Tuscany chauffeured tour itinerary in 9 days. This private tour starts and finish in Florence. Tuscany  is one of the important regions of Italy, popular for its art, museums, great history, food and excellent wines. Six localities of Tuscany have been declared as UNESCO protected sites, during the last three decades. This tour provides an opportunity to view beautiful countryside and historic architecture while exploring the region where the Renaissance began more than 600 years ago.
Overnights: 4 nights in Florence, 4 nights in Chianti area.

Note: this itinerary can be customized according to your needs

Day 1 – Florence, 4 hours
Our friendly English speaking driver picks you up at Florence airport, train station or at your hotel – if from a different location please advise. Driving up the beautiful Viale dei Colli, we reach the marvellous terrace called Piazzale Michelangelo square. Here you get the most impressive view of the city.  Nearby you can also see the white and green marble façade of the S. Miniato al Monte church – one of the purest examples of the Florentine Romanesque style. We follow an uphill road, bordered by the ancient city walls, until we reach Forte Belvedere (exteriors), built around 1590 by the Grand-duke Ferdinand to protect the Medici villas. Driving down from the Fort, passing the old gate to the city, the Porta Romana, we come to Pitti Palace (exteriors) which hosts many galleries and museums (Gallery of Modern Art, Costume Gallery, Palatine Gallery, Royal Apartments, Coach Museum, Silver and Porcelain museums) and a magnificent park called the Boboli Gardens. Next we head for the city center, to the Piazza della Repubblica, surrounded by the historical literary cafés, where long ago important intellectuals gathered together. Here we’ll meet our Tour Guide for a relaxing 3 hours walking tour of the old city: following the Via De’Calzaiuoli, which connects Piazza del Duomo (S. Maria del Fiore, the Baptistery, Giotto’s Bell tower) to Piazza Signoria ( Palazzo Vecchio, Uffizi , etc.)  breathing in the magical atmosphere that only Florence can offer. Last visit will be at the famous Accademia Museum, house of the Michelangelo’s masterpiece The David. For your first dinner in the city our driver or guide will be more than happy to suggest and reserve a table for you in a typical florentine restaurant…buon appetito!

Day 2 – Pisa, 4 hours
With your personal driver, travel to Pisa (approx. 1 hour from Florence), where you’ll meet our local guide for a two-hour walking tour. This calm and charming town reflects the history of the Pisan Republic, and its river system helped it avoid decline after the fall of the Roman Empire. The tour focuses on the Piazza dei Miracoli (Square of Miracles), a UNESCO World Heritage Site. The Duomo, a medieval cathedral, impresses with its massive bronze doors, golden ceiling, intricately carved pulpit, and striking black-and-white marble interior. Nearby, the round-shaped Baptistery features an octagonal font that contrasts beautifully with its spacious circular interior. Finally, admire the world-famous Leaning Tower, originally built as the cathedral’s bell tower (campanile), which began to lean shortly after its completion in 1173. Afterwards, enjoy some free time to relax and have lunch.

Day 3 – Lucca & wine, 6 hours
Today we head to charming Lucca (just about 1 hour from Florence) to meet our local guide for a relaxed two-hour walking tour of the historic city center. Famous as the birthplace of composers Giacomo Puccini and Luigi Boccherini, Lucca is full of history and character. Its Renaissance walls and gates make for a scenic and interesting stroll, brought to life by our guide’s stories. Inside the Duomo, discover the Holy Face of Lucca, a wooden representation of Christ on the cross, which plays a central role in the city’s annual procession. Be sure not to miss the magnificent San Michele in Foro church, built in 1070, with its intricate façade full of sculptures, arcades, and delicate blind arcades. After the tour, enjoy about an hour to relax and explore on your own. Around noon, we’ll venture into the beautiful Lucca countryside to visit a typical family winery. Take a guided tour of the property, then sit down to a delicious light lunch featuring local delicacies: ham, salami, bruschette, cheese, fresh bread, olive oil… and, of course, a tasting of several local wines! We’ll return to Florence in the early afternoon, leaving the rest of the day free for you to relax or explore at your leisure.

Day 4 – Arezzo and Cortona, 9 hours
In the morning, depart from your hotel and head south to Arezzo, one of Tuscany’s oldest and most charming cities. Upon arrival, meet our local guide for an engaging two-hour walking tour through the narrow streets of this historic town. Arezzo is famously featured in the award-winning film “Life is Beautiful” with Roberto Benigni. Explore the picturesque town center, enjoy its medieval atmosphere, and browse the many shops along the way. Highlights include the breathtaking frescoes by Renaissance painter Piero della Francesca and a visit to the Duomo. Arezzo is also renowned for its culinary delights, so consider enjoying lunch here before continuing to your next destination. In the early afternoon, continue to Cortona, the hilltop town made famous by “Under the Tuscan Sun.” Originally an Etruscan settlement, Cortona played an important role during the Middle Ages. Its narrow medieval streets, charming old buildings, and stunning views over the surrounding countryside make it one of Tuscany’s most beautiful towns. Enjoy the scenery as we drive up the winding roads and again from the small piazza at the top. Cortona is home to the Accademia Museum, which houses fascinating Etruscan, Roman, and Egyptian artifacts. Take a leisurely stroll through the town’s lovely Tuscan gardens, relaxing in the shade of Holm oak trees. Wander the streets lined with shops offering locally handcrafted jewelry, leather goods, clothing, and ceramics—no designer labels, just authentic artisan work. For a quintessential Tuscan experience, stop at a street café for a drink and enjoy some slow-paced “la dolce vita,” watching the world go by.

Day 5 – Chianti,  San Gimignano, 8 hours (change of hotel)
Today we leave Florence and head into the heart of the Chianti region. No visit to Tuscany is complete without a stop in San Gimignano, famous for its stunning skyline of 13 medieval towers. Perched 334 meters above the Elsa Valley along the historic Via Francigena—a route once traveled by traders and pilgrims on their way to Rome—this 11th-century town flourished thanks to the many inns built for travelers. Like much of Italy, San Gimignano suffered greatly during the Black Plague of 1348, which drastically reduced its population and led to economic decline, ultimately bringing the town under Florence’s rule in 1353. Over the centuries, however, San Gimignano rediscovered its cultural importance and agricultural wealth, emerging today as the beautifully restored town we visit. You’ll explore part of it with your driver and part on your own. Next, drive along the panoramic roads of the Chianti wine region, enjoying breathtaking scenery and charming small towns. Stop at a top-rated winery for a guided tour of the cellars and a tasting of exceptional wines, including Chianti Classico, Riserva, Super Tuscan, Vin Santo, and even Grappa (for the brave!). For lunch, your driver can suggest a traditional trattoria where you can savor authentic Tuscan dishes—or, if you prefer, you can enjoy your meal at the winery. Simply let your driver know. The day ends with drop-off at your hotel nestled in the peaceful countryside.

Day 6 – Siena, Monteriggioni, 7 hours
Leave at 9.30am for the day on a private tour to Siena with your driver. At the arrival to the Siena you’ll find our tour guide waiting for take you to an informative 3 hours walking tour of the old city: the historic centre has been declared as the World Heritage Site by the UNESCO. This beautiful city made of brown Siena-coloured bricks (so that’s how they named the colour!), its jumble of narrow streets and delightful squares, the medieval towers that make such a spectacular skyline, its spectacular cathedral, the tall and trim Torre del Mangia, all together create an enticing atmosphere almost like stepping back in time. Siena, the famous antagonist city of Florence during the twelfth century, is built on three hills and is home to one of the most authentic and important Gothic cathedrals south of the Alps. Despite the city’s architectural masterpieces, it is the unusual shell-shaped Piazza del Campo that receives the most consideration having been seen in numerous films and photographs. This brick covered square is used twice a year for the famous “Palio” horserace, an event that involves the entire population and is considered one of the most important events in the life of the Sienese people. This reckless bareback race is run on July 2nd and August 16th, has Roman origins but has first been officially recorded in 1283. After the guided walking tour you’ll have some free time on your own for relax, shopping, lunch. On the way back to your accommodation make a stop in Monteriggioni, one of the best known and classic walled towns in Tuscany. This village was built on a hill by the Sienese between 1213 and 1219 to overlook the ancient Roman road, the Via Cassia. This was a perfect position allowing for surveillance of the valleys below in the direction of the city of Florence, which was the historic enemy of Siena.

Day 7 – Volterra, 5 hours
After breakfast we set off from Chianti towards Volterra, about 30 miles away. The road itself is a pleasure, with rolling hills, olive groves and cypress-lined ridges that slowly lead us into a different part of Tuscany. Volterra is an ancient town whose roots go back as far as the Neolithic era and which later became an important Etruscan settlement. As you walk through its gates, you can still sense the layers of history that shaped this unique hilltop town. Here you will meet our private local guide who will bring the city to life during a 2-hour walking tour. You’ll stroll through atmospheric streets paved with stone, admire artisan shops and discover remarkable landmarks such as the Piazza dei Priori, considered one of the most beautiful squares in Italy. At its center stands the Palazzo dei Priori, the oldest town hall in Tuscany, built in 1239, with its elegant pentagonal tower rising above the skyline. Inside, the magnificent cross-vaulted council hall still echoes with the spirit of the medieval meetings once held there. Along the way, your guide will weave stories of Etruscans, Romans, and noble families, giving you a vivid picture of Volterra’s past and present. After your visit, we leave the town behind and head to the peaceful Tuscan countryside to visit a family-run Pecorino cheese producer. Here you’ll discover how this traditional sheep’s milk cheese is made, following ancient methods passed down through generations. The visit culminates in a relaxed farmhouse-style lunch, where you’ll taste different types of Pecorino, paired with fresh local products and a local wine — a true Tuscan experience of authenticity and flavors.

Day 8 – Montepulciano, Pienza, Montalcino, 9 hours
Today your driver will pick you up at 9:00 AM and take you to Montepulciano, one of Tuscany’s highest hilltop towns. Enclosed by ancient walls, its streets are lined with Renaissance-style palaces and churches. Wander through the town and enjoy the charming streets and historic buildings, while taking in stunning views of the surrounding rolling hills and vineyards. Next, continue to Pienza, originally a small village called Corsignano and the birthplace (1405) of Aeneas Silvius Piccolomini (Italian: Enea Silvio Piccolomini), a Renaissance humanist who later became Pope Pius II. Once Pope, Piccolomini rebuilt the village as an ideal Renaissance town, applying early humanist urban planning concepts that influenced other Italian and European towns. Explore the main sights with your guide, including the Duomo, Palazzo Piccolomini, and Palazzo Comunale. The drive through the Val d’Orcia offers breathtaking landscapes, perfect for a photo stop to capture the iconic rolling hills, cypress-lined roads, and the famous valley featured in the movie The Gladiator. Finally, head to Montalcino, a hilltop town renowned for its wine production, especially the world-famous Brunello di Montalcino. Stop at a top-rated winery for a guided tour of the cellars and enjoy a delicious lunch paired with a tasting of Brunello and other local wines. After lunch, take some time to explore Montalcino’s narrow, winding streets or visit the Fortezza (Fortress), built by Cosimo I in 1571, where you can admire spectacular panoramic views over the Val d’Orcia and surrounding countryside. Return to your hotel in the late afternoon, with memories of a day filled with history, culture, and the most iconic Tuscan landscapes.

Day 9 – Departure
Depending on your schedule and the departure time of your flight or train, we will pick you up and ensure a comfortable and safe journey to your final destination. Along the way, we hope you’ll take in a few last glimpses of the Tuscan landscapes, the rolling hills, charming villages, and vineyards that make this region so unforgettable. Our goal is to make your farewell as pleasant as your stay, leaving you with a heart full of fond memories and a lasting impression of the beauty, culture, and warmth of our beloved Tuscany.

• Private Mercedes-Benz sedan or minivan
• Pick up & drop off at your hotel everyday
• English speaking driver at your disposal during the all tour. Our driver will personally attend to your needs not only taking care of directions and getting around, but also introducing you to friendly Italians, general explanations about the area, history and customs & traditions of the regions you'll visit, suggestions of best stores for shopping, reservation or suggestions of restaurants, etc. In few words your personal travel assistant - a unique and genuine tourism experience that group tours are unable to offer. 
• Accommodations in 4 or 5 star hotels according to your preference, our booking office will offer some suggestions
• Daily breakfast
• Personal Tour guide in Florence, Pisa, Lucca, Volterra, Siena, Arezzo
• Admission fees to all musuems of your tour
• Light lunch & wines on Lucca tour
• Visit of wineries in Chianti and Montalcino, with wine tasting
• Assistance 24 hours of our booking office
• Wi-fi in the car
• Porterage
• Tax, tolls, parking fees, gasoline