Best Tuscany Cities And Towns – Where To Day Trip From Florence

Every year, tourists flock to Tuscany, Italy, in droves, drawn by its stunning landscapes, quaint villages, and world-renowned wine and cuisine. While the region as a whole is undoubtedly beautiful, there are a few Tuscan cities and towns that stand out above the rest.

In this blog post, we’ll explore what the best cities and towns in Tuscany have to offer. We will also share a brief history of these towns and their locations. 

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Where Is Tuscany Italy

Tuscany is a region in west-central Italy, and its regional capital is the City of Florence. It covers an area of about 8,900 square miles with a population of 3.8 million. Tuscany is a traditional region that occupies much of the former grand duchy near the Italian peninsula’s base. 

Geographyically, Tuscany is located along the Ligurian and Tyrrhenian seas and consists of the provinces of Lucca, Massa-Carrara, Pistoia, Florence, Pisa, Livorno, Siena, Grosseto, Arezzo, and Prato.  

Tuscany is not far from Bologna. It is approximately a 65-mile driving distance that will take about an hour. Alternatively, you can fly from Bologna to Tuscany in just 35 minutes. You can also take a trip from Rome to Tuscany and enjoy the beautiful and scenic rolling hills.

The easiest way to explore Tuscany is to hop a half-hour train from Bologna for a day trip. We love Bologna food so much, we recommend staying in Bologna and day-tripping to Florence than the other way around.

Best Tuscany Cities And Towns - Where To Day Trip From Florence
Best Tuscany Cities And Towns – Where To Day Trip From Florence

Is It Worth Visiting Tuscany Italy?

Tuscany is well-known for its history, artistic legacy, landscapes, and influence on culture. It is considered the origin of the Italian Renaissance and the foundation of the Italian language.    

The towns and cities of Tuscany are home to numerous figures influential in Italy’s art, science, and history. The region contains famous museums, architectural, and historical sites. It is also renowned for its wine, including Chianti Classico, Vino Nobile di Montepulciano, and Brunello di Montalcino.

Tuscany is the second most famous Italian region for visitors after Veneto, home to Venice. Visiting Tuscany allows you to avoid the tourist crowds of Rome, Milan, Venice, Florence, and other major cities. In addition, the region has over 120 protected nature reserves, and eight places in Tuscany are UNESCO World Heritage Sites worth visiting. 

The Italian food in the region is also some of the tastiest, with rustic dishes like pasta with wild boar ragu. One of our best tips for Italy is to visit the small towns, like those outside of Florence, to eat some of the best, regional dishes.

Traveling to Tuscany? See our tips for what to pack for Italy.

How To Book Hotels In Italy

In the 20+ years of traveling to Italy, we’ve learned a thing or two about booking a hotel in Italy. We’ve stayed at some stunning hotels like the Westin Excelsior Rome and St. Regis in Florence. And we’ve stayed at some not-so-great hotels mainly around train stations in Italy. Do yourself a favor and avoid hotels near train stations at all costs.

When planning a trip to Italy, we use for our accommodations. In addition to booking hotels, we’ve used them for booking apartments for longer stays or booking villas in Italy when we want something special. We’ve even found some charming and less expensive guest houses in Italy on

Our Favorite Cities In Tuscany To Visit

Tuscan cities and towns are laden with rustic villages, enthralling mazes of marble and stone, and ancient Etruscan settlements, which make the region one of the most beautiful in Italy. 

Here is our list of the best towns in Tuscany.


Best Tuscany Cities And Towns

Lucca is one of the best cities in Tuscany, located in the Province of Lucca on the Serchio river in Central Italy. It is sandwiched between the marble frontispieces of Pisa and the Tyrrhenian Sea. Lucca is close to Florence, which is only 39 miles away.   

This Italian city in Tuscany has a lot to offer. The city walls of Lucca let you enjoy panoramic views of the city. The 16th-century walls surround the old town of Lucca. You can also visit the Piazza dell’Anfiteatro, an oval amphitheater square constructed around the elliptical structure. It is lively with restaurants, shops, events, and concerts.

Lucca is sometimes referred to as the city of 100 churches. Though it is challenging to visit them all, don’t miss the San Michele in Foro, the Basilica of San Frediano, and the cathedral, II Duomo. 

We visited Lucca the first time during a winter trip to stay with local friends. We ate giant steaks in the countryside and dined in small osterias outside of the city. What I loved the most, though, was wandering along the old city walls. It’s a magical Italian town.


Best Tuscany Cities And Towns

Siena is a Tuscan city and the capital of Siena province. The major Italian cities near Siena include Florence, 32 miles away, and Bologna, 81 miles away.  

Siena, the second Tuscan city, is more intimate and smaller than Florence. It is historically linked to banking and commercial activities after being a significant banking center during the 13th and 14th centuries. This city is home to the world’s oldest bank, The Monte dei Paschi bank, founded in 1472.

This Italian city in Tuscan is renowned for its art museums, medieval cityscape, cuisine, and the Palio, a horse-racing event held biannually in Piazza del Campo.  Fans of the movie Twighlight might recognize the horse-racing event and Italian village from one of the films.


Best Tuscany Cities And Towns

Volterra is one of the Tuscan towns in the province of Pisa, Tuscany region, Italy. It is one of the towns in Tuscany whose nearest city is Frolence, which is 33 miles away.  

This walled mountaintop town dates before the eighth century BC and features substantial structures from the Medieval, Roman, and Etruscan periods. Volterra was a Bronze Age settlement and an important Etruscan center of the Proto-Villanova culture. It was one of the twelve Etruscan League cities.

Today, Volterra is one of Tuscany’s best places for Etruscan and medieval art. It also hosts the remains of the Etruscan walls that were enlarged in the third and fourth centuries BC, circular tombs from the sixth BC, and two Etruscan-Roman getaways.    


Best Tuscany Cities And Towns
World famous leaning tower of Pisa, Italy

Pisa is an Italian city in Tuscany and the Province of Pisa’s capital. It is located in central Italy, straddling River Arno just before it drains into the Ligurian Sea. Pisa is 43.5 miles from the capital of the Tuscany region, the city of Florence.

The most original hypothesis of the origin of the name Pisa is from the Etruscan word, which means mouth, because the city sits at the mouth of River Arno. Archaeological excavations between the 1980s and 1990s discovered a fifth-century BC tomb with the remains of an Etruscan prince, further proving the city’s Etruscan origin     

Although this Tuscan city is famous worldwide for the leaning Tower of Pisa, it contains several medieval palaces, over 20 historical churches, and several bridges across the River Arno. Most of Pisa’s architecture was funded by its history as an Italian maritime republic.     


Best Tuscany Cities And Towns

Cortona is one of the towns of Tuscany, Italy, in the province of Arezzo. It is the main artistic and cultural center of the Val di Chiana, after Arezzo. Its closest cities are Perugia in Umbria and Arezzo in Tuscany.

This town in Tuscany was originally an Umbrian city before the Etruscans conquered and enlarged it. They called it Curtun, which joined the Etruscan League in the seventh century BC. It eventually became a Roman colony known as Corito.

In the 13th century, Cortona became a Ghibellinian city-state with its own currency. After the Italian Wars of Independence, it became part of Italy. 

Cortona is one of the best places in Tuscany for anyone seeking to experience delicious cuisine, stunning country views, and a quintessential Italian historical town. It was also the setting for the film Under The Tuscan Sun.

Greve In Chianti

Greve is a town in the Florence, Tuscany region of the Metropolitan City of Florence. It is only 19 miles south of Florence and 26 miles north of Siena. This small Italian town is the Chianti wine district’s principal town and is located in Val di Greve.

Greve’s location and neighboring territory were probably occupied before the Romans, and the Etruscans dominated the region. Historical documents from the 11th century allude to an ancient monastic settlement located on a nearby hill, now referred to as the Hill of San Francesco.   

The town of Greve has numerous small and delightful villages worth visiting. It is also worth visiting the picturesque castle of Montefioralle. The castle is a medieval military center that retains its historical traces. 

We spent a wonderful weekend at a villa in Greve in Chianti during one of our anniversary trips to Italy. We sipped local super Tuscans poolside and dined outdoors overlooking the vineyards. It was a romantic trip to Tuscany for sure.

San Gimignano

Best Tuscany Cities And Towns

San Gimignano is one of the walled medieval hilltop towns in the province of Siena, north-central Italy. This town is approximately 24 miles from Florence.

A small Etruscan village sat on the current site of the San Gimignano in the third century. The town was significantly developed during the first three centuries. 

Also called the Town of Fine Towers, this Tuscan town is famous for its medieval architecture. Architecture plays a critical role in preserving numerous tower houses in the town. 

The hilltop setting, encircling walls, and tower houses form a breathtaking skyline. Enclosed by the walls are well-preserved buildings such as notable examples of Gothic architecture and Romanesque.  

San Gimignano is one of the more popular Tuscan towns to visit, particularly on day trips from Florence or via tour buses that pop into various Tuscan villages in one day. To really experience the magic of the town, stay overnight and wander around counting all of the towers the village is known for.


Best Tuscany Cities And Towns

Montepulciano is one of the Renaissance and medieval hilltop towns in Tuscany. It is in the province of Siena and sits high on a 1,985 feet limestone ridge. This Tuscan town is eight miles east of Pienza, 43 miles southeast of Siena, and 116 miles east of Rome.

Lars Porsena, an Etruscan king, is believed to have founded the town. Recent findings also allude to a settlement during the third and fourth centuries. 

Montepulciano is a famous wine-producing region and the source of well-known Italian wines such as Vino Nobile di Montepulciano and Chianti Classico. The town is also a great tourist destination thanks to its rolling landscapes, medieval architecture, world-class wine bars, and sumptuous dishes.  

Depending on how you are traveling to Montepulciano, especially with a car, it’s very important to follow the driving rules in Italy. Illegal parking or restricted driving zone can result in fines as well as your rental car being towed. Make sure to follow all the signs in the town. You’ve been warned.

Looking to explore the coast of Italy? Check out our recommendations for the best Italian Riveria towns to visit.


Montalcino is yet another hilltop town in the province of Siena, central Italy. It is located west of Pienza, near Crete Senesi in Val d’Orcia. Furthermore, the town is 26 miles from Siena, 68 miles from Florence, and 93 miles from Pisa.

The history of Montalcino suggests that the town has probably been occupied since the Etruscan times. Historical documents first mention it in 814 AD and suggest there was a church in the ninth century. The church was most likely constructed by the monks allied with the neighboring Abbey of Sant’Antimo.

 Montalcino is a lovely tourist destination famous for producing delicious Italian wines such as Brunello di Montalcino and Rosso. The best time to visit Italy for wine is during the fall harvest!


pecorino cheese in Pienza Italy

Pienza is one of the towns in Tuscany, the province of Siena, Italy. It is in the historical region of Val d’Orcia, between the towns of Montalcino and Montepulciano. Pienza is only a 20-minute drive from Montepulciano and a 60-minute drive from Siena. 

This town was established during the medieval ages as Corsignano. Pope Pius II redesigned and renamed the town in the late 15th Century.

Pienza is the city of cacio, the Italian cheese. The town is famous for pecorino cheese. But there are other sites in the town worth visiting, like the Palazzo Piccolomini and Palazzo Vescovile.  

Tuscany, Italy, is a great tourist destination because it has some of Europe’s most beautiful villages and small towns. You can visit hilltop towns, medieval towns, and the best wineries. Our guide on the best Tuscan cities and towns gives you a sneak peek of what to expect. 

Culinary Travel To Italy

Food Traveler's Guide To Emilia Romagna

Our Italy Travel Experience

Check out Food & Drink Destinations original founder Amber Hoffman’s book, the Food Traveler’s Guide To Emilia Romagna, which is available on Amazon. In addition to being a culinary travel guide to the region, it walks through how many of the typical Italian food products are made, like mortadella, prosciutto, and Parmigiano Reggiano.

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