Tuscany Travel Guide: Best Places to Visit, Things to Do & Travel Tips

Growing up in Florence, I was always surrounded by the beauty and history that make Tuscany one of the most famous regions in Italy. While many travelers visit Florence for its Renaissance art and architecture, the landscapes beyond the city are just as remarkable. Rolling hills, vineyards, and medieval hill towns stretch across the countryside, creating some of the most iconic scenery in Europe.

Living here, I quickly learned that the real magic of Tuscany often lies just outside the city. A short journey from Florence can lead you to historic towns like Siena, the famous towers of San Gimignano, or the quiet countryside landscapes of Val d’Orcia. Other places, like Pisa with its Leaning Tower, or charming villages such as Pienza and Montepulciano, reveal different sides of the region’s culture, history, and food traditions.

In this Tuscany travel guide, I’ll share the best places to visit, the top things to do, practical travel tips, and more to help you explore the region. Whether you’re visiting historic cities, discovering hill towns, or enjoying the famous Tuscan countryside, Tuscany offers a mix of culture, landscapes, and experiences that make it one of the most unforgettable destinations in Italy.

If you’re planning a broader trip across the country, this region fits perfectly into a larger Italy itinerary. For a complete overview of destinations, travel tips, and planning ideas across the country, you can also read our Italy Travel Guide.

Where Is Tuscany in Italy?

Tuscany is a region in central Italy, located between the Tyrrhenian Sea and the Apennine Mountains. It borders Liguria to the northwest, Emilia-Romagna to the north, Umbria to the east, and Lazio to the south.

The region’s capital is Florence, one of Italy’s most important cultural and artistic cities. Other famous destinations across Tuscany include Pisa, home to the world-famous Leaning Tower, and Siena, known for its medieval streets and the historic Piazza del Campo.

Beyond the major cities, Tuscany is also famous for its countryside landscapes filled with vineyards, olive groves, and hill towns such as San Gimignano, Pienza, and Montepulciano. These towns are spread across the rolling hills of the region and are part of what makes Tuscany one of the most beautiful areas in Italy.

Map of the Best Places to Visit in Tuscany

Before planning your trip, it helps to see where Tuscany’s main destinations are located. The map below highlights the region’s most famous cities, hill towns, and countryside areas, making it easier to understand distances and plan a route through the region.

Some of the key places included on the map are:

• Florence – the capital of Tuscany and the birthplace of the Renaissance
• Siena – a historic medieval city famous for Piazza del Campo and the Palio
• Pisa – home to the iconic Leaning Tower of Pisa
• San Gimignano – known for its hilltop views and medieval towers
• Val d’Orcia – a UNESCO-listed countryside landscape with rolling hills and scenic villages
• Montepulciano – a charming hill town famous for wine and panoramic views
• Pienza – a Renaissance village known for architecture and local pecorino cheese
• Lucca – a beautiful walled city with walkable historic streets
• Volterra – an ancient hill town with Etruscan history
• Cortona – a picturesque town overlooking the Tuscan countryside
• Chianti Wine Region – famous for vineyards, wineries, and scenic countryside roads

Use this map as a visual guide to see how Tuscany’s most famous destinations connect across the region.

Tuscany map showing Florence, Siena, Pisa, Val d’Orcia, and the best towns to visit in the region.

How to Get to Tuscany

Reaching Tuscany is fairly easy thanks to its central location in Italy and its good connections by air, train, and road. Most travelers arrive through Florence or Pisa, which serve as the main gateway to the region.

By Plane

The two main airports for reaching Tuscany are Florence Airport (Amerigo Vespucci) and Pisa International Airport (Galileo Galilei).

Florence Airport is the most convenient if your trip begins in the city itself. It’s located only a short distance from the historic center and is well-connected to other European destinations.

Pisa Airport is the largest airport in the region and often offers more international flights and budget airline options. From Pisa, travelers can easily reach cities like Florence, Lucca, and Siena by train or car.

By Train

Traveling by train is one of the easiest ways to reach Tuscany from other major Italian cities. High-speed trains connect Florence with cities like Rome, Milan, and Venice, making it possible to reach the region in just a few hours.

For example, the high-speed train journey from Rome to Florence takes about 1 hour and 30 minutes, while trains from Milan to Florence usually take around 2 hours.

By Car

Driving is another convenient way to get to Tuscany, especially if you plan to explore smaller towns and countryside areas. Major highways connect the region with the rest of Italy, including the A1 motorway between Rome and Florence.

If you’re arriving from major cities like Milan or Rome, driving allows you to turn the journey into a memorable Italy road trip with incredible stops along the way. Many routes pass through charming villages, historic cities, and some of the most beautiful landscapes in the country.

Travel times to Tuscany are relatively manageable:

• Florence to Siena: about 1 hour
• Rome to Florence: about 3 hours
• Milan to Florence: about 3.5 hours

Along the way, you can stop in historic towns, explore vineyards, and enjoy some of the most scenic countryside routes in Italy.

If you’re planning a road trip to Tuscany, these guides can help you plan the best routes:

• Driving from Milan to Florence through Tuscany – a food-focused road trip through some of the region’s most famous culinary stops.
• Driving from Rome to Siena – a scenic route connecting central Italy with one of Tuscany’s most beautiful medieval cities.
• Driving from Rome to Pisa – a great option for visiting the Leaning Tower and exploring the Tuscan coast.
• Driving from Rome to Florence with scenic stops – a classic route linking two of Italy’s most famous cities.

Why Visit Tuscany

There are many beautiful regions in Italy, but Tuscany stands out for the way it combines history, culture, landscapes, and food into one unforgettable destination. From world-famous Renaissance cities to peaceful countryside villages, the region offers an incredible variety of experiences within a relatively small area.

Living in Florence, it’s easy to understand why people fall in love with Tuscany so quickly. Leave the city, and within a short drive, you’ll find rolling hills, vineyards, olive groves, and medieval hill towns sitting on top of the landscape. The scenery is so iconic that sometimes it almost feels staged—like someone carefully arranged the vineyards and cypress trees just for photos. Even locals still pause to admire views that visitors travel across the world to see.

One of the biggest reasons travelers visit Tuscany is the mix of historic cities and hill towns. Cities like Florence, Siena, and Pisa are filled with art, architecture, and landmarks that shaped Italian history, while smaller towns such as San Gimignano, Pienza, and Montepulciano offer a slower rhythm and timeless charm.

The landscapes are just as memorable. The famous Tuscan countryside is known for its rolling hills, vineyards, and scenic valleys like Val d’Orcia, a UNESCO World Heritage area and one of the most photographed landscapes in Italy.

And of course, there’s the food. Tuscany is home to some of Italy’s most famous wine regions, including Chianti, where long lunches, local wines, and traditional dishes are taken very seriously. Honestly, if you come to Tuscany planning to diet… you might want to reconsider.

Maybe I’m not the most objective person here since Florence is home, but after spending so much time exploring the region, it’s easy to understand why Tuscany is one of the most loved destinations in Italy.

Best Places to Visit in Tuscany

Tuscany is a fairly large region, and one of the first things I usually tell friends when they plan a trip here is that it’s impossible to see everything in a single visit. Between historic cities, medieval hill towns, and beautiful countryside landscapes, there are far more places worth visiting than most itineraries can realistically include.

For most trips of 3 to 7 days in Tuscany, it’s best to focus on a few key areas rather than trying to cover the entire region. Many of Tuscany’s most famous destinations are surprisingly close to each other, which makes it possible to explore several highlights without spending all your time traveling.

In general, the region’s main highlights are concentrated around four areas: Florence and its surroundings, the Pisa and Lucca area, Siena and the Chianti wine region, and the scenic countryside of Val d’Orcia. Together, these areas include some of the best places to visit in Tuscany, from Renaissance cities to historic hill towns and iconic landscapes.

Below are some of the most beautiful and memorable destinations in Tuscany, places that many travelers include in their first visit to the region.

Florence

Florence, my home and the capital of Tuscany, is usually the first stop for many travelers visiting the region. Known as the birthplace of the Renaissance, the city is filled with art, history, and architecture that shaped much of European culture.

Walking through Florence’s historic center often feels like exploring an open-air museum. Landmarks such as the Florence Cathedral (Duomo), the Uffizi Gallery, Ponte Vecchio, and Piazza della Signoria are all located within a compact area, making the city surprisingly easy to explore on foot.

Florence is also a perfect starting point for visiting Tuscany. From here, many of the region’s famous destinations—such as Siena, Pisa, San Gimignano, and the scenic countryside of Val d’Orcia—are just a short drive or train ride away, making it easy to combine the city’s cultural highlights with the beauty of the Tuscan landscape.

If you’re planning your time in Florence, read our Florence Travel Guide to discover the best things to do, top attractions, and travel tips.

Siena

If Florence represents the Renaissance side of Tuscany, Siena feels like stepping back into the medieval world. The city is famous for its beautifully preserved historic center and the stunning Piazza del Campo, a shell-shaped square that hosts the traditional Palio horse race twice a year.

Compared to Florence, Siena has a quieter and more intimate atmosphere. Its narrow streets wind between historic buildings, small piazzas, and viewpoints overlooking the surrounding Tuscan countryside.

There has always been a bit of competition between Florence and Siena, going back to medieval times when the two cities competed for power and influence in Tuscany. Today it’s mostly friendly, but if you ask someone in Florence which city is better… well, you can probably guess the answer.

Planning your time in Siena? Take a look at our Siena Travel Guide to see the best things to do and how to organize your visit.

Pisa

Most people visit Pisa to see the famous Leaning Tower of Pisa, one of the most recognizable landmarks in the world. The tower stands in the beautiful Piazza dei Miracoli, alongside the impressive Pisa Cathedral and the Baptistery, creating one of the most striking architectural squares in Italy.

While the leaning tower is the main attraction, Pisa has more to offer than many visitors expect. The city has a lively atmosphere thanks to its large university, historic streets along the Arno River, and several interesting churches and squares beyond the famous monument.

For many travelers exploring Tuscany, Pisa makes an easy stop, whether as a short visit or as part of a broader trip connecting nearby destinations like Lucca, Florence, and the Tuscan coast.

For more info, read our complete travel guide to Pisa.

San Gimignano

Rising above the Tuscan countryside, San Gimignano is one of the most recognizable hill towns in Tuscany, famous for its medieval towers that dominate the skyline. Because of these towers, the town is often called the “Medieval Manhattan” of Tuscany.

Walking through San Gimignano feels like stepping back in time. Its narrow streets, stone buildings, and historic squares have remained largely unchanged for centuries, giving the town a unique atmosphere that reflects Tuscany’s medieval past.

Today, visitors come not only for the history but also for the views and local specialties. The town is known for the Vernaccia di San Gimignano wine, as well as the famous Gelateria Dondoli, often mentioned as one of the best gelato shops in Italy.

Val d’Orcia

If you’ve ever seen photos of rolling hills, cypress trees, and winding country roads, there’s a good chance they were taken in Val d’Orcia. This beautiful valley in southern Tuscany is one of the region’s most famous landscapes and has been recognized as a UNESCO World Heritage Site.

The area is known for its peaceful countryside, historic villages, and panoramic viewpoints that seem to appear around every corner. Tuscany towns like Pienza, Montepulciano, and Montalcino sit on hilltops overlooking vineyards and farmland, creating some of the most iconic scenery in Tuscany.

One of my favorite ways to experience Val d’Orcia is simply driving through the countryside. Exploring Val d’Orcia is less about visiting a single attraction and more about enjoying the landscape itself. Driving through the valley, stopping in small villages, and taking time to admire the views is part of what makes this area so special.

Montepulciano

Perched on a hilltop overlooking the surrounding countryside, Montepulciano is one of the most beautiful towns in southern Tuscany. The town is famous for its elegant Renaissance buildings, historic streets, and panoramic views across the rolling hills of the Val d’Orcia.

Walking through Montepulciano feels like exploring a classic Tuscan hill town. The main street climbs steadily toward Piazza Grande, the town’s historic square surrounded by impressive palaces and the Montepulciano Cathedral.

Montepulciano is also known for its wine, particularly Vino Nobile di Montepulciano, one of Tuscany’s most respected red wines. Many visitors stop here not only for the views and architecture but also to enjoy wine tastings in historic cellars carved beneath the town.

A visit to Tuscany wouldn’t feel complete without spending some time in towns like Montepulciano, where historic streets, local wine culture, and countryside views come together perfectly.

Pienza

Located in the heart of Val d’Orcia, Pienza is one of the most charming small towns in Tuscany. Unlike many medieval hill towns, Pienza was redesigned during the Renaissance and is often considered one of the first examples of an “ideal Renaissance town.”

The historic center is small and easy to explore, with elegant buildings, quiet streets, and beautiful viewpoints overlooking the surrounding countryside. Walking through Pienza, you’ll quickly notice how the town seems perfectly positioned to admire the rolling hills of Val d’Orcia.

Pienza is also famous for its local specialty, Pecorino di Pienza, a traditional sheep’s milk cheese that you’ll find in many shops and restaurants throughout the town. Between the views, the architecture, and the food, Pienza is a wonderful stop while exploring southern Tuscany.

Lucca

Surrounded by impressive Renaissance walls, Lucca is one of the most charming cities in Tuscany. Unlike many historic cities where the walls were removed over time, Lucca’s walls remain completely intact and today form a wide promenade that circles the entire historic center.

One of the best experiences in Lucca is walking or cycling along these city walls, which offer peaceful views over the rooftops, church towers, and tree-lined paths. The atmosphere here feels relaxed compared to larger cities like Florence, making Lucca a wonderful place to slow down and explore.

Inside the walls, the city is filled with narrow streets, small squares, and landmarks like Piazza dell’Anfiteatro, a unique oval-shaped square built on the remains of a Roman amphitheater.

Volterra

Perched high on a hill in western Tuscany, Volterra is one of the region’s oldest and most atmospheric towns. Its history stretches back thousands of years, with roots in the Etruscan civilization, long before the rise of the Roman Empire.

The town has a distinctive character shaped by its ancient stone streets, historic buildings, and dramatic hilltop setting. Volterra feels slightly more rugged and authentic than many other Tuscan destinations, which adds to its charm.

Some of the highlights include the impressive Palazzo dei Priori, the well-preserved Roman Theater, and sections of the original Etruscan walls that still stand today. Volterra is also known for its traditional alabaster craftsmanship, with local workshops displaying this art throughout the historic center.

Thanks to its elevated location, the town also offers sweeping views of the surrounding Tuscan countryside, making it a memorable stop while exploring this part of the region.

Cortona

Perched on a hillside overlooking the wide Val di Chiana valley, Cortona is one of those towns that immediately feels peaceful and welcoming. With its stone streets, small piazzas, and sweeping countryside views, it captures the relaxed charm that many people imagine when thinking about Tuscany.

The town became internationally known after the book and movie “Under the Tuscan Sun”, which brought a lot of attention to Cortona and its beautiful setting. Even so, it still manages to keep a more laid-back atmosphere compared to some of Tuscany’s bigger destinations.

Spending time in Cortona is really about enjoying the simple things—wandering through the historic streets, stopping at a small café in the piazza, and taking in the panoramic views over the surrounding hills and valleys.

Chianti Wine Region

If there’s one place that truly captures the spirit of Tuscany, it’s the Chianti wine region. Located between Florence and Siena, this area is famous for its rolling vineyards, olive groves, hilltop villages, and of course its world-known Chianti wine.

Driving through Chianti feels like traveling through one of those classic Tuscan countryside landscapes people imagine before even arriving in Italy. Vineyards stretch across the hills, cypress trees line the roads, and small villages like Greve in Chianti, Radda, and Castellina appear along the way.

One of the best ways to experience the region is simply taking time to stop at local wineries, enjoy a wine tasting, and sit down for a long Tuscan lunch. Between the scenery, the wine culture, and the relaxed atmosphere, Chianti easily becomes one of the highlights of any trip to Tuscany.

Best Things to Do in Tuscany

Beyond its beautiful towns and landscapes, Tuscany offers many memorable experiences. From exploring historic cities and medieval villages to enjoying local food, wine, and nature, there are plenty of activities that make a trip to this region special.

Many travelers arrive with a list of what to do in Tuscany, but quickly realize that the region offers far more than just famous landmarks. Whether you’re visiting Renaissance cities like Florence, tasting wine in the Chianti region, relaxing in natural hot springs, or simply enjoying the views of the Tuscan countryside, the experiences here are just as rewarding as the destinations themselves.

Below are some of the best things to do in Tuscany to help you experience the region beyond its historic towns and iconic landscapes.

Explore Renaissance Cities

One of the most rewarding things to do in Tuscany is exploring its historic Renaissance cities, where art, architecture, and centuries of history are present around almost every corner. Cities like Florence, Siena, and Pisa are filled with famous landmarks that shaped the cultural history of Italy.

In Florence, visitors can admire masterpieces at the Uffizi Gallery, climb the dome of the Florence Cathedral (Duomo), and cross the historic Ponte Vecchio. In Siena, the beautiful Piazza del Campo and the impressive Siena Cathedral showcase the city’s medieval heritage. Meanwhile, Pisa attracts travelers from around the world with the famous Leaning Tower of Pisa, located in the spectacular Piazza dei Miracoli.

These cities are among the most important cultural destinations when visiting Tuscany, offering a fascinating glimpse into the region’s artistic and historical legacy.

Visit Tuscany’s Hill Towns

Another highlight of any trip to Tuscany is visiting its famous hilltop towns. Scattered across the countryside, these historic villages sit on elevated hills and offer stunning views of the surrounding landscape.

Places like San Gimignano, Montepulciano, Pienza, Volterra, and Cortona are among the most beautiful towns in the region. Their stone streets, historic piazzas, and medieval towers create a timeless atmosphere that makes them some of the best places to visit in Tuscany.

Exploring these towns is also a great way to experience the slower rhythm of life in the Tuscan countryside, where small cafés, family-run restaurants, and local markets are part of everyday life.

Go Wine and Olive Oil Tasting in Chianti

No trip to Tuscany would be complete without experiencing its famous wine culture. The Chianti wine region, located between Florence and Siena, is one of the most well-known wine areas in Italy.

Here, visitors can stop at local wineries to taste Chianti Classico, learn about traditional wine production, and enjoy vineyard views stretching across the hills. Many wineries also offer guided tastings paired with local products such as extra virgin olive oil, cheeses, and cured meats.

In fact, olive oil tasting is another classic Tuscan experience. The region produces some of the best extra virgin olive oil in Italy, and many farms invite visitors to taste freshly pressed oil while learning about the traditional harvesting and production process.

Wine and olive oil tastings in Chianti are among the most enjoyable activities when exploring Tuscany, combining beautiful landscapes with the region’s rich culinary traditions.

Enjoy Tuscan Food

Food plays an essential role in the experience of traveling through Tuscany. The region is known for its simple but flavorful cuisine that highlights fresh local ingredients.

Some of the most famous specialties include bistecca alla fiorentina, a large grilled steak from Florence, pecorino cheese from Pienza, and truffles from areas like San Miniato. Many visitors also enjoy joining cooking classes, where they can learn how to prepare traditional Tuscan dishes such as handmade pasta and sauces.

For food lovers, discovering the local cuisine is easily one of the most enjoyable things to do in Tuscany.

Relax in Natural Hot Springs

Tuscany is also home to several beautiful natural hot springs, where warm mineral waters flow through scenic landscapes. These thermal baths have been used since Roman times and remain popular places to relax.

Some of the most famous spots include the cascading pools of Saturnia, the historic village springs of Bagno Vignoni, and the natural pools of Bagni San Filippo. Surrounded by nature, these locations offer a unique and relaxing experience during a trip to Tuscany.

Explore the Tuscan Countryside

Finally, one of the best ways to experience the region is simply spending time in the Tuscan countryside. The landscapes here are famous for their rolling hills, vineyards, olive groves, and cypress-lined roads that stretch across the hills of central Italy.

Areas such as Val d’Orcia and the Chianti region are especially beautiful and offer some of the most iconic scenery in Tuscany. Many visitors choose to explore these landscapes by car, stopping in small villages and scenic viewpoints along the way.

Another wonderful way to enjoy the countryside is to rent a bike and cycle along the quiet country roads, where you can take in the stunning views of vineyards, olive groves, and hilltop towns. Cycling through Chianti or Val d’Orcia allows you to experience the peaceful side of Tuscany at a slower pace.

For many travelers, these landscapes are what make Tuscany one of the most beautiful regions in Italy.

Visit the Tuscan Coast and Beaches

The coastline of Tuscany is often overlooked, but it offers some beautiful beaches and seaside landscapes. The Maremma coast in southern Tuscany is especially known for its wild nature, sandy beaches, and clear water.

One of the most scenic areas is Monte Argentario, a rocky peninsula connected to the mainland by narrow strips of land. Small seaside towns like Porto Santo Stefano and Porto Ercole offer charming harbors, fresh seafood restaurants, and access to beautiful coves and beaches.

Nature lovers can also explore Parco Naturale della Maremma, a protected coastal park where forests, wetlands, and quiet beaches create one of the most unspoiled landscapes in Tuscany. The park is ideal for hiking, wildlife spotting, and enjoying nature away from the more crowded tourist areas.

For travelers looking to combine historic towns with time by the sea, the Tuscan coast is a wonderful addition to a trip through the region.

How Many Days in Tuscany?

The ideal amount of time to spend in Tuscany depends on how much of the region you want to explore. Between historic cities, medieval hill towns, vineyards, and countryside landscapes, there’s a lot to see.

For most travelers, spending 3 to 7 days in Tuscany allows enough time to visit the main highlights while also enjoying the relaxed pace that makes the region so special.

3 Days

A 3-day trip to Tuscany is perfect for a short visit focused on the region’s most famous destinations.

During this time, many travelers base themselves in Florence and take day trips to nearby cities such as Pisa, Siena, or San Gimignano. This itinerary offers a great introduction to Tuscany’s art, history, and landscapes.

5 Days

Spending 5 days in Tuscany gives you the opportunity to explore both historic cities and the countryside.

In addition to visiting Florence, Siena, and Pisa, you’ll have time to explore charming hill towns like Montepulciano or Pienza, enjoy wine tasting in the Chianti region, or spend time in the beautiful landscapes of Val d’Orcia.

For many travelers, five days offers the best balance between sightseeing and relaxing while exploring the region.

7 Days

With 7 days in Tuscany, you can travel at a slower pace and experience more of the region’s diversity.

A week allows time to visit several hill towns, enjoy scenic countryside drives, explore the Chianti wine region, relax in small villages, and even spend time along the Tuscan coast or the Maremma region.

This longer stay makes it easier to discover some of the quieter and less crowded corners of Tuscany.

Where to Base Yourself in Tuscany

Choosing where to stay in Tuscany depends on the type of trip you’re planning. Some travelers prefer staying in a historic city with museums and restaurants nearby, while others prefer a quieter countryside base surrounded by vineyards and rolling hills.

Fortunately, the region offers a variety of excellent options, from lively cities to peaceful hill towns. Here are some of the best areas to stay in Tuscany, depending on what you want to experience.

Florence

Florence is one of the best places to stay in Tuscany for first-time visitors. As the region’s capital and largest city, it offers easy access to major attractions like the Duomo, Uffizi Gallery, and Ponte Vecchio.

Florence is also well connected by train, making it convenient for day trips to cities like Pisa, Siena, and Lucca.

Siena

If you prefer a smaller and more atmospheric city, Siena is another great base. Its historic center feels more intimate than Florence, with narrow medieval streets and beautiful squares like Piazza del Campo.

Staying in Siena also places you close to the famous Chianti wine region and the scenic landscapes of Val d’Orcia.

Val d’Orcia

For travelers dreaming of classic Tuscan countryside views, staying in Val d’Orcia is an unforgettable experience. Small towns such as Pienza, Montepulciano, and Montalcino offer peaceful surroundings, beautiful landscapes, and easy access to vineyards and hill towns.

This area is also famous for its traditional agriturismo accommodations, countryside farm stays where visitors can experience authentic rural life in Tuscany. Many agriturismos are located on working farms surrounded by vineyards and olive groves, offering homemade food, local wine, and incredible views of the rolling hills.

For travelers who want to slow down and fully enjoy the scenery, staying in an agriturismo in Tuscany is one of the most memorable ways to experience the Tuscan countryside.

Lucca

Located near the Tuscan coast, Lucca is a charming walled city known for its relaxed atmosphere. It’s a wonderful base for travelers who want to explore both the countryside and nearby destinations like Pisa and the Cinque Terre region.

With its historic streets, cafés, and famous city walls, Lucca offers a pleasant and less crowded alternative to the larger Tuscan cities.

How to Get Around Tuscany

Getting around Tuscany depends on the type of trip you’re planning. While the region has a good train network connecting major cities, exploring the countryside and smaller towns often requires a bit more flexibility.

By Train

Traveling by train works well if you plan to visit the main cities such as Florence, Pisa, Siena, and Lucca. These destinations are well connected by regional trains, making it easy to move between them without needing a car.

For travelers focusing mostly on historic cities and day trips, trains can be a convenient way to explore Tuscany.

Book Train / Bus / Ferry / Flight

Public Transport in Rural Areas

Public transportation exists in many parts of Tuscany, but it can be limited in rural areas. Buses connect some smaller towns, though schedules may be less frequent compared to trains.

For this reason, many travelers combine both options—using trains to reach major cities and renting a car for exploring the countryside.

Renting a Car in Tuscany

In my experience, renting a car is the easiest way to explore the Tuscan countryside, especially if you want to visit places like Val d’Orcia, the Chianti wine region, or smaller hill towns that are harder to reach by public transport.

Car rental offices are easy to find in major cities such as Florence, Pisa, and Siena, as well as at the region’s airports. Most international rental companies operate here, and it’s usually simple to book a car online before arriving.

Driving in Tuscany is generally straightforward. Roads are well-maintained, clearly signposted, and traffic outside the main cities is usually light. The only thing to watch for is ZTL zones (limited traffic areas) in historic city centers, where driving without permission can result in fines. For more info, read our Guide to everything you need to know about ZTL zones in Italy.

Prices vary depending on the season, but compact cars are often the most practical option for navigating the region’s narrow roads and countryside villages.

To compare prices and availability, I usually recommend checking DiscoverCars, which lists both international and local rental companies across Italy.

Scenic Drives Through Tuscany

One of the best ways to truly experience Tuscany is simply getting in the car and exploring the countryside. While the historic cities are incredible, it’s the quiet roads between vineyards, rolling hills, olive groves, and medieval villages that make this region unforgettable.

Many of the most beautiful places in Tuscany are small hill towns and rural landscapes, and having a car allows you to discover them at your own pace. Around almost every bend, you’ll find postcard-perfect views: cypress-lined roads, golden wheat fields, vineyards, and ancient stone villages perched on hilltops.

Whether you’re exploring for a few hours or planning a longer trip, these scenic drives in Tuscany offer some of the most breathtaking landscapes in Italy.

Val d’Orcia Scenic Drive

The Val d’Orcia is one of the most iconic landscapes in Tuscany and a UNESCO World Heritage Site. This region looks exactly like the Tuscany most people imagine: soft rolling hills, winding roads lined with cypress trees, vineyards, and historic villages.

A classic route begins in San Quirico d’Orcia and continues toward Pienza and Montepulciano, passing some of the most photographed landscapes in Italy. Along the way, you’ll find countless viewpoints where you can stop to take photos or simply enjoy the peaceful scenery.

Highlights of this drive include:

• The famous cypress-lined roads of Val d’Orcia
• The charming Renaissance town of Pienza
• The historic wine town of Montepulciano
• Endless views of the Tuscan countryside

The Chianti Wine Road

The road between Florence and Siena passes through the heart of the Chianti wine region, one of the most famous wine areas in the world. Traveling through Chianti means winding through vineyards, olive groves, and picturesque villages surrounded by rolling green hills.

The route along SR222, also known as the Chiantigiana road, is especially scenic. Small towns such as Greve in Chianti, Radda in Chianti, and Castellina in Chianti are perfect stops to enjoy a relaxed lunch, visit a local winery, or stroll through a quiet piazza.

Along this route you can:

• Visit traditional Chianti wineries
• Stop in charming hill towns
• Enjoy beautiful vineyard landscapes
• Taste some of the best wines in Tuscany

Florence to San Gimignano Drive

Traveling from Florence to San Gimignano is another beautiful route that showcases Tuscany’s classic countryside scenery. As you leave Florence, the landscape quickly transforms into rolling hills dotted with vineyards, farmhouses, and small villages.

The destination, San Gimignano, is one of Tuscany’s most famous hill towns, known for its dramatic skyline of medieval towers rising above the countryside.

Highlights of this route include:

• Scenic vineyard landscapes
• Historic Tuscan farmhouses
• Panoramic countryside views
• The spectacular medieval skyline of San Gimignano

Local Tip: The best time for scenic drives in Tuscany is early morning or late afternoon, when the light is softer, and the countryside glows with warm golden colors — perfect for enjoying the views and taking photos of the beautiful Tuscan landscapes.

Best Time to Visit Tuscany

The best time to visit Tuscany depends on the type of experience you’re looking for. The region is beautiful throughout the year, but each season offers something slightly different—from blooming countryside landscapes in spring to the famous wine harvest in autumn.

If you’re wondering when to travel to Tuscany, here’s what to expect during each season.

Spring (April – June)

Spring is often considered one of the best times to visit the region. The countryside becomes green and vibrant, vineyards start to grow, and temperatures are usually mild and comfortable for sightseeing.

This is a great time for exploring cities like Florence, Siena, and Pisa, as well as visiting hill towns and enjoying the landscapes of Val d’Orcia and Chianti.

Summer (July – August)

Summer is the busiest season in Tuscany, especially in popular destinations like Florence and San Gimignano. The weather is warm and sunny, making it ideal for outdoor activities and countryside drives.

Many towns host festivals, outdoor events, and local celebrations during the summer months. If you plan to visit during this period, booking accommodations in advance is recommended.

Autumn (September – October)

Autumn is another excellent time to travel to Tuscany. The weather remains pleasant, and the countryside takes on beautiful golden colors.

This season is also known for the wine harvest, making it a perfect time to visit the Chianti wine region, enjoy wine tastings, and experience local food festivals across the region.

Winter (November – March)

Winter is the quietest season in Tuscany. While some smaller towns can feel sleepy, major cities like Florence remain lively with museums, restaurants, and cultural attractions.

Travelers visiting during winter often enjoy fewer crowds, lower accommodation prices, and a more relaxed atmosphere when exploring the region.

Tuscany Itinerary Ideas from 3 to 10 Days

Planning a Tuscany itinerary can feel overwhelming at first, since the region offers so many historic towns, scenic landscapes, and cultural landmarks. The good news is that many of Tuscany’s highlights are located relatively close to each other, making it possible to explore several destinations even on a shorter trip.

Whether you’re spending 3 days in Tuscany or enjoying a longer 10-day trip, the itineraries below offer ideas for combining the region’s famous cities, hill towns, wine regions, and countryside landscapes.

3-Day Tuscany Itinerary – Highlights

Day 1: Florence
Start your trip in Florence, the heart of Tuscany and one of Italy’s most important cultural cities. Visit the Florence Cathedral (Duomo), explore the Uffizi Gallery, and walk across the historic Ponte Vecchio.

Day 2: Pisa and Lucca
Visit Pisa to see the famous Leaning Tower of Pisa, then continue to nearby Lucca, a charming walled city where you can cycle along the historic city walls and explore the lively piazzas.

Day 3: Siena and San Gimignano
Spend the day exploring Siena, famous for Piazza del Campo and its medieval streets. On the way back, stop in San Gimignano, known for its iconic medieval towers.

5-Day Tuscany Itinerary – Cities and Countryside

Days 1–2: Florence
Explore Florence’s historic center, museums, and viewpoints.

Day 3: Pisa and Lucca
A classic day trip from Florence.

Day 4: Siena and Chianti
Travel to Siena, then explore the Chianti wine region, stopping at vineyards and scenic villages.

Day 5: Val d’Orcia
Visit Pienza and Montepulciano, two of the most beautiful towns in the Tuscan countryside.

7-Day Tuscany Itinerary – Classic Tuscany

Days 1–2: Florence
Day 3: Pisa and Lucca
Day 4: Siena
Day 5: San Gimignano and Monteriggioni
Day 6: Val d’Orcia – Pienza and Montepulciano
Day 7: Chianti Wine Region

This itinerary allows more time to enjoy the famous Tuscan countryside, vineyards, and hilltop villages.

10-Day Tuscany Itinerary – Slow Travel

With 10 days in Tuscany, you can explore the region more slowly and discover places beyond the main highlights.

Days 1–2: Florence
Day 3: Pisa and Lucca
Day 4: Siena
Day 5: San Gimignano and Monteriggioni
Days 6–7: Val d’Orcia – Pienza, Montepulciano, Montalcino
Day 8: Chianti Wine Region
Days 9–10: Tuscan Coast or Maremma

Finish your trip by visiting the Maremma coast, Monte Argentario, or relaxing in one of Tuscany’s natural hot springs, such as Saturnia.

Bonus Idea: 14 Days in Italy Including Tuscany

If you’re planning a two-week trip to Italy, Tuscany can easily become the centerpiece of your itinerary.

One great option is to start in Rome, spending 3 days exploring the capital—visiting landmarks like the Colosseum, the Vatican, and the historic center. If you’re planning your time there, this 3 Days in Rome itinerary will help you see the city’s highlights before heading to Tuscany.

From Rome, you can travel north to Tuscany and follow a 10-day Tuscany itinerary, exploring cities like Florence, Siena, and Pisa, visiting hill towns such as San Gimignano and Montepulciano, and enjoying the famous landscapes of Val d’Orcia and the Chianti wine region. You can then fly home from Florence, which makes the route simple and convenient.

Another option is to start your trip in Florence and spend 10 days exploring Tuscany at a relaxed pace. Afterward, you can head to the Cinque Terre, one of the most beautiful coastal areas in Italy, and spend 2–3 days visiting the colorful seaside villages. The region is easy to reach from Pisa or La Spezia, making it a natural extension to a Tuscany itinerary. From there, you can return to Florence for your flight home.

This type of route allows you to combine historic cities, Tuscan countryside landscapes, and coastal villages in one memorable Italian trip.

Travel Costs in Tuscany

Traveling in Tuscany can be moderately expensive compared to other regions in Italy, especially in popular destinations like Florence, Siena, and San Gimignano. However, costs vary depending on the season, the type of accommodation you choose, and your travel style.

Here are some typical mid-range prices travelers can expect when visiting Tuscany.

Major attractions such as the Uffizi Gallery, Accademia Gallery, and Siena Cathedral complex typically cost around €15–€25 for entry.

Wine tastings in the Chianti region often include multiple wines and small snacks, making them a popular and affordable experience when visiting Tuscany.

Overall, Tuscany offers options for many budgets, from luxury countryside villas to affordable guesthouses and agriturismo farm stays.

Travel Tips for Visiting Tuscany

To make the most of your trip, here are some practical Tuscany travel tips that can help you avoid common mistakes and enjoy the region more fully.

Book popular attractions in advance

Famous sites like the Uffizi Gallery or the Accademia Gallery in Florence often sell out quickly. Booking tickets in advance can save you time and help you avoid long queues.

Consider renting a car for the countryside

While trains connect major cities like Florence, Pisa, and Lucca, many of Tuscany’s most beautiful destinations—such as Val d’Orcia, Chianti, and small hill towns—are easier to reach by car.

Stay in smaller towns or the countryside

Large cities can get busy, especially during the summer. Staying in places like Pienza, Montepulciano, or a countryside agriturismo offers a more peaceful and authentic Tuscan experience.

Visit early or late in the day

Popular towns such as San Gimignano and Siena are much quieter in the early morning or evening, once the day-trip crowds leave.

Take time to slow down

One of the best parts of traveling in Tuscany is the relaxed rhythm of life. Enjoy long lunches, stop at scenic viewpoints, and take time to explore villages and countryside roads.

FAQs About Visiting Tuscany

Continue Planning Your Trip to Tuscany

Planning a trip to Tuscany? These guides will help you explore more of the region, from historic cities and famous landmarks to scenic countryside destinations.

• Things to Do and see in Florence – Discover the top attractions, museums, and viewpoints in Tuscany’s cultural capital.
• 2 Days in Florence Itinerary – A complete guide to exploring Florence’s top landmarks, museums, and viewpoints over two days.
• Complete Guide to Siena – Discover the best things to do, main landmarks, and practical tips for visiting Siena.
• Pisa Travel Guide – Everything you need to know before visiting the famous Leaning Tower and the historic city of Pisa.
• Italy Driving Guide: Everything You Need to Know – Helpful tips about ZTL zones, toll roads, parking, and driving rules across Italy.

Final Words

Tuscany is one of the most unforgettable regions to visit in Italy. From historic cities like Florence, Siena, and Pisa to the rolling hills of Val d’Orcia and the vineyards of the Chianti wine region, the landscapes and cultural heritage here create a travel experience unlike anywhere else.

Exploring medieval towns, tasting local food and wine, driving through the countryside, and discovering quiet villages are all part of what makes traveling through Tuscany so special. Every corner of the region offers something unique, from famous landmarks to peaceful rural scenery.

Take your time, enjoy the journey, and allow space in your itinerary to stop in small towns, admire the landscapes, and experience the relaxed rhythm of life that makes Tuscany so memorable.

With its rich history, incredible scenery, and welcoming atmosphere, Tuscany remains one of the most beautiful places to visit in Italy.

Buon Viaggio!

Get our FREE Italy
Travel Guide
E-Book

This printable guide is your ultimate companion for exploring Italy, with insider tips, detailed itineraries, transportation advice, must-see attractions, and more.

Name*

Email*

Sign up