17 Prettiest Tuscany Villages & Hill Towns in Tuscany + Tips How to Visit in 2022

Tuscany is a truly Dream Destination, and it is not an easy task to choose the most beautiful Tuscany villages, because there are all amazing. So, if your are looking for the best towns in Tuscany to visit during your next trip, you have come to the right place!

After visiting Tuscany a couple of times, I have a piece of advice for you: Whatever you choose to visit Tuscany, you cannot go wrong! Every hilltop town or village in Tuscany is so unique, and you find something magical in each one of them.

In this article, you will not only learn the most incredible Tuscany villages to visit, but also, you will find very helpful tips.

Here you will find an overview of the main hill towns in Tuscany, the best places to stay and how to get to each town in Tuscany – This is your one stop guide for how to plan and visit the best towns in Tuscany!

So, without further ado, I really hope you enjoy this very unique guide.

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Best Small Towns in Tuscany

READ MORE: Best way to travel from Rome to Tuscany: Car, train, bus, or private tours

The Best Towns & Villages in Tuscany Overview

Before we jump into the most beautiful towns in Tuscany, let’s do an overview of the Tuscan Region. It has a triangular shape in the heart of Italy. Tuscany is one of the largest regions in Italy, with 67% of the territory being hills, 25% being mountains, and the remaining 8% being coastal plains.

Tuscany is made up of 10 provinces: Florence, Arezzo, Grosseto, Livorno, Lucca, Massa Carrara, Pisa, Pistoia, Prato and Siena – and these are the main cities in Tuscany.

  1. Florence
  2. Pisa
  3. Siena
  4. Lucca
  5. Pontedera
  6. Civita
  7. Castelnuovo de Gafagnana
  8. Monteriggioni
  9. Arezzo
  10. Cortona
  11. San Giminiano
  12. Pitigliano
  13. Pienza
  14. Manciano
  15. Montepulciano
  16. Montalcino
  17. Volterra
Where to stay in Tuscany Map

Plan your Trip to Tuscany Villages

Just because the Tuscan Region has so much to do and to see, I highly recommend coming to Tuscany with a well-defined priority of places you want to visit, in order to maximize your time. The good news is that if you are short on time, you can visit Tuscany on a day trip from Rome.

But of course, ideally, you will spend a few days the Tuscany. You will want more time to adventure in the medieval towns while experiencing the incredible local cuisine and exploring the Italy wine regions in the spectacular Tuscan countryside.

Also, make sure you choose accommodation in a good area, where you can walk to the main attractions. Making your reservations in advance is also part of a well-planned visit to Tuscany, and here you can find the best accommodations in Tuscany for every budget and also, best areas to stay in Florence.

Lastly, some popular towns in Tuscany are busy throughout the year, so I highly recommend booking a group tour in advance.

Read More: The most dreamy accommodations in Tuscany

Famous Towns in Tuscany

1. Florence

Amazing Small Towns in Tuscany
CONTRIBUTED BY: Cynthia & Alexander from Travel your Memorie
Florence Highlights
  • Here you will find the beautiful Duomo Santa Maria Del Fiore, a cathedral that astonishes you.
  • The famous Ponte Vecchio is the post-card of Florence.
  • The Uffizi Gallery with an incredible collection of ancient paintings and sculptures
  • the Galleria dell’Accademia, where you can admire the sculpture David by Michelangelo.

The incredible Florence should be the start point of any town in the Tuscany itinerary. Florence is the provincial capital of Tuscany and one of Italy’s most popular cities to visit Italy. This is because Florence has something to offer everyone.

Here, you can find many masterpieces from the Renaissance period. The architecture of the buildings will also amaze you. Especially when you stand in front of the entrance and look at the details, it’s really beautiful.

Florence is a romantic city where you can discover all the highlights on foot. The historic center is the most beautiful thing to see in Florence.

When you walk here it is like being in a large open-air museum. You need at least a 3-day itinerary in Florence to get to visit the main sites and explore the beauty of this city.

How to Get There

Depending on where you are, you can reach Florence by plane, car or public transport. For most travelers, it is recommended to book a plane ticket to Aeroporto Amerigo Vespucci. You can also check the train or bus options from Rome to Florence, which takes about 3 hours. Another option is to book a private driver from the international airport in Rome to Florence.

Where to Stay

Hotel Paris is located in the historic center so you can do everything on foot. The rooms are very nice and the price-quality ratio is very good. If you are looking for a 4-star hotel with the River Arno views, the Hotel Berchielli is a great option.You can also check here for the best areas to stay in Florence.

Read More: Best Areas do Stay in Tuscany + Hotel Guide

2. Pisa

Magic Small Towns in Tuscany
CONTRIBUTED BY:  Lyndsay from The Purposely Lost
Pisa Highlights
  • The post-card is the Leaning Tower of Pisa.
  • You will get a good sense of the local culture by walking along the Arno River and its side streets.
  • You can relax on the beach, and eat out at a restaurant by the water, by renting a car or go on a private tour from the city center.

Pisa is one of the most well-known towns in Tuscany. Most people come to visit the Leaning Tower of Pisa, which is arguably the city’s most recognizable Italian landmark. The good news is that you can add a day tour from Florence to Pisa very easily.

Building on the tower began in the 12th century, but it was already leaning by the time the second story was started. The Tower was used as a bell tower for the Cattedrale di Pisa, and the cemetery and a baptistry are also nearby.

The rest of the city is a bit quieter because most tourists only come to see the Tower. Stop for coffee, take a peek into different shops, and enjoy street art from world-renowned artist Keith Haring. Even though the major city center is inland from the coast, Pisa still has a lovely shoreline.

How to Get There

The easiest way to reach Pisa is by the Italian train system or by driving – If you are traveling from Rome to Pisa check here for all options. Several tours can also bring you to Pisa for a day trip from Florence.

Where to Stay

Just a 10-minute walk from the Leaning Tower of Pisa, Rinascimento Bed & Breakfast is a beautiful hotel in the city that offers free breakfast and beautiful rooms.

3. Sienna

an incredible Towns in Tuscany
CONTRIBUTED BY: Caroline from Veggie Wayfarer
Siena Highlights
  • The Piazza is lined with the Torre del Mangia, the Palazzo Pubblico, and the Fountain of Gaia.
  • The heroic travelers can climb up the Torre del Mangia to see the best views over the town.
  • After marveling at the Piazza, walk through the narrow little streets and make your way to the Cathedral of Santa Maria Assunta, the gothic masterpiece was built in the 13th century with austere pink, white and black marble on the outside and lavish gold adornments on the inside.
  • Be sure to visit the Piccolomini library hidden inside, the small library has the most intricate frescoes painted from floor to ceiling.

Set amidst the famous rolling hills and one of the most beautiful towns in Tuscany. Siena is one of those beautiful gems that made exploring Umbria and Tuscany an absolute must for many visitors. The historical old town has been on the UNESCO list for well over 30 years as an important cultural heritage, and it is not hard to see why.

The old town was built between the 12th and the 15th century and has been maintained beautifully with at its center the breathtaking Piazza del Campo. Keep enough time to try some of the local delicacies: Capocollo and finocchiona, panforte senese and pecorino of Pienza, and one of the many, many local restaurants.

How to Get There

Siena is an easy 1h15 min drive from Florence, or alternatively, you can hop on a direct train from Florence to Siena which takes between 1h30 door to door – Or take a group tour from Florence. Or you can visit Siena on a trip from Rome and the easiest option is by bus – check here for all the details.

Where to Stay

If you are looking to spend the night, try and find accommodation in the quaint old town at one of the many family-run B&Bs dotted around. The B&B il Barbero is rated as Exceptional, with an incredible location and great breakfast.

4. Lucca

One of the most amazing Towns in Tuscany
CONTRIBUTED BY: Jes from Tourists to Travellers
Lucca Highlights
  • Walk on the charming Roman Amphitheater, which was originally built in the second century,
  • Visit the massive Guinigi tower with holm oaks growing on its top,
  • Admire the scenic Baroque garden at the Palazzo Pfanner-Controni
  • the medieval engineering marvel across the Sergio river; the dramatic Ponte Della Maddalena.

Tuscany is famous for its fine art, beautiful countryside, rolling hills, and of course its vineyards. A trip to visit the towns in Tuscany would be incomplete without a visit to this quiet quintessential town of Lucca, with cobblestone streets leading to historical buildings that transport you into the olden era.

Lucca oozes history and it has preserved its heritage. Tall buildings stand where once the city’s amphitheater stood and this town in Tuscany consists of many towers that offer gorgeous views of the countryside.

Torre Guinigi and Torre Delle Ore are amongst the most iconic towers. Unlike the more crowded towns like Florence, Lucca is pedestrian-friendly, and you can explore the town of Lucca on foot without worry. History buffs can soak in the beautiful architecture of the marble churches and cathedrals.  The elaborate façade and design of the church leave one in awe.

How to Get There

If you are visiting Lucca from Florence, it is only 1:15 hour driving. Another option is to visit Lucca on a day tour from Florence with a private tour. You also have an option to travel from Florence to Luca by taking a train from Firenze Santa Maria Novella station to Lucca. If you are visiting Lucca from Rome you can take a direct train.

Where to Stay

While there are great accommodation options in Lucca, if you are on a budget then B&B Anfiteatro is a great option, very well located, overlooking the Roman amphitheater

Unique Small Tuscany Villages

5. Pontedera

Tuscany Villages
CONTRIBUTED BY: Paulina from Paulina on the Road
Pontedera Highlights
  • The main sights to visit in Pontedera include the first Vespa prototype,
  • Piaggio Museum
  • Rocca di Vico Pisano
  • Veranos Bar

Pontedera is one of the most beautiful Tuscany villages, situated between Pisa and Florence. It is near the highway but around a quiet location, near the sights of northern Tuscany. It is also just ten minutes from the Mediterranean beaches. Travelers can find nearby shopping markets and shop some popular sustainable shoe brands and more local goods, such as mesmerizing bars, remarkable museums, and more.

Pontedera is a hidden gem in Tuscany that doesn’t get as much appreciation as other places like Florence, Siena, Pisa, and San Gimignano. However, the ones who have visited love it, especially because of the famous wine, fun scooter rides, and delicious chocolates. Moreover, a few kilometers away from this town, there is a small village named Montecastello, situated between the hills. People also appreciate Pontedera due to Villa Torrigiani Malaspina and the Church of Santa Lucia virgin and martyr situated in this charming village.

How to Get There

There are several ways to get to Pontedera, including trains and cars. You can reach there by renting a car or hopping on your own car via the Florence-Pisa-Livorno route. You can also reach there via train as the railway station connects to the main parts of the city.

Where to Stay

The best-rated places to stay in Pontedera are the Le Sodole Country Resort with an amazing vineyard landscape around.

6. Civita Di Bagnoregio

Civita Highlights
  • Piazza San Donato or Piazza del Duomo is located in the center of the village
  • Nearby the Chiesa San Donato (8th century – the only church in town, built upon a pagan temple) there is a Romanesque bell tower or campanile (8th century)
  • The church of San Donato was the cathedral of Bagnoregio until
  • Near the church, there is a wine cellar and an olive press that dates back to Etruscan times.

Even if Civita di Bagnoregio is NOT really in Tuscany, it is actually located in Lazio Region, it made it to this list because it is located between Rome and Tuscany, and it makes an easy stop to visit this fascinating medieval village, not only because of its history but also, its unique location.

While driving on the road you can see signposts pointing the way to “Civita, The Town That is Dying“. This village in Tuscany sits on top of a canyon, a pinnacle ruled by wind and erosion. You get to Civita by a narrow pedestrian bridge, with spectacular views, connected to the town of Bagnoregio (where you park your car). The original bridge that connected the two villages eroded away over the centuries and was bombed out during WWII.

In order to preserve the remnants of this town, and to avoid over-tourism in 2013, it became the first Italian town to charge visitors an entry fee. On weekends and holidays, the fee is about $6. On weekdays, it’s $3.50.

How to Get There

The best way to get to Civita is by car. Civita is located about 2:00 hr driving from Rome via highway A1. A good option is also to go on a day tour from Rome. Another option is by train – you can get to reach Bagnoregio are Viterbo and Orvieto.

Where to Stay

Right in the heart of Civita you can stay at the iRoom Civita, which is a wonderful place, with great restaurants & bars within meters of the apartment, or the La Grotta Su Civita where the rooms were converted from a cave and with fabulous views overlooking Civita di Bagnoregio

7. Castelnuovo Di Garfagnana

one of the most magical Towns in Tuscany
CONTRIBUTED BY: Terri at FemaleSoloTrek.com
Castelnuovo Highlights
  • The Cathedral of Saints Peter and Paul was constructed in the Renaissance (16th century). Visitors will enjoy the Baroque interior as well as the Madonna with Saints painting by Domenico Ghirlandaio.
  • The Rocca Ariotesca (Ariosto’s fortress), the symbol of Castelnuovo di Garfagnana,
  • Mont’Alfonso Fortress, built in the late 1500s, represents the House of Este’s last throw of the dice.
  • For the more athletic, a hike or job in the Parco dell’Orecchiella, featuring a nature park and botanical garden.

Castelnuovo di Garfagnana is one of the historic Tuscany villages, perched in the province of Lucca, Italy. This “new fortified settlement” town is nestled in the shadows of the Italian Apennine Mountains and the Apuan Alps.

Located in northern Tuscany, the town’s history dates back to the 8th century. Castelnuovo di Garfagnana offers a glance back at Italy’s medieval days. Rocco Ariostesca (Ariosto’s Castle) was built in the 12th century. Named after an Italian poet, the castle has been converted to an archaeological museum. It has frequently been the site of Italian battles when Italian states waged war. Napolean Bonaparte’s army invaded the town and held it in the siege.  

How to Get There

Castelnuovo di Garfagnana is a great day trip from Lucca by train, it takes less than 1-hour over a distance of around 20 miles (32 km). You can check the train times here.

Where to Stay

Agriturismo Braccitcorti offers a stay in a traditional Italian farmhouse in Northern Italy. It features homecooked meals, fresh produce, and wines grown on its own turf. There are other local Agriturismos, B&Bs, and farmhouses nearby to stay, such as the amazing Villa Belvedere with breathtaking views.

8. Monteriggioni

A fascinating Small Towns in Tuscany
CONTRIBUTED BY: Haley of Gathering Waves
Monteriggioni Highlights
  • Piazza Roma is located in the heart of the old town, gathering great restaurants and cafes
  • Church Santa Maria Assunta, with its façade still in the original state
  • Medieval Museum “Monteriggioni in Arms” at the entrance showcases different medieval warfare strategies that were implemented in the actual town of Monteriggioni!  

Monteriggioni is one of the most charming medieval Tuscany villages, located just outside of Siena. The town was built in 1214 by the Sienese people during their war against Florence. The town is strategically built atop a hill and was used as the first line of defense in the war.

Walking through this medieval town, or even standing on its walls, one can really get a feel for the conflict that occurred so many years ago. Monteriggioni has truly had a medieval feel. The majority of the walls built around the town still stand, and in certain sections, you can even walk along the top of the walls! Because of Monteriggioni’s strategic defensive position, there is a very picturesque view of the Tuscan countryside one can only see standing along the walls.

How to Get There

Monteriggioni is easily accessed on a day trip from Siena. There are busses that run from Siena to Monteriggioni all day, and it is also a quick 25-minute drive by rental car from Siena.

Where to Stay

Hotel Monteriggioni is the only accommodation option located inside the actual fortress, making it a very cool option for a truly immersive historical experience. Also, the Borgo dé Brandi with its breathtaking castle views and the picturesque landscape is highly recommended.

The Best Tuscan Hill Towns

9. Arezzo

one of the best Small Towns in Tuscany
CONTRIBUTED BY: Martina & Jurgen from PlacesofJuma
Arezzo Highlights
  • Beautiful and absolutely worth a visit is definitely the historic old town, as the center is full of interesting places to visit.
  • Piazza Grande, a breathtakingly beautiful main square and a really unique popular photo motif, sloping downwards at an angle, creating an almost surreal backdrop.
  • Also worth seeing are the numerous interesting museums and beautiful churches, where art treasures and masterpieces by famous artists such as Piero Della Francesca or Giorgio Vasari can be admired.

A visit to Arezzo in Italy is one of the best highlights of any visit the fascinating Tuscan hill towns. This town is a real hidden pearl and should not be missed on any round trip!

The city of Arezzo is world-famous for ceramic and metal processing. Crafts and jewelry have always been produced here, which has brought over the years wealth to the city. Hard to believe, but ten tons of gold are processed here every month. A stroll through this Tuscan hill town takes you to the countless shops, selling the finest jewelry and beautiful ceramics, such as the world-famous Aretin vases.

How to Get There

Arezzo is located only 1 hour’s drive south-east of Florence and is therefore easy and quick to reach by car, but also by public bus. Guided tours are also available if you prefer to travel in groups. 

Where to Stay

If you want to stay in the fascinating Tuscan hill town of Arezzo, you will find a fantastic offer of amazing accommodation. Really lovely is the BioBenessere, a very nice, clean, and lovingly furnished B&B in Arezzo.  Another great option is the iConic Resort & Grand Spa, very peaceful, very modern, and functional but surrounded by nature.

10. Cortona

Tuscany Villages and Small Towns in Tuscany
CONTRIBUTED BY: Renee of Dream Plan Experience

Cortona Highlights
  • Diocesan Museum where you can admire a beautiful panel painting of the Annunciation by Beato Angelico
  • Santa Margherita Sanctuary, patron of the city
  • Great red wines are made in the area (we are just a few kilometers from Montepulciano and Montalcino) and all of the wine bars offer a wide selection
  • Franciscan hermitage Le Celle, the first monastery built by Saint Francis of Assisi in 1211

The beautiful Tuscan hill town of Cortona was put on the map with the release of Under the Tuscan Sun, first the book by Francis Mayes, and then the movie, and it should be one of the must-visit Tuscany Villages in your itinerary.

There is so much to see and do in Cortona, and one of the best things to do is to get lost in Cortona’s endless narrow alleyways, or vicoli as Italians call them and take in those epic Tuscan countryside views. The heart of this charming town is the main square, Piazza Della Repubblica. It features many historical buildings from the 13th century.

A well-preserved town hall, clock tower, and former palace are just some of the significant landmarks you will find. The lively piazza is where you will find the locals constantly coming and going, catching up with one another, and stopping in on their favorite shops and cafés. Try and visit on Saturday – market day – and watch the town really come alive. 

How to Get There

The Tuscan hill town of Cortona sits in the eastern part of Tuscany about 1-hour drive from Florence. The best way to see Cortona is by renting a car, so you can also visit many villages in Tuscany along the way. You can also take a tour from Rome and add Arezzo to your visit.

Where to Stay

The best place to stay in the Monastero San Silvestro dating back to the 14th century this place has breathtaking views. and with authentic rooms, you feel you are living in a castle.

11. San Giminiano

one of the most amazing Tuscany Villages
CONTRIBUTED BY: Dan Bagby from HoneymoonAlways.com
San Gimignano Highlights
  • In town, visit Collegiata, the Romanesque cathedral with frescoes
  • Hike the 218 steps of the Palazzo Comunale, the tallest medieval tower in San Gimignano.
  • Wine Tour in San Gimignanogoing
  • Horseback riding through the Tuscan landscape.

San Gimignano is of the must-visit Tuscany Villages and a great destination for a Tuscan honeymoon. The medieval village is a UNESCO World Heritage site built on a hilltop, providing amazing viewpoints of the rolling Tuscan hills. It feels as if you have stepped back in time as you wander the walled town and see the towers built to show the wealth of prominent families in the past.

For food, there are so many good restaurants in this charming town where you can enjoy authentic Tuscan food it’s hard to recommend a specific one. The area is also ideal for wine lovers, with its vineyards producing more than 16 million bottles of wine every year.

How to Get There

You can reach San Gimignano on a day tour from Florence or Siena. I recommend renting a car to stay at least for one night when it is quieter after the day trip tourists leave.

Where to Stay

A great option is to stay outside the old town at one of the farmhouses at the Hotel Sovestro where you can enjoy the countryside and take a horseback ride through the vineyards and olives trees.

12. Pitigliano

one of the most amazing Tuscany Villages
CONTRIBUTED BY: Or from My Path in the World 
Pitigliano Highlights
  • Visit the Fontana delle Sette Cannelle,
  • Explore the Museum of Palazzo Orsini
  • Try some local Bianco di Pitigliano wine in the town’s restaurants and bars.
  • Located at a scenic position perched on a cliff is simply iconic, you can admire one of the most beautiful Tuscany Villages views

A perfect addition to an Italian road trip through Tuscany, the hill town of Pitigliano is an enchanting place that will make you feel like you’ve stepped back in time, making it one of the most fascinating villages in Tuscany.

From Etruscan remains at Museo Archeologico Alberto Manzi to medieval landmarks like the Acquedotto Mediceo to the only synagogue in the entire province of Grosseto. Pitigliano offers a fascinating mix of historical points of interest. Also, unlike other towns in Tuscany, Pitigliano boasts a strong Jewish heritage since the Jewish community fled Rome and found a haven here in the 16th century, which is why it is called “Little Jerusalem”. 

How to Get There

The most convenient way to get here is to rent a car. Although it is possible to reach Pitigliano by public transportation, you will have to switch 2 or 3 buses if you are coming from the main cities like Rome or Siena.

Where to Stay

There are a few accommodations in Pitigliano, but you can also stay in the nearby Saturnia at the lovely Agriturismo Le Cascatelle to be at an easy reach of both Pitigliano and Saturnia’s natural hot springs.

13. Pienza

one of the most amazing Tuscany Villages
CONTRIBUTED BY: Katy from Untold Italy
Pienza Highlights
  • Piazza Pio II has a perfect harmonious shape which gives great dignity and solemnity to all of the surrounding buildings
  • The imposing Palazzo Piccolomini to the right of the Duomo was used for filming some scenes of his famous romantic movie Romeo and Juliet,
  • The Duomo or Cattedrale dell’Assunta hosts very fine paintings by the most renowned artists of the period
  • Pieve di Corsignano, the Romanesque church with three naves has its ancient origins in the 7th century but the present Romanesque style is from the 12th century.

One of the most beautiful Tuscany Villages is Pienza, because of its dreamy position overlooking the spectacular Val D’Orcia. Designed as the perfect Renaissance town by Pope Pius II in the fifteenth century, it lives up to that objective with cobbled streets full of romantic names like Via del Bacio (Kiss Street) or Via dell’Amore (Love Street).

Along these charming cobblestone roads, you can stop at cheese stores filled to bursting with rounds of pecorino sheep’s milk cheese while browsing boutiques along your way before reaching the town’s impressive cathedral and the main piazza. Here you’ll find the pope’s former residence, Palazzo Piccolomini – with stunning views of the valley below.

How to Get There

Pienza is a 2-hour drive from Florence and just over 1-hour from Siena. Public transportation in that part of the world is very slow so you will need to rent a car to the there. You can also visit Pienza on a group tour. Visiting the town is doable as a day trip but when you arrive, you will wish you were staying longer as this part of Tuscany is sure to win your heart.

Where to Stay

To enjoy one of the most fascinating Tuscan hill towns, book yourself into Relais II Chiostro di Pienza. This lovely 4-star hotel has a charming atmosphere and fabulous views.

14. Manciano

one of the most amazing Tuscany Villages
CONTRIBUTED BY: Lisa of Travel Connect Experience
Manciano Highlights
  • Visit the stunning churches of San Leonardo and the Church of Santissima Annunziata
  • Walk around the town and stop for some pictures at the Clock Tower and The Fountain of Piazza Garibaldi
  • To taste some typical dishes of the area, take a seat at the café-winery “Il Covo dei Briganti” in Via Dell’Imposto, 1. This café is famous for offering hearty dishes at reasonable prices, try, next to a glass of good Tuscan wine, the “tagliere” with croutons, cheeses, and cold cuts, or the first course of homemade pasta such as “pici with ragu”.

Manciano is one of the medieval Italian towns located in southern Tuscany, only a few kilometers from the border with Lazio. This is a Tuscan hill town with a privileged position on top of a hill, allowing you to admire the terraces scattered around the historic center, all the surrounding countryside, and even the Tyrrhenian Sea.
The most interesting monuments of the town are of renaissance or medieval origin, such as the castle, called “Cassero”, which rises in the highest part of the village and was founded by the noble Aldobrandeschi family in the 12th century.

The Cassero houses the Prehistoric Museum of the Fiora River Valley, which exhibits the findings belonging to the Neolithic period near the most important river in the area, and is also the seat of the town hall of Manciano.

Even if you are not interested in museums, you should still reach the castle to walk by the delightful architecture of this small undiscovered, medieval Italian town. Manciano was once entirely surrounded by walls and had 11 defensive towers, while today only 2 remain.

How to Get There

You can reach Manciano by public transport, by taking a train to Albania and then a bus to Manciano. Or if you are driving from Florence, it is 144 miles (232 km) and should have a drive time of 3 hours.

Where to Stay

In southern Tuscany, the best accommodations are in farmhouses, known as agriturismo. The Fattoria Pianetti is rated as s superb, and this beautiful 16th century stone farmhouse is located in the Tuscan countryside.

15. Montepulciano

Tuscan Hills towns
CONTRIBUTED BY: Lori Sorrentino Travlinmad
Montepulciano Highlights
  • You’ll love Montepulciano for its amazing intact architecture, historic buildings, and renowned wines, with plenty to see and do for a week or more.
  • Walking through Montepulciano is the best way to view the town and its beautiful landmarks like the Sanctuary of the Madonna di San Biagio.
  • On the Piazza Grande is the 14th-century Palazzo Comunale, with a tower offering views of the surrounding countryside.

The historic Tuscan hill town of Montepulciano is undoubtedly one of the most beautiful Tuscany villages, and it makes a superb base from which to explore the surrounding iconic landscape of the famous Tuscan Val d’Orcia.

The town itself sits high on a hill and boasts many elegant Renaissance palaces, churches, and piazzas, and the panoramic views from just about everywhere in town are nothing short of breathtaking. Surrounded by vineyards, Montepulciano is one of Tuscany’s famous wine towns, known for its red, thick-skinned Montepulciano grape which produces Montepulciano d’Abruzzo wine.

Although the local grape is in the Sangiovese family, it is not the same grape used to make the famous Vino Nobile di Montepulciano, though it’s widely available and often attributed to the town. For a unique wine tour and tasting, visit the sustainable Salcheto Winery, a local winery that’s completely off-the-grid.

How to Get There

Montepulciano is located in the Siena region of Tuscany. If you are driving it’s easy to get to Siena, Florence, and Arrezzo via major highways. Another option is to go on a wine and food tour and this tour is very high-rated and recommended.

Where to Stay

Stay at the amazing 4-star La Locanda di San Francesco with incredible views of the sunset and sunrise view over Tuscany, spacious rooms, and fantastic service.

16. Montalcino

Tuscan Hills towns
CONTRIBUTED BY: Dhara from It’s Not About the Miles
Montalcino Highlights
  • The biggest highlight is to appreciate the local wine, so enjoy the wide array of tasting opportunities
  • Piazza Grande is the heart of Montepulciano and the setting for its main events
  • Montepulciano Cathedral was built between 1586 and 1680 and was finally consecrated in 1712. 
  • Museum-lovers will want to pop into the Civic Museum and the Glass Museum.

Montalcino is one of the prettiest villages in Tuscany. Whether you are visiting as part of a drive through the Val d’Orcia or you plan to spend a few days here enjoying a relaxing vacation, you will love Montalcino!

As the home of the world-famous Brunello wine, Montalcino is a must-visit for wine tasting. Created in the late 19th century, the red wine made with Sangiovese grapes has firmly placed Montalcino on the wine world map, and there are several vineyards right outside town where you can enjoy tastings. Montalcino is also worth visiting if you are not a wine fancier. Its medieval fortress is still standing, and the town’s pretty streets make for fun wandering.

Browse the small shops for artisanal food products and gifts. The views of the surrounding countryside from Montalcino are outstanding, particularly if you climb the ramparts of the fortress.

How to Get There

You can visit Montalcino (and tour the Val d’Orcia) independently by renting a car, or you can join a tour from Florence or Siena.

Where to Stay

There are several hotels if you wish to stay in town, or you can opt for an agriturismo stay in the countryside nearby. One of the best options is the Colle al Matrichese, rated as “exceptional” by the guests, located in the heart of the Tuscany wine region.

17. Volterra

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Volterra Highlights
  • Visit many of the Roman ruins, like the Roman Theater, dating back to the end of the first century AC, built in a natural amphitheater. 
  • Visit the Piazza dei Priori and walk around the narrow medieval streets
  • Spend some time admiring the amazing Duomo, the Cathedral of Santa Maria Assunta dated back to 1120
  • Giarmacco Etruscan Museum is one of the oldest public museums in Europe, opened in 1761
  • Admire the Roman Amphitheater and the Archeological Area, located just outside the medieval walls and built in the 1st century AD.

Last, but not least of this amazing list of the best Tuscany Villages is Volterra. A very charming town situated in the province of Pisa, and not far from Florence and Siena.

Volterra is known for its Etruscan origins and for many remains from this era. But today, Volterra is renowned for its peculiar urban layout, and you still can visit the majestic protective walls built during the 5th and 4th centuries, including the two very well preserved gates entering the city – Porta dell’Arco and Porta Diana.

Walk around the historical center of Volterra, and step back in time, while enjoying the timeless atmosphere that surrounds the town. Taste its typical products and visit the handicraft workshops, where you’ll find many ideas for souvenirs from Tuscany, especially alabaster hand-made objects, which Volterra is famous worldwide for.

How to Get There

Volterra is about 70 km from Florence and if you are driving to head to the Firenze-Siena roadway alongside the A1. Another option, you can take a full-day tour to Volterra.

Where to Stay

There are plenty of accommodation options in Volterra, I stayed and recommend the Hotel La Locanda as it is perfectly located right in the city center, the rooms were recently renovated and they offer excellent breakfast.

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Tuscany Villages Travel Planning

Every time I visited the villages and towns in Tuscany, I tried different itineraries and lengths of time. If you are traveling from Rome to Tuscany, I have prepared this very detailed guide on the best options you can travel – by train, bus, car, or book a group tour – and here you can find what fits your budget and itinerary better.

If you are planning just a day trip to Tuscany, I would recommend staying in Florence and booking a private tour or renting a car for the day to travel around the Tuscan countryside and visit some villages and towns.

Best Ways to Visit the Tuscany Villages


Driving from Rome to Tuscany is the best way to experience the stunning Tuscany Villages. It’s a beautiful and relaxing road trip. Highways in Italy are easy to navigate and most of the driving will be on the A1, except for occasional stops in small towns. 

You can get a 15% off your rental car when you book through this site. I use and recommend RentalCar because it is the most reliable rental car source, and it allows you to compare the prices of different places.

  • Trenitalia and Italo Treno chigh-speed trains connect the Firenze-Santa Maria Novella railway station (Florence’s main station) to Milan, Turin, Rome, Verona, Bologna, Naples, Venice, Salerno. From Florence, with Trenitalia direct regional trains, you can reach Pisa, Siena, Lucca, Arezzo, Livorno, Viareggio, Montecatini Terme.
  • The company Trasporto Ferroviario Toscano operates rail connections in the province of Arezzo.

READ MORE: The Best way to travel from Rome to Tuscany: Car, train, bus or private tours


There are many bus companies operating across Tuscany. Most companies operate from the “Firenze Santa Maria Novella” railway station and the airports of Florence and Pisa:

  • BusItalia: operates the Vola in bus connections between Florence airport and the city center, as well as local public transport services in the Florence, Arezzo, Siena, Mugello, Valdisieve, Casentino, and Valdarno areas.
  • ACV Bus: connects 20 districts of the province of Florence, Poggibonsi, and five districts in the province of Arezzo.
  • FlyBus: operates connections between Florence Airport and Prato, Montecatini Terme and Pisa Airport, and five districts in the province of Siena
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You can reach Tuscany by air using the airports of Florence and Pisa.

  • PISA INTERNATIONAL AIRPORT: with connections to and from all major European cities. The airport is only a few kilometers away from the city center, which you can easily reach by taking the Pisa Mover, the shuttle that connects the airport to the Pisa Centrale railway station. From Pisa Airport you can catch connections by bus to Florence (via Montecatini – Pistoia – Prato), and to Lucca and Viareggio/Pietrasanta with Vaibus.
  • FLORENCE INTERNATIONAL AIRPORT:  offers connections to and from many European cities. From here, you can reach downtown Florence in a few minutes using the T2 tramway line and by bus with Vola in Bus. The FlyBus service connects the airport to Prato, Montecatini Terme, and to Pisa Airport  (via Prato-Pistoia-Montecatini).
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Best Time to Visit the Tuscany Villages

The best time to visit Italy is during spring and fall when the temperatures are comfortable and there are fewer crowds:

SPRING: Temperatures start to warm up in spring, going from the late teens to mid-twenties, although it’s still advisable to wear layers in case of colder spells.

SUMMER: The summer months of July and August see higher temperatures and visitor numbers reach their peak. Temperatures are normally around 81 °F and often reach over 88 °F at the height of the day.

FALL: Temperatures cool down gradually, so September is still very pleasant, with an average of around 77℉. Expect crisp fall leaves and some sunnier days, but plan for wet weather too.

WINTER: Temperatures in the south remain mild in winter. However, northern Italy is normally wet and cold, and it’s not unusual for snow to fall, especially in the mountains.

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Best Tuscany Villages Conclusion

I hope this list of the most magical Tuscany villages has added plenty of options for your bucket list.

Traveling to Tuscany from Rome, or any other major city is very easy. You can rent your own car and drive, or there are several tours that you can join that offer great options from a day trip to Tuscany to wine and food taste to multi-day tours.

Now, choosing which Tuscan Villages or small towns you want to visit, is up to you!

If you are planning a trip to Italy, you may enjoy the following:

Tuscany Villages and small towns Pinterest

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11 thoughts on “17 Prettiest Tuscany Villages & Hill Towns in Tuscany + Tips How to Visit in 2022”

  1. I really need to book a trip to Tuscany and tour around to these amazing places! I’d definitely love to see Florence, but I always enjoy checking out smaller villages that are less touristy, so thanks for the tips!

  2. All of these towns are so beautiful! Florence is one of my favorite places in Italy and I’ve been fortunate enough to visit 7 of these stunning Tuscany locations. Three that I haven’t been to but would love to are Civita di Bagnoregio, Pitigliano and Volterra! Each of them look so romantic, lovely architecture that it would be easy to spend time at each of them!

  3. I love the hill towns of Tuscany. They each have a unique feel and there is always good food to be found in them! It’s constantly a struggle to decide whether to go back to the same places or find a new one to love. The views from Volterra, especially at sunset, are the most remarkable I’ve ever seen!

  4. Tuscany is one of my favourite parts of Italy. Sienna is one of my favourite towns, but I’d love to visit some of the others on your list. Your photos make them all look beautiful!

  5. Thanks, Rachel – and I agree with you. Tuscany is one of my favorite spots in Italy and all the towns are so magical

  6. I agree with you, sunset is Volterra is a must-see for anyone who loves traveling and loves Italy. Yeah, I have been in Tuscany a few times, and I do a mix of visiting my favorite hill towns plus exploring new places too.

  7. HI Vanessa – Yes, Tuscany is so unique and magical. I love just to take my time and stroll around and observe the amazing architecture and stop for a coffee or a prosecco, while I just observe the slow lifestyle – to me, it is a perfect destination for a relaxing and exploration vacation.

  8. HI Krista – you will love both, Florence is incredible – busy, but still incredible. And there are many towns in Tuscany that are still little explored and you can only travel in time just walking around the medieval streets. I hope you get to visit Tuscany soon.

  9. Que lindo e completo artigo, onde pude conhecer e desfrutar de algumas destas preciosidades italianas. Tudo é muito intenso nesta maratona de conhecer estas pérolas históricas. Tudo isto em 20 dias corridos pela Bella Itália em minha última viagem antes da pandemia e louca para retomar minhas idas ao mundo.

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