This road trip around Tuscany is perfect for those looking to delve into Italian wine culture. Start in Florence, the birthplace of the Renaissance, stroll around its medieval plazas and cathedrals and see for yourself the history that permeates the city. Visit picturesque Tuscan villages and local wineries, getting a taste for local life and in some incredible surroundings.

Highlights

  • Tour Florence's beautiful medieval piazzas & cathedrals
  • Enjoy a wine tasting in the Tuscan city of Siena
  • Travel back in time visiting the town of San Gimignano and Monteriggioni
  • Discover Montepulciano and its famous wine
  • Wander through the cobblestone streets of Cortona

Brief Itinerary

Day Highlights Overnight
Day 1 Arrival in Florence Florence
Day 2 Historic Walking Tour of Florence Florence
Day 3 Drive to Siena, Afternoon Wine Tasting Siena
Day 4 Self Guided Visit of San Gimignano & Monteriggioni from Siena Siena
Day 5 Drive from Siena to Montepulciano, stop in Pienza Montepulciano
Day 6 Wine Tasting in Montepulciano Montepulciano
Day 7 Visit Cortona, Guided Tour Montepulciano
Day 8 Drive to Florence, Depart  

Detailed Itinerary

Day 1: Arrival in Florence

Various cured meats in the Mercato Centrale
Various cured meats in the Mercato Centrale

Welcome to Florence, the capital of Italy's Tuscany region! Arrive at Florence Airport and transfer to the city center to check in to your hotel. Spend the rest of the day relaxing and settling in, or head out for a relaxing stroll and dinner downtown.

Florence is home to many masterpieces of Renaissance art and architecture, including the iconic Duomo, a terracotta-tiled dome, and the Galleria dell'Accademia, which displays Michelangelo's 'David' sculpture. Make the most of your time at some of these spots:

  • Head to Studio Artemisia, located steps away from the Ponte Vecchio for a class in ancient fresco painting techniques
  • Visit the Mercato Centrale, a 19th-century open-air market, to browse for a wide selection of vegetables, fruits, meats and cheeses, and a variety of lunch spots  
  • Take a walk through the peaceful Boboli Gardens to see the oval-shaped Isolotto, a small island surrounded by various sculptures and lots of greenery 

In the evening, stroll around the historic L-shaped Piazza della Signoria, located in front of the Palazzo Vecchio, for some people watching followed by dinner and drinks in the hip Sant'Ambrogio neighborhood.

Day 2: Historic Walking Tour of Florence

Piazza della Signoria, a UNESCO site
Piazza della Signoria, a UNESCO site

Spend the day exploring the city's top sites, starting with a guided half-day walking tour. 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 explore the beautiful squares and architecture that make Florence so picturesque. Soak in the atmosphere before heading over to the Ponte Vecchio, where you can admire the Arno River.

You'll then make a stop at the iconic Duomo, with its terracotta-tiled dome, where across the way Giotto's Bell Tower and the Baptistery with its bronze doors create an unforgettable scene. Finally, with Skip the Line entrance tickets in hand, you'll head to the Galleria dell’Accademia to see Michelangelo’s David. Your guide will share stories of Michelangelo and how this masterpiece came to be.

After your tour, continue your exploration of Florence on your own.  Head across the Arno River to visit to Piazzale Michelangelo. It's a bit of an uphill climb or a quick taxi ride away. This spectacular viewpoint offers an incredible view of all of Florence and is the perfect place to watch the sunset before you head over to Piazza Santo Spirito for some pre-dinner aperitivos

Day 3: Drive to Siena, Afternoon Wine Tasting

Brick houses in Siena
Brick houses in Siena

After breakfast, pick up your rental car and hit the road for the 1.5-hour drive to Siena, then check into your accommodation. The city's historic center is one of Italy's most popular attractions and is a UNESCO World Heritage Site. Siena is famous for its medieval architecture, museums, and for Palio, a popular horse race that takes place twice a year in the Piazza del Campo (the main square).  

Make the most of your time in Siena with some recommended activities: 

  • Learn about 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)
  • See art at the Museo dell'Opera Metropolitana
  • Learn about the ceramics manufacturing process and shop for gifts at the Ceramiche Bianco e Nero di Staccioli 

In the afternoon, head to the city center of Siena for a wine tasting. This local wine school will offer you the perfect way to start your crash course on all things wine. Sample a variety of Tuscan classics paired with some regional snacks while learning about the most important and traditional wines of the region and the history embedded in each glass.

Plan your trip to Italy
Customize your trip with help from a local travel specialist.

Day 4: Self Guided Visit of San Gimignano & Monteriggioni from Siena

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. It's for these reasons that the town is a UNESCO World-Heritage Site.

Also, be sure to 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 make a stop to visit the impressive medieval fortress of Monteriggioni. The intact castle walls surround this town perched on a hillside, and are a sight to behold. Take in the views before continuing on your way back to Siena. 

Arriving back in Siena, don't miss the city highlights, such as the 13th-century Palazzo Pubblico; the Torre del Magnia, a bell tower with fantastic city views; the green-and-white-striped Duomo; and the Piccolomini Library, which is famous for its soaring Pinturicchio frescoes. Besides these, there's the Museo dell'Opera Metropolitana art museum as well as Siena's many churches, including the Basilica dell' Osservanza, Santo Spirito, and Sanctuary of Santa Caterina.

Day 5: Drive from Siena to Montepulciano, stop in Pienza

Montepulciano
Montepulciano

Time to head further into the Tuscany countryside, visiting the famous village and surrounding wine region of Montepulciano. Set out from Siena with your rental car and enjoy the views along the way. We'd recommend opting for the slightly longer route, heading down along the SR2 and later the SP146 roads for a more scenic experience and stopping in the village of Pienza. 

Stretch your legs in the tiny village of Pienza, which stands atop a high hill above the Orcia Valley. The charming town is known as the "ideal city of the Renaissance" and was designed by Enea Silvio Piccolomini, who later became Pope Pius II. Piccolomini used his money and influence to transform his birthplace village, then known as Corsignano, into his ideal Utopian Renaissance city.

The harmonious composition of the city includes the Cathedral, the Papal or Piccolomini Palace, the Town Hall, and the central square which sits between the buildings. Visit the Duomo or Cattedrale dell'Assunta to see unique paintings and the octagonal bell tower. Visit the Palazzo Piccolomini to see the hanging gardens, as well as 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 and is surrounded by walls and fortifications. Montepulciano is famous for its Renaissance buildings, churches, and historical Corso main street which leads through town, ending at the Piazza Grande—the town's main civic and religious center.

Tour the Piazza to see the Palazzo Comunale, the castle-like town hall with an iconic clock bell. Climb to the top for views of the Tuscan hillside, then visit the spartan 15th-century Duomo, whose unfinished facade stands out from the surrounding buildings. Continue to the Palazzo Cappelli and Gothic Palazzo Neri Orselli, home to the civic museum, to see regional and national art.

Day 6: Wine Tasting in Montepulciano

Wine region of Chianti

Today, delve deeper into the wine culture of the Tuscany region with a wine tasting right in the heart of Montepulciano. 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. 

Tour one of the most ancient wine cellars the town holds, where the wine bottles age to perfection. Go back in time in this centuries-old cellar, which holds vast barrels full of the town's namesake red wine. Finally, with a better appreciation of the history, taste for yourself a variety of wines emblematic of the area.

The tour wouldn't be complete without a local lunch to pair with your wine tastings. You are sure to leave full and satisfied from these local dishes, enjoyed in your beautiful surroundings.

Back in Montepulciano, visit 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.

Day 7: Visit Cortona, Guided Tour

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 subsequent movie with Diane Lane, Under the Tuscan Sun. But although it is more well-known these days, Cortona still holds on to its authentic Tuscan charm.

After arriving and strolling around its main plaza and cobblestone streets, meet your local guide for a 2-hour tour and fall in love with this postcard-worthy town. Stops include the Piazza della Republica, Cortona's main 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 and the Diocesan Museum is home to an array of Renaissance paintings. Head just outside of 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 8: Drive to Florence, Depart

Florence skyline
Florence skyline

After one last cappuccino, make the 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. Arrivederci, Italia!

Map

Map of Tuscany Road Trip: Florence, Siena, & Montepulciano - 8 Days
Map of Tuscany Road Trip: Florence, Siena, & Montepulciano - 8 Days