views.

Lucca

This walled city is known for its Renaissance fortifications and charming atmosphere. Take a stroll or bike ride along the top of the walls for panoramic views, explore the historic center, and enjoy authentic Tuscan cuisine in one of Lucca’s cozy trattorias.

Want to explore Europe even more? We have prepared the most convenient European itineraries for you to explore the continent.

How to get to Tuscany

Starting your Tuscan adventure is easy, with several convenient travel options available.

By air

Fly into Florence or Pisa, both of which offer regular connections to major European cities. Florence Airport is close to the heart of Tuscany, while Pisa Airport provides access to the western coast and nearby attractions.

By train

Italy’s extensive rail network makes it simple to reach Tuscany by train. High-speed trains connect major cities like Rome and Milan to Florence, allowing you to enjoy scenic countryside views as you travel.

By road: rental car

For maximum flexibility, consider renting a car. Tuscany’s well-maintained highways make it easy to explore the region at your own pace, giving you the freedom to visit charming hilltop towns, vineyards, and hidden gems along the way.

7-day Tuscany itinerary

Tuscany is a region that’s rich in culture, food, and beautiful views. This 7-day Tuscany itinerary is designed to give you a great mix of all that. You’ll start in Florence, head to San Gimignano, explore the countryside, and enjoy some of Tuscany’s best food and wine experiences.

Want to skip the hassle of planning? Have us create your trip for you.

Day 1: Arrive in Florence

Florence is a city with so much history. It’s where the Renaissance started, and you’ll find reminders of that everywhere. Michelangelo carved the statue of David here from a block of marble that others thought was too flawed, and Galileo first spotted the moons of Jupiter from the Torricelli gardens.

As you explore the city, you’re walking in the footsteps of legends like Leonardo da Vinci, who tested the acoustics of the Duomo by singing inside its dome.

While Florence is all about history, it also has plenty to offer in the present. There are amazing restaurants, art galleries, and boutiques to check out. You could easily spend your whole time in Italy exploring the classic sights here, but take a moment to just walk around the city. 

Where to stay in Florence

When deciding where to stay in Florence, you have some options—here are some of our favorite parts of town: 

• Oltrarno: The "other side of the Arno" is where local artisans still work in centuries-old workshops. It's authentic Florence, with fewer tourists and more traditional trattorias.
• Santa Croce: A vibrant area combining nightlife with history, featuring some of Florence's best restaurants and bars alongside historic churches.
• Santo Spirito: Perfect for food lovers, this neighborhood centers around a bustling square filled with cafes and markets, offering a genuine slice of Florentine life.

Day 2: San Gimignano

Caffè Gilli, which has been around since 1733, is one of the best spots for a classic Florentine cappuccino. You’ll stand at the marble counter (worn smooth by two centuries of elbows) alongside locals who are just starting their day. Their cornetti are fantastic, and the whole experience is a great way to start your second day of this week-long Tuscany itinerary.  

Then head to San Gimignano. Famous for its towers and well-preserved medieval architecture, it’s one of the most iconic towns in Tuscany. While many other towns lost their towers over time, San Gimignano still has 14 of the original 72. It’s a rare opportunity to see what a medieval Tuscan town actually looked like.

Toree Grossa

Start your day with a climb up Torre Grossa, the tallest tower in the city. The views from the top are worth it—vineyards, cypress trees, and the distant Apennine Mountains all laid out before you. These towers were once used as status symbols by wealthy families, and some still have traces of the original wooden floors. Back then, when families needed more space, they would just build another level, like a medieval version of vertical living.

How to get from Florence to San Gimignano

The drive from Florence to San Gimignano takes about an hour, and it’s a beautiful route. You’ll pass through the Tuscan countryside, complete with vineyards and medieval castles. If you’ve got some extra time, stop in Monteriggioni, a small walled town perched on a hill. It’s so picturesque that Dante mentioned it in his Divine Comedy, and you’ll see why when you get there.

Where to stay in San Gimignano

San Gimignano isn’t huge, but there are some options when it comes to areas to stay:

• Historic Center: Staying in the heart of San Gimignano puts you right near the main attractions, like the towers and medieval streets. Many hotels offer great views of the countryside.
• South of town (near Porta SG): If you’re after something quieter, stay near Porta San Giovanni. It’s still close to the center, but you’ll get a more relaxed atmosphere.
• Countryside: For a peaceful retreat, look for accommodations in the surrounding countryside. The views are beautiful, and it’s a great spot for unwinding.

Day 3: Explore San Gimignano

On day three of this Tuscany itinerary, spend some time wandering around San Gimignano.

Take a hike

If you’re in the mood for a hike, the San Gimignano Ring Trail (Anello di San Gimignano) is an 8-mile (13 km) circular route that takes you around the town and through olive groves, vineyards, and past historic farmhouses and churches. Alternatively, the Vernaccia Wine Trail (Sentiero della Vernaccia) is another scenic route that winds through the vineyards where the famous Vernaccia white wine is made. Both trails will give you beautiful views of the town and the surrounding countryside.

Have a Tuscan lunch

For lunch, head to Dal Borgo, a family-run trattoria in the historic center. They serve homemade pici pasta and hearty Tuscan soups like ribollita. The family has been making pasta here for generations, and the wooden boards they use have been worn smooth from years of rolling dough by hand. It’s a little less touristy than the places around the main square. Having a Tuscan meal is by far one of the best things to do in Tuscany.

Another great option is Le Vecchie Mura, which is located along the town’s walls. The terrace overlooks the Tuscan countryside, and it’s the perfect spot to enjoy traditional dishes like pappardelle with wild boar ragù, paired with local Vernaccia wine.

Day 4: Montepulciano

Montepulciano is famous for its Vino Nobile wine and stunning Renaissance architecture. Unlike other Tuscan towns that were built by merchants, this one was designed by nobles, and you can see that in the grand palaces around town. Each one seems more impressive than the last, thanks to wealthy families of the time competing for prestige. 

Take a wine tour

To really experience Montepulciano’s wine, check out one of its historic cellars, many of which are tucked beneath Renaissance palaces. If you want a thorough experience, book a tour at Avignonesi for tastings and vineyard tours. For something a bit more atmospheric, De' Ricci offers an unforgettable experience in their medieval underground cellars. Gattavecchi, near San Biagio Church, pairs wine tasting with amazing views, while Salcheto is known for its eco-friendly practices and great hospitality.  

Piazza Grande

If you’re not into wine, take a stroll through the historic center. Start by walking up Via di Gracciano nel Corso, the main street that leads to the highest point in town. The walk is steep but filled with beautiful palaces and shops, and the views only get better as you go.

How to get from San Gimignano to Montepulciano

Take the SR2 south towards Siena, then the SR438 towards Asciano. The journey takes about 1.5 hours by car, but plan for 2-3 hours with stops. You'll pass through the stunning Crete Senesi region, known for its distinctive gray clay hills that create an almost lunar landscape.

Where to stay in Montepulciano

For easy access to Montepulciano's main attractions, stay in the historic center around Piazza Grande. There are plenty of charming boutique hotels here with views of the vineyards. If you prefer a quieter vibe, try staying near San Biagio Church in the lower town. It’s a bit more peaceful and offers sweeping views of the countryside.

Day 5: Castalina in Chianti

Castellina in Chianti is a quieter, more authentic medieval town in the heart of the Chianti Classico wine region. It’s a great escape from the more tourist-heavy spots, but just keep in mind that many places close in the afternoon for riposo (the Italian siesta), so plan accordingly. 

Walk along the Via della Volte

The Via della Volte is a covered medieval walkway that runs along the city walls, originally used by soldiers defending the town. Now it’s a peaceful spot for a walk, with shops and restaurants built into the ancient arches. There are some great viewpoints to the Chianti countryside along the way.

Wine tasting

Castellina is right in the middle of the Chianti Classico region, so it’s the perfect place to try some of the area’s famous wines. The combination of altitude, soil, and climate makes it ideal for growing Sangiovese grapes. Castello di Fonterutoli, owned by the Mazzei family since 1435, offers a great tasting experience, with a modern winery and historic cellars. If you’re looking for something more intimate, check out Cantina Geggiano. Those who are traveling to try great wines might want to consider an Italy wine tour.

Tenuta di Corsano olive oil tours 

If you want to try something a little different, Tenuta di Corsano offers tours of their olive oil production. You’ll get to visit the olive groves and learn about the harvesting process, as well as see the traditional stone mill used to produce the oil.  

Where to stay in Castellina in Chianti

If you want to be close to Castellina, Greve is just a short drive away. It has a lovely town center with good restaurants, shops, and access to wine tours. For a more peaceful stay, try Radda, a small town surrounded by vineyards. It’s quieter and gives you a more rural experience.

Day 6: Day trip to Pienza and the Val d’Orcia

Start day six of this week-long Tuscany itinerary in Pienza. 

Pienza

This UNESCO World Heritage town was shaped by Pope Pius II during the Renaissance, and it’s a great place to explore. The streets and squares are beautifully laid out, and you’ll enjoy a relaxed walk through the town. Don’t miss the Via dell'Amore, a scenic path along the town walls with amazing views of the Val d'Orcia.

Drive through the Val d’Orcia countryside

From Pienza, head into the Val d’Orcia. This area has been inspiring artists for centuries, and it’s easy to see why. The landscape is full of rolling hills, cypress trees, and tiny chapels like the Cappella della Madonna di Vitaleta, tucked among wheat fields. Take a stop in San Quirico d'Orcia, a peaceful village with lovely gardens—perfect for a quiet stroll. From there, make your way to Bagno Vignoni, a village known for its historic thermal pool in the main square.

Route to take

To get from Pienza to Bagno Vignoni, follow the SP146 toward San Quirico d'Orcia. You’ll pass by some of the most beautiful views in Tuscany. From San Quirico, continue along SP137 to reach Bagno Vignoni. 

Day 7: Relaxed drive to Pisa

The drive from Montepulciano to Pisa takes about three hours, but you’ll want to make a few stops along the way.

How to get from Montepulciano to Pisa

Head west from Montepulciano, passing through the Val d'Orcia on your way to San Quirico d'Orcia. This part of the drive is classic Tuscany—rolling hills and vineyards stretching out on either side.

Stop in Siena

Siena is about halfway to Pisa, so it’s a perfect place to stop for a break. The city is famous for Piazza del Campo, a large square where the Palio horse race is held twice a year, and its cathedral, with beautiful art by Donatello and Michelangelo. It’s definitely worth a couple of hours to explore.

From Siena, continue on the SS429 through the Chianti region, and then take the FI-PI-LI highway (SGC Firenze-Pisa-Livorno) to finish your drive to Pisa.

Campo dei Miracoli in Pisa

When you reach Pisa, head straight to the Campo dei Miracoli (Field of Miracles). This large green space is home to four main attractions: the Leaning Tower, the Cathedral, the Baptistery, and the Monumental Cemetery. The entire complex represents different stages of life: the Baptistery (birth), the Cathedral (life), the Tower (calling to prayer), and the Cemetery (death). 

End at Pisa airport

Galileo Galilei Airport (PSA) is conveniently located just over a kilometer from the Campo dei Miracoli. It's Tuscany's main international airport, and the end point of this Tuscany itinerary.

Create your Tuscany itinerary with us

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