Combine historic hill towns, fine wines, and the Tuscan countryside for an Italian eight-day road trip to remember. Get your bearings amid the Renaissance splendor of Florence, then set out into the surrounding landscapes—basing yourself first in Siena and then in Montepulciano. Along the way, you'll experience wine tastings and workshops focused on local Chianti vintages and set off on day trips to hilltop villages like San Gimignano, Monteriggioni, and Cortona.


  • Get a crash course in Renaissance history on a walking tour of Florence
  • Learn about the many intricacies of Tuscan wine in Siena
  • Take day trips to the hill towns of San Gimignano, Monteriggioni, and Cortona
  • Get to know the fortified medieval town of Montepulciano
  • Taste your way through the best wines of the Chianti region

Brief Itinerary

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

Day 1: Arrive in Florence, Explore

You'll land in Florence, the birthplace of the Renaissance

Welcome to Florence, the capital of Italy's Tuscany region! Arrive at Firenze-Peretola 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 to start exploring. Long considered a cultural capital and the "Jewel of the Renaissance," Florence is home to many masterpieces of Renaissance art and architecture, including the iconic Duomo and Galleria dell'Accademia.

Channel some of the city's artistic flair and head to Studio Artemisia for a class in ancient fresco painting techniques, or visit the Mercato Centrale, a 19th-century open-air market, to browse for a wide selection of vegetables, fruits, meats, and cheeses. For something more sedate, 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.

As evening falls, make for La Terrazza Continentale next to the Ponte Vecchio bridge for a predinner cocktail on the terrace while you enjoy the sunset, then continue to the Sant'Ambrogio neighborhood for dinner accompanied by a glass of Tuscan wine.

Day 2: Historic Walking Tour of Florence

Artisan shops line the covered Ponte Vecchio bridge over the River Arno

Spend the day exploring the city's top sites 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 architecture that makes Florence so picturesque. Soak in the atmosphere before heading over to the Ponte Vecchio, where you can admire the River Arno. 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 bronze doors of the Baptistery 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 bring the iconic piece to life as they share stories of Michelangelo and how the masterpiece came to be. After working up an appetite with all that walking, head over to the trendy Piazza Santo Spirito as evening falls for some predinner aperitivi.

Day 3: Pick Up Rental Car, Drive to Siena & Afternoon Wine Tasting

Drive to Siena, then sit back and enjoy a wine-tasting workshop

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 its historic Palio, a popular horse race that takes place twice a year in the Piazza del Campo (the main square).

You could start your exploration of the city by learning about its archaeology and history at the Complesso Museale Santa Maria della Scala (National Archaeological Museum of Siena) and the Museo Archeologico di Siena (Museum of Archaeology and History). See works of medieval art and architecture at the Museo dell'Opera Metropolitana, or discover 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.

Day 4: Day Trip to San Gimignano & Monteriggioni

Take a day trip to one of Tuscany's loveliest hill towns: San Gimignano

Head out today to explore the surrounding countryside and picturesque villages near Siena. First, visit San Gimignano, a quintessential Tuscan village comprised of medieval buildings perched atop one of the iconic hills that dot the countryside. 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. Located in the Elsa Valley, the UNESCO-listed village is also known for producing Vernaccia di San Gimignano, a white wine with floral and fruity notes.  

Pop in at one of San Gimignano's famous gelaterias, which has a well-earned reputation for producing some of the best gelatos in the world, before getting back on the road to Siena. On the way, make sure to visit the impressive medieval fortress of Monteriggioni. Intact castle walls surround this hilltop town, and the views over the surrounding countryside are well worth the stop.

Arriving back in Siena, you'll have the rest of the day to discover more of the city's 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. 

Day 5: Drive to Montepulciano via Pienza

See Renaissance architecture and countryside views from the walled town of Montepulciano

Time to head farther 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. While the drive only takes about an hour, opt for the slightly longer route, heading down along the SR2 and later the SP146 roads for a more scenic experience and a stop in the village of Pienza. Stretch your legs in this tiny village that stands atop a high hill above the Orcia Valley. Known as the "ideal city of the Renaissance," Pienza 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 town includes the Cathedral, the Papal 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. Don't miss 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. Get settled in at your hotel, then head out for a stroll to get your bearings. Renaissance buildings and churches surround its Piazza Grande—the town's main civic and religious center. See the Palazzo Comunale, the castle-like town hall with an iconic clock bell, and climb to the top for views of the Tuscan hillside. 

Day 6: Wine Tasting in Montepulciano

Sample the best reds of the Chianti region with a wine tasting in the heart of Montepulciano

Today, delve deeper into the wine culture of Tuscany 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.

In the afternoon, you could see more of Montepulciano's sights at your own pace. Visit the Spartan 15th-century Duomo, whose unfinished facade stands out from the surrounding buildings, and continue to the Palazzo Cappelli and Gothic Palazzo Neri Orselli, home to the civic museum, to see regional and national art. See 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: Day Trip to Cortona, Guided Tour

Take a day trip to postcard-pretty Cortona

Just a 40-minute drive away from the town of Montepulciano sits Cortona. This charming hilltop village was made more famous in recent years thanks to its starring role in the book "Under the Tuscan Sun" by Frances Maye and its subsequent film adaptation. 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 two-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 through Tuscany's rich history. The MAEC Museum holds precious Etruscan artifacts, while the Diocesan Museum is home to an array of Renaissance paintings. For something more tranquil, 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, hit the road back to Montepulciano, where you can spend your final Tuscan evening however you choose.

Day 8: Return to Florence, Depart

Florence skyline
Bid farewell to Florence as you catch your departing flight. 

After one last cappuccino, make the scenic 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!

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