24 Ultimate Things to Do in Florence and Tuscany

Sandro Botticelli’s Venus floats on a scallop shell on the sea in Florence’s Galleria degli Uffizi. The famous 1400s painting shows the golden-haired goddess of love blown to shore by the wind god. You may have seen it countless times on postcards, but you’ll be in awe as you stand before the original.

David, 17 feet of Carrara marble carved by Michelangelo in the 1500s, could be the most famous man in the world. See him “in the flesh,” poised before his battle with Goliath at Florence’s Galleria dell’Accademia. It’s best to buy tickets in advance because David is one of the most popular attractions in the city, and the line to enter the museum often stretches for several blocks. If you don’t want to wait, you can see copies of the sculpture in two other spots: Piazzale Michelangelo and in front of Palazzo Vecchio in Piazza della Signoria.

The terracotta-tiled dome of Cattedrale di Santa Maria del Fiore stands as a symbol of Florence and Filippo Brunelleschi’s 1400s engineering innovation. The cupola, called Il Duomo, is two domes connected by an intricate interior support system, while the exterior is a design marvel of structurally supportive tiled herringbones. Climb 463 steps through narrow passageways that were used during the dome’s construction and out to the terrace surrounding its lantern for incredible views of Firenze and the surrounding hills.

If you are searching for green in Florence, head to the 111-acre manicured and sculptured grounds of Palazzo Pitti (which was once home to the Medici, one of the city’s most powerful and successful dynasties) at the Giardino di Boboli. (Flowers are not the draw here—if you want blooms go to Giardino delle Rose.) Instead, appreciate the vastness and explore vine-covered pergolas, stone paths leading to hidden bubbling fountains, and grand staircases decorated with outdoor sculptures. It’s an ideal picnic spot and from certain vantage points you’ll have skyline views.

After David and Il Duomo, Ponte Vecchio may be the most well-known attraction in Florence. Rather than walking across the “Old Bridge” (literally the oldest of Florence’s six Arno-spanning bridges, dating from the 1300s), which is overcrowded and lined with jewelry shops, gaze at the bridge from a distance. It’s best to stand on Ponte Santa Trinita, or anywhere on the walkway along the Arno as the sun is setting, to see the sky changing hues, and lights from the bridge reflecting off the placid river.

The tradition of leather craftsmanship in Florence dates back to the Middle Ages. If you want to buy high quality, this is the city for it. There is such an abundance of stores selling handbags, shoes, jackets, wallets, and gloves, that shopping here can be overwhelming. While it’s tempting to go to the bustling Mercato di San Lorenzo or Mercato Nuovo, you’ll find a better shopping experience (and quality), elsewhere. For gloves, try Madova; for leather jackets, Benheart; and for bags and small leather goods, Scuola del Cuoio—Florence’s leather school. Scuola del Cuoio has been in operation since the 1950s and prides itself on products that are “fatto a mano” (handmade).

Bistecca alla fiorentina is a common menu item at traditional Florentine restaurants. This a huge (typically at least 2½ pound) T-bone steak, cut from Chianina cows, which are bred in Tuscany’s Val di Chiana valley south of Florence. The usual preparation is cooked rare (do not ask for it well-done as you’ll be told this is impossible), on a wooden grill, and side dishes (contorni) like roasted potatoes, or grilled vegetables, are ordered separately. Try Buca Lapi near Santa Maria Novella, or Alla Vecchia Bettola in the Oltrarno.

You can’t leave Florence without seeing the sunset over its terracotta skyline. Many people will advise you to head to Piazzale Michelangelo for the best views, and while this is an incredible lookout point, it’s so crowded at sunset hour that you may not see much. Instead, climb the hill to San Miniato al Monte to the Romanesque basilica’s courtyard where the views are as spectacular and fewer people are vying for the perfect photo-op.

The Oltrarno, or “other side of the Arno,” was one of Florence’s original neighborhoods at the city’s founding in the 1st century B.C. This has traditionally been home to Florence’s working class, filled with leather makers, jewelers, artists, and other craftspeople. Some of that character remains today. Visit Palazzo Pitti in the Oltarno, then spend some time walking down narrow side streets and lingering in cafés or wine bars (particularly around Piazza Santo Spirito and Piazza del Carmine). You can also visit Cappella Brancacci in Santa Maria del Carmine to see a Renaissance master fresco by Masaccio, Masolino, and Filippino Lippi.

Wild boars, or cinghiale, roam freely throughout Tuscany and are a symbol of the region. But there’s more to the bronze wild boar outside Mercato Nuovo than that. Il Porcellino (“the piglet”) is said to bestow good luck on people who touch his snout. He’s also a fountain, and if you throw a coin to him and it falls through the grates, it means you are destined to return to Florence. If it bounces out, legend says you might never see the city again.

In the northeast hills above Florence is the town of Fiesole, where you can explore Roman baths, a Roman amphitheater, and Etruscan walls. The church of San Francesco has a small park overlooking Florence. The roads leading to Fiesole are lined with vine-covered walls and Tuscan villas. Nearby is Monte Cerci, where Leonardo da Vinci’s flying machine is said to have been tested.

During the Middle Ages, Tuscan hill town San Gimignano, 25 miles northwest of Siena, was one of the most popular stopping points for pilgrims traveling to and from Rome on the Via Francigena (road to France). From the 1100s to 1200s patrician families who controlled the town built more than 70 towers to highlight their status (the taller it was, the more powerful they appeared to be)—some were as tall as 164 feet. Today, 14 of the Medieval high-rises remain, and you can climb them for sweeping Tuscan hillside views.

How is it not falling over? The Leaning Tower of Pisa (Torre Pendente) is the most popular site in Pisa and one of the most famous in Tuscany. It is said to have begun its famous incline during construction in the 1100s and it has continued ever since, with various buttressing techniques used to ensure that the tower does not actually topple over. Buy tickets in advance to climb it, especially during high tourist season.

The city of Lucca, 48 miles west of Florence, is surrounded by ramparts built in the 16th and 17th centuries to protect the city’s residents. Today it can be enjoyed as a park. This elevated, tree-lined walkway is the site of what for some is a daily ritual of passeggiata delle mura (“walk along the walls”). You’ll also see people running, biking, or just admiring the several sculptures around the park.

Legend says that the Roman god Saturn, irritated by the behavior he saw on earth, threw a thunderbolt down, creating the bubbling mineral-rich waters of Saturnia. Etruscans, Romans, and even pre-Greeks lived in this Tuscan town frequenting its thermal waters, and today one of its main draws is still Terme di Saturnia. The springs at this spa and resort are kept at 99.5 degrees Fahrenheit (the temperature of the amniotic fluid), for ultimate relaxation.

The central piazza is a main feature of any Italian town or city, and Siena’s Piazza del Campo is one the most distinctive you can find. Il Campo’s sloping expanse is divided into nine quadrants, which represented the nine governors who ruled Siena in the early 14th century during its political heyday. As the focal point of city life, Il Campo was (and still is) the place of Palio di Siena, where 10 horse racers representing 10 of the city’s neighborhoods compete in July and August. Any time of year, Il Campo is an ideal spot for people-watching while sitting on the cobblestone piazza like a local, or in one of the restaurants and cafés around its perimeter.

At the end of cena (dinner) in Tuscany, it is customary for your waiter to ask if you’d like a coffee or dolce. To follow local tradition, order cantucci with vin santo for your dolce. Cantucci are crunchy, twice-baked, oblong-shaped almond biscuits with origins in the city of Prato (about 11 miles west of Florence). They are a bit too crunchy to eat on their own (though not impossible), but when dipped in sweet Vin Santo wine, the consistency becomes perfect.

If the main piazza of Arezzo looks familiar, it could be because scenes in Roberto Benigni’s film Life is Beautiful were shot here. The city, about 50 miles southeast of Florence, is also the birthplace of art historian Giorgio Vasari (and you can visit his house), and Renaissance scholar and poet, Francesco Petrarca. You won’t want to miss seeing Piero della Francesca’s Legend of the True Cross fresco cycle in the Basilica di San Francesco’s Capella Bacci.

The Chianti region encompasses the provinces of Florence, Arezzo, Pisa, Prato, Pistoa, and Siena, and it’s also one of Italy’s best-known wines. With 17,000 acres of vineyards, sipping your way through Chianti is a fine way to spend a day (or longer) and learn the difference between this full-bodied Sangiovese red’s Chianti, Chianti Classico, Chianti Classico Riserva, and Chianti Rufina.

Assisi, birthplace of Saint Francis—founder of the Franciscan religious order—in Umbria, has been a Christian pilgrimage site since he was buried there in the 1300s. The town was declared a UNESCO World Heritage site in 2000 for its Basilica di San Francesco and the tomb of St Francis. In the basilica, you can see celebrated works of Italian Medieval art. In the Basilica Superiore (upper church), Giotto painted the Legend of St. Francis during the late 1200s, and in Basilica Inferiore (lower church), Cimabue, Simone Martini, and Pietro Lorenzetti decorated the walls with Franciscan themes.

By the end of the 1500s, the Medici, Florence’s most powerful family, had more than 16 villas across Tuscany. One of them was built at Il Parco di Pratolino, and although the villa located about a 25-minute drive north of Florence is no longer standing (Villa Demidoff replaced it in the 1800s), you can still see art that were created for it, like Flemish sculptor Giambologna’s Fontana dell’Appenino (Fountain of the Appenines). You can picnic at the park (open from April to October), or eat lunch or dinner at Zocchi—a traditional Tuscan restaurant that has been in business since 1783 and has a terrace with countryside views.

Between Tuscany and Emilia-Romagna are more than 400 miles of trails in the Foreste Casentinesi. The forest’s natural beauty is unmistakable, with waterfalls, sweeping vistas, and soaring eagles, and its history adds to the wonder. It is said that wood used to build Florence’s Duomo came from this forest. Throughout the trails you’ll find churches like La Verna Santuario Francescano, where you can stay for the night among a community of Franciscan friars.

If you are exploring the Tuscan hills, you might want to add Volterra, southwest of Florence and San Gimignano, to your list. Volterra was inhabited by Etruscans and has the walls to prove it. Visit Palazzo dei Priori, which is considered the oldest town hall in Tuscany (it’s said that the Palazzo Vecchio in Florence was modeled after it), with its central tower built in the 1200s. The Museo Etrusco Guarnacci has a collection of funerary urns and other Etruscan relics that are worth exploring, as is the town’s Roman theater from the 1st century BC.

Soak up views of rolling hills, sunflowers, and Cypress groves in what might be considered one of the most scenic areas of Tuscany. The Val d’Orcia (Orcia Valley) spans south from Siena to Grosseto and gets its name from the river Orcia. You could spend a day exploring the hill town Montalcino and sipping wine from its Brunello vineyards. Or, taste distinctive Pecorino cheeses in Pienza at Podere Il Casale or Fattoria Pianporcino. If you want ultimate relaxation, try the Piscina val di Sole public hot springs in Bagno Vignoni.