12 Must-See Towns in Tuscany

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There are few places in the world that compare to Tuscany.  Known 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 you will consistently find Tuscan towns on the list of the best places to visit in Italy.

Just thinking of Tuscany brings about visions of villages with beautifully tiled roofs and cobblestone streets.  The charming towns in Tuscany will steal your heart while making any Italy itinerary feel complete.

It can get a little overwhelming planning a visit to this area.  I mean, there are so many amazing Tuscan towns that narrowing down the list to a manageable size can be challenging. 

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

We hope this article empowers you to know exactly which towns in Tuscany fit your travel style.

*This post contains affiliate links.  By purchasing through these links, we get a small commission at no additional cost to you. That Texas Couple is also a participant in the Amazon Services LLC Associates Program.  As an Amazon Associate, we earn from qualifying purchases.

Towns in Tuscany

Florence

By Me, Michelle of That Texas Couple

Known for its Renaissance masterpieces and its incredible Duomo, Florence is the quintessential town in Tuscany.  Few people venture to Italy and not spend at least a couple of days in Florence.

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

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

Of course, there are a lot of sights in Florence, so be sure and plan ahead if there is something that you have your heart set on seeing.

Many of Florence’s masterpieces like David, can get very crowded during the busy season.

While here, you have to visit Florence’s Duomo.  The Piazza del Duomo contains the famous Duomo (church), the Baptistery, and Giotto’s Campanile (the bell tower).

The ornate and gorgeously decorated structures are a perfect introduction to the city and give you a glimpse into the grandeur of Florence.

Another noteworthy site is the Uffizi Gallery, one of Florence’s most popular tourist sites.  Here you will find masterpieces from Italy’s greatest artists like Leonardo and Michelangelo.

After viewing some of the masterful work of Florence, make your way to Ponte Vecchio bridge.  This bridge, which dates back to 1345, still has shops on it just as it originally did.

Be sure and notice the corridor at the top of the bridge.  This was used by Cosmo Medici so that he could travel from his home, Pitti Palace, to Piazza della Segnoria while avoiding the townspeople.

No matter where you turn in Florence, there is a treasure waiting to be explored.  I think you will agree it is one of the marvelous towns in Tuscany.

Greve in Chianti

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 of people come to Tuscany every year to visit its historic cities, hilltop medieval towns, and to 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 lies at the gateway to the Chianti wine region.

This small market town has no notable sights but at its heart, you’ll find the Piazza Matteotti. Its triangular-shaped piazza features a small church and a portico that frames the square and houses a host of 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. Part butcher, part wine cellar and part cheese shop, this small shop is famous for its salami with fennel, using a recipe that has been passed down generations.

Most people visit Greve to enjoy a local style lunch and sample some local wines. You can do this at Antica Macelleria Falorni or visit any of the restaurants in the square.

They will all serve local dishes and you can order a bottle of Chianti wine to accompany your lunch. You’ll see the symbol of the rooster on the neck of the bottle, which signifies it is an authentic bottle of Chianti wine.

For wine tasting, you can visit the Falorni Enoteca just a few steps from the shop, which offers a plethora of Tuscan wines for you to sample and buy.

Montepulciano

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.

Roughly an hour and a half south of Florence, the stone-walled medieval town imposingly sits atop a hill overlooking the surrounding countryside. Buses run regularly but to make the most of your time, we recommend renting a car and driving yourself.

You can then stop where you like for as long as you like.Parking at Montepulciano in one of the metered parking lots outside of the wall is easy. Just a short walk through the wall along a narrow lane brings you into the main street of the town, a narrow cobbled street lined with centuries-old buildings, shops, trattorias, and small corner markets.

When it comes to food, Montepulciano has some of the best in the area. But the highlight of a visit for many is stopping at any of the many enotecas, small wine shops featuring tastings of local wines. Without question one of the very best wines to try is Vino Nobile di Montepulciano, one of Italy’s most prized wines. Walk a short distance up a hill to the center of the old town to the 16th-century Cathedral of Santa Maria Assunta, Saint Mary of the Assumption, situated on one of Italy’s most beautiful piazzas. 

Spend the night at any of the fine small hotels and inns just outside of town. Our favorite is Salcheto Winehouse which has lovely accommodations and an excellent enoteca featuring their own wines, cheeses, bread, and fresh seasonal produce.

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

Montalcino

Submitted by Coni from Experiencing the Globe

If you want to see Italy off the beaten path, look no further than Montalcino, one of the amazing towns in Tuscany. If you’re a wine lover, for sure you’ve heard this name.

Brunello di Montalcino is among the country’s best. What you might not know is that it’s named after the little town where it’s produced. In the southeastern part of Tuscany, in the Val d’Orcia, between rolling hills dotted by cypresses and full of vines, dominating the area, you’ll see it from the distance –a gorgeous medieval top-of-the-hill town.

Even though the name is popular, the town is not. Here you’ll hear little English and you’ll be treated with the best of Italian hospitality, together with the amazing views and delicious wine.

The best place to visit is the Enoteca –wine bar/shop– in the old fortress, where the owners know their wine, and can entertain you for hours with stories and lessons. Stroll around the town before you go in. They have an extensive selection of wine and they offer tastings of the best of the region, so it’s better to pose for photos before venturing into the fortress.

As for the rest of the town, see the clock tower on the Palazzo dei Priori, the city’s town hall, which lies in the main square, known as Piazza del Popolo, and then get lost in the little narrow cobblestone streets.

You’ll find plenty of bars and restaurants offering a pairing of wine and food, making it a great break from walking up and down the hill.

Bolgheri

Submitted by Michelle from Intentional Travelers

Tuscany’s Etruscan Coast boasts the beautiful rolling hills, vineyards, olive groves, 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 for the summer sun, and bicycle tours cycle through on a regular basis, the area still feels relatively undiscovered and uncrowded.

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 that this area is also home to world-class wineries like Sassicaia.

From the town of Bolgheri heading toward Castagneto, a road lined with cypress trees has been declared a national monument and continues 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 or hopping from town to town, walking to the village gelato shop, or tasting wines and olive oils, there’s something for everyone in this part of Tuscany.

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 that distinct medieval look and feel, complete with cobblestone streets and 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 sort of thing, you’ll be happy to learn that Lucca is filled to the brim with beautiful old churches, grand squares, and historical towers.

This might be considered the standard in Italy, but this place really 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.

There are plenty of sidewalk cafes and restaurants as well, so it won’t be an issue to find a place to have a delicious Tuscan lunch.

You can, in fact, also stroll around on top of the walls. The ramparts are so wide that even cars can drive there, although those are thankfully prohibited.

Go for a long walk, or rent a bike, and take in the panoramic views at a leisurely pace instead.

Lucca can be visited on a day trip from Florence, which is only about an hour away. It’s also located very close to the famous town of Pisa (30 minutes), so if you are in a hurry, the two could be combined.

However, it would be a shame not to spend a bit more time in Lucca, because it truly is the kind of unique bucket list destination that you just 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 one of the most charming towns in Tuscany!

Siena

Written by me, Michelle from That Texas Couple

Siena is one of the quintessential medieval towns in Tuscany.  Famous for its rust-colored medieval brick buildings and the fan-shaped town square, Il Campo, which hosts the twice-annual world-famous horse races, Siena is a must-see while visiting the Tuscan region.

Originally dating back to the Middle Ages, Siena has a long history associated with it.  Of course, you should spend some time exploring the famous Siena square.

Grab a meal or a coffee in this area and enjoy the life that surrounds you in Siena.

You will notice the tall, towering structure on the square, the Torre del Mangia.  This tower is one of Siena’s most recognizable landmarks and well worth a climb up the 400 steps to get a great view of the city.

Siena is also home to a gorgeous cathedral, Duomo di Siena.  This church is so unique.

Donned with black and white striped marble, both inside and out, the Duomo di Siena is mesmerizing.  Like most grand churches in Europe, the cathedral took several years to complete.

Work began in 1196 and the church was continually worked on until the Black Death overtook much of the country in 1348.  The work on the ornate facade is breathtaking!

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 surface of the city, you may want to plan more time in this great town to explore a little slower!

Elba Island

Submitted by Amandine from Les Berlinettes

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

Do you know that Tuscany has its own island called Elba? It is reachable with a one-hour ferry ride from the mainland.

Elba is famous for its history, as it was Napoleon’s exile island but also for its beautiful villages, dream beaches, and wine.

While Chianti is made in Tuscany, Elba has it’s own wine as well called Elba Aleatico wine. In terms of activities, there are plenty of things to do in Elba, from kayaking, wine tasting, snorkeling (indeed Elba has some amazing clear water), diving, and of course, just enjoying the island.

I recommend to rent 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 a lot of things.

For accommodation, we stayed in a chic camping area, but there are plenty of small hotels and bed and breakfast to choose from. No big hotel chains on this island, 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, but the architecture and layout we see today were designed by Pope Pius II (who was born Aeneas Silvius Piccolomini in Corsignano) in the  1400s.

The Pope wanted to rebuild Corsignano as an ‘ideal Renaissance town’ and 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 was 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, which was 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. This church was the place where Pope Pius II (and later his nephew who became Pope Pius III) was baptized.

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 situated 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 of amazing cities you would charm after setting your foot in.

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

For over a pretty long decade, Pontedera has been a commercial center, manufacturing artisanal towns and moving 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 completely occupied with public art projects, providing the town a unique charm to exhibit.

La Via Della Seta is the most famous attraction in Pontedera. It is a contemporary colorful installation with nine architectural works sculpted over it.

The city is also the landmark of the oldest church building in town, which is the Church of the Santissimo Crocifisso, built-in 1272. The city offers a great tour of the archeological history and magnificent heritage and culture, that motivates the upcoming generation.

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 the Arno’s natural beauty, provided with a riverboat tour that almost en route 6-kilometer pathway to witness the beautiful scenario of the lush green vegetation and the extraordinary wildlife with unique species.

Pontedera believes in the interest of flora and fauna and tries level best to secure them. Therefore, I recommend bringing your vegan hiking boots while traveling since they are vegan friendly and are produced without any animal ingredients or byproducts.

Overall, Pontedera serves you with its ethnicity and unique culture, making Pontedera one of the beautiful towns in Tuscany.

Pisa

Submitted by Lyndsay from The Purposely Lost

The beautiful city of Pisa is one of my favorite towns in Tuscany. Although most people only go to Pisa for one day, there are more than enough activities all around to fill your time for several days.

The most famous landmark in the city is the Torre di Pisa, also known as the Leaning Tower of Pisa.

The stunning structure was built beginning 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 Tower actually served as the nearby Cattedrale di Pisa’s bell tower. In addition to the Tower and the Cathedral, you can also visit the baptistry and a cemetery, all on the same grounds.

Since most tourists only visit Pisa for the Tower, the rest of the city fairly quiet. You’ll get a great feel for the local culture by walking along the Arno River, which cuts straight through the town, and along its side streets.

You’ll also find coffee shops and local stores surrounding the many different 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 to visit when you’re in Tuscany.

Cortona

Submitted by Ivan from Mind the Travel

Situated not far from the border with Umbria, a traditional walled Etruscan town of Cortona is the embodiment of quintessential Tuscany.

Sitting at about 600 meters above sea level, the town offers mind-boggling views extend over the green plains and hills of both provinces.

Although Cortona is small, it is packed with interesting sites to visit. Make your way to the Diocesan Museum that 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 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 the town and well worth a visit.

At a few kilometers’ distances, the 13th-century Franciscan Convent located in Le Celle is an amazing place of silence and mysticism where you can appreciate the devout and meditation of Saint Francis.

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 to Camucia-Cortona train station, the closest station to Cortona (3 km.)

The train takes about 2 hours and 25 minutes. There are also fast trains that 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 of the towns within the province of Arezzo.

Final Thoughts on Must-See Towns in Tuscany

As you can see, Tuscany is full of incredible towns just waiting to be explored.

Of course, we have only scratched the surface of the amazing towns in Tuscany. This area is rich in history and culture, making it an outstanding place to spend some of your time while in Italy.

Take your time while exploring Tuscany and immerse yourself in all of the grandeur that this region has to offer.

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