A Guide to the Most Beautiful Cities in Tuscany

Written by Rem Malloy, since 1995 Rem has been guiding and designing trips to Italy and all of Western Europe and is considered an expert in his field for over 30 years.

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Tuscany is Italy’s most renowned region for natural beauty and artistic landscapes. Between the acres of vineyards and the rolling hills, this area of the country is drop dead gorgeous. Tuscany is dotted with fantastic cities, medieval towns, and tiny mountain villages. The food culture is immense and the selection of art and history is quite impressive. If you’re visiting Tuscany and aren’t sure where to start, we’ve come up with a handy guide to some of the most beautiful cities in the region.


This postcard-perfect town can be found between Tuscany and Lazio. The entire city looks like it was carved out of a rock face by the Etruscan people, who once used this place as a settlement. It’s certainly a gem that’s a bit off the beaten path. While it may be small, the winding alleyways, stone archways, and cobblestone streets make it feel like a grand adventure to explore. Pitigliano is known for its collection of grand synagogues, so make sure to give those a visit before you leave.


This small, colorful city can be found on top of the Tuscan hills. The views here are incredible, especially when looking out over the rolling hills and vineyards. It’s located just outside of Florence, which makes it a great city for a day trip. Arezzo is a top spot to see Florentine architecture outside of Florence, and offers tons of natural beauty. If you want to see the city at its best, make sure to visit in the summer. Those stopping by in July will be met with plenty of live entertainment and markets. It’s not a very common stop for tourists, so you can expect to soak up lots of authentic, local culture amongst local residents.


Visiting the Leaning Tower of Pisa is an absolute must while visiting Italy. Lucky for Tuscan road travelers is that Pisa is located in Tuscany. Spend some time getting the perfect photo of the tower and then lounging on the grass beside it to rest your feet.

While many travelers check out the tower and leave right away, the city of Pisa does have more to offer. Take a walk along the River Arno to view the lovely scene of houses and gardens. Other highlights include the Baptistery, Camposanto, and the Duomo di Pisa. If you’d like to do some shopping and get yourself a few souvenirs, visit the Corso Italia, a pedestrian-only shopping street that’s less crowded and touristy than the one in Florence.

San Gimignano

Once a bustling medieval town, San Gimignano was the hot spot for wealthy Tuscans. Many of the wealthy families who lived there built massive towers to show off their clout. The city skyline was once scattered with 75 of these towers. Only 13 remain today, but they still give this city an interesting edge and great vantage points to check out the view. Many of the remains of former towers can be seen scattered around the city.

The historic downtown has been dubbed a World UNESCO Heritage Site, so make sure to give it a visit while you’re there. Other highlights include the Piazza del Duomo, Piazza del Cisterna, the City Hall tower, and the Salvucci twin towers. This is a great city to spend a night as the daytripper crowds can get quite overwhelming during the day. Spend some time trying out the restaurants and definitely get yourself a glass of Vernaccia di San Gimignano, one of the most famous white wines in Tuscany.


This town may be one of the smaller ones in Tuscany but it’s big on beauty. It’s located near the Mediterranean, nestled in the forests of Livorno Province. The entire region is surrounded by greenery and rugged hills that make it look picture-perfect.

Some of the highlights here include the Renaissance castle, historic stone buildings, and the ability to get lost in the cobblestone alleyways that line the town. Suvereto is full of twists and turns that can lead to beautiful and unusual squares, cafes, and houses. Try out the local specialties in whichever restaurant you happen to wander into.


Found in the Tuscan highlands is Barga, a scenic city located just below the Pania della Croce mountains. The views are stunning and often include misty mountains, snow-capped peaks, and lush forests of chestnut and olive trees. The city is scattered with wonderful examples of Renaissance architecture, which are painted in bright yellows, contrasting perfectly with the dark mountain ranges.

Wander the small side streets, lounge in the piazzas, and enjoy the atmosphere that is oddly like that of a UK city. They even have a Fish n’ Chips festival, setting the scene even more.


Named after Pope Pius II, this city was designed to look like the ideal Renaissance town. It was listed as a World UNESCO Heritage Site, and is considered one of Tuscany’s most scenic hill towns. The charming city is dotted with colorful gardens, beautiful works of architecture, and lots of history. Make sure to visit Piazza Pio II, the main town square and the location of some of the city’s best buildings. Highlights include the Duomo di Pienza, Palazzo Piccolomini, and Cappella della Madonna di Vitaleta, which is a famous chapel that can be reached just outside the city by car. After a long day of sightseeing, reward yourself with some of the fantastic food and wine on offer in the restaurants.


Located in the high hills, this town can be found just 40 miles from Siena. It offers stunning views of the iconic, Tuscan countryside, but also has a main hub for dining, drinking, and exploring. Spend some time walking down the Corso, the main street, which leads up to the top of the hill. It’s a scenic walk that ends in a vantage point that’s perfect for photos. Check out the small shops, cafes, and eateries around the town if you want to pick up some souvenirs or try local dishes. Highlights include the Piazza Grande, the main town square, which is a great place to rest your feet and watch the locals go about their daily routines. Try climbing the Palazzo Comunale tower if you’d like some of the best views the city has to offer. And, definitely don’t leave the city until you have a class of the famous white wine, Nobile de Montepulciano, which is known all over the world.


This charming medieval town is a lesser-known gem that should definitely make your Tuscan itinerary. It’s quite small but still offers a charming atmosphere and intriguing architecture. Check out the city wall and take in the views of the city. Some of the highlights on a visit to Volterra include the Museo Civico, Baptistery, the Palazzolo dei Priori, and the Pinacoteca. History lovers will thoroughly enjoy a visit to the Roman remains like the Medicean Fortress and Roman Theatre.


This small, medieval city can be found on the fringes of Tuscany. It’s a maze of winding, cobblestone alleyways, colorful gardens, and charming homes. It looks out over the Valdichiana plains so expect fantastic views and great photo opportunities. You’ll also get incredible views of Lake Trasimeno, the historic architecture, and the rugged valleys below. Highlights here include the bustling weekend markets, Garibaldi Square, and the Santa Maria Cathedral. It’s also a nice place to stay a while and enjoy some wine so make sure to enjoy a glass.


If you’re spending some time in Pisa or Florence, make sure to add a day trip to Lucca. In fact, spending a night here will do you good as you can avoid the day tripping crowd. This historic city is known for its history and culture, and features a city wall that is loved by visitors. It’s 80 feet wide and 2.5 miles long, so you can spend half a day exploring Lucca from above. Walk or bike the wall and stop off at a picnic area, park, or a cafe. This is one of Lucca’s main highlights so take your time and enjoy the view. This city is sprinkled with historic churches so make sure to visit as many as you can on your own self-guided walking tour. Other highlights to check out include San Michele in Foro, Piazza dell’Anfiteatro, and Duomo di Lucca. Lucca is also famous for its opera so try to catch a show if you can.


This small city can be found among the Apuan Alps. It is known for its terracotta buildings and is home to a 12th century castle that brings in lots of tourists. Other highlights include the historic citadel that can be explored while looking out over the Tyrrhenian Sea. This city is a bit off-the-beaten-path so the best thing to do is just wander around, take in the seaside views, and leisurely dine on wine and local cuisine.


This Tuscan city is exactly what you’d expect from the countryside of this region. It’s flanked by rolling hills and is full of natural beauty. The locals take the natural beauty seriously, and take pride in their home-grown food. You’ll find plenty of farm-to-table restaurants in Montaione, not because it’s trendy, but because that is how the locals live. Take in the beauty of the olive groves, forests, and historic buildings that dot the city. Foodies will love a visit to this city as the food is fresh and the wine is bright. Make sure to try some handmade pasta, which shouldn’t be too hard to find as most of the restaurants here offer it.

Punta Ala

Need a change of scenery? Swap the rolling Tuscan hills for the coastal town of Punta Ala. It’s a real beauty, with seaside views instead of rolling hills. It’s mostly untouched, so the natural beauty is there in a big way. Visitors will find forests of pine, calm beaches, rocky outcrops, and mostly locals enjoying the views. This spot is not a big place for tourists so you can bring a book, a bottle of wine, and enjoy the sun in peace and quiet.


This is one of the top cities to visit in Italy as it’s packed to the brim with art, culture, food, and beauty. You’ll definitely need a few days to fully experience Florence, especially if you love museums. Make sure to stop at the Uffizi Gallery to check out the impressive collection of Renaissance era artworks. The Accademia is the spot to visit if you want to see the original David statue by Michelangelo. There are so many museums in Florence that you won’t have time to see them all so make sure to do your due diligence to figure out which ones are best for you. Spend some time wandering the city center as it’s filled with impressive architecture and even considered a World UNESCO Heritage Site. If you can find a high vantage point, spend some time up there overlooking the landscape of the city. Photographers, don’t forget your camera. Make sure to check out the San Lorenzo Market, Piazza Della Signoria, the Duomo, and Ponte Vecchio. And whether you’re a foodie or not, don’t forget to spend time taste testing the various gelato shops and pizzerias. The food in Florence is incredible.


Elba can be found in the Tuscan Archipelago. It’s the largest of the islands that make up the national park here. It’s history dates back to the time of the Etruscans, The Romans, and even Napoleon who was once exiled here. Now, people flock to this destination because of its sunny atmosphere and crystal clear waters. Some even compare the water here to that of the Caribbean! Highlights include visits to Napoleon’s former residences as well as the historic fortresses.


Siena is one of the larger cities that Tuscany has to offer. While it’s smaller than Florence, it’s absolutely brimming with culture, beauty, and charm. The city center is considered a World UNESCO Heritage Site, making it a great place for history lovers to wander. Highlights include the Piazza Del Campo at the heart of the city as well as the Siena Cathedral. This medieval city has a lot to offer in the way of architecture so make sure to look up every once in a while to check out the buildings and houses. Don’t leave Siena without visiting the Piazza del Campo, which is one of the most famous public squares in all of Europe. The people watching here is pretty fantastic.

Tuscany is a beautiful and culturally rich part of Italy. If you’re visiting, expect to be kept busy exploring the Tuscan cities and all they have to offer. Between the food, wine, culture, and architecture, you’ll be too busy to even think about Italy’s other regions.

About the Author

Rem Malloy started Italy4real back in 1995 with his mother, Deborah de Maio.

He specialises in Italian tours as well as customised tours to France, England, Ireland, Germany, Switzerland, Greece and Spain. He was also featured in the Travel Channel show Mysteries at The Museum in 2016.

Rem has family in Italy and his mothers home town is Cava di Terrani, near the Amalfi Coast. The family has a street named after them in Sorrento, Via Luigi de Maio; a relative who was mayor of Sorrento.

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