12 Must-See Towns in Tuscany That Will Amaze You

Few places in the world compare to Tuscany. 

The towns in Tuscany are famous for gorgeous rolling hillsides dotted with vineyards, medieval villages, Renaissance art, and, of course, amazing wine and food; Tuscany is unequal to any other region in the world. 

That’s probably why Tuscan towns consistently appear on the list of Italy’s best places to visit.

Just thinking of Tuscany brings about visions of villages with beautifully tiled roofs and cobblestone streets protected by ancient city walls. 

The charming towns in this area will steal your heart while making any Italy itinerary feel complete.

Just imagine visiting Florence, Siena, Pisa, and many more beautiful towns in Tuscany!

It can get a little overwhelming planning a visit to this area.  There are so many amazing Tuscan towns that narrowing the list to a manageable size when planning your trip to Tuscany can be challenging. 

I am willing to bet that Tuscany is on everyone’s couple’s bucket list.

Whether you are looking for big cities or a small town in Tuscany, we have you covered.

That is why we have teamed up with some incredible travel bloggers to bring you this list of incredible Tuscan towns worth visiting! 

We hope this article lets you know which Tuscany towns fit your travel style.

*This post contains affiliate links. If you purchase through these links, we will receive a small commission at no additional cost to you. That Texas Couple also participates in the Amazon Services LLC Associates Program, through which we earn from qualifying purchases.

Florence-The Heart of the Italian Renaissance

By Me, Michelle of That Texas Couple

Known for its Renaissance masterpieces and incredible Duomo, Florence is the quintessential town in Tuscany and a UNESCO World Heritage Site. 

Few people venture to Italy and do not spend at least a few days in Florence.

Overflowing with charm and personality, Florence will likely make you fall in love with it and keep you coming back repeatedly.

Even though Florence is a large city, it will make you feel like you are in one of the small towns in Tuscany!

Exploring Florence on foot ensures that you feel immersed in the charm and action of this fabulous town.

Just note that the masterpieces, like the David, can get very crowded during the busy season.

While here, you have to visit the town center, Florence’s Duomo. 

The Piazza del Duomo contains the famous Duomo (one of the best-preserved churches in Italy), the Baptistery, and Giotto’s Campanile (the bell tower).

The ornate and gorgeously decorated structures are a perfect introduction to the city.

They immediately give you a glimpse into the grandeur of Florence.

Another noteworthy site is the Uffizi Gallery, one of Florence’s most popular tourist attractions.

Here, you will find masterpieces from Italy’s greatest artists, like Leonardo and Michelangelo.

After viewing some of Florence’s masterful works, go to the Ponte Vecchio bridge. 

This bridge, which dates back to 1345, still has shops, just as it originally did.

Take note of the corridor at the top of the bridge.

Cosmo Medici used this to travel from his home, Pitti Palace, to Piazza della Signoria without being seen by the townspeople.

You can imagine stepping back in time and experiencing the city!

Florence is truly one of the most beautiful towns in Tuscany!

San Gimignano-Historic Medieval Town

By Michelle of That Texas Couple

Known as the medieval town on the hill, this town should be on your list of Tuscan towns as it is one of the most beautiful towns in Tuscany!

Approaching San Gimignano, you immediately notice the terra cotta roofs on the Tuscan hillside.

But it is the towers that get your attention here.

In addition to the towers, San Gimignano also boasts a well-preserved medieval wall!

San Gimignano is a UNESCO World Heritage site that has been attracting tourists for centuries. It served as a resting point for pilgrims traveling to and from Rome.

14 of the original 72 towers of the city remain today.

You will find these towers in the historic center still standing tall, watching over the Tuscan countryside below (along with the Church of San Gimignano.

Surrounded by the city wall, this is one of those beautiful towns that make you feel you have been transported back to the Middle Ages.

During your visit, visit the Church of San Gimignano to see a historic Italian church.

Visitors to this small town are in for a fabulous treat as this historic town is unlike any other in Italy.

Walking down the cobblestone streets and visiting the Duomo in San Gimignano immediately transports you back in time.

Be sure to see the historical exhibits at Palazzo Comunale.

Then explore the stores to buy some of the local crafts.

We found fabulous leather purses, incredible wine, and impeccable olive oil during our time in San Gimignano.

You have to try the Vernaccia di San Gimignano, the well-known white wine produced from the Vernaccia grape grown around San Gimignano.

Vernaccia di San Gimignano white wine is amazing and one of my favorites!

Some unique museums in San Gimignano, like The Museum of Torture.

The San Gimignano Museum of Torture allows visitors to view over 100 instruments used to torture people.

Some date as far back as the 16th century.

Honestly, you may want to stay in the hilltop town of San Gimignano forever!

Greve in Chianti-Wine Lovers Paradise

Submitted by Samantha of The Wandering Wanderluster

The Tuscany region in the heart of Italy is one of the most popular travel destinations in the world.

Thousands visit Tuscany annually to visit its historic cities and hilltop medieval towns and enjoy its delicious cuisine and world-renowned wines.

One town which has become popular with tourists is Greve in Chianti. Situated just 30km from Florence, it is the gateway to the Chianti wine region.

This small market town has no notable sights, but the Piazza Matteotti is at its heart.

The town’s triangular piazza and main square feature a small church and a portico.

The area also includes houses, boutique shops, artisan workshops, and restaurants.

A visit to the Antica Macelleria Falorni, a local butcher shop, is a must.

It has been in the same spot since 1806. This small shop is famous for its salami with fennel, using a recipe that has been passed down to generations.

Most people visit Greve to enjoy a local-style lunch and sample local wines.

You can do this at Antica Macelleria Falorni or visit restaurants in the main square.

They will all serve local dishes, and you can order a bottle of Chianti wine to accompany your lunch.

The neck of the bottle will bear the symbol of the rooster, which signifies it is an authentic bottle of Chianti wine.

You can visit the Falorni Enoteca for wine tasting. It offers many Tuscan wines that you can sample and buy.

This is one of the must-see towns for sure!

Montepulciano-Amazing Red Wine Town

Submitted by Lori from Travlinmad

Tuscany is one of Italy’s premier destinations, and there’s no better way to explore this idyllic region than on one of several Tuscany road trips through the stunning Val d’Orcia to the historic town of Montepulciano.

The Val d’Orcia is a Tuscany region extending from the hills south of Siena to Monte Amiata.

It is noted worldwide for its beautiful rolling hills, with gorgeous towns and villages.

Honestly, the Val d’Orcia region is not to be missed.

Roughly an hour and a half south of Florence (in the Val d’Orcia), the stone-walled preserved medieval town imposingly sits atop a hill overlooking the surrounding countryside.

Buses run regularly, but we recommend renting a car and driving yourself to maximize your time.

You can then stop where you like for as long as you like. Parking at Montepulciano in a metered parking lot outside the city walls is easy.

A short walk through the wall along a narrow lane leads to the town’s main street and the Piazza Grande.

Piazza Grande is the official main square, surrounded by quaint cobbled streets, centuries-old buildings, shops, trattorias, and small corner markets.

Regarding food, Montepulciano is a Tuscan town with some of the best in the area.

A highlight of this small town is stopping at any of the many enotecas. Enotcas are small wine shops featuring tastings of local wines. 

One of the best wines to try is Vino Nobile di Montepulciano, one of Italy’s most prized wines. 

Vino Nobile di Montepulciano is a must-try when visiting!

Walk a short distance up a hill to the town center of the old town to the 16th-century Cathedral of Santa Maria Assunta.

The Cathedral of Santa Maria is situated on one of Italy’s most beautiful piazzas, making the Cathedral of Santa Maria a place that cannot be missed.

No matter where you plan to visit in Tuscany, Montepulciano should be on your bucket list.

This is one of the fabulous small towns in Tuscany.

Montalcino-Fabulous Wine Town In Tuscany

Submitted by Coni from Experiencing the Globe

If you want to see Italy off the beaten path, look no further than the small towns, specifically Montalcino.

If you’re a wine lover, you’ve heard this name.

Brunello di Montalcino is among the country’s best. You might not know it’s named after the little town where it’s produced.

In the southeastern part of Tuscany, in the Val d’Orcia, you will find Montalcino.

You will see Montalcino in the distance, between rolling hills dotted with cypress trees and full of vines. Look for a gorgeous medieval town at the top of the hill.

Even though the name is popular, the small town is not.

Here, you’ll hear little English, so be ready. Despite the possible communication barrier, you’ll be treated with the best of Italian hospitality.

Combining this with amazing views and delicious wine will make you feel at home.

The best place to visit is the Enoteca –wine bar/shop– in the old fortress.

The owners know their wine and can entertain you for hours with stories and lessons.

They have an extensive selection of wine and offer tastings of the best in the region.

Be sure to see the clock tower and the city’s town hall and explore the narrow cobblestone streets.

When you need a break, you can find plenty of bars and restaurants offering wine and food pairings!

Bolgheri

Submitted by Michelle from Intentional Travelers

Tuscany’s Etruscan Coast boasts the great small towns, beautiful rolling hills, and charming villages that you probably associate with Tuscany.

But the sunny, sandy beaches and ocean vistas make it even more spectacular.

Though vacationers flock to the beach towns, the area still feels relatively uncrowded and is a great small.

The small town of Bolgheri brings together the very best of the region – Tuscany’s old-world village life, complete with a castle; warm climates and views of the Etruscan Coast; and bountiful landscapes, with wineries and olive groves in every direction.

Not everyone knows this area is also home to world-class wineries like Sassicaia.

A road lined with cypress trees has been declared a national monument and continues from the town of Bolgheri toward Castagneto. It passes through olive groves and fertile vineyards.

This Wine and Olive Road is the perfect place to do a few tastings and admire the scenery.

Whether you prefer easy bike rides to the beach, hopping from town to town, walking to the village gelato shop, or tasting wines and olive oils, this part of Tuscany offers something for everyone.

For more things to see and do around Bolgheri, visit this Guide to Tuscany’s Etruscan Coast.

Lucca

Submitted by Nick from The Danish Nomads

Lucca is a beautiful old town in the northern part of Tuscany. It has a distinct medieval look and feel, complete with narrow streets, renaissance walls, and ramparts.

The air is thick with history, which is no wonder because the city dates back to the Roman Empire.

If you like that, you’ll be happy to learn that Lucca is filled with beautiful old churches, grand squares, and historical towers.

This might be considered the standard in Italy, but this place takes it up a notch. It’s even known as “the city of a hundred churches”!

You can have a very enjoyable day in Lucca simply by strolling around within the walls of the old town, stopping for the occasional gelato, and just enjoying the Piazza Dell’Anfiteatro.

There are plenty of sidewalk cafes and restaurants near Piazza Dell’Anfiteatro, so finding a place to have a delicious Tuscan lunch will be no problem.

It would be a shame not to spend more time in Lucca because it is a unique bucket list destination you won’t find anywhere else.

Upon visiting, most people will agree that the city is plenty interesting for at least a few days’ worth of exploration and is one of the most charming small towns in Tuscany!

Siena

Written by me, Michelle, from That Texas Couple

Siena is one of the quintessential medieval Tuscan towns and another UNESCO World Heritage Site in Tuscany. 

Siena is a must while visiting the Tuscan region. It is famous for its rust-colored medieval brick buildings and the fan-shaped town square in the town center, the Piazza del Campo, which hosts the twice-annual world-famous horse races.

Originally dating back to the Middle Ages, Siena has a long history. 

Of course, you should explore the famous town square, Piazza del Campo, and the great shops, restaurants, and attractions that border it.

You will notice the tall, towering structure on the Torre del Mangia square. 

This tower is one of Siena’s most recognizable landmarks and is well worth climbing the 400 steps to get a great view of the city.

Follow the narrow streets to one of Siena’s top attractions: the Duomo.

Siena is also home to a gorgeous cathedral, the Duomo di Siena, which is so unique.

The Duomo di Siena is mesmerizing and, both inside and out, is adorned with black and white striped marble. 

Like most grand churches in Europe, the cathedral took several years to complete.

Once inside, you will find works by Michelangelo, Bernini, and Donatello, making it almost like visiting a museum.

While a day in Siena is enough time to explore the city’s surface, you may want to plan more time in this great town to explore a little slower! Siena is truly one of the most beautiful towns in Italy!

Be sure to visit Siena on your trip to Tuscany!

Elba Island

Submitted by Amandine from Les Berlinettes

If you plan to go to Tuscany, Italy, you probably think of the countryside, the small villages, and the cypress trees. But what about a beach holiday in Tuscany?

Did you know that Tuscany has its own island, Elba?

It is reachable by a one-hour ferry ride from the mainland.

Elba is famous for its history- Napoleon’s exile island- and its beautiful villages, dream beaches, and wine.

While Chianti is made in Tuscany, Elba has its own wine called Elba Aleatico. 

There are plenty of activities in Elba, including kayaking, wine tasting, snorkeling (Elba has amazing clear water), diving, and enjoying the island.

I recommend renting a car from the mainland to go around Elba as you won’t be able to rely on public transportation, and taxis can be expensive if you would like to do many things.

We stayed in a chic camping area for accommodation, but plenty of small hotels and bed and breakfasts exist.

This island has no big hotel chains, as it is still a secret gem!

Pienza

Submitted by Chrysoula from Athens and Beyond

The picturesque Tuscan town of Pienza lies in the Orcia Valley in the province of Siena and has been a UNESCO World Heritage Site for over 20 years.

The town, which was originally known as Corsignano, dates back as far as the 9th century.

Still, the architecture and layout we see today were designed in the 1400s by Pope Pius II (who was born Aeneas Silvius Piccolomini in Corsignano).

The Pope wanted to rebuild Corsignano as an ‘ideal Renaissance town,’ once he was happy with its design, he renamed it Pienza, meaning the City of Pius.

This ‘utopian city’ was created as a retreat from Rome, and new architectural gems such as the Cathedral, the Piccolomini Palace, and the Town Hall were built.

These buildings still stand proud in the heart of Pienza, on the hilltop overlooking the Val d’Orcia.

The town also features a central square, Piazza Pio II, designed to balance the layout of the buildings.

Elsewhere in the town lies the Pieve di Corsignano, a simple yet beautiful Romanesque church that dates back to the 12th century.

Pope Pius II (and later his nephew, who became Pope Pius III) was baptized in this church.

Aside from its architecture, Pienza is also known for its fine cuisine, with dishes often highlighted by the tasty Pecorino of Pienza cheese.

One such dish is an Italian Fondue made with a mix of rich sheep cheese.

Pienza is between the equally stunning hill towns of Montepulciano and Montalcino, so it’s well worth visiting them all in one trip.

Pontedera

Submitted by Paulina from Paulina on the Road

Situated in central Italy with an approximate area of about 23,000 square kilometers, Tuscany is home to the world’s most recognizable Renaissance art and distinguished architecture.

The place is laden with ancient Etruscan settlements, rustic villages with slanting red-tiled roofs, enthralling mazes of gorgeous stones and marbles, and breathtaking landscapes.

It’s one of the most beautiful regions in Italy, comprising amazing cities you would charm after setting foot in.

Located between Pisa and Florence, Pontedera is situated on the northern side of Tuscany, Italy.

For over a decade, Pontedera has been a commercial center, producing artisanal goods and transporting goods since it is built upon the confluence of Era River and the Arno.

Besides the commercial requirements, Pontedera is quite famous for its civic sculptures.

The town is full of public art projects, providing a unique charm.

Moreover, the city offers a variety of restaurants, coffee bars, pastry shops, grocery stores, designer clothes, gadgets, and accessories scattered all over the countryside.

The river park situated in Pontedera displays an amazing glimpse of Arno’s natural beauty.

Pontedera believes in the interest of flora and fauna and tries its best to secure them.

Therefore, I recommend bringing your vegan hiking boots while traveling since they are vegan-friendly and produced without animal ingredients or byproducts.

Overall, Pontedera serves you with its ethnicity and unique culture, making Pontedera one of the most beautiful places to visit in Tuscany.

Pisa

Submitted by Lyndsay from The Purposely Lost

The beautiful city of Pisa is one of my favorite cities in Tuscany, Italy.

Although most people only visit Pisa for one day, there are more than enough activities around Pisa and the old town area to fill several days.

The city’s most famous landmark is the Torre di Pisa, also known as the Leaning Tower of Pisa, located in the Piazza Dei Miracoli.

The Leaning Tower was built in the 12th Century, but by the time the second floor was started, it was already tilting.

Although some think it was a lookout, the Leaning Tower was actually the bell tower of the nearby Cattedrale di Pisa.

In addition to the Tower and the Cathedral, you can also visit the baptistry and a cemetery, all on the same grounds in the city center at the Piazza Dei Miracoli.

Since most tourists only visit Pisa for the Tower and the Piazza Dei Miracoli, the rest of the city is fairly quiet, making it worth a visit.

You’ll get a great feel for the local culture by walking along the Arno River, which cuts through the historic town and its side streets.

You’ll also find coffee shops and local stores surrounding the many town squares.

And, since the main city center of Pisa is inland from the coast, it has a beautiful coastline, Marina di Pisa.

From large, famous landmarks to smaller local areas and a beautiful beach, Pisa is a great city in Tuscany.

Cortona-Under the Tuscan Sun Town

Submitted by Ivan from Mind the Travel

Situated near the border with Umbria, the traditional walled Etruscan town of Cortona is quintessential Tuscany.

Made famous by the movie Under the Tuscan Sun, Cortana now welcomes visitors from all over the world who want their own “under the Tuscan sun” experience in one of the small towns in Tuscany.

Although Cortona is small, it has interesting sites to visit, especially in the historic center.

Make your way to the Diocesan Museum, which houses remarkable works of art made by the Lorenzetti brothers, Fra Angelico, Bartolomeo della Gatta, Luca Signorelli, and Giuseppe Maria Crespi.

Another place you should not miss out on visiting is the Museo dell’Accademia Etrusca (MAEC), a revamped civic museum in the old town where you’ll find some of the most fascinating artifacts produced by the Etruscan civilization.

Beautiful churches, like the pretty 15th-century Chiesa di San Niccolo and the Santuario di Santa Margherita (Sanctuary of St. Margaret), are dotted around this Tuscan town and are well worth a visit.

You can reach Cortona by a slow train from Rome, Pisa, Florence, or Venice.

If you travel from Rome, take the Regionale train RE (local train). This will stop at Camucia-Cortona train station, the closest station to Cortona (3 km.)

The train takes about 2 hours and 25 minutes. Fast trains arrive at Terontola train station (10 km from Cortona.

Then, you can hop on a bus at the railway station to Piazza Garibaldi or take a bus from any town in the province of Arezzo.

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About The Author

Michelle Snell is a travel writer, history buff, wine lover, and enthusiast of different cultures. Michelle enjoys bringing places to life through her informative writing style on her blogs, That Texas Couple and Totally Texas Travel.  Her practical tips and suggestions help make travel dreams a reality while immersing her readers in the history, culture, and food of a region.  She is happiest sipping wine in Italy or chilling on a beach with her husband, Marty.