21 Beautiful Places to Visit in Tuscany (Plus Umbria) for A Road Trip

Discover 21 beautiful places to visit in Tuscany, from Florence and Pisa to Val d’Orcia hill towns, plus stunning Umbria detours like Assisi, Perugia, and Spello.

I’m always in love with Tuscany. What a beautiful region! I visited it once, but the atmosphere, the colors, the vibes, and the peaceful rhythm of life there are still in my heart. Tuscany is a place where every hilltop town looks like a painting and every road feels like a scenic drive. Even a small village can surprise you with stunning views, historic streets, and delicious local food.

While researching for our Tuscany trip, we listed out 21 places we wanted to visit. Of course, we did not have enough time to see them all during my 5-day trip in Tuscany 😀 I could only manage to visit more than half of the places on this list, but the rest have become my motivation for future trips to Tuscany.

I hope this post can give you some ideas and inspiration for your upcoming Tuscany road trip. To make it easier for trip planning, this list is arranged roughly from the places closest to Florence down to the farthest destinations toward southern Tuscany and some in Umbria. Although Umbria is a different region from Tuscany, they are very close and easy to add to a Tuscany road trip. The scenery there is breathtaking, and some of these villages became the most impressive stops during my Tuscany journey.

Florence

Florence (Firenze in Italian) is the heart of Tuscany and one of the most famous cities in Italy. Known as the birthplace of the Renaissance, the city is filled with incredible art, architecture, and history. Walking through Florence feels like walking inside an open-air museum.

The iconic Duomo, or Cathedral of Santa Maria del Fiore, dominates the skyline with its massive red dome designed by Brunelleschi. Climbing to the top rewards you with one of the best views over the city. Nearby, the historic Ponte Vecchio bridge spans the Arno River and is lined with small jewelry shops.

Florence is also home to world-famous museums like the Uffizi Gallery and the Accademia, where you can see Michelangelo’s David. Even if you are not an art lover, simply wandering the streets and enjoying the atmosphere makes Florence unforgettable.

Pisa

Pisa is famous worldwide for its Leaning Tower, but the city has more to offer than just this iconic landmark. The tower is part of the beautiful Piazza dei Miracoli, a large square that also includes the Pisa Cathedral and the Baptistery.

The white marble buildings against the green lawn create one of the most recognizable views in Italy. Standing next to the Leaning Tower and seeing its dramatic tilt in person is a unique experience.

After visiting the famous square, it’s also nice to explore the rest of the city. Pisa has charming streets, small cafés, and a lively university atmosphere thanks to its large student population.

Lucca

Lucca is a charming city surrounded by perfectly preserved Renaissance walls. Unlike many historic cities, these walls are wide and tree-lined, creating a beautiful park that circles the entire old town.

One of the best things to do in Lucca is to rent a bike and ride along the walls. From there you can enjoy views of the red rooftops and church towers inside the city.

The historic center is full of elegant squares, churches, and hidden alleyways. Piazza dell’Anfiteatro, built on the site of a Roman amphitheater, is one of the most unique and beautiful squares in Tuscany.

San Gimignano

San Gimignano is known as the “Town of Towers.” During the Middle Ages, wealthy families built tall towers as symbols of their power and influence.

Today, 14 of these towers still stand, creating one of the most distinctive skylines in Tuscany. From a distance, the town looks like a medieval Manhattan rising from the countryside.

Walking through the stone streets feels like traveling back in time. The town is also famous for its gelato shops, including a world-champion gelateria that many visitors love to try.

Volterra

Volterra is one of Tuscany’s oldest towns, with a history that dates back to the ancient Etruscans. Over the centuries, the town developed layers of history including Roman and medieval influences.

One of the highlights is the impressive Roman theatre located just outside the town walls. The historic center itself is filled with narrow streets, stone buildings, and beautiful viewpoints.

Volterra is also known for its traditional alabaster craftsmanship. Small shops throughout the town sell sculptures and decorative objects made from this local stone.

Chianti Region

The Chianti region lies between Florence and Siena and is one of the most famous wine areas in the world. The landscape here is exactly what many people imagine when they think of Tuscany.

Rolling hills, endless vineyards, olive groves, and winding roads create a peaceful and picturesque countryside. Driving through this region is an experience in itself.

Along the way, you will find charming villages, family-run wineries, and small restaurants serving delicious Tuscan food. Wine tasting in Chianti is one of the highlights of any Tuscany trip.

Siena

Siena is one of the best preserved medieval cities in Italy. Its historic center has remained largely unchanged for centuries, giving visitors a true sense of the Middle Ages.

The heart of the city is Piazza del Campo, a large shell-shaped square that hosts the famous Palio horse race twice a year. The square is surrounded by historic buildings and lively cafés.

Siena Cathedral is another major highlight. Its stunning black and white marble exterior and richly decorated interior make it one of the most beautiful churches in Tuscany.

Asciano (Crete Senesi)

Asciano is located in an area called the Crete Senesi, known for its distinctive clay hills. The landscape here looks very different from the typical green Tuscan countryside.

The rolling hills are smooth and almost wave-like, creating a unique and dramatic scenery. During sunrise or sunset, the warm light makes the hills glow with beautiful colors.

This area is especially popular with photographers. Many of Tuscany’s most artistic landscape photos are taken along the roads near Asciano.

Val d’Orcia

Val d’Orcia is one of the most iconic landscapes in Italy and a UNESCO World Heritage site. The region is famous for its sweeping hills, golden fields, and winding cypress-lined roads.

Many of the classic images of Tuscany come from this area. It is a place where the scenery changes beautifully with the seasons. Driving through Val d’Orcia feels like moving through a living painting. Every hill seems to reveal another stunning viewpoint.

San Quirico d’Orcia

San Quirico d’Orcia is a small village located right in the center of Val d’Orcia. Although it is less famous than some neighboring towns, it has a wonderful peaceful atmosphere.

The village is surrounded by some of the most photographed landscapes in Tuscany. Just outside town you can find the famous cypress tree roads that appear in many travel photos.

Inside the village, visitors can explore medieval streets and the beautiful Horti Leonini gardens.

Bagno Vignoni

Bagno Vignoni is one of the most unusual villages in Italy. Instead of a traditional town square, the center of the village is occupied by a large thermal pool.

These hot springs have been used since Roman times and were once visited by nobles and pilgrims traveling through the region.

Although the main pool is not for bathing today, nearby natural thermal baths allow visitors to enjoy the warm mineral waters while surrounded by beautiful scenery.

Pienza

Pienza is a small town that sits on a hill overlooking the Val d’Orcia valley. It was redesigned during the Renaissance to become an ideal model town.

The result is a charming village with elegant streets and a beautiful central square. From the town walls, visitors can enjoy breathtaking views across the countryside.

Pienza is also famous for its pecorino cheese, which is sold in many small shops throughout the town.

Monticchiello

Monticchiello is a small fortified village located near Pienza. It is much quieter than many other Tuscan towns, which makes it feel very authentic and peaceful.

The village is surrounded by the stunning landscapes of Val d’Orcia. From its walls and streets, you can see endless rolling hills stretching into the distance.

Walking through Monticchiello feels like discovering a hidden corner of Tuscany.

Montalcino

Montalcino is a dream destination for wine lovers. The town is famous for producing Brunello di Montalcino, one of the most prestigious wines in Italy.

Perched on a hill, the town offers panoramic views of vineyards and countryside. The medieval fortress at the top of the town is another highlight.

Visitors can explore wine cellars, enjoy tastings, and relax in small restaurants serving traditional Tuscan dishes.

Montepulciano

Montepulciano is another stunning hill town famous for its wine culture. The town rises along a narrow ridge surrounded by vineyards.

Its historic streets are lined with Renaissance palaces and charming squares. The main square, Piazza Grande, offers beautiful views and impressive architecture.

Montepulciano’s wine cellars are often located underground, creating a unique atmosphere for wine tastings.

Cortona

Cortona is a beautiful hilltop town overlooking the wide Val di Chiana valley. The town’s location provides spectacular panoramic views of the surrounding countryside.

Cortona became famous internationally after the book and movie “Under the Tuscan Sun.” Many visitors come to experience the romantic atmosphere described in the story.

The town’s narrow streets, historic squares, and old stone houses make it a lovely place to explore slowly.

Pitigliano

Pitigliano is one of the most unique towns in Tuscany. Built dramatically on top of a volcanic rock cliff, the town looks like it is growing out of the stone itself.

Its historic center is full of narrow alleys, stone houses, and hidden staircases. Walking through the town feels like exploring a maze of medieval architecture.

Pitigliano is also known as “Little Jerusalem” because of its historic Jewish community and preserved synagogue.

Saturnia Thermal Springs

Saturnia is famous for its natural hot springs, especially the beautiful Cascate del Mulino. Here, warm mineral water flows through a series of natural limestone pools.

The turquoise pools are open to the public and can be enjoyed year-round. Many visitors come here to relax in the warm water while surrounded by peaceful countryside.

It is one of the most unique natural experiences in Tuscany.

Perugia (Umbria detour)

Although Perugia is not in Tuscany, it is very close and makes a wonderful addition to a Tuscany road trip. The city is the historic capital of the Umbria region.

Perugia sits on a hill and is full of medieval streets, historic buildings, and lively squares. The central Piazza IV Novembre is one of the most beautiful piazzas in central Italy.

The city is also known for its chocolate tradition and vibrant cultural festivals.

Assisi (Umbria detour)

Assisi is one of the most famous towns in Umbria and an important pilgrimage destination. The town is best known as the birthplace of Saint Francis.

The Basilica of St. Francis dominates the town and contains remarkable medieval frescoes. From the basilica and town walls, visitors can enjoy sweeping views of the Umbrian countryside.

Assisi’s peaceful atmosphere makes it one of the most memorable stops in the region.

Spello (Umbria detour)

Spello might be one of the prettiest villages in Italy. The town is famous for its beautiful flower displays decorating balconies, windows, and streets.

Walking through Spello feels like stepping into a postcard. Every corner reveals colorful flowers, stone houses, and charming little alleys.

Despite its beauty, Spello remains quiet and relaxing compared to more famous destinations.

Tuscany has an incredible mix of historic cities, charming hill towns, stunning countryside, and relaxing natural springs. Every town has its own personality and unique scenery. Even after visiting many of these places, I still feel there is so much more to explore. That is exactly why Tuscany keeps calling travelers back again and again.

I hope you have a wonderful Tuscany road trip this year!

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