K.C. was a featured writer for Yahoo! Travel before joining trips to discover in 2013. She is the author of Best Travel Guide for First Time Visitors to Ireland, an Amazon bestseller every year between 2013 and 2016. She has been a featured expert on Newsweek, Travel + Leisure, Travelocity, among others.
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Who hasn’t dreamed of visiting Tuscany? After all, it’s one of the most popular destinations, not only in Italy but the world. It’s also quite a vast region, making it a bit of a challenge when trying to decide exactly what charming towns to visit. This list of breathtaking destinations is sure to make that task a whole lot easier.
A favourite Italian city for many, Florence has got a long list things to do. Florence is one of the most important Renaissance architectural and art centers, with its museums, palaces and churches home to some of the greatest artistic treasures on the planet. If you have time for just one museum, head to the Accademia Gallery which houses Michelangelo’s works, including the imposing marble statue of David, which stands over 13 feet tall. If you want to enjoy one of the city’s most enchanting views, climb the hill to the church of San Miniato al Monte. Florence is also a shopper’s paradise, offering everything from amazing bargains to high-end goods in a highly concentrated shopping experience.
The Chianti region, which has inspired artists, poets and travelers for centuries, offers one of Tuscany’s most diverse and scenic landscapes, with its scenery varied as much as its legendary wines. Discover gentle rolling hills covered with endless rows of grapes, low lying forests and charming hamlets as well as stone farmhouses and luxurious villas that offer unforgettable accommodation. Its main attraction, of course, is the wine, and many of the vineyards have areas dedicated to wine tasting and offer the chance to visit wine cellars and see the production of its famous Chianti Classico. But Chianti isn’t just about wine, you can check out Etruscan tombs, the many fortresses built to protect the boundaries between Florence and Siena, and taste delicious eats, like cheeses, honey, special local dishes and prized meats from Falorni and Macelleria Cecchini.
Certaldo was built back in the 12th century as a lookout point for the Via Francigena, the pilgrim’s walk, from Canterbury in England to Rome. It’s the quintessential Tuscany hilltop town, with a peaceful, laid-back atmosphere, magnificent architecture, cobbled streets and lots of picture-perfect photo ops. Make the trek up the hill and you’ll find small shops, delicious eateries and interesting museums like the Museum of Holy Art which features a collection of religious artwork that spans the centuries. Of course, it also has the requisite palace – Palazzo Pretorio was originally a residence for Florentine governors who once ruled the town. Open to visitors, you can step inside and gaze at its beautiful frescoes that date between the 13th and 16th centuries.
A top city to visit in Italy, Siena is a classic medieval hill town renowned for its vast, fan-shaped piazza, Piazza del Campo, and the horse race known as Il Palio which is hosted here twice each year in the summer. The piazza is dominated by the red Palazzo Pubblico and its tower, the Torre del Mangia. The Campo is one of the most remarkable squares in the country and continues to play an active part in the life of the city. In the Pinacoteca, Museo dell’Opera del Duomo and the Palazzo Pubblico, you can see the fabulous Sienese school of painting works that were created in the 13th and 14th centuries by masters like Simone Martini and Duccio di Buoninsegna. By climbing the more than 500 steps of the civic palace, you’ll be rewarded with a spectacular view of Siena and its surroundings.
There’s a good chance you’ve at least heard of Cortona. It’s the Tuscan hill town that was made famous by the book and subsequent movie, “Under the Tuscan Sun.” This “Pearl of Tuscany” is surrounded by Etruscan walls and has some 3,000 years of history. Much of that history has been retained through its architecture, with layers built upon the Etruscan core that dates back to the 7th century BC. Situated on a hill, it also offers impressive views of the valley below, and as it sits near the border of Umbria, it makes a great base for exploring both Tuscany and Umbria. After a day spent wandering through picturesque villages and endless alluring landscapes, you can come back and enjoy a glass of Tuscan wine paired with a tasty Tuscan dish in one of the many restaurants and wine bars.
Set on the slopes of the hills overlooking the Costa degli Etruschi in the green valley of the River Cornia, Suvereto is considered to be one of the best villages in all of Italy, and it’s just 12 miles from the Etruscan coast. While its culture and traditions are decidedly rural, it’s surrounded by the typically lush Tuscan hills. The alluring medieval village still has its circuit of walls intact, and every summer, it hosts many events right inside. Those ancient walls enclose paved streets lined with historical buildings, stone houses and lovely churches, with the old town hall, Palazzo Comunale, dating all the way back to 1200, considered one of Italy’s most stunning examples of civic architecture. St. Justus’ Church was constructed around the year 1000 in Romanesque style, and stands between the walls, the parish church and the gate to the town, while the Museum of Sacred Art hosts a number of important paintings, sculptures and paraments.
Volterra is in central Tuscany, a little south of San Gimignano, and while it’s overshadowed by its neighbor, as one of Tuscany’s most evocative hilltop towns, it really shouldn’t be missed. Volterra was one of the 12 Etruscan power centers between the 4th and 6th centuries BC, and its medieval center remains one of Italy’s best-preserved. Visitors can see unique remains that date back to Etruscan and Roman times, including a Roman theater built in the 1st century that sits just outside the city walls, as well as multiple medieval and renaissance treasures. Stroll its many lanes and stop to marvel at the 13th century Palazzo dei Priori, the oldest town hall in all of Tuscany, be wowed by the ceiling in the Duomo and stop by one of the many alabaster shops, with the hand-made products considered the town’s crown jewel. Like a museum of beautiful works of art, you can admire boxes, bowls, sculptures and other pieces made by artisans that still follow the traditional methods of working alabaster that has been passed down through generations.
Collodi is best known as the birthplace of Pinocchio, a figure created by Italian author Carlo Collodi in his best-seller, The Adventures of Pinocchio. You can even visit the Monumental Park of Pinocchio to see fascinating sculptures of the novel’s characters. The park boasts a large, beautifully-kept garden, along with Pinocchio, the Fairy with Turquoise Hair, the Cat, the Fox and many other figures you might recall from the book. The Garzoni Garden, considered one of Italy’s most stunning, is located just a short walk away and features well-manicured walkways, fountains, statues and flower beds. The adjacent Butterfly House is a large greenhouse with an exotic garden populated by thousands of colorful tropical butterflies.
San Gimignano, known as the City of Beautiful Towers, is a classic medieval walled hill town renowned for its 14 surviving medieval towers which create a magnificent skyline visible from the surrounding countryside. Its Duomo is considered a must-visit, offering the chance to admire frescoes that recount tales from the New and Old Testaments painted by 14th-century Sienese school artists, as well as the exceptional Renaissance jewel, the Chapel of Santa Fina. You should also be sure to check out the Pinacoteca, Palazzo Comunale and Torre Grossa. Torre Grossa is the tallest tower in the city, and from there you can take in a panoramic view of San Gimignano and the surrounding landscape. In addition to the history and gorgeous vistas, you should also come to sample the dry white Vernaccia wine that’s local to the area.
Surrounded by the Apuan Alps and the Apennines, Garfagnana is considered to be one of Italy’s most outstanding areas of beauty – and it’s also one of its less-discovered destinations, affected little by tourism. There are no big cities or upscale restaurants in this rugged, mountainous corner of northern Tuscany, but adventurers will appreciate the opportunity for a multitude of outdoor activities like biking, hiking, caving and rock climbing, along with the many charming villages that boast architectural treasures and enchanting works of art.
One of the most popular hikes in the area is the day hike to Monte Forato in the Apuan Alps, because of its natural arch which joins twin peaks, creating a hole that can be seen from the valley. The moderately challenging hike starts in the little village of Fornovolasco and follows the Turrite stream in a continuous climb up Foce di Petrociana pass. A short but steep climb will then bring you to the crest, which you’ll follow to reach the great stone arch.
The Val D’Orcia is an enchanting land of rolling hills, secluded hilltop towns, medieval castles, charming farmhouses, rows of vineyards, olive groves and avenues of cypress trees. It’s bordered to the north by the hill towns of Montepulciano and Pienza, while Montalcino lies just to the west. The area is protected as a natural and cultural park, and it’s also been recognized as a UNESCO World Heritage Site. After a day exploring museums, ancient castles and abbeys, you can enjoy soaking in one of the many thermal baths found in the area, like Bagno Vignoni with its series of ancient buildings surrounding a Renaissance pool with gorgeous arcades, and relaxing with a glass of the region’s famous wines, like Rosso Orcia and Brunello di Montalcino.
This medieval village with Etruscan origins is a haven on Tuscan hilltops. One of the region’s most compelling places, while it’s not quite undiscovered, it’s remained below the radar enough to prevent it from becoming overloaded with tourists. It has one of the most intact historic centers of any other town in Italy. Other than a few minor repairs, no major building work has taken place since the late 16th century. The main street winds up to Piazza Grande, which sits at the town’s peak, with green-shuttered medieval houses rising like cliffs on either side. Its main sights include the Romanesque-style town hall, several churches, the Sanctuary of the Madonna di San Biagio and the piazza. Montepulciano is renowned for its production of food, including lentils, Pici pasta and pork, as well as for its famous Vino Nobile red wine that’s a must-try while you’re here.
Located in the countryside of Siena, Monteriggioni is another must-visit Tuscan hill town that features remarkably preserved fortified walls that rise nearly 33 feet, as well as 14 towers that can be seen from afar. The castle was built by the Sienese in the early 13th century for defensive purposes, with its strategic location atop the hill allowing it to be on the lookout for approaching enemies. It became especially famous after being mentioned by Dante Alighieri in his most famous work, The Divine Comedy.
One of the best times to be here is in late July when the village hosts the Medieval Festival of Monteriggioni, one of the most spectacular medieval festivals in the region. The town goes back in time to the Middle Ages, with the streets filling up with people in period costumes, craftsmen and cavaliers, while music, theater, duels, storytellers and more offer outstanding entertainment while recreating what life in the castle may have been like.
This town located in the beautiful Val d’Orcia mentioned previously, is well-deserving of a mention on its own. A fabulous gem, it’s a UNESCO World Heritage Site as well as the spot where Zeffirelli filmed “Rome and Juliet.” Pope Pius II, for whom the town is named after, was born here. After becoming pope in 1458, he had it completely rebuilt as the perfect Renaissance town, and it’s changed very little since complete with awe-inspiring architecture and a harmonious layout. It’s a superb example of Renaissance architecture, with its Piazza Pio II serving as the town center on which all of its main monuments are located.
The piazza is flanked by the cathedral and three palaces: one for the government, one for the bishop and one for Pope Pius II. The cathedral was built on the remains of the Romanesque church of St. Mary and houses works of art, including five altar paintings from the Sienese School. The Palazzo Piccolomini, considered the second most important building in Pienza, is Rossellino’s masterpiece, while Palazzo Borgia is home to the Diocesan Museum which features religious artifacts and local textile works.
Barga is a tiny hill town set between Lucca and the Garfagnana mountains in the Media Valle (Middle Valley) of Serchio River. It’s considered Italy’s “most Scottish town,” due to the many locals that left for Scotland in the late 19th-century following the demise of the town’s silk industry. There they became successful street traders, selling gesso figures (plaster figurines) they were so skilled at making. Eventually, the wealth they made was brought back to Barga and used to construct the beautiful villas that now form the new area known as Il Giardino, located just outside the historic center.
Today, you’ll see a number of Scottish touches throughout Barga, including the annual fish and chip festival it hosts, and you’re even likely to be greeted in a Glaswegian accent in the restaurants and bars. Its main attractions are the Romanesque Duomo, the Renaissance buildings and the theater.
The medieval hill town of Pitigliano is situated in a dramatic position nearly 1,000 feet high above a plain. The natural defensive position that is further enhanced by the presence of fortified walls, and it’s an extraordinary sight to see when approaching. It’s not uncommon for jaws to literally drop as this remarkable village comes into view, with its tall medieval houses squeezed together along a rocky spur. Sometimes referred to as Little Jerusalem due to the presence of Jewish in its past, today, you can admire the restored synagogue as well as attractions like the great Palace of the Orsini, which can be seen in the Piazza della Repubblica. It stands as a veritable fortress and is built in a variety of styles, particularly medieval and renaissance. There are also some interesting walks, including one that will bring you to the bottom of the rocky outcrop where you get a new perspective on the town and see ancient Etruscan caves and tombs that were carved into the soft rock along the ancient Etruscan ‘sacred ways’ known as Vie Cave.
Located along the northern Tuscany coast between the Marinas of Ronci and Pietrasanta, this chic seaside resort is often referred to as the Tuscan Riviera. It’s long been a popular summer getaway for the wealthy and well-connected from Florence. Forte Dei Marmi was one of the very first beach resorts in the country, started around the turn of the 20th century. It became an instant favorite with royalty and the rich “beautiful people” who still flock here. Private beach areas, which can be entered for a price, have loungers, umbrellas, cafes and restaurants. One beach, in particular, Santa Maria Beach, was singled out at one point as one of the top 10 topless beaches in the world. The promenade is a lovely place for an evening stroll and people-watching, while its famous weekly market, is a Wednesday market that’s centered around designer clothing – it’s considered the place to go to get reproductions of expensive designer clothes at a bargain price.
Arezzo is one of Tuscany’s wealthiest cities, thanks to its tradition in goldsmithery. The city has ancient origins verified by stone tools and the Man of Elm from the Paleolithic era that was discovered here. Its well-preserved center boasts lots of monuments, museums and churches, with the Church of San Francesco arguably the most famous. It showcases an amazing early Renaissance fresco cycle by Piero della Francesca that depicts the Legend of the True Cross. Uphill at the Piazza Grande, you’ll find the Loggiato Vasariano and Palazzo delle Logge. Other highlights include the Medicean Fortress, the cathedral dedicated to San Donato and a Roman amphitheater. Be sure to make time for a stop into Museum of Medieval and Modern Art as well, housed in the Bruni-Ciocchi del Monte Palace, which Donato, son of humanist Leonardo Bruni, had built during the middle of the 15th century.
This famous medieval village is a must see for those heading to Arezzo and the surrounding area. It’s mostly known for the famous battle of Anghiari, which was fought between the army of Florence and Milan in 1440, but it’s also included in the “most beautiful villages in Italy” list. Set on a hill made of stone and built up over the centuries from the Tiber River, it’s enclosed in huge 13th-century walls that preserve the original, ancient atmosphere. Wander around its narrow streets, and you’ll noticed a decided air of proud history. The stone houses overlooking the streets have little windows, wooden shutters and doors, and while some are damaged, it only adds to the character of the village. Many of the home’s entrances and balconies are decorated with flowers, further enhancing its allure.
Lucca is another fantastic walled city with one of the country’s best-preserved walls. Atop the walls, you’ll find walking and biking paths as well as gardens, so you can walk completely around the city center on top of the wall. There are nearly two-and-a-half miles of walls, with six gates and 11 bastions. Lucca also has a number of well-preserved towers – and from them, if you climb to the top, you’ll enjoy outstanding views of the city. San Michele Church, built between the 11th and 14th centuries, sits in the large square the was once the Roman Forum. Today, it’s a lively square lined with medieval buildings that host shops, cafes and homes. The Villa Giunigi National Museum, located within a 15th-century villa near the east wall, features local works of art and artifacts dating from prehistoric times through the 17th century.