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 you will consistently find Tuscan towns 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 exactly which Tuscany towns fit your travel style.
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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 very 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 sites. You will find masterpieces from Italy’s greatest artists, like Leonardo and Michelangelo, here.
After viewing some of the masterful works of Florence, make your way to the Ponte Vecchio bridge. This bridge, which dates back to 1345, still has shops, 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 Signoria while avoiding the townspeople.
You can just 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 definitely 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 really get your attention here. In addition to the towers, San Gimignano also boasts a well-preserved medieval wall!
A UNESCO World Heritage site, San Gimignano has been attracting tourists for centuries as 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 help you to feel like you have been transported back in time immediately.
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.
Speaking of wine, 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 are found 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 just 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 of people visit Tuscany every year 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 lies at the gateway to the Chianti wine region.
This small market town has no notable sights, but the Piazza Matteotti is at its heart.
Its triangular-shaped piazza and main square feature a small church and a portico. You will also find houses, boutique shops, artisan workshops, and restaurants here.
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 any restaurants in the main 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, which offers many Tuscan wines to 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. Noted worldwide for its beautiful rolling hills dotted 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 make the most of 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 brings you into the town’s main street and the Piazza Grande.
Piazza Grande is the official main square with quaint cobbled streets with 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.
Without question, one of the very 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 of Italy, 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 from the distance, between rolling hills dotted by cypress trees and full of vines. Just look for a gorgeous medieval top-of-the-hill town.
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 right 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.
You’ll find plenty of bars and restaurants offering a pairing of wine and food when you need a break!
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.
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, 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.
Submitted by Nick from The Danish Nomads
Lucca is a beautiful old town in the northern part of Tuscany that you want to visit. It has that distinct medieval look and feels, 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 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, 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 won’t be an issue.
It would be a shame not to spend more time in Lucca because it truly is a unique bucket list destination 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 small towns in Tuscany there is!
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.
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, Siena is a must while visiting the Tuscan region.
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: Duomo. Siena is also home to a gorgeous cathedral, Duomo di Siena. This church is so unique.
The Duomo di Siena is mesmerizing and donned with black and white striped marble, both inside and out. 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!
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?
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, 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 to do in Elba, from kayaking, wine tasting, snorkeling (indeed, Elba has some 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 there are plenty of small hotels and bed and breakfasts. There are no big hotel chains on this island, as it is still a secret gem!
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 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,’ 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.
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 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 occupied with public art projects, providing a unique charm to exhibit.
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.
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 go to Pisa for one day, there are more than enough activities around Pisa and the old town area 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, 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 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 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 really worth a visit.
You’ll get a great feel for the local culture by walking along the Arno River, which cuts straight 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 to visit when you’re 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 the embodiment of 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 of the towns within the province of Arezzo.
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Book Your Trip: Logistical Tips and Tricks
Book Your Flight:
We love using CheapOAir, Kayak, and Kiwi to search for the best flight prices. We love using these search engines because they search the web for airlines worldwide to ensure you get the best deal! In addition to flights, you can also find great hotel prices on Kayak and Kiwi.
Book Your Vacation Package:
If you want to book an entire vacation package, we suggest using Expedia. We love how easy Expedia is to use, and we always find good deals on entire vacation packages on their site.
Another great site for vacation packages is BookVIP. BookVIP offers super cheap vacation packages to incredible destinations. You are sure to save money using their site!
For full guided vacations, including hotels, some meals, transportation, and guides, then we book with Trafalgar. Trafalgar is a trusted tour company that will meet all your needs while ensuring a great experience.
Trip.com allows you to book flights, hotels, train tickets, rental cars, airport transfers, tours, and more all on one site. Owned by the parent company that also owns Skyscanner, this is a trusted resource for travel booking and a great “one-stop shop.”
Book Your Accommodations:
We always begin our search by checking out honest reviews on TripAdvisor hotels. This allows us to narrow our search for specific properties once we are ready to book. Of course, you can also book directly on the TripAdvisor site!
There are several accommodation sites that we like to use. One of our favorites is Booking.com because it offers a wide variety of hotels and guesthouses at a good price.
Another “go-to” hotel booking site for us is Hotels.com. We love their loyalty program that allows you to earn free nights, and their “secret prices” for members are fabulous deals!
If you want a luxurious all-inclusive vacation, consider checking out the Sandals/Beaches properties. Sandals properties are for couples only and Beaches are for families. We have visited Sandals in the past and absolutely love the attention to detail and the service they provide.
Tour Companies We Trust:
We love taking guided tours when visiting new places. Our go-to tour companies are Viator.com and Get Your Guide. Both of these companies have been in business for years and provide excellent customer service. You can trust booking tours from their sites for sure!
CityPass is a great way to save money when visiting large cities. CityPass allows you to get free admission to major attractions once you buy their pass. The savings add up quickly with this pass, often saving 50% with combined admissions.
Another great pass to save money in larger cities is the Sightseeing Pass. This pass allows you to save valuable time and money by combining admissions to major attractions. They also have a handy app that keeps everything you need at your fingertips.
Looking to Save Time and Money?
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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.