A Guide to the Most Beautiful Cities in Tuscany

Tuscany has long been known as one of Italy’s most beautiful regions. The rolling hills, acres of vineyards, and world-class architecture make Tuscany look postcard perfect from every angle. From historic cities to quaint and charming hill towns, this part of Italy is an absolute wonder for everyone who visits. If you have the time, you could spend your entire trip to Italy just exploring this stunning region. There’s a lot to see and do so you’ll need a great starting point if you want to see the best and most beautiful of what Tuscany has to offer. Ready to explore? Here’s a guide to the most beautiful cities in Tuscany.

Florence

This is one of Italy’s most famous cities, especially for art, architecture, and culture. It’s a top city to visit while on an Italian getaway, and one that deserves at least a couple of days to explore. The historic city center is a World UNESCO Heritage Site, and the architecture alone is enough to marvel at for hours. Photographers, you’re going to love this part of the city. Find a high vantage point to view the city from as the site is absolutely incredible. The colors, architecture, and looming mountain peaks makes Florence a true beauty. Aside from eating pizza, pasta, and gelato, make sure to explore the museums here. The top highlights include Michelangelo’s David statue in the Accademia, and the collection of masterpieces from the Renaissance era that can be found in the Uffizi Gallery. Make sure to visit the Duomo, San Lorenzo Market, Ponte Vecchio, and the Piazza Della Signoria. If you happen to be a foodie, Florence will be an absolute dream for you. It’s home to some of the best gelato shops in the country, and is a fantastic city to take a cooking class too. Spend as much time eating as you do in the museums if you want a well-balanced trip.

Pitigliano

Located between Lazio and Tuscany is Pitigliano, a town that is so postcard perfect that it’s startling. The city looks like it was cut out of the surrounding rock faces by Etruscans who once thrived here. It’s an intricate city lined with small shops, stone archways, cobblestone streets, and winding alleys that seem to lead nowhere. Make sure to see the synagogues that are one of the town’s most famous features.

Pisa

You can’t visit Italy, let alone Tuscany, without visiting the Leaning Tower of Pisa. It’s one of Italy’s most iconic sites, and it’s definitely worth the photo opportunity. However, the tower isn’t the only thing Pisa has to offer. Make sure to walk along the River Arno to photograph the charming houses and take in the lovely scene. You can also check out the Duomo di Pisa, the Camposanto, and the Baptistery. If you want to get in some shopping while you’re in Pisa, make sure to visit the pedestrian only shopping district on Corso Italia. Pisa is great because it’s less touristy than Florence but still has beautiful views and interesting architecture.

Lucca

Lucca makes a great day trip from Pisa or Florence. It’s a historic city, surrounded by ancient city walls and full of culture. This medieval town’s main draw are the city walls which run for 2.5 miles overlooking the city. You’ll get incredible views without all of the hustle and bustle of the city streets. This isn’t your average walkway either as the walls are 80 feet wide and feature greenery and trees. Make sure to walk or bike and stop off at the picnic areas, parks, and cafes that line the wall. Lucca is full of historic churches so once you finish your journey on the walls, make sure to tour some of these beautiful buildings. Make sure to visit Piazza dell’Anfiteatro, Duomo di Lucca, and San Michele in Foro. After a busy day of sightseeing, attend one of the local operas that Lucca is famous for.

San Gimignano

This medieval town is known for its towers and stunning views. It’s kind of what you did if you were wealthy and lived in San Gimignano during its heyday. Now, visitors have plenty of vantage points to take in the views and take stunning photos. In fact, there was once 72 towers in the city! Today, there are only 13 still standing, and some remains of the others-still pretty impressive compared to most Tuscan cities. Make sure to wander around the historic downtown area, which is considered a World UNESCO Heritage Site. Take some time to explore Piazza del Cisterna, Piazza del Duomo, the Salvucci twin towers, and the City Hall tower. The best way to explore San Gimignano is to come early in the day and stay overnight. You can avoid the daytripper crowds this way and have plenty of time to wander, dine, and taste some of Tuscany’s most famous white wine, Vernaccia di San Gimignano.

Suvereto

Located right near the Mediterranean, this is one of the most beautiful small towns in Tuscany. It can be found situated amongst the forests of Livorno Province, which is surrounded by rugged hills and greenery. Visitors here will find historic stone buildings, a Renaissance castle and small alleyways throughout the town. This is a great city to get lost in as it’s too small to really lose your way, but is filled with hidden gems that can be hard to find. Wander around until you find a quaint cafe or hole-in-the-wall restaurant to rest up and try the local specialties.

Pienza

This city was named after Pope Pius II, and was designed to be an ideal Renaissance town. It’s now known to be a charming hill town that has been deemed a World UNESCO Heritage Site. Pienza as quaint and beautiful, featuring wonderful works of architecture and colorful gardens. Start by visiting the main square, Piazza Pio II, where you can see some of the city’s most notable buildings. Explore the beautiful gardens of Palazzo Piccolomini, the lovely interior of Duomo di Pienza, and Cappella della Madonna di Vitaleta, the famous chapel that is just 15 minutes from Pienza. After taking in all of the history and architecture, make sure to spend some time taste testing the local cuisine and wine in the cafes.

Montepulciano

Just 40 miles from Siena, this town is located high in the hills, offering absolutely gorgeous views of the Tuscan countryside. Wander the main street, the Corso, which is a scenic route that leads to the very top of the hill. Spend some time wandering in and out of the tiny shops and eateries to pick up souvenirs and try out some of the local dishes. Visit the Piazza Grande, the main square, which is a great place for relaxing and people watching. Make your way up to the Palazzo Comunale tower, which you can climb up to get incredible views. Don’t leave without trying the city’s most famous wine, Nobile de Montepulciano, which is known and loved all throughout Italy and the world.

Volterra

Yet another medieval town, Volterra is a charming stop on a Tuscan road trip. It isn’t the biggest of cities, but it does have interesting architecture and a charming atmosphere. Take in the views of the city wall, and spend some time wandering around the town’s main attractions. Stop into the Baptistery, the Pinacoteca, the Palazzolo dei Priori, and the Museo Civico. And, if you love history, make sure to visit the Roman remains such as the Roman Theatre and the Medicean Fortress.

Cortona

Located on the fringes of Tuscany is Cortona, a medieval town that is full of winding alleyways, charming homes, and colorful gardens. Because it’s located high above the Valdichiana plains, the views from this city are absolutely incredible. Visitors can take in the sights of Lake Trasimeno, rugged valleys, and historic architecture. While visiting, make sure to check out the Santa Maria Cathedral, Garibaldi Square, and the bustling markets that take place during the weekends. And if you like red wine, this is definitely the place to get yourself a glass or two.

Fosdinovo

Found amongst the Apuan Alps is Fosdinovo, a small city dotted with terracotta buildings and a historic castle from the 12th century. Visitors will find an ancient citadel to explore while looking out over the Tyrrhenian Sea. Make sure to wander around town to take in the quaint buildings and seaside views before stopping off for some wine and a hearty meal.

Barga

This city is located in Tuscany’s highlands, right beneath the Pania della Croce mountain summits. Visitors here will find views of snow-topped mountains as well as forests of chestnut trees and olive trees. Most of the buildings are displays of Renaissance architecture, with bright yellow facades that contrast nicely with the mountains that surround them. The town is made up of small streets and piazzas, with an atmosphere that’s reminiscent of a Scottish city. In fact, they even have a Fish n’ Chips festival here each year.

Montaione

This rural village is quintessentially Tuscan. It’s surrounded by rolling hills and is full of old world charm and natural beauty. Visitors will be treated to farm-to-table restaurants, groves of olive trees, and locals who take pride in living off the land. There’s a few small, historic attractions, but the best thing to do is taste the food and wine. The handmade pasta is particularly delicious so make sure to get yourself a heaping plate at whichever restaurant you stumble upon.

Punta Ala

If you’ve had enough of the rolling hills and want a different kind of atmosphere, this is the place. This coastal town is mostly untouched, leaving its charm and natural beauty intact. Expect a variety of calm beaches, rocky outcrops, pine forests, and primarily Italian visitors. It’s not too well-known on the typical tourist trail so it’s often quiet and peaceful.

Elba

Located within the Tuscan Archipelago, this is the largest island that makes up the National Park here. The island has history that dates back to the Etruscans, The Romans, and even Napoleon who was sent here in exile. With clear, blue waters and sandy beaches, it’s now a getaway for visitors in Tuscany. Make sure to visit the former residences of Napoleon as well as the historic fortresses. If it’s hot, bring a bathing suit because the water is just as clear as the Caribbean.

Siena

While smaller than Florence, Siena packs in a whole lot of beauty and culture. The charming city center is considered a World UNESCO Heritage Site, and is full of historic architecture. Make sure to wander around the central area, Piazza Del Campo, which is known as the heart of the city. Tour the Siena Cathedral, wander the intriguing museums, and soak up as much knowledge as you can. Siena is a medieval hub in Tuscany, and it certainly looks the part. Expect lots of ancient architecture and plenty of chances to learn all about the history. Before you leave, make sure to spend some time in one of Europe’s most famous squares, Piazza del Campo, where the people watching is fantastic and the views are top notch.

Arezzo

Sitting atop the Tuscan hills is this small and colorful city. Visitors who climb to the top of this city will be met with a beautiful Tuscan view of vineyards and rolling hills. Outside of Florence, Arezzo has one of the best displays of Florentine architecture in the world. Visit in the summer if you want to really see this city come alive. July is full of live entertainment and artisan markets that are visited mostly by Italians. The city is a bit under the tourist radar so you won’t have to deal with large crowds while visiting.

If you’re visiting Tuscany you’ll never be short of places to visit. This beautiful region is packed with cities and towns that all offer something beautiful and interesting. No matter where you go, be sure to take in the natural scenery, drink some wine, and relax your way through every day.