This sophisticated 10-day trip is ideal for travelers looking to experience art, culture, food, and wine—all things that make Tuscany one of Italy's most sought-after regions. Start in Florence, the birthplace of Renaissance art and architecture, to experience the city's rich history and walkable center. Then begin a self-guided road trip around Tuscany, visiting UNESCO-listed monuments, picturesque hill towns, and notable vineyards, including a memorable sit-down lunch and wine pairing in Montepulciano.


  • Take a walking tour through Florence's beautiful medieval piazzas
  • Learn how to make fresh pasta during a class that begins with a glass of prosecco
  • Wander around Siena's UNESCO-listed center, home of a famous horserace
  • Travel back in time to visit the town of San Gimignano and Monteriggioni
  • Discover Montepulciano's famous wines and the nearby village of Cortona

Brief Itinerary

Day Highlights Overnight
Day 1 Arrive in Florence, Explore Florence
Day 2 Historic Walking Tour of Florence Florence
Day 3 Local Cooking Class in Florence Florence
Day 4 Pick Up Rental Car & Drive to Siena, Afternoon Wine Tasting Siena
Day 5 Day Trip to San Gimignano & Monteriggioni Siena
Day 6 Day Trip to Volterra  Siena
Day 7 Drive to Montepulciano, via Pienza Montepulciano
Day 8 Wine Tasting in Montepulciano Montepulciano
Day 9 Guided Tour of Cortona Montepulciano
Day 10 Return to Florence, Depart  

Detailed Itinerary

Day 1: Arrive in Florence, Explore

The 13th-century Duomo frames Florence's iconic skyline

Welcome to Florence, the capital of Italy's Tuscany region! Upon arrival at the airport, transfer to the city center and check into your hotel. Once you've had time to rest and settle, step outside and begin exploring the elegant, pedestrian-friendly streets at your own pace.

Florence's compact city center is home to many masterpieces of Renaissance art and architecture, including the iconic Duomo, a terracotta-tiled dome that's impossible to miss, and the Galleria dell'Accademia, which displays Michelangelo's "David" sculpture. To start, you might consider heading to Studio Artesia, steps away from the Ponte Vecchio, to learn more about ancient fresco painting techniques. Alternatively, walk through the peaceful Boboli Gardens to see an oval-shaped island called Isolotto, surrounded by various sculptures and greenery.

In the evening, you can sit at La Terrazza Continentale next to the Ponte Vecchio bridge for a predinner aperitivo on the terrace while enjoying the sunset. Then make your way to the hip Sant'Ambrogio neighborhood for dinner with a glass of Tuscan wine.

Day 2: Historic Walking Tour of Florence

Let your private guide point out Florence's architectural marvels on today's walking tour

Today's exploration of Florence begins with a half-day walking tour. First, meet your guide and then stroll through the picturesque historic center, where you'll find the most important squares and monuments, from the Piazza della Repubblica to the Palazzo Vecchio. You'll then stop at the iconic Duomo, followed by visits to Giotto's Bell Tower and the Baptistery, with its bronze doors. Finish at the Galleria dell'Accademia, where your guide will share stories of the famous Renaissance artists who called Florence home.

After your tour, continue exploring on your own. Consider taking a short walk over to the Mercato Centrale on the second floor of the Mercado di San Lorenzo, where you'll be able to meander through the stalls of local goods. If you're up for an uphill climb, cross over the Arno River to visit Piazzale Michelangelo (or take a taxi). This viewpoint offers an incredible view of Florence and is the perfect place to watch the sunset before heading to Piazza Santo Spirito for a bite to eat. 

Day 3: Local Cooking Class in Florence

Learn How to Make Traditional Italian Pasta
Learn how to make traditional Italian pasta with a local chef

Enjoy a leisurely morning in Florence with breakfast at your hotel and a stroll through the historic center. Popular highlights you may not have seen yet include the sprawling 15th-century Pitti Palace and the world-famous Uffizi Gallery, considered one of the best art museums in Europe. Be sure to purchase your tickets to the Uffizi online to avoid disappointment!

In the afternoon, you'll meet your host near the center of Florence for a traditional Italian cooking class. He or she will first welcome you with a glass of prosecco as you begin the three-hour experience with an appetizer of Italian cheeses and other local products.

Then roll up your sleeves and learn to cook four regional Italian dishes from recipes passed down through generations. Observe the chef's different tricks and techniques in cooking Italian family recipes. In the summer months, you might be able to use the small vegetable and herb garden in the courtyard where zucchini, tomatoes, and herbs are grown. No matter what the season is, the best part comes at the end when you and your hosts will sit down and enjoy your freshly-made dinner together.

Day 4: Pick Up Rental Car & Drive to Siena, Afternoon Wine Tasting

Siena is your first stop on this Tuscan road trip

After breakfast, pick up your rental car and hit the road for the 1.5-hour drive to Siena. Upon arrival, check into your accommodation and head for the UNESCO-listed historic center. Siena is one of Italy's most popular attractions thanks to its medieval architecture, impressive museums, and famous horse race called Palio, which takes place twice a year in the main square, Piazza del Campo.  

To start your self-guided tour, learn about the area's archaeology and history at the Complesso Museale Santa Maria della Scala (the National Archaeological Museum of Siena) and Museo Archeologico di Siena (Museum of Archaeology and History). You can also wander around an extensive art collection at the Museo dell'Opera Metropolitana. Or, learn about ceramics (and shop for gifts) at the Ceramiche Bianco e Nero di Staccioli.

In the afternoon, take a break for a wine tasting at a local wine school—the perfect way to start your crash course on all things grape related. Sample a variety of Tuscan classics paired with regional snacks while learning about the region's most essential and traditional wines and the history embedded in each glass.

Plan your trip to Italy
Chat with a local specialist who can help organize your trip.

Day 5: Day Trip to San Gimignano & Monteriggioni

Wander slowly through the photogenic streets of San Gimignano

Head out today to explore the surrounding countryside and picturesque villages near Siena. First, visit San Gimignano, a quintessentially Tuscan village comprised of medieval buildings perched atop one of the iconic hills that dot the countryside. Located in the Elsa Valley, the village is known for producing Vernaccia di San Gimignano, a white wine with floral and fruity notes. However, San Gimignano is most famous for the 13th-century walls that encircle it, as well as its medieval plazas, churches, and stone towers dominating the skyline. For these reasons, the town is a UNESCO World Heritage Site.

Also, pop in at one of San Gimignano's famous gelaterias. They have an earned reputation for producing some of the best gelato in the world. On the way back from San Gimignano, be sure to stop to visit the impressive medieval fortress of Monteriggioni. The intact castle walls surrounding this town perched on a hillside are a sight to behold.

Return to Siena in the afternoon and explore more of the city's highlights, such as the bell tower at Torre del Magnia, with fantastic city views, and the Piccolomini Library, with its soaring Pinturicchio frescoes. Siena's many churches are also worth a visit, including the green-and-white-striped Duomo, the Basilica dell' Osservanza, and the Sanctuary of Santa Caterina.

Day 6: Day Trip to Volterra

Visit Volterra's Roman Theater to see an impressive archaeological site

Today you'll continue to explore the surroundings of Siena, venturing into the town of Volterra. To get there, you'll drive toward San Gimignano and continue onward before arriving at this hilltop town, about an hour from Siena. The last stretch of road before getting to Volterra is steep and windy, so be prepared!

Volterra's walled town has deep roots in Etruscan history, and to this day, visitors can still see parts of the protective walls and ancient gates when entering. Start in the center square, Palazzo dei Priori, whose bell tower offers impressive views. Then venture inside the Volterra Cathedral to see the marbled entrance and unique ceiling. Finally, visit the ancient ruins of the Roman Theater and wander through this amazing archaeological site.

Apart from its historical importance, Volterra is known for its alabaster production. Stroll through the artisanal shops and handicrafts and see why the town has become famous for this beautiful stone. When you're ready, head back to your accommodation in Siena in the evening.

Day 7: Drive to Montepulciano, via Pienza

Keep your camera close as you drive to the historic village of Montepulciano

After breakfast in Siena, it's time to head deeper into the Tuscan countryside, where you'll visit the famous village and surrounding wine region of Montepulciano. Set out from Siena with your rental car and enjoy the views.

You might want to take the slightly longer route for a more scenic experience and the chance to stop in Pienza. This tiny village stands atop a high hill above the Orcia Valley and was designed by Enea Silvio Piccolomini, who later became Pope Pius II. Visit the Duomo or Cattedrale dell'Assunta to see unique paintings and the octagonal bell tower. Another attraction is the Palazzo Piccolomini to see the hanging gardens and the shooting locations for Franco Zeffirelli's film, "Romeo and Juliet."

Continue on your way to the historic village of Montepulciano, which sits along a ridge surrounded by walls and fortifications. Montepulciano is famous for its Renaissance buildings, churches, and historic main street, which leads through town, ending at the Piazza Grande—the town's leading civic and religious center. Tour the piazza to see the Palazzo Comunale, the castle-like town hall with an iconic clock bell. If you still have energy, climb to the top for views of the Tuscan hillside, then visit the 15th-century Duomo, whose unfinished facade stands out from the surrounding buildings. 

Day 8: Wine Tasting in Montepulciano

Sample some of Montelpuciano's wines during a sit-down lunch

Today, delve deeper into the wine culture of the Tuscany region with a wine tasting right in the heart of Montepulciano. This is your chance to learn the tradition of local winemaking firsthand and experience the culture and history embedded into the production of each bottle. You'll soon understand why this region has been famous for wine production for centuries.

During the tour, you'll head to one of the most ancient wine cellars that the town holds, where the wine bottles age to perfection. This is where vast barrels provide the namesake red wine. After learning about various wines emblematic of the area, you'll sit down for lunch, where each course is paired with a proper tasting. You will surely leave full and satisfied with these local dishes, enjoyed in Montelpuciano's beautiful surroundings.

Finish your day by visiting anything you missed on the first day. Walk around the Church of Sant'Agnese, dedicated to Montepulciano's patron saint, and don't miss the recognizable 16th-century Chiesa di San Biagio, which rests on a hill below the town. You can also visit Palazzo Cappelli and Palazzo Neri Orselli to see regional and national art.

Day 9: Guided Tour of Cortona

Finish your Tuscany tour with a trip to Cortona

Just a 40-minute drive away from the town of Montepulciano sits Cortona. This village was made more famous in recent years thanks to the book by Frances Maye and the subsequent movie with Diane Lane, "Under the Tuscan Sun." Although it is more well-known today, Cortona still holds on to its authentic Tuscan charm.

After arriving and strolling around its central plaza and cobblestone streets, meet your local guide for a two-hour tour where you'll likely fall in love with this postcard-worthy town. Stops include the Piazza della Republica, Cortona's central square that dates back to the Roman age, Palazzo del Capitano del Popolo, the 16th-century residence of Cardinal Passerini, and the Palazzo Comunale.

Spend the rest of the day enjoying Cortona on your own. Venture inside some of its museums to travel back in time. The MAEC Museum holds precious Etruscan artifacts, while the Diocesan Museum is home to various Renaissance paintings. You can also head just outside Cortona to the Monastery of  Saint Francis "Le Celle" for a peaceful experience and spectacular views of the surrounding valley. When you're ready, head back to your accommodation in Montepulciano. 

Day 10: Return to Florence, Depart

Florence skyline
Until next time, Florence!

After one last cappuccino in Montepulciano, it's time to say goodbye, or ciao, to Italy! At the appropriate hour, drive back to Florence and head to the airport for your international flight. Be sure to give yourself plenty of time to drop your rental car. Safe travels!

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Map of Explore Tuscany: Florence, Siena & Montepulciano - 10 Days
Map of Explore Tuscany: Florence, Siena & Montepulciano - 10 Days