Gorgeous Towns in Tuscany for First-Timers

No region in Italy evokes the sense of la dolce vita better than Tuscany. When you set eyes upon the beautiful landscape with its rolling hills, you will want to jump up and down with joy and take a million photos. Love history and culture? Tuscany’s great cities, filled with world-class art and architecture, will delight you. If you are a foodie, you will love sampling the delectable cuisine of Tuscany, paired with its famous wines. Read on to discover the most charming cities and towns in Tuscany to visit as a first-time visitor!

Charming towns in Tuscany

Although Tuscany has lots of beautiful towns, big and small, to keep you occupied for several visits, this first-timers’ list will take you on a tour of the classics: the places that jump to your mind when you think of Tuscany. Because they are famous, they also tend to be popular, so plan your visit for the outer fringes of the shoulder seasons.

When you visit, try to do some overnight stays in the smaller towns instead of relegating all of them to day trips. In the quiet of the late evenings and early mornings in Tuscany, you will truly experience the sweet life that you equate with this beautiful region. Here’s my pick of some must-visit towns in Tusancy oozing with charm…

Get your fill of art and architecture in Florence

Florence has so much to offer that you can never really say you’re truly done. And many sights are so iconic that you could see them multiple times and still not be satisfied. So Florence definitely deserves to always be first on your list of the most stunning places to visit in Tuscany!

If you haven’t visited yet, then focus on the classics in the historic center, a UNESCO World Heritage site. Climb to one of the several high spots in the city for breathtaking views of the red rooftops of the city. Gaze at Michelangelo’s David (the original) in the Accademia. View the masterpieces of great Renaissance artists at the Uffizi Galleries. Wonder at the enormity of scale of Brunelleschi’s dome and the beauty of Ghiberti’s Doors of Paradise. Of all the (cities and) towns in Tuscany, spending 1 day in Florence needs to be top of your list.

duoma florence


If you are a foodie, sample the famous Florentine bistecca. Go on a gelato crawl: Florence is where you will find the best gelato on the planet. Pop into the Mercato Centrale for bits and bites of Italian favourites, from pizza to fresh pasta to cheeses, fruity olive oil, and biscotti.

If you want the leather bag from Firenze, walk past the stalls and stores on the streets and visit the Scuola del Cuoio in Santa Croce, where you will find exquisite workmanship and great choices. Of course, it will be pricey, but it’s a once-in-a-lifetime purchase and you’ll be glad you bought the best. Plus, they will engrave your initials on the bag for you while you watch!

things to do in florence

Enjoy more than just the Leaning Tower in Pisa!

Pisa’s main claim to fame is, of course, the Leaning Tower. An unintended tilt, caused by unstable soils at the site, has made Pisa’s campanile one of the most recognized structures in the world. Although you may be tempted to dismiss Pisa as a tourist trap, a full day trip to the city will let you experience more of Pisa than just the tourist-heavy Leaning Tower. Even better, spend the night, and head to Lucca the following day.

If you are visiting Pisa as a day trip, walk to the Field of Miracles from the train station, or hop into a taxicab to get there is just 7-8 minutes. If you walk, it should take you about 20-25 minutes, and on the way, you can get pretty photos of the houses along the River Arno.

Besides the Leaning Tower, the Field of Miracles houses the Duomo di Pisa, the Baptistery, and the Camposanto. The complex is a UNESCO World Heritage Site. Walk around the beautiful green field and enjoy the pristine white buildings with their beautiful facades. If you have the time and the energy, climb to the top of the tower for gorgeous views over the city.

Next, leave the selfie-focused tourists behind and head to the stunning Piazza dei Cavalieri, for more gorgeous architecture in less touristy surroundings. Take a break for lunch at the highly regarded Osteria dei Cavalieri. Browse the stores on Corso Italia: the pedestrian-only street is much less crowded than the shopping areas of Florence, and you may find that pair of strappy leather sandals you’ve been coveting, at a better price than in Florence!

In Pisa, you’ll get a glimpse of life in a Tuscan city without the huge crowds of Florence, especially if you decide to stay overnight. So the city should definitely be on your list of top places to visit in Tuscany!

views of pisa

pisa field of miracles

Walk or bike the old city walls of Lucca

Next on your list of the most wonderful places to visit in Tuscany should be Lucca. Another historic gem, Lucca can be visited as a day trip from Florence or Pisa. Arrive early in the day though, so you have one entire day to explore this charming medieval town.

Lucca’s main draw is its boundary wall. The old city walls are well preserved and offer about 2.5 miles of scenic pathway overlooking the city. Walking or biking the walls of Lucca should be the first thing you do here. The tree-lined walls are about 80 feet wide! You’ll come across parks, picnic areas, and a cafe along the walls. Walking will let you enjoy the sights on the way in a more leisurely fashion. It will take you about an hour.

lucca tuscay

lucca italy rooftops

Next head to the Duomo di Lucca, home to the famous Holy Face of Lucca, a revered wooden crucifix. Also worth a visit in the city of 100 churches is the stunning San Michele in Foro. At the top of the church is a 13-foot statue of the Archangel, and the story goes that as long as St. Michael remains in this spot, Lucca is protected.

While in St. Michael’s square, pop into the Buccellato Taddeucci cafe and refuel with a slice of buccellato, the sweet bread of Lucca. Made since medieval times, the bread is stuffed with sweet raisins and flavoured with anise, and tastes absolutely divine.

Wander around and admire more of Lucca’s treasures, including the Piazza dell’Anfiteatro, shaped like a Roman amphitheatre, and the roof garden at Torre Guinigi. If you have the time, climb to the top of the tower for fabulous views!

Lucca is the birthplace of Puccini, so if you enjoy opera, check if a performance is being offered on the evening you visit, for the perfect ending to your day.

lucca cathedral

Spend a delightful day exploring Siena

In Siena, you’ll find the essence of medieval Tuscany perfectly preserved. Beautiful brown palazzos line winding streets, and the flags of the different districts fly proudly on every building in the district. Come July and August, the districts take their rivalry to another level at the racetrack. The Palio is a time not just for the famed race, but also for parades and pomp. You will love being in Siena during the exciting event, held twice a year.

Although the Palio is a huge draw, Siena is a lovely Tuscan town to visit any time of year. The Duomo di Siena can compete with any cathedral anywhere. A fabulous facade is complemented by an equally gorgeous interior. And the Duomo di Siena has two additional surprises that set it apart: the absolutely stunning Piccolomini Library, and the floor that is covered with art. If you plan to visit in the fall, check for the window of time the entire floor is uncovered. One of the prettiest towns in Tuscany, it would be such a shame not to visit picturesque Siena.

siena italy ceiling

And the cherry on Siena’s cake is the majestic Piazza del Campo. It’s one of the most magnificent squares in Europe, and the venue for the Palio. It is also home to Siena’s clock tower, the graceful Torre del Mangia. You can climb to the top for panoramic views.

So set aside a day to spend in the historic centre of Siena, designated a UNESCO World Heritage site. It definitely deserves a spot among the top places to visit in Tuscany!

sienna tuscany town square

Admire the many towers of San Gimignano

Keeping up with the Joneses took on a whole new meaning in medieval San Gimignano. If you wanted to display your wealth, you had to build a tower, preferably taller than your neighbour’s! As a result, San Gimignano once boasted 72 tall towers. Today, only thirteen are still standing in their entirety. But you can still see the remains of some others that were ordered to be cut off or fell down on their own.

Wander through the historic center, a UNESCO World Heritage site. See the old well at Piazza del Cisterna. Visit the Romanesque cathedral on Piazza del Duomo. The frescoes on the left wall are from the Old Testament and the frescoes on the right wall from the New Testament. Admire the Salvucci twin towers. They aren’t identical, but they look harmonious together! Climb the City Hall tower, the only one in the town you can climb, for rooftop views.

San Gimignano

San Gimignano

San Gimignano is one of the most interesting places to visit in Tuscany because of its unique tower-filled skyline. To escape the worst of the crowds, arrive in the early evening and spend the night. That way, you can enjoy the town in the relative peace of the evening and the early morning, when day trippers are not around.

If you haven’t tried ribollita yet, start your dinner with a bowl of the hearty Tuscan soup, made from a variety of vegetables and thickened with day-old bread. This is also your chance to try a glass of Vernaccia di San Gimignano, Tuscany’s most famous white wine.

Decide whether Pienza is the ideal Renaissance town

The Val d’Orcia town of Pienza is named after Pope Pius II, who was born here when it was called Corsignano. Pope Pius II wanted to transform the town into the “ideal” Renaissance town and hired a Florentine architect to realize his vision. Four years of construction ensued, using humanist urban principles, before the Pope’s death halted further changes.

Today Pienza is a UNESCO World Heritage site, a charming hill town with stunning architecture and beautiful views over the Tuscan countryside. You will fall in love with the picturesque town as soon as you first set eyes on it from the road.



Once in town, start at the main square, the Piazza Pio II. Many of the town’s most important structures are built around this plaza. Begin with the Duomo di Pienza, with its simple facade and light airy interior. Next, explore the Palazzo Piccolomini, with its gorgeous gardens. The views from the balcony are beautiful.

Wander the streets of the town. Browse the small shops selling Italian foods and souvenirs. Sample the famous pecorino di Pienza. It’s considered special because it’s made from the milk of sheep that graze on the plants of the Crete Senesi, the gray clays of Tuscany.

Although it’s not in Pienza, it’s worth doing the 15-minute drive to see the tiny Cappella della Madonna di Vitaleta, just off the highway to San Qurico d’Orcia. This is the chapel you may have seen on Tuscany postcards or on Instagram, and if you have a good zoom lens, you can get your own beautiful photo of the gem!

Take in the views from Montepulciano

Located high on a hilltop about 40 miles southeast of Siena is the charming town of Montepulciano. From here you get absolutely breathtaking views of the Val d’ Orcia and the Val di Chiana. This is some of the most beautiful countryside in Tuscany! Although you can take either a bus or a train from Siena, a car is the best way to explore the Tuscan countryside. If you’re like me, you will want to stop and take photos every few yards!

Arrive at one of the main gates to the town and then walk up the main street, the Corso, which goes all the way to the top of the hill. The street, flanked by magnificent palazzos on either side, is a joy to walk. Browse the little stores selling local foods and souvenirs. When you find an intriguing alley to explore, make sure you find your way back to the Corso to continue your walk.

Eventually you will come to the Piazza Grande, the main square, where you will find the Duomo, and three beautiful palazzos. Climb the tower of the Palazzo Comunale for gorgeous views. On a clear day, you can all the way to Siena! If you like churches, visit the lovely Church of San Biagio, set down the hill a little ways outside the town.

Don’t forget to relax on a terrace with a glass of Nobile de Montepulciano, one of the region’s most famous red wines, and for lunch, try pici pasta with local pecorino. While you can visit Montepulciano just for the day, you can also spend a few days here, making it your base to explore more of the beautiful Val d’ Orcia.


So there you have it: my list of the top places to visit in Tuscany. Which of these beautiful places have you visited?

Author bio:

This was a guest post written by Dhara from the travel blog Not About The Miles. Be sure to follow her for more travel adventures on Instagram or Facebook.

Last updated on October 13th, 2023 at 12:29 pm

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