Siena and Tuscany’s Wine Country

Siena, once a proud and independent city-state, retains its confidence and unique traditions. We'll enjoy a front-row seat at its wild horse race — the venerable Palio — and marvel at cultural treasures from the days when it rivaled Florence for leadership of Tuscany. Then we'll head into wine country for a little dolce vita under the Tuscan sun.

Travel Details

City Tower

The tower's Italian nickname, Torre del Mangia, comes from a hedonistic bell-ringer who consumed his earnings like a glutton consumes food. The tower's nearly 400 steps get pretty skinny at the top, but the reward is one of Italy's best views (closed in rainy weather but otherwise open daily in summer until 19:00, off-season until 16:00).

Civic Museum

Siena's City Hall (Palazzo Pubblico), still the seat of city government, symbolizes a republic independent from the pope and the Holy Roman Emperor. It also represents a rising secular society, one that appeared first in Tuscany and then spread throughout Europe in the Renaissance. City Hall also has a fine and manageable museum that displays a good sampling of Sienese art, including Siena's first fresco (with a groundbreaking down-to-earth depiction of the Madonna). It's worth strolling through the dramatic halls to see fascinating frescoes and portraits extolling Siena's greats, saints, and the city-as-utopia, when this proud town understandably considered itself the vanguard of Western civilization.

Santa Maria della Scala

This museum, opposite the Duomo, operated for centuries as a hospital, foundling home, and pilgrim lodging. Many of those activities are visible in the 15th-century frescoes of its main hall, the Pellegrinaio. Today, the hospital and its cellars are filled with fascinating exhibits (well-described in English).

Roberto Bechi

Tours by Roberto, led by Roberto Bechi or one of his guides, offers off-the-beaten-path minibus tours of the Sienese countryside (up to eight passengers, pickup at hotel). Regardless of the size of your group, they charge per person, so these minibus tours are economical. The first participants to book choose one of seven itineraries — then others join until the van fills. Roberto and his team share the same passion for Sienese culture, Tuscan history, and local cuisine. Roberto also offers Siena walks and multiday tours.

Siena's cathedral

Siena's 13th-century duomo and striped bell tower are one of the most illustrious examples of Romanesque-Gothic style in Italy. This ornate but surprisingly secular shrine to the Virgin Mary is slathered with colorful art inside and out, from inlaid-marble floors to stained-glass windows. The cathedral's interior showcases the work of the greatest sculptors of every era — Pisano, Donatello, Michelangelo, and Bernini — and the Piccolomini Library features a series of 15th-century frescoes chronicling the adventures of Siena's philanderer-turned-pope, Aeneas Piccolomini. Lines can be long here — before buying a ticket, check to see if there's a long wait. If so, I'd head to the "reserved/fast entrance" queue and pay a small "reservation" fee, which lets you skip the line.

Taverna San Giuseppe

Enjoy this taverna's chic grotto ambience as you dine on beautifully presented Tuscan cuisine from a creative and enticing menu. Attentive Matteo and his wonderful wait staff enjoy showing off their Etruscan wine cellar — be sure to venture down. Reservations are a good idea here.

Il Palio

The city's world-famous horse race happens twice a year, on July 2 and August 16. This is not some folkloric event — it's a real medieval moment. If you're packed onto the square with 60,000 people, all hungry for victory, you may not see much, but you'll feel it. (Go with an empty bladder as there are no WCs, and be prepared to surrender any sense of personal space.) While the actual Palio packs the city, you can more easily see the horse-race trials on any of the three days before the main event (usually at 9:00 and after 19:00, free seats in bleachers). And keep in mind that finding a room in Siena is tough at Palio time. Many hotels won't take reservations until the end of May for the Palio, and even then they might require a four-night stay.

Agriturismo Cretaiole

Ideally situated in pristine farmland just outside Pienza, this agriturismo is perfect for setting in and fully experiencing Tuscany. They offer a full slate of activities, and those with a car can use this as a springboard for exploring virtually all of Tuscany. This family-friendly farm welcomes visitors for weeklong stays (Sat–Sat) in six comfortable apartments. One of my favorite agriturismo experiences in Italy, Cretaiole is warmly run by reformed city-slicker Isabella, who came here on vacation and fell in love with country-boy Carlo. Now Carlo and his father, Luciano, tend to the farm, while Isabella and her helper Carlotta assist guests in finding the Tuscan experience they're dreaming of — including thoughtfully planned optional activities such as pasta-making and olive-oil tasting classes, winery tours, and artisan studio visits. The same family runs two properties in the atmospheric medieval village of Castelmuzio, five miles north of Pienza (both with access to activities at the main agriturismo): Le Casine di Castello is a townhouse with two units, while the more upscale Casa Moricciani is a swanky villa with dreamy views, a garden terrace, and loads of extras. For special offers, short stays, and discounted rates for all three properties, check their umbrella website.

Altesino winery

Elegant and stately, Altesino owns perhaps the most stunning location of all the wineries in this region, just off the back road connecting Montalcino north to Buonconvento. You'll twist up on cypress-lined gravel lanes to this perch, which looks out over an expanse of vineyards and Montalcino in the distance. Reserve ahead for tours and tastings.

Santa Giulia winery

On the outskirts of the town of Torrenieri, this is a quintessential family-run winery, with an emphasis on quality over quantity (only 20,000 bottles a year). They also produce excellent olive oil, prosciutto, and salami. Less picturesque and much more rustic than most other wineries in the area, a tour at Santa Giulia is a Back Door experience. The son, Gianluca, and his wife, Kae, enjoy showing off their entire working farm — ham hocks, cheese, and winery — before giving you a chance to taste their produce. Call to find a time that fits their schedule; around lunchtime, you can arrange a "Zero Kilometer" tasting, with everything farm-made.


See the Travel Details above for recommendations highlighted in bold, excerpted from Rick's guidebooks.

Hi, I'm Rick Steves back with more of the best of Europe. This time we're in Italy for the wildest horserace in the world and we're not alone! It's Siena, the Palio, and a whole lot more! Thanks for joining us.

Tuscany seems to be every Italy connoisseur's favorite region, and for good reason. Here in the heart of Italy, the rustic soul and historic charm collaborate, seducing travelers into tossing their itineraries and settling in.

We'll enjoy an aperitivo on a great square, marvel at exquisite art, eat cheese in an Etruscan cellar, settle into a farmhouse B&B, learn to make pici pasta, taste one of the world's finest wines, prepare for a festival, and go to the races.

Italy packs 55 million people into an area about the size of Arizona. Between Florence and Rome is the region of Tuscany. We start in Siena, explore the Chianti region, and then visit wineries near Montepulciano and Montalcino.

Back in the 1300s, Siena was a major banking, trading, and military power. It was in a league with Venice, Florence, and Genoa. It had a population of about 50,000 people — that was one of the biggest cities in Europe — about as big as Paris. But after being weakened by a devastating plague and conquered by its bitter rival, Florence, it's been a backwater ever since.

Siena's loss became our sightseeing gain, as its political and economic stagnation preserved its purely Gothic identity. Its population hasn't changed for centuries: It's still around 50,000.

Siena's great central piazza is Il Campo. Like a people-friendly stage set, it's the heart of Siena, both geographically and metaphorically. The historic junction of Siena's various neighborhoods, or "contrade," it fans out from City Hall as if to create an amphitheater. The square and its buildings are the color of the soil here: a color known to artists and Crayola users as "burnt Sienna."

Sprawling before the City Hall backdrop, the gently tilted piazza offers the perfect invitation to loiter. This is a major university town, and a mix of students, locals, and tourists lounge comfortably, as if it's their community living room.

The great sights of Siena date from long before the country of Italy existed. And these sights have a consistent theme: The Republic of Siena is independent and perfectly capable of ruling itself.

The Mangia Tower [City Tower], built nearly 700 years ago, remains one of Italy's tallest secular towers. Medieval Siena was a self-assured republic, and this tower stands like an exclamation point — an architectural declaration of independence from both the pope and the emperor.

Three hundred winding steps take you high above the town. Your reward: a bird's eye view down at the uniquely shaped square and a commanding view of the Tuscan countryside.

Beneath the tower, the City Hall [Civic Museum] is open to visitors. Its historic rooms were, for centuries, the home of Siena's government. In the "room of peace" the republic's council met under instructive 14th-century propaganda showing the effects of good and bad government — with a message that seems remarkably applicable today. Bad government — a dictatorship counseled by greed and tyranny — results in a place you wouldn't want to call home, with run-down buildings and violence in the streets.

But good government — with wise and virtuous leadership — results in a utopian republic where the shopping's brisk, construction's booming, students are attentive, and women dance freely in the streets. The message: A community ruled by a just government enjoys peace, prosperity…and is a great place to raise your kids.

For a portrayal of that "good government" in action, drop by the historic hospital of Santa Maria della Scala. A series of idealized frescos show medieval Siena's innovative health care and progressive social welfare system at work. The city, rather than the Church, ran this hospital, illustrating how far secular society had come in Siena by the 1400s.

It took in and raised orphans — from wet nurse through schooling — to a civil wedding. And this wedding is not arranged; it's based on love.

Sienese society cared for its poor. Bread was given to the needy. Note the loaves are cleverly stamped — to prevent resale. The hospital was run by secular doctors and nurses. In a slap to Church authorities, the well-fed monk looks bored as he seems to ignore a dying patient's confession.

Siena is a stony wonderland where people rather than cars fill the streets. It's that time in the early evening when friends gather and stroll. Like in any Italian city, the people of Siena are out and making the scene. This ritual is called the "passeggiata" — it's like cruising without cars. In fact, throughout the Mediterranean region, early evening is the time to be out and about.

The passeggiata is ideal for getting together with friends…and I'm joined by my friend and fellow tour guide, Roberto Bechi. With Roberto, my passeggiata includes a little history.

Rick: I just feel there's so much history all around.
Roberto: Yes. Especially on this road here.
Rick: What happened on this road?
Roberto: This road, in the Middle Ages, was called "Via Francigena" —
Rick: The way of the French.
Roberto: Yes. It's where all the pilgrims were passing through, from France to Rome.
Rick: This is the pilgrims' route!
Roberto: Yes.
Rick: For centuries! And people are walking, to this very day.
Roberto: Yeah, but they do passeggiata.
Rick: But now…passeggiata today.
Roberto: Oh, I love the passeggiata. All the Italians love the passeggiata.
Rick: Everybody's out. Every generation.
Roberto: Every generation going up and down on the main road, shopping, looking at the last fashion…
Rick: What are the fashions, who's got a new baby…
Roberto: Absolutely.

Italy is a culture of piazzas — ever since Roman times, the piazza has been the heartbeat of the community. And in Siena Il Campo is perfect for a nice aperitivo. We've grabbed a front-row table to enjoy a spritz — that's a favorite drink: mixing Aperol, white wine, and fizzy water.

Rick: I love the aperitivo. "Aperitivo" is Italian for "happy hour," basically. Get a cocktail — and, you know, it's not a cheap cocktail — but it comes with lots of nice munchies and…the best view in town.
Roberto: Yes, in the main square in Siena.
Rick: I love it.

Siena's 13th-century Gothic cathedral, with its striped tower, is dedicated to the Virgin Mary and covered with art. The richly ornamented facade bristles with ornamentation: Its striking mosaics framed by patriarchs and prophets, saints, and gargoyles.

Grand as Siena's cathedral is, it's actually the unfinished rump of a failed vision. After nearby Florence began building its huge cathedral, proud Siena — not about to be outdone by its rival — planned to build an even bigger church…in fact the biggest church in all Christendom.

But Siena was so hilly, there wasn't enough flat ground to support such a enormous church. What to do? Build the church oversized anyway, and prop up the overhanging edge by building the Baptistery underneath.

The cathedral we see today was intended only to be a transept, or wing, off the envisioned nave, or main part of the church. These towering marble arches hint at the immensity of the vision. But the arches were as far as Siena got before construction problems and a devastating plague scuttled the project.

I'm standing atop what would have been the front of that church. Had it been completed, this square would have been not a parking lot, but the nave itself.

It's fun to imagine that if Siena's grandiose plans had succeeded, I'd be looking straight down the nave of that massive church toward the altar.

The resulting church is still impressive. It's richly decorated from top to bottom. Peering down from above are 172 heads. They represent the popes who reigned from the time of St. Peter to the 12th century.

The exquisite marble floor is paved with Bible scenes, intricate patterns, and allegories. This one features Siena as a she-wolf at the center of the Italian universe, orbited by such lesser lights as Rome, Florence, and Pisa.

The greatest artists of their day helped decorate Siena's cathedral. In this side chapel, St. John the Baptist, carved by Donatello, wears his iconic rags. And high above, playful cherubs dangle their feet.

This memorial to the Sienese pope Pius II features a statue of St. Paul carved by Michelangelo himself. And in another chapel, you'll see why Lorenzo Bernini is considered the greatest Baroque sculptor. His St. Catherine is in spiritual ecstasy. And St. Jerome caresses the crucifix like a violinist lost in heavenly music.

A highlight is the church's Piccolomini Library: Brilliantly frescoed, it captures the exuberance and optimistic spirit of the 1400s, an age of humanism when the Renaissance was born. The frescoes look nearly as vivid now as the day they were finished, over 500 years ago. They celebrate the life of one of Siena's hometown boys — who became Pope Pius II. Each of the scenes is framed with an arch, as if opening a window into the real world.

The back streets of Siena have changed little since the days of the Renaissance. Make a point to get away from the crowds and enjoy a quiet moment with the timeless magic of Siena.

All over town, shops tempt you with edible Sienese specialties — gourmet pasta, vintage Chianti, wild-boar prosciutto…

Rick: Looks very good! Tutti Toscana?
Butcher: Qui prodotti di Siena. [Products here are from Siena.]
Rick: Siena!?

…and delicious Sienese salami.

Rick: This is salami?
Butcher: Assaggio della casa: Si chiama "finocchiona," un salami fatto… [House sample: It's called "finocchiona," a salami made...]
Rick: Mmmm! Complimenti!

Siena's claim to caloric fame is panforte — a chewy local delicacy that tempts even fruitcake haters.

Siena offers a delicious range of opportunities to enjoy the hearty Tuscan cuisine. Characteristic tavernas serve local dishes in a grotto-chic atmosphere — this one [Taverna San Giuseppe] under a fine old medieval vault.

I love bruschetta, and my favorite is without toppings — just the olive oil and garlic.

Rick: I like it as simple, because you can taste the oil.
Roberto: The olive oil. You can use your hands here.
Rick: You can use your hands?
Roberto: Yes, absolutely.
Rick: That's nice.
Roberto: Like this…

I've ordered my pasta "bis." That gives me half portions of two different pastas for the cost of one, doubling my taste treat.

Rick: Mmmm, oh! That's light and nice, with the truffle. I like that!
Roberto: Yes, absolutely. It's a good match.

Rick: Wow, tell me the story!

And we cap our meal by descending into their ancient Etruscan wine cellar. Dating from 300 B.C. and roughly hewn by hand, this former tomb now houses the taverna's fine wine and cheese. Year round it's the perfect temperature for wine…and the perfect humidity for cheese. And, as a travel writer, I feel it's my solemn duty to confirm this.

Rick: It's nice.
Matteo: It's perfect.
Rick: I bet the Etruscans liked this.
Matteo: Definitely!

Across Europe, festival traditions go back centuries, and are filled with time-honored pageantry and ritual. Entire communities hurl themselves with abandon into the craziness. There's no better example than here in Italy: Siena's Palio.

Twice a year that spirit shows itself in a five-century-old city-wide competition that culminates in a crazy horse race.

Siena is divided into 17 neighborhoods, or contrade. With their mascots and flags, these have long been competitive and filled with rivalry.

Each July and each August the entire city readies itself for the big race. Its centerpiece, Il Campo, is transformed into a medieval racetrack as tons of clay are packed atop the cobbles, and bleachers are set up.

Before the race, competing neighborhoods gather for communal dinners that last well into the night. There are rousing choruses with everybody cheering their contrada.

For days, processions break out across the city. With waving flags and pounding drums, it all harkens back to the Middle Ages, when these rituals boosted morale before battle. A highlight of the parade is the actual banner, or "palio." This palio, featuring the Virgin Mary (to whom the race is dedicated), will be awarded to the victorious contrada.

Finally, with what seems like the entire city packed into Il Campo, it's race time. Bleachers and balcony seats are expensive, but it's free to join the masses in the middle.

The snorting horses and their nervous riders line up, jockeying for the best spot. Silence takes over. Once the rope drops, there's one basic rule: There are no rules. They race bareback like crazy while spectators go wild.

Life stops for these frantic three laps…just 90 seconds.

When the winner crosses the line, the winning contrada goes berserk. Tears of joy flow, people embrace. The winners thunder through the streets and eventually into the cathedral — filled with jubilation. Then the winners raise their coveted palio high: Champions…until the next race.

While the Palio takes Siena by storm just two days a year, the charms of the Tuscan countryside can be enjoyed all year long. The fortified farmhouses and castles of the Chianti region are reminiscent of medieval days, when this was part of the battlefield where Florence and Siena fought. Today the stony walls are peaceful…growing ever more graceful with age.

Chianti, with its rugged hills and farmland, charms visitors with a slower, more rustic lifestyle. This farmer prunes his olive trees, employing a lifetime of experience to maximize the fall harvest. In his vineyard, as they do each spring, tender shoots are bursting out of their gnarly vines filled with promise.

South of Chianti is a region called the Crete, where the hills are more gentle. This quintessential Tuscan landscape features clay hills — the topsoil washed away by ages of rain and wind — and iconic lanes of cypress trees, planted to slow that erosion. The dramatic beauty of the countryside changes with the season, and with the time of day. In the springtime the rolling fields are splashed with colorful flowers.

The Tuscan terrain is dotted by rustic yet noble farmhouses. All over Europe, farms are renting rooms to travelers — now harvesting their rural charm as well as their produce to help make ends meet. Here in Italy, farmhouse B&Bs are called agriturismos.

Our agriturismo [Agriturismo Cretaiole], perched on a bluff overlooking pristine farmland, is perfect for those who want to settle in and fully experience Tuscany.

After enjoying a great day out, the guests gather for a convivial happy hour. Under the oak tree…enjoying the view…sharing today's experiences, and dreaming about tomorrow's — the relaxing vibe is a vacation dream come true. It's a family business as Isabella keeps the hospitality flowing, while husband Carlo mans the BBQ.

As evening falls, we gather for a cultural experience. Tonight we're learning to make the local favorite — a pasta called "pici." Isabella is a patient and engaging teacher. It's a hands-on experience — and it's great to have a coach.

Isabella: We'll recognize that.
Rick: We'll recog — ha HA!

The kids take part as well, as everybody's learning and having fun.

Then, as if a reward for all the kneading and rolling, we sit down together and enjoy the fruits of our labor. This is good travel — a crossroads of American and Italian cultures, eating and drinking together, while creating memories of a lifetime.

With our Tuscan farmhouse as a base, there are plenty of things to experience within a short and scenic drive.

This is wine country, home of the famous and much-loved Brunello di Montalcino. And vineyards welcome guests who call ahead. We've got appointments with two wineries — a large corporate winery first, and then a smaller family-run farm.

The Altesino winery is elegant and stately. It looks out over an expanse of vineyards with the hilltown of Montalcino on the horizon.

Guides take visitors on an informative stroll through the entire wine-making process.

Rick: So how old to the vines get?
Guide: Think a sangiovese vine naturally arrives at 50, 60 years old. But there are wineries that still have the vine from a century ago.

Here it's clear modern technology complements tradition, and after centuries of trial and error, wines are better today than ever before. Each year 70,000 bottles of this producer's prized Brunello work their way through this exacting process. It's a labor-intensive industry…but right now the grapes are doing all the work as they age in their oak casks.

And each tour ends up in the tasting room, to help visitors appreciate why Brunello is so highly regarded.

Nearby, the much smaller winery of Santa Giulia offers a more intimate visit. Taking visitors into his vineyard, Gianluca enjoys sharing the fine points of producing his Brunello wine.

Gianluca: The grape that is used for Brunello is called sangiovese. Sangiovese grosso. By law, by the DOCG, Brunello di Montalcino must be 100 percent sangiovese. This is the most important difference between Brunello and other imported red wine from Tuscany. This soil is a mix of clay and sand. The characteristic of the clay is that it keeps the water, the humidity, underground. If you give water, you stimulate the root to grow up to find the water. If you don't give water, you stimulate the root to go down, to go deep, to find the water. And they find minerals, too, underground. So the taste of the grapes, and then taste of the wine, then, is different.

Producing such a fine wine requires a huge investment and lots of expertise. Surrounded by stainless steel vats that produce 10,000 bottles a year, father and son monitor the process, carefully tasting and discussing the potential of this year's vintage.

The aging process carries on in oak barrels. There's more tasting as the wine continues its long journey to the bottle. Seeing father, son, and grandson together amid these towering casks is a reminder that this is a rural art form passed from generation to generation.

To cap our visit, Gianluca's mother is orchestrating the final touches of a delightful lunch — which of course includes homemade pasta. It's a local feast with everything farm made here in Tuscany. The enticing array of pecorino cheeses, prosciutto, and salami are all an ideal complement to what this family believes is the best wine in Italy.

As they share their Brunello, it's clear the family appreciates the happiness their work brings to wine lovers not only here but all over the world. If anything characterizes the Tuscan lifestyle, it's a knack for taking time to savor simple quality…

Rick: Here's to good wine, and good family.

…whether it's wine, food, art, or friendships.

I hope you've enjoyed our taste of Tuscany — from rich and exuberant Siena to the rustic and equally rich countryside. I'm Rick Steves. Until next time, la vita è bella — that's "life is beautiful." And keep on travelin'! Ciao.