With its lively piazzas, Gothic monuments, and well-preserved city walls, the Siena Historic Center (Siena Centro Storico) is one of Italy’s most impressive medieval cityscapes. A UNESCO World Heritage Site since 1995, the old town is an open-air museum of striking historical architecture, including the Piazza del Campo and the Gothic cathedral.
Facing the Florence Cathedral (aka the Duomo) and flaunting matching green and white marble, the Baptistery of St. John (Battistero di San Giovanni) is one of the oldest structures in the Tuscan capital. The octagonal building is thought to have been built in the fourth century, with artistic masterpieces added over time. These include Byzantine-style mosaics covering the ceiling and Lorenzo Ghiberti’s intricate bronze entry doors, which an impressed Michelangelo declared the “Gates of Paradise.”
Visitors flock to Pisa’s famous leaning tower, which is part of a magnificent cathedral complex centered around the 17th-century Duomo and adjacent baptistery. A splendid example of Pisan Romanesque architecture, the Duomo’s original and renovated elements include a splendid apse mosaic, ornate pulpit, golden coffered ceiling, and more.
Picturesque Monteriggioni is the quintessential Tuscan village, encircled by medieval walls and perched on a hilltop above a rolling expanse of olive groves and vineyards. Stroll through its postcard-perfect center of cobblestone piazzas, pretty churches, and Renaissance townhouses and enjoy the authentic atmosphere.
San Gimignano’s Collegiate Church of Santa Maria Assunta, known simply as the Duomo, is one of the most impressive sights in this Tuscan hill town’s UNESCO-listed historic center. Behind the church’s plain facade you'll find exquisite 14th- and 15th-century frescoes inside, remarkable for their bold colors and painstaking details.
Montalcino is known as the heart of Tuscany’s Brunello di Montalcino wine production, but oenophiles shouldn’t overlook this hill town’s spectacular Fortezza di Montalcino, an imposing 14th-century fortress set above the town’s medieval center with sweeping views from its watchtowers and an atmospheric wine shop.
Though Brunelleschi’s soaring cupola may be the most recognizable part of the Florence Duomo, the cathedral wouldn’t be complete without Giotto’s Bell Tower (Campanile di Giotto). Rising 278 feet (85 meters) above the rooftops of Florence, the Gothic tower is covered in multicolored marble, with impressive sculptures and bas-reliefs on its lower levels and a panoramic terrace on top—which you can reach by climbing 414 steps.
Florence’s Santa Croce Basilica has a grand piazza and an instantly recognizable neo-Gothic facade—but what’s on the inside is even more impressive. One of the most important churches in the city, the 13th-century basilica is a treasure trove of Renaissance artwork and history, with masterpieces by Brunelleschi, Donatello, and Giotto. It’s also the final resting place of luminaries, including Michelangelo, Galileo, and Machiavelli.
This Gothic church and museum has a long history. The site was once home to an oratory to the archangel Michael (San Michele, in Italian). In the Middle Ages, it was replaced by a grain market, with the upper floors serving as a storehouse to ward off famines. But Catholics still saw Orsanmichele as a holy site, attributing miracles to an image of the Madonna inside. It was eventually converted into a place of worship.
Perched on a hill in Tuscany’s unspoiled Val d’Orcia is Pienza, surrounded by the cypress trees and rolling hills for which the region is famed. A town without a train station in the middle of the countryside, Pienza isn’t the easiest place to reach. However, those who do make the effort to get there are rewarded with a pristine Renaissance town, city walls for panoramic views, and the town’s famous pecorino cheese.
The image of Michelangelo’s David—one of the world’s best-known works of art—is so ubiquitous in Florence that it’s become a symbol of Italy’s Renaissance capital. Carved between 1501 and 1504, then installed at the custom-built Accademia Gallery (Galleria dell’Accademia) in 1873, the sculptural masterpiece symbolizes the liberty of Florence and the beauty of the human form.
Dominated by the Basilica Santa Croce, the sweeping Piazza Santa Croce is one of the largest squares in Florence’s historic center. Created in grand style to accommodate more churchgoers in medieval times, the square now serves as the pitch of the annual calcio storico—the spectacle of a combative (and even brutal) 15th-century game that suggests soccer, rugby, and wrestling, which takes place in the square every June.
The historic and happening Oltrarno—which sits just across the Arno River from central Florence—is one of the city’s most dynamic neighborhoods. It’s home to Pitti Palace (Palazzo Pitti) and Boboli Gardens (Giardino di Boboli), as well as Brunelleschi’s Santo Spirito Basilica and Santa Maria del Carmine’s Brancacci Chapel, frescoed by Filippino Lippi. Panoramic Piazzale Michelangelo perches just above, and lively artisan workshops, restaurants, and wine bars line the district’s narrow lanes.
Pisa’s Leaning Tower may be more famous, but the nearby baptistery (battistero) is equally captivating. Clad in white marble with intricately carved rows of Romanesque and Gothic arches and a cupcake dome, the baptistery is one of the essential sights in the city’s UNESCO-listed cathedral (duomo) complex.
Pass through the arched entrance of Florence’s stately Pitti Palace (Palazzo Pitti) and into the serenity of the sweeping Boboli Gardens, once the private playground of the Medici family. Dating back to the 16th century, the Italian gardens are a veritable open-air museum, covering an enormous stretch of cypress-studded hillside with ornate fountains, grottoes, and sculptures from ancient Rome through the 17th century.
It may not have an ornate marble facade like the neighboring Duomo, but the Basilica of San Lorenzo (Basilica di San Lorenzo) is one of the oldest and most important Renaissance churches in Florence. Commissioned by Cosimo the Elder—patriarch of the Medici dynasty—the church is home to magnificent sculptural and architectural works by Michelangelo, including the Medici Chapels and Laurentian Library.
Florence’s 19th-century Central Market (Mercato Centrale) has all the gastronomic variety you’d expect from the city’s largest covered market. Some Florentines still do their daily shopping on the ground floor—a great place to sample Tuscan cheeses and Chianti wine, then stock up on gourmet goods to take home. Upstairs, a modern food court offers everything from fresh pasta with truffles to burgers made with local Chianina beef, as well as a cooking school.
For a glimpse into the sumptuous life of Florence’s powerful Medici family, look no further than the Medici Riccardi Palace (Palazzo Medici Riccardi). Designed by the architect Michelozzo for Cosimo the Elder, the 15th-century palace is now a museum displaying masterpieces collected by members of the Medici and Riccardi families. Get a feel for the palace’s Renaissance glory with Filippo Lippi’s Madonna With Child, then see its baroque era in the lavishly frescoed Mirror Gallery.
Art enthusiasts are drawn to the Lucca Cathedral for its paintings by masters like Ghirlandaio and Tintoretto; architecture aficionados appreciate the church’s unique mix of Gothic and Romanesque styles. But the Duomo di Lucca is revered by locals primarily as home to the city’s most precious relic: the Holy Face of Lucca (Volto Santo.
The Medici Chapels are the burial place of several members of Florence’s most powerful family, and they’re decorated with all the Renaissance bells and whistles you’d expect. Part of the Basilica of San Lorenzo, the marble-filled mausoleum’s New Sacristy houses some of Michelangelo’s best-known masterpieces: the reclining figures of Night,Day,Dawn, and Dusk, expertly sculpted for the tombs of Medici dukes.
With so many cultural treasures in Florence, San Miniato al Monte, perched high up on a hilltop outside the city, would be easy to skip. However, this handsome church is considered among the finest examples of Romanesque architecture in Tuscany. Its intricate exterior stonework, 13th-century apse mosaic, and sweeping views over Florence make the effort to reach it worthwhile. Be sure to visit the church’s crypt, decorated with frescoes by Taddeo Gaddi.
If one structure embodies the resilience of Renaissance humanism, it is this 16th-century bridge in the heart of Florence. All but destroyed by retreating Nazis during World War II, the Ponte Santa Trinita was painstakingly rebuilt with original stones salvaged from the Arno River. Ponte Santa Trinita is often overshadowed by Ponte Vecchio, just downriver; however, its elegant elliptical arches and dramatic history make it one of Florence’s most beloved landmarks.
Piercing the sky above Siena, the soaring Mangia Tower (Torre del Mangia) is a notable feature of the medieval town’s skyline. It affords views across the rooftops to the surrounding Tuscan countryside. Climb the hundreds of steps to the top, or admire this imposing bell tower in Piazza del Campo from below.
One of the most historically important churches in Siena, the Basilica of San Domenico (Basilica di San Domenico) is famous for another saint: the city’s own Saint Catherine. It was here that Catherine took her vows in 1363 at the age of 15, and the church holds a number of her relics, including her head, thumb, and whip used for self-flagellation.
The Mall is Tuscany’s premiere luxury outlet shopping area, where goods made by dozens of high-fashion designer brands are sold at discounted prices. Come for gorgeous clothing, shoes, and accessories from world-famous fashion houses like Armani, Burberry, Stella McCartney, Fendi, Versace, Valentino, Balenciaga, Yves Saint Laurent, and many more.
A literal walk through history, the Vasari Corridor (Corridoio Vasariano) was the Medici family’s private passageway through central Florence. Giorgio Vasari designed the elevated, covered walkway over the Arno River in the 16th century, allowing the Grand Dukes to discreetly get from work at the Palazzo Vecchio to their home in the Pitti Palace. You can follow in their footsteps today—and admire the views from the corridor’s windows atop the Ponte Vecchio.
One of the most important squares in Lucca’s medieval center, Piazza dell'Anfiteatro was built on the site of a Roman amphitheater, from which it got its unique oval shape. Today, the piazza is the vibrant heart of the city’s historic center, and the perfect spot to enjoy the friendly vibe of this picturesque Tuscan town.
This glorious Renaissance church is set below the hill town of Montepulciano, and its soaring dome and pyramid-topped bell tower turn heads from miles away. Designed in the 16th century by Antonio da Sangallo (Sangallo il Vecchio), the Temple of San Biagio (Tempio di San Biagio) has an elegant travertine exterior and airy pastel interior.
Palazzo Strozzi once was a lavish private residence, belonging to the aristocratic Strozzi family in the 15th century. After a makeover, it opened to the public in 1940 as Florence’s largest exhibition space. Today, the trendy museum and cultural center is still going strong, regularly hosting blockbuster shows and retrospectives from contemporary art world A-listers such as Tracey Emin, Anish Kapoor, and Damien Hirst.
No visit to Lucca’s medieval center is complete without a passeggiata (stroll along Via Fillungo, the main thoroughfare stretching through the heart of the old town from the ancient city gate of Porta dei Borghi to Canto d'Arco. Lined with bustling shops and cafés, this street is ideal for experiencing Lucca’s lively atmosphere.
