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  • Horses from Siena's various contrade race on a dirt track...

    Horses from Siena's various contrade race on a dirt track in the Piazza del Campo, which is transformed every year for the annual Palio.

  • The crowd goes wild at the end of the Palio,...

    The crowd goes wild at the end of the Palio, waving flags from Siena's contrade.

  • The bustling Piazza del Campo

    The bustling Piazza del Campo

  • The Corteo Storico, a historical costume parade, takes place in...

    The Corteo Storico, a historical costume parade, takes place in the Piazza del Campo before the Palio begins.

  • The Giraffe contrada's horse is brought onto the track at...

    The Giraffe contrada's horse is brought onto the track at the Palio.

  • View of Siena at night from the terrace of the...

    View of Siena at night from the terrace of the Hotel Bernini

  • Drinks at the Ram contrada's bar

    Drinks at the Ram contrada's bar

  • The Palio gets ready to get underway at the end...

    The Palio gets ready to get underway at the end of the Corteo Storico.

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Go There  
Florence is the closest airport.
The hour-long bus ride from
Florence to Siena is a commuter
bus running early morning to
late in the evening. Albergo
Bernini is a very reasonably
priced, family-run B&B, 10
rooms, some with shared baths.
:: albergobernini.com/en/
:: discovertuscany.com/siena

On the final lap of the race, Montone has lost momentum and fallen to third place. Oca is in front, but Lupa is coming up fast on the inside. With one final spurt, Lupa closes the gap at the last turn, bringing the horses neck and neck. Oca’s jockey lashes out with his whip at Lupa’s horse (and jockey), pushing them into the rail, where they both fall. Oca crosses the finish line, victorious.

The cannon goes off, and so ends the year’s Palio, the most popular – and most dangerous – horse race in Italy, and one of the most thrilling in the world. Oca (Goose), Montone (Ram) and Lupa (She-Wolf) aren’t the names of the horses or the jockeys, but of the contrade, the fiercely competitive neighborhoods they run for.  

Someone once told me (and guidebooks echo this sentiment) that Siena, a little Italian city tucked into three hills that spring up from the Tuscan countryside, could be done in a day. I’ve been there three times, for five days each, and haven’t “done” it yet.

Not much has changed in Siena through the centuries. The population was 55,000 in the Medieval period, and it’s 55,000 today. There are still two runnings of the Palio each year, on July 2 and August 16, and during the days before the race, members of each contrada still march through the streets, led by a drummer and flag bearers. They are in full Palio dress, but don’t call what they’re wearing “costumes.” These are “clothes,” unchanged since 1656 (the year of the first Palio as we know it today).

A little background: During the Middle Ages, Siena vied with Florence, Pisa and Rome for dominance, landed on top for most of the 15th century and then lost out for a couple of reasons. Even though the city was on the route from Rome north, there was no waterway, and the plague wiped out one-third of the population.

So the Renaissance virtually passed this city by, but that doesn’t mean it lacks cultural splendor; it simply means the architecture is mostly Gothic, the art heavily Byzantine. And there are spectacular examples of both.

Visiting them during one of the two summer Palios is very doable, indeed.
Yes, the crowds are huge and the noise relentless, but the excitement is palatable, and everything is more fun because it’s Palio time. Yet tourists are often perplexed because it all seems to just happen. Cross a street and there are flags waving, turn a corner and there’s a parade. But don’t be fooled; it’s beautifully organized and carried off with aplomb. After all, the Sienese have had centuries to get it right.

Everything begins in earnest three days before the Palio with the tratta, the drawing that matches horses by number with the contrada they will run for. It’s followed later in the day by the prova, the first of six trial races. The action happens in the Campo of Siena, Italy’s (and maybe the world’s) greatest Medieval square, a shell-shaped piazza surrounded by uniformly beautiful Gothic homes and dominated by the great tower (Torre del Mangio) and Town Hall (Palazzo Publico, which houses the Civic Museum).

This is the center of Siena and one of its most stunning sites. Today, and for the following three days, bleachers are set up around the Campo, and the outer pavement is covered with hard-packed dirt to form a race track unlike any other.

The Campo’s restaurants are pricey because of the location, but the fare is better than most that overlook famous European squares (and less likely to be a rip-off.) Try a bowl of ribolitta, and maybe a Campari and soda or a prosecco, at Al Mangia.

By 12:30 p.m. on tratta day, the Campo is the most crowded it will be until the day of the big race. Visitors will wonder why, but for the Sienese nothing is more important than the horse; in fact, if a jockey falls off (and many do) and the horse finishes in first place, its contrada wins. So this is the moment they’ve been waiting for.

The drawing takes place on an elaborate stage in front of the town hall. High up, on the facade of the Palazzo Publico, the flags of all 17 contrade fly, seven above and 10 below. Those are the 10 that will race because that’s all the track can accommodate. Seven of the 10 are contrade that didn’t run the previous year; the others have been chosen by lottery.

As each number is drawn, bedlam ensues (especially if the contrada gets a favorite horse). Each horse is led out, followed by singing, flag-waving, screaming contrada members, to a private stable where the trainer will sleep in the stall and the jockey will be closely watched to avoid bribery, doping and even kidnapping. After all, this is the Palio, and while all contrade have at least one friend, with the exception of Bruco (Caterpillar), they also have enemies, and next in importance to winning the Palio is making sure the enemy doesn’t win.

After the tratta, the Campo clears in minutes, and the Museo Civico opens its doors. Never a huge fan of Byzantine art, on my first visit I approached the museum with disinterest, aware that what awaited were copious renditions of the Madonna and child in which the “child” resembles nothing more than a little old man. And there are many of those; however, there are also grand frescoes, made more appealing by virtue of being painted on the spot many centuries ago.

This building is the original town hall, and in the room where the governing body met is the mural commissioned to keep them honest, Sienese artist Ambrogio Lorenzetti’s Allegory of Good and Bad Governments and Their Effects on the Town and Countryside. Of course, the good are very good and the bad are not only very bad, but also, fittingly, in worse repair.

The mural is considered one of the most important pieces of secular art to have survived Medieval Europe, but my favorite is Guidoriccio da Fogliano, by the Sienese master Simone Martini, in which the captain of the Sienese army rides his steed through conquered land.

By early evening, it’s time for the first prova, a one-lap race in which jockeys are concerned less with winning than getting a feel for the track and, more important, checking out the weaknesses of the other horses and riders.

Skip it, because there are five more, and the nighttime crowds are enormous. Instead, have an early dinner (7 p.m., early for Sienese) at La Taverna di San Giuseppe, where they claim the world’s best tiramisu. The entrées aren’t bad either.

There’s an abundance of churches in Siena, and fitting them into Palio activities can be challenging fun, made easier by starting early in the morning with San Dominico, the home of all things St. Catherine, including her thumb, for those into relics. The patron saint of Siena spent much of her time here, and her birthplace is a pleasant sanctuary just down the hill.

After visiting San Dominico, I often walk down the street to Ci Ritorno and choose from the scrumptious assortment of meats and cheeses, stop next door for a bottle of Chianti Classico, and enjoy an antipasto brunch on the terrace of Albergo Bernini. This is the 10-room B&B that I – and others not into expensive many-starred hotels – call home. Here is the best panoramic view of Siena and the most gracious of hosts, Daniela, and her daughters, Eugenia and Carlotta. They serve breakfast on the terrance, which is open for guests throughout the day and night. Bernini is the one exception to my lifelong belief that hotels are only for sleeping.

The day’s big event is the procession to Basilica di Provenzano for the blessing of the Palio. A note: While the race is called the Palio di Siena, or Il Palio, the “palio” itself is a silk banner hand-painted by commissioned artists for each of the two summer races, and topped by a silver platter. The palio goes to the winning contrada; the platter is engraved with its name.

It’s a short stroll down to Provenzano from the center of town, which means a steep one back. Walking is the mode of transportation in Siena, and while everything is within walking distance, don’t forget that every hill down has its opposite hill up.

After the procession, it’s possible to squeeze in with the masses for the blessing and hang around afterwards for a look at the church and the palio, which will remain here until the race. You’ll see contrada members tossing their scarves to touch it for luck.

These scarves are sold on the street, and it adds to the fun to check out the websites of each contrada and choose one to support before leaving home. Then buy a scarf and wear it everywhere; you’ll feel naked – and look like a confused tourist – without it.

There’s one more church on the day’s agenda, Basilica Dei Servi, with its stunning view and paintings by some of the finest Sienese artists. For those who might balk at three churches in one day, remember that the best art in Italy is often found in the churches, and Siena is no exception.

Servi is a long but leisurely and not particularly hilly stroll along Via Roma, through two contrade – Lecorna (Unicorn) and Montone (Ram) – easily identified by their flags, which fly from all the buildings and nearly every window. The walk offers a chance to watch the playful Unicorn guys, who pause as they set up dinner tables in the street to gleefully spray water on the passersby, and to join the Montone crowd for a cold Campari in their tavern next to the basilica.

With friendly contrade visiting each other daily in full dress, flags soaring and drums sounding, and with impromptu celebrations everywhere, walking almost any street provides opportunities to feel a part of things. Choose a contrada, locate their neighborhood, and you’ll find a welcome.  
Finding the best restaurants, however, is often accidental. Near the end of Via Roma, but still away from big crowds, I stumbled on one of the best.

Osteria La Sostadi Violante boasts a selection of mouthwatering pasta entrées and cannoli that’s cold and creamy inside, served with sauce that’s hot and sweet. The Corleones never tasted cannoli like this. Get there early for dinner because I’m not the only one who has discovered this little gem.
The day before the Palio, there’s only one dinner that matters. It’s the Cena della Prova Generale, the blowout event attended by literally hundreds of paid guests. (Ticket information is available at the contrade websites.) All the contrade bustle with activity as members prepare for it. While the Sienese are busy, for visitors, it’s Duomo time.

Those who spend only a day in Siena will likely spend it here. The cathedral’s facade is a gothic wonder of white marble with dark green, nearly black, stripes that give off – somehow – a pinkish aura. Across the piazza, there’s room to sit and absorb the majesty of it.  

Inside, in addition to its great paintings, two statues by a young Michelangelo and a Nicola Pisano pulpit that rivals Pisa’s, is the amazing floor, a wonder of decorated pavings with religious, mythological and allegorical motifs by many artists through time, from the 14th to the 19th century.

And under it all is the crypt, uncovered in its present condition only 15 years ago. Part of an old buried church, its walls are covered with murals depicting biblical scenes and dating from the 13th century. Don’t miss this “discovery.”

Once preparations are complete for the big dinner, everyone, and I mean everyone, attends that night’s race (the Prova Generale). So, like the first Prova, skip it. This time, take a nap in preparation for the long evening ahead, because dinner never begins before 10 p.m., the courses are many, the wine flows, and the speeches soar (don’t worry, someone will happily translate).

The next morning, with all of Siena sleeping it off, it’s easy to get a place at the rail for the final Prova, followed by lunch in a restaurant where nary a tourist can be found. Choices are made at the counter and written on brown paper which serves as the bill. Il Grattacielo is my favorite down home (if such an expression exists in Italian) eatery.
Then, if you’ve missed a parade, today’s the day for that, too, beginning with the blessing of the horse in each contrada’s oratory, where the animal is taken right up to the altar and sent away with, “Vai e torna vincitore!” (“Go and return victorious!”).

After the blessing, the contrade come together for the biggest parade of all, with stops along the way (I catch them at Piazza Salimbeni) before entering the Campo.

Each contrada has its own fountain, including the Lupa contrada. Because Lupa had a horse (the one that fell, along with its rider) in the July 2 Palio, I became an avid fan. I was a Bruco supporter the season before; their horse didn’t win, either. But I remain devoted to both contrade and will add another next season, when Chicolio (Snail), the contrada of my friends at Hotel Bernini, will run.  

Those interested in sitting in bleachers or hanging out of windows for the Palio pay upwards of $300 for tickets and need to be in place a couple of hours before the spectacle of the Corteo Storico, which lasts another two hours and ends when the palio enters the Campo in an oxen-drawn cart.
Then come the horses, to the singing and cheering of their contrade. Post positions are determined by the order of swirling balls (painted in contrada colors) in a long-necked bottle. Getting the horses to the post can take up to another hour. Don’t expect an electric gate here; they line up between two ropes, where they fight ferociously for position. Finally, when the number 10 horse passes the first rope, the second one is dropped and, “La mossa e valida!” or, roughly translated, “They’re off!” for a three-lap race that lasts about 90 seconds.

Is it worth it? Or does it make more sense to join the pack in the Campo and stand cheek to jowl with 5,000 others? Or – here’s another possibility – be there for everything during the four days of the Palio and then watch the final race on TV at Bernini.

I’ve done it all, cheering for a different contrada each time (and never winning, but there’s always next year) and have no expert advice. It depends on Siena’s weather (Palio day can be excruciatingly hot or quite pleasant) and your stamina. One thing is certain: If you’re in Siena at Palio time, and if you choose a contrada and get into the spirit, there’s no travel experience like it in the world.