Things to Do in Tuscany

David Cicconi

From Montepulciano, the most impressive Tuscan hill town, head to Pienza (the most romantic hill town). Continue on to San Quirico though the bucolic... Read More

Guarded by vast sandstone cliffs and groves of dark cypresses, this monumental monastic complex, built all of brick, is one of the world’s most serene... Read More

In absolute contrast to the elaborate three cathedrals above, this serene Romanesque church of travertine and alabaster—set below hills of olive trees... Read More

Built of dramatically white travertine and alabaster and standing below green hills, this elegant Romanesque church gained fame when, in 781,... Read More

Carved horse heads and Roman gods crowd the studio’s shelves. But collector-worthy contemporary pieces, such as transparent spiral candleholders... Read More

The most visually impressive and romantic area of Tuscany is the Val D’Orcia: the valley of the Orcia River. It was declared a UNESCO World Heritage... Read More

Brother and sister Alessio and Cecilia Tessieri launched the chocolate company Amedei in La Rotta 18 years ago. Alessio sources the cocoa beans, while... Read More

Silk items may not be the most well-known Tuscan product, but Lucca’s and Florence’s wealth (which enabled the artistic explosion of the Renaissance)... Read More

The most memorable of Tuscan beaches—dramatic coves, pebble shores with crystalline waters, and remarkable windswept vegetation. They are often isolated... Read More

The town’s mayor, Fabio Tinti, loves the area’s Casentino wool overcoats, sold here. Read More

Sniff out a whole world—licorice, citrus, tobacco—in slow twirlings of fabled Avignonesi vin santo on the winery’s property... Read More

B&M is Florence’s answer to a full-service English language indie bookstore. The shelves here are piled with gorgeous books on art and design,... Read More

This jewel of a hamlet built around a Roman vasca, or community baths. There are two main places here for partaking in the thermal waters—the Hotel... Read More

Just off the Piazza del Duomo in the medieval town of San Gimignano, near the cathedral’s bell tower, is the stone storefront of Balducci Ceramics. Part... Read More

The cooking school at the elegant Belmond Villa San Michele Hotel offers two kinds of culinary instruction: group cooking classes using local and... Read More

This beautiful, coastal region south of Pisa is best known for the stellar success (and astronomical prices) of its Ornellaia and Sassicaia... Read More

This is as different from the rest of Tuscany as can be. Start from the many-towered town of San Gimignano (it had fifty-two towers in its twelfth... Read More

Beneath the vaulted showrooms of Busatti sit the original looms that the Busatti-Sassolinis have used to make linens since 1842. Traditional striped... Read More

Stop in at Caffé della Posta, on the main square, to try one of Bolgheri’s reds: first produced in the 1980’s, these wines now rival... Read More

Parco Uccellina, is a vast protected nature preserve on the most dramatic and pristine twenty-mile stretch of Tuscan coast. South of the Ombrone River’s... Read More

This is the best art festival in Tuscany. For the past thirty-eight years, the summer evenings and nights of Montepulciano have come alive with song,... Read More

The jewelry shop is divine with a 17th-century safe, bright frescoes, and its outstanding collection of silver, watches, and unusual objects such as... Read More

Carlo Fagiani's leather workshop, specialising in shoes, handbags, belts, wallets and jackets, is one of the best in Tuscany. He makes shoes to... Read More

This ceramics shop is a home-goods and kitchenware-lover’s paradise in the historic center of Siena. Wall-to-wall mugs, plates, bowls, teapots, and more... Read More

In this classic Italian spa town, you can soak, veg out, eat like a king, then shop until you drop in classy boutiques. There are more than a dozen spa... Read More

This is the land of one-hill views, meaning the hilly terrain lets you see only the hill before you. Wonderful for gazing close up at vineyards, ruins,... Read More

The oldest and most respected part of the much larger Chianti region, this series of hills lies between Florence and Siena. The wines produced here are... Read More

A few miles from this town’s small but densely packed Etruscan museum is the perfectly preserved, deep, and complex Tomb of the Monkey.  Discovered... Read More

A wild, romantic place to watch a Tuscan sunset. This tiny town atop limestone cliffs overlooks the spectacular Abbey of Monte Oliveto, and layers of... Read More

Years as agent: 21. Other specialty: Italian countryside. Consulting fee: From $300. Read More

On the grounds of the 800-year-old estate you'll find Etruscan ruins dating to 600 B.C., a 12th-century fortress, a Gothic chapel, and an amazing... Read More

On a remarkable bluff overlooking the sea, this enormous, ancient walled town is not to be missed. The architecture incorporates huge stones that have... Read More

While admittedly the single most impressive Roman structure in Tuscany is the theater of Fiesole 5 miles north of Florence that’s still in use today,... Read More

Under the tutelage of chefs Elena Mattei and Lapo Magni—a mother-and-son team— you’ll learn to cook the sorts of dishes that Tuscan grandmas have been... Read More

Okay, get out your wallets! You’ll be thankful that you did. On a bank of the Arno River adjacent to the Ponte Vecchio is Davide Cerasi, specializing in... Read More

De Bondt concocts award-winning chocolates with everything from rose oil to fennel plus gives tasting tours. Read More

This artisanal chocolate shop near the Arno River in Pisa offers an array of luxurious chocolates, truffles, nut clusters, chocolate bars, and other... Read More

Sienese fashion tends to be less flamboyant than that of Florence, leaning toward a timeless elegance. So the owners of Dolci Trame, Elisabetta Terli... Read More

An absolute must. This magnificent, much-photographed cathedral complex includes a majestic dome, a freestanding graceful bell tower and a spectacularly... Read More

This is a twofer. Not only does a visit here let you see the enormous cathedral, made from slabs of sensuously pale marble set in an open green field... Read More

A marvel of alternating layers of pale and dark green marble, this cathedral has a façade—covered with opulent carvings and figures—that is worth its... Read More

This is an international company that coddles you through a six-day, five-night bike tour of the most gorgeous parts of Tuscany. The level is active,... Read More

You’ll amaze your friends at your next dinner party if you’ve spent a session with the chefs at Ecco La Cucina. The classes offered are either single... Read More

Beneath the unassuming storefront are block-long subterranean caves filled with unexpected finds, such as 1970’s California Cabernets. The vaults... Read More

Okay, so this is no cerebral event but colorful and noisy and fun. Dating back centuries of Easter Sunday mornings, a street procession of flag throwers... Read More

The pre-Romanesque Farneta Abbey now doubles as a chic spot for weddings and a museum showcasing the wealth of local Roman-era artifacts from the church... Read More

The shop makes Tuscany's most exclusive, sought-after cheeses. Read More

Strips of sand—about 4 miles long each—and sand dunes and pine forests that connect the mainland to the Argentario Peninsula. Partially wild, with some... Read More

The ancient Etruscan city of Arezzo is home to fabulous monuments and art museums; it’s also where this astounding flea market is held on the first... Read More

This store is a unique take on fashion: a combination of quality, elegance, and ethics. They feature rising designers, and dedicated craftsmen of small... Read More

To fill your eyes with wonder made by man, there is simply no Tuscan place like Florence.  It is of course in almost every church and palazzo you... Read More

At the foot of the Apuan Alps, lies Tuscany’s most famous beach town. Its stellar visitors go back to Thomas Mann, Henry Moore, and Visconti. Its villas... Read More

Siena’s large outdoor market runs every Wednesday outside the city’s massive fortress, Fortezza Medicea. You can find well-priced designer clothes here,... Read More

Michelangelo’s Slaves, which seem to be trying to erupt form the coarse marble encasing them, are themselves worth a visit here. But of course, his... Read More

This contemporary gallery showcases Tuscan artist Sandro Chia and avant-garde duo Christo and Jeanne-Claude. Read More

Really a fortress, this sprawling 11th-century ridge-top ruin, set among dark hills, will ignite the imagination. It will have to, for there is not much... Read More

Best flavors: ginger, pumpkin, and saffron. Read More

Set in the San Martino quarter of Pisa, this garden inside the walls of a medieval fortress provides a wonderful break from more touristy activities in... Read More

Warning! If you have a shoe fetish, do not go within a mile of Goccia Shoes. If you do, its vortex will suck you in, the quality and design of their... Read More

Treat yourself and stay overnight at Castello Ripa D’Orcia (very reasonable with good food) and start an unforgettable hike from here. From Ripa D’Orcia... Read More

A company started ten years ago by passionate bike racer Marco Vignoli, I Bike Tuscany offers tours around Florence and the Tuscan hillside but with a... Read More

Choose from over 450 wines and from a seemingly endless selection of whiskies to taste at the restored Renaissance building. The wine bar takes its name... Read More

Twice each summer, July 2nd and August 16th, Siena undergoes a miraculous transformation. The town is festooned in medieval splendor of the seventeen... Read More

This sparsely inhabited island, population 1,400, is a place of easy day hikes with breathtaking views, punctuated by good eating. Isola del Giglio ... Read More

One of Tuscany’s true hidden treasures, this stupendous granite island off the Tuscan coast is home to just a handful of wine growers. They produce... Read More

This fancy foods market in the center of Lucca stocks many local, high-quality cooking ingredients at affordable prices. You can bring back herbs and... Read More

This modern Italian bookstore chain is probably the closest you’ll find to the expansive, brightly lit Borders (R.I.P.) experience in Tuscany. There are... Read More

An Italian department store (with roots in Milan and an outpost in Florence), La Rinascente is Florence’s answer to Macy’s, where you can find... Read More

Stark and haunting, this enormous landscape sculpture is possibly the most dramatic and silent in all of Tuscany. From Siena, take a quick road to... Read More

Tucked away on a steep street in the medieval hill town of Montepulciano, Legatoria Koine specializes in unique handmade leather-bound journals, diaries... Read More

This cheerful little bookshop off the Sieve River in Pontassieve—a small town outside of Florence—features a mix of contemporary literature, most of it... Read More

This gorgeous bookshop is nestled in a gorgeous location: right in Siena’s Piazza del Campo. The historic two-story space offers an English books... Read More

Since 1688, every 16th and 17th of June, Pisa stops and celebrates. The 16th is the eve of the city’s patron saint San Ranieri. Through the night, on... Read More

A long neglected charmer close to the sea, Massa Marittima features mysterious Etruscan ruins and the esteemed wine district of Bolgheri. The central... Read More

On the banks of the Arno River, leather tanners have been plying their trade since the 13th century. To tan their leather, they used to soak the skins... Read More

This is a country of wide, low hills and long, beautiful views. From our house, we see eleven layers of hills misting toward the sea. The region... Read More

When I first tasted Brunello di Montalcino, this region’s famous varietal, 30 years ago, I thought, “Oh, sweet mystery of life, at last I’ve found you!”... Read More

Montechiello is a respite for the soul, a secluded, ultra-romantic version of Pienza, and a perfectly restored village in a fifteenth-century landscape.... Read More

This winding medieval hill town is one of the most dramatic seen from any direction—yet the best view is from the very top. Its lovely Piazza Grande is... Read More

Grown mostly in clay, the Sangiovese grapes of this medieval hill town yield a robust, signature wine—Vino Nobile di Montepulciano—that’s perfect with... Read More

Vino Nobile di Montepulciano is one of Tuscany’s oldest wines dating back centuries. Vino Orcia is a fledgling appellation with interesting blends but... Read More

This vast fortressed village sits among the rolling hills of Siena. Its massive walls, surrounded by olive groves and vineyards, are dotted with... Read More

Start with these three museums in Siena; all three contain early works that predate Florence’s Renaissance. Among them are Duccio’s magnificent Maesta;... Read More

Michelangelo’s Pietà, which he carved at the age of 80, is the showstopper here; a more somber highlight is Donatello’s heartrending Mary Magdalene,... Read More

Similar to the Frick collection in New York City, Museo Stibbert is the acclaimed personal collection of Frederick Stibbert, which was donated to the... Read More

Housed in a former 15th-century convent, this museum contains the largest collection of frescoes by Fra Angelico, a Dominican monk whose religious works... Read More

Officina Della Pelle (a recent name change from Legatoria D’Arte) began 40 years ago by Antonio Capuozzo, a binder of precious antique volumes for the... Read More

A cool new gallery with works by emerging contemporary artists. Read More

A hydrangea-scented refuge abutting the walls, and the most geometrically lovely spot in Lucca, a copse of bamboo reaching up to the San Frediano bell... Read More

Tons of English-language titles—both new and used, fiction and nonfiction—are offered at this book exchange in Florence. It’s an especially great place... Read More

For a quieter outdoor shopping experience in Florence, pop over to the Piazza Santo Spirito, where vendors set up shop each morning to sell local... Read More

Pienza is the ideal city. Commissioned by Pope Pius II—a humanist poet of the fifteenth century—as the epitome of Renaissance town planning, it’s set in... Read More

One of Tuscany’s most popular zoos, this attraction in the city of Pistoia is located outside of Florence and great for kids of all ages. All manner of... Read More

Start with the Galleria Palatina. If you can still remember your name after it, move on; you’ll find Titian’s sultry The Concert and sensuous Mary... Read More

Set among hundreds of acres of vineyards, olive groves, and lakes, this ninth-century castle has been sensitively restored. It’s modest in size, perfect... Read More

This imposing tenth-century castle looms over the medieval town of Poppi. It has perfectly preserved dungeons, and a unique library housing 25,000... Read More

This spectacular ruined city is one of the only Etruscan sites that overlooks the sea. Thought to have once been a major hub of metalworking in the... Read More

Let’s start with this ancient site of the Etruscans—and even pre-Etruscans—found behind a beautiful promontory off the Tuscan coast. It would be a... Read More

This hidden, isolated jewel in farm country is known mostly to locals. It has wonderfully nature-rimmed beaches with dense pine forests yet all the... Read More

Set at the foot of Monte Amiata (in the middle of a gorgeous nowhere) this tiny hamlet within beautifully fortified walls is as romantic as a medieval... Read More

Perched on a rocky outcropping, this early medieval fortress has views of the whole Val d’Orcia (a UNESCO site), plus a winding gorge, castles, hill... Read More

Take a walk through Lucca’s Piazza dell’Anfiteatro, a sun-bleached ellipse of medieval houses built upon the ruins of a Roman amphitheater. Read More

This site is historically and culturally deep; the ruined architecture here was started by the Etruscans, continued by the Romans, and finished with the... Read More

Hidden deep in Tuscany’s southeast corner is this perfectly charming, lovingly cared for medieval hill town—home to the refined Fonteverde Tuscan Resort... Read More

These are the “wild ones” of Tuscany’s hot springs. San Filippo, hidden in the woods of Monte Amiata, has an enormous white mineral wall, and natural... Read More

This popular Florentine market boasts an indoor and outdoor section—inside, a food hall with Tuscan snacks and eats; outside, a street market with... Read More

The church's sacristy contains Jacopo della Quercia’s magnificent Gothic tomb of a poor young dear who died in childbirth, her noble dog loyally... Read More

In the heart of Brunello country sits this town with its panoramic view. To the north are wild Tuscan woods; to the east, rolling vineyards; to the... Read More

The Brancacci Chapel in this church houses Masaccio's frescoes, arguably Renaissance painting's most important works. If Expulsion from the Garden of... Read More

Siena’s Santa Maria della Scala was one of Europe’s first hospitals. It remained in operation for almost 1,000 years, until the entire complex began... Read More

Hidden in the bucolic countryside of Maremma, these giant natural pools of swirling milky water draw visitors from all over Italy. A village of resorts... Read More

A long but unforgettable day involving wild, empty mountain roads where Morellino di Scansano is made, then coastal cliff hangers where you can taste... Read More

I can’t imagine a greater contrast to the austere medieval Abbey of Sant’Antimo than the gingerbread, birthday cake, glitzy, high-Gothic Duomo of Siena... Read More

Florence’s Signum is a high-quality stationery shop where you can pick up wax seals, handmade paper, leather-bound journals, artwork, historical maps,... Read More

A barely known trio of villages, Sorano, Savona, and Pitigliano are picturesquely set in the wildest, most unvisited corner of Tuscany, full of baffling... Read More

Not only does this tiny, two-street village contain a 150-foot deep, incredibly narrow road that the Etruscans sliced through a mountain; it also houses... Read More

Everything about this Tuscan outlet is designed to obscure its true purpose as the best place in the world to find Miuccia Prada's gems off-price. There... Read More

Stefano Bemer, who died in 2012, had a simple philosophy: A shoe is an object which, if of excellent quality, helps us walk and live more comfortably.... Read More

Angiolini's three modernized palazzi carry the latest looks from Gucci, Prada, and Marni, along with niche labels, such as Dosa and Haute by Vincenzo De... Read More

I love this dramatic rocky point that juts into the Tyrrhenian Sea; it’s unique on this coast of long sandy beaches and pine forests. Adjoining the wild... Read More

A tiny fishing village, Talamone is a sea lover’s dream. Located on a spur of land with magnificent views, the10,000-acre Parco D’Uccelina, and a... Read More

The Cabernet-dominated Ornellaia has the big name, but the lush, all-Merlot Masseto is the collector’s prize. Read More

This pioneering Bolgheri estate makes Tuscany’s most famous wine, the Cabernet-based Sassicaia. Read More

These beautiful gardens set behind Pitti Palace comprise one the largest parks in Florence, spanning 11 acres (about the size of eight football fields).... Read More

This trail is a good climb of about a thousand feet, through some of the most famous vineyards in the world and you’ll end at the walled town of... Read More

From Torrenieri, take the old Cassia turning toward the medieval castle of Cosona. Do a side trip northwest to Lucignano d’Asso, a magical hamlet with a... Read More

Imagine Palm Beach's Worth Avenue transplanted to a Tuscan hillside with prices slashed up to 70 percent. None of the stores here is a makeweight&mdash... Read More

OK here it is. Just outside of Florence, in Leccio, is the fabled Mall: luxury outlets for those who like to show labels in public. Prices are not... Read More

Relax in one of Tuscany's thermal baths at this Bagno Vignori spa complete with an updated image, sleek rooms, and amenities. Read More

If you are a lover of wine and want to drive through the best zone for wine tasting, this trip is for you. From Montalcino head to Castelnuovo dell... Read More

Classes are intimate, home-style affairs at the Toscana Mia farmhouse. You can choose from several single, half-day classes or packages that include... Read More

A beautiful loop with lots of worthwhile stops in tiny medieval towns. From San Quirico, take Old Cassia road to Torrenieri. Go on to San Giovanni D... Read More

If I had one last bike trip to take, this would be it. It’s mostly empty, unpaved roads with unlimited views, and stops at castles, a monastery, and... Read More

This hillside estate in Suvereto produces an inky Merlot called Redigaffi that has a cult-like following. Read More

At this small cooking school in Cortona, a one-day class will teach you everything you need to know about creating a typical Tuscan meal—including menu... Read More

This tour company, covering Florence and the nearby Chianti hills, offers one-day bike tours that are the ultimate in luxurious sightseeing. Only... Read More

Tuscany Now has been offering Italian rentals to its clients worldwide. We have more than 200 exclusive Italian properties that vary from the small... Read More

This Florentine museum is one of the world’s very best—but don’t make your first visit here an endurance test. Just make sure to see the true... Read More

These new-style Brunellos balance their heft with caressing fruit. Read More

Colle di Val d'Elsa's fairy tale-like Vilca studio produces some of the area's most imaginative crystal ware. Call ahead to watch craftsmen transform... Read More

Every third and fourth Sunday of August, Volterra in the province of Pisa, steps back eight centuries. The streets and piazzas throng day and night with... Read More

This small very personal company has been looking after hikers for 15 years. They can arrange single-day to eight-day tours—you can go either alone or... Read More

The southern part of Tuscany, divided from the north by the great volcano Monte Amiata, is even more pastoral than the rest. Rugged, wild, almost... Read More

On the grounds of the 800-year-old estate you'll find Etruscan ruins dating to 600 B.C., a 12th-century fortress, a Gothic chapel, and an amazing... Read More

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