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HomeRoad TripsEuropeSouth EuropeItalyTuscan Wine Trail
Wineyard Tuscany

Tuscan Wine Trail Road Trip

Florence - Greve in Chianti - Siena - Montalcino - Montepulciano

Expect on your itinerary

Historical sites Historical sites
Landscape Landscape
Benefit-stress ratio Benefit-stress ratio
Culture Culture
Comfort Comfort
Urban life Urban life
Road conditions Road conditions
Security Security
Tuscan Wine Trail Road Trip ACTIVATE MAP Stages4 km184 h/stage1.3

Best months to drive

I II III IV V VI
VII VIII IX X XI XII

Road Trip Costs

How much does it cost to go on a Tuscan Wine Trail Road Trip in Italy?

Economy
Low budget options by car rental, accommodation and catering. In- and Out-bound travel expenses are not included.
rent & more 135EUR drive & more 25EUR sleep & more 198EUR eat & more 144EUR Total (est. for 2 prs.) 367EUR Total (est. for 2 prs.) incl. rented car 502EUR
Standard
Mid budget options by car rental, accommodation and catering. In- and Out-bound travel expenses are not included.
rent & more 243EUR drive & more 38EUR sleep & more 319EUR eat & more 216EUR Total (est. for 2 prs.) 573EUR Total (est. for 2 prs.) incl. rented car 816EUR
Premium
High budget options by car rental, accommodation and catering. In- and Out-bound travel expenses are not included.
rent & more 324EUR drive & more 50EUR sleep & more 517EUR eat & more 288EUR Total (est. for 2 prs.) 855EUR Total (est. for 2 prs.) incl. rented car 1,179EUR
Camper
On the road in RV, overnight at camp grounds with self-catering. In- and Out-bound travel expenses are not included.
rent & more 675EUR drive & more 50EUR sleep & more 165EUR eat & more 144EUR Total (est. for 2 prs.) 359EUR Total (est. for 2 prs.) incl. rented car 1,034EUR
Car rental Book hotel Flights
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Tuscan Wine Trail Road Trip Itinerary

Experience the best of the Tuscan region with the Tuscan Wine Trail Road Trip! Starting in Florence, you'll make your way through the towns of Greve in Chianti, Siena, and Montalcino, before ending in Montepulciano. Along the way, you'll take in the breathtaking landscapes, historical sites, and UNESCO Heritage Monuments. The total distance is approximately 182km, and can be completed in 3 days. The best time of year to drive the route is during the spring and summer months, when the fields are in bloom and the weather is mild. The Tuscan Wine Trail Road Trip is the perfect way to experience this stunning region of Italy. Good road conditions make the drive enjoyable, and the experience is one that will stay with you for a lifetime. It's suitable for any driver and can be managed on a moderate budget. Don't miss out on this incredible journey through the heart of Tuscany!
number of days 3 number of days
route length 184 km route length
budget fair budget
good for tourist good for
traffic direction on the right traffic direction
accident level moderate accident level

START Florence

Distance 184 km Driving time 5.3 h Pace: slow 42.3 kWh Airports FLR
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Florence, Italy, is the perfect starting point for the Tuscan Wine Trail Road Trip. Located in the heart of Tuscany, this city is the ideal place to start exploring the region’s best vineyards and wineries. Florence is also a city rich in culture and art. From the iconic Duomo to the Ponte Vecchio, there are plenty of sights to explore in and around the city. The Uffizi Gallery, one of the most famous museums in the world, is a must-see for art lovers. For travelers flying into Florence, the closest international airport is the Florence Airport (FLR), located just 6 miles from the city center. There are numerous car rental agencies located at the airport, giving visitors the opportunity to explore the Tuscan countryside in their own vehicle. From Florence, travelers can easily access some of the best wineries in Tuscany. With a car, it is possible to visit the Chianti and Montepulciano regions and explore the many vineyards and wineries located in these areas. Florence is the perfect starting point for the Tuscan Wine Trail Road Trip. With its abundance of culture, art, and vineyards, this city is sure to provide an unforgettable experience.

1 Florence - Greve in Chianti

Distance 45 km Driving time 1.2 h Pace: slow 10.3 kWh View map Itinerary
junction of road trips UNESCO World Heritage Site interesting  historic site accommodation options camping sites
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Embark on an exciting road trip from Florence to Greve in Chianti! The 44km drive will take you less than an hour. Along the way, you will pass by some amazing UNESCO Heritage sites. Make sure to keep an eye out for the historical sites as you drive! At the end of the journey, you will be rewarded with the stunning views of Greve in Chianti. For more information about attractions, accommodation options, recommended restaurants, and campsites along the route, check out the “Itinerary” of this stage. Get ready to explore the beauty of Florence and Greve in Chianti!

2 Greve in Chianti - Siena

Distance 41 km Driving time 1.1 h Pace: slow 9.3 kWh View map Itinerary
junction of road trips UNESCO World Heritage Site interesting  historic site accommodation options camping sites
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Are you ready to embark on an unforgettable road trip from Greve in Chianti to Siena? This 40 km journey will take you less than an hour, but you will have plenty of time to explore the historical sites along the way. You will pass through some of the most beautiful countryside in Italy, with vineyards, olive groves, and cypress trees all around. As you drive, you will also be able to admire UNESCO World Heritage Sites, such as the Val d'Orcia and the San Gimignano Historic Centre. Once you reach Siena, you can explore the many attractions in this beautiful city, including the Piazza del Campo, the Torre del Mangia, and the Palazzo Pubblico. You can also visit the Siena Cathedral, which is one of the most important Romanesque-Gothic churches in Italy. For more information on attractions, accommodation options, recommended restaurants, and campsites along the route, please refer to the Itinerary of this stage. Enjoy your journey!

3 Siena - Montalcino

Distance 63 km Driving time 2.2 h Pace: slow 14.4 kWh View map Itinerary
accommodation options junction of road trips interesting  historic site UNESCO World Heritage Site camping sites
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Welcome to the Siena-Montalcino road trip stage! This is one of the most beautiful stages of the tour, leading you through the stunning Tuscan countryside. The distance between Siena and Montalcino is only 62km and the driving time is fewer than 2 hours. Start your journey in Siena, where you can explore the city’s historical centre and its iconic Piazza del Campo. The city’s main square is a UNESCO World Heritage Site and is the perfect place to get an idea of the city’s unique atmosphere. Continue your journey to Montalcino, located on a hilltop surrounded by vineyards. Here you can explore the city’s medieval architecture and the impressive Fortezza di Montalcino. The city is also home to the world-famous Brunello di Montalcino wine. Along the way, you will have the opportunity to explore the Tuscan countryside and its charming villages. Make sure to take some time to relax and enjoy the magnificent views. For more information regarding attractions, accommodation options, recommended restaurants, and campsites along the route, please check the “Itinerary” of this stage. Have a great journey!

4 Montalcino - Montepulciano

Distance 36 km Driving time 0.8 h Pace: modest 9.3 kWh View map Itinerary
junction of road trips interesting  historic site accommodation options UNESCO World Heritage Site
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Embark on a unique road trip from Montalcino to Montepulciano, two of the most beautiful hill towns in the Tuscan countryside. This 35 km journey will take you less than an hour to complete, but you will want to take your time to explore the many historical sites along the way. Start your journey in Montalcino, known for its Brunello di Montalcino wines and its fortress, built in the 14th century. Don’t forget to take in the panoramic views of the Val d’Orcia and the Val di Chiana valleys. From there, your journey will take you to the charming town of Pienza, famous for its pecorino cheese. Take a break to explore the cobblestone streets and admire the Renaissance-style palaces. Continue your journey to the enchanting town of Montepulciano, with its ancient churches and palaces. Here, you can sample the local Vino Nobile di Montepulciano and take in the views from the terraces of the Palazzo Comunale. This is just one stage of a larger tour, and more information about attractions, accommodation options, recommended restaurants, and campsites along the route is available in the “Itinerary” of this stage. So, get ready to explore the beauty of the Tuscan countryside on this unforgettable road trip.

  Montepulciano

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Montepulciano is a delightful hilltop town in the Tuscany region of Italy, and the perfect end to the Tuscan Wine Trail Road Trip. It is home to some of the most renowned wines in the world and the main attraction for visitors is the wine tasting tours. With its cobblestone streets, terracotta-tiled homes, and stunning views of the rolling hills, Montepulciano is a must-see for any traveler. When in Montepulciano, be sure to visit the Piazza Grande, a stunning square adorned with stunning architecture. The Palazzo Comunale is the town hall and boasts a grand staircase and beautiful frescoes. Also, the Duomo di Montepulciano is a breathtaking cathedral with a bell tower and a terrace offering stunning views of the surrounding countryside. For wine lovers, Montepulciano is a paradise. There are many wineries to explore and taste the local wines. The most popular wine is the Vino Nobile di Montepulciano, a full-bodied red that is aged for years in the cellars. Be sure to check out the Cantina Contucci, where you can taste wines, purchase bottles, and learn about the history of the region’s wine production. The closest international airport to Montepulciano is Florence Airport (FLR), which is approximately 90 km away. From there, you can rent a car and take the scenic drive through the Tuscan countryside to Montepulciano. The drive is about 1.5 hours and offers stunning views of the countryside. At the end of your Tuscan Wine Trail Road Trip, you’ll find yourself in Montepulciano, a hilltop town with stunning architecture, world-renowned wines, and breathtaking views of the Tuscan countryside. From here, you can savor the local wines, explore the cobblestone streets, and enjoy the beauty of the Italian countryside.

Tuscan Wine Trail Road Trip at a glance

Enhanced Overview:

Embark on the Tuscan Wine Trail Road Trip for a captivating journey that takes you through the verdant heart of Italy's famed wine country. Starting from the iconic city of Florence, the birthplace of the Renaissance, this route winds through the rolling hills and vineyard-clad landscapes of Tuscany. Along the way, you'll visit charming towns like Greve in Chianti, Siena, Montalcino, and Montepulciano. This 182-kilometer (approximately 113 miles) Scenic Drive is ideally spread over at least three days, granting you the opportunity to immerse yourself in the stunning vistas, profound history, and rich cultural heritage that define the region.

Detailed Key Destinations and Top Sights:

  • Florence: Not only the cradle of the Renaissance, Florence brims with masterpieces like Michelangelo's David, Botticelli's Birth of Venus, and the awe-inspiring Duomo. The city's historic center is a UNESCO World Heritage site.
  • Greve in Chianti: Known as the entrance to the Chianti wine region, this town offers exceptional wine-tasting experiences and vineyard tours set amid classic Tuscan scenery. Don't miss the triangular-shaped piazza lined with artisan shops and the Wine Museum.
  • Siena: This well-preserved medieval city is famous for the biannual Palio horse race. Its stunning cathedral, known as the Duomo di Siena, is a masterpiece of Italian Romanesque-Gothic architecture, and the shell-shaped Piazza del Campo is one of Europe's greatest medieval squares.
  • Montalcino: Nestled atop a hill, Montalcino is the birthplace of the highly esteemed Brunello di Montalcino wine. Visitors can explore the 14th-century fortress that offers panoramic views and a chance to sample local wines.
  • Montepulciano: A medieval town perched on a limestone ridge, Montepulciano is lauded for its Vino Nobile wines. The town is also a treasure trove of Renaissance buildings and offers breathtaking views of the surrounding countryside.

Optimal Timing:

The best time to venture on this Road Trip is during the spring (April to June) when the lush landscapes are in full bloom, and the weather is mild, or in the summer (July to August) when Tuscany is bathed in glorious sunshine, making the vineyards come alive.

Traveler Considerations:

Navigating the Tuscan Roads can be an adventure in itself, with narrow, winding routes that offer a quintessentially rustic Italian driving experience. Be prepared for potential traffic and limited parking in smaller towns, especially during the tourist-heavy summer months.

Invaluable Facts for Roadtrippers:

  • Non-EU drivers should obtain an International Driving Permit (IDP) to drive in Italy legally.
  • The region accommodates a range of budgets with diverse lodging and dining options, from agriturismos to luxury villas.
  • Responsible wine tasting is a must-do activity, so plan ahead for a designated driver or organized tour if you intend to indulge.
  • Tuscany's culinary offerings are an integral part of the experience, with local specialties like ribollita soup, pappa al pomodoro, and bistecca alla fiorentina providing a true taste of the region.

Concluding Insights:

The Tuscan Wine Trail Road Trip is a quintessential Italian experience that marries the joy of discovery with the pleasures of gastronomy and viticulture. Ideal for oenophiles, history buffs, and romantics alike, this journey is a splendid way to soak in the timeless allure and epicurean delights of Tuscany's countryside.

Facts for safer driving in Italy

drink drive limit drink drive limit 0.5
max speed urban max speed urban 50 km/h
max speed rural max speed rural 90 km/h
max speed highway max speed highway 130 km/h
headlights at daytime headlights at daytime on
fire extinguisher fire extinguisher no
tolls tolls yes
seat belts seat belts yes

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