The city on a hill - and on a crayon

The burnt sienna in every big box of crayons is named for the color of the earth around Siena, Italy - a reddish-brown hill town of medieval buildings, narrow alleyways, and old squares surrounded by vineyards, olive groves, and cypress trees.

Seen from the high ground of its nearby fortress, Siena's massive white cathedral with its gleaming zebra-striped bell tower stands in startling contrast to the sienna-colored town.

The proportions of the town - laid out on three hills by medieval architects and town planners - delight the eye.

Although Siena is a small city(about 60,000 inhabitants, 15,000 of them inside the town walls), it has been an important center of civilization since the Roman Empire, and has an artistic heritage in Tuscany that is second only to Florence.

Small and free of cars, virtually unchanged inside its ancient walls since the Middle Ages, Siena provides quite a contrast to bustling Florence, which is less than an hour away. (The two cities are centuries-old enemies.)

The centerpiece of the town is the Piazza del Campo, "the most beautiful square in Italy," according to the Renaissance writer Montaigne. The Campo resembles a giant scallop shell ringed with Gothic palaces whose facades curve to follow its outline, anchored by the Palazzo Pubblico (town hall) with its slender Mangia Tower.

All the palaces were designed to be seen from the Palazzo Pubblico; from any other vantage point, the buildings look slightly askew.

Twice a year, in July and August, there's a colorful, historic horse race around this square called the Palio. (See story.) No quaint custom revived for the tourist trade, the Palio is serious business and has been since the 14th century.

This ancient festival between Siena's districts, or contrade, offers an insight into the quirkiness of the Sienese character. "My wife and I are from different contrade," confides Mario Pescini, a Siena hotelier. "During Palio, we hardly talk to each other.

"We Sienese," he adds proudly, "we are not normal."

Fierce pride in all things Sienese and a passionate love for their beautiful city have always been characteristic of the city's inhabitants. They had planned to build a cathedral larger than St. Peter's Bascilia in their town, but that was before the plague decimated their ranks in the mid-14th century.

The old town records (on view in the Palazzo Piccolomini) are bound between wood panels painted by the city's greatest artists.

Every paving stone of the local pietra serena on Siena's narrow streets is smooth and perfectly fitted - and carefully replaced by hand when needed.

The usual Italian promenade, the passeggiata, goes on most of the day here, up and down the curving Banchi di Sopra (Il Corso to the Sienese). This stroll - a hilly one like all walks in Siena - leads past tasteful shops in 14th-century buildings of sienna-colored brick and passes the world's oldest surviving bank, founded when these buildings were new.

Pick up a snack of Siena's specialties - panforte or the spicier panpepato, both sweets, or ricciarelli, an almond- and orange-flavored cookie. Then, as you munch, continue the walk along Via di Citta.

If you're visiting in late June or mid-August, some glimpse of preparations for the Palio are sure to surface along the way - a youth in sumptuous velvet hurrying down the street toward a rehearsal of little boys twirling brightly colored flags, which they bear with pride in the historic procession before the horse race.

When further exploring inside the old town walls, try to avoid the few streets that permit cars: Walking along a medieval street with no sidewalks and 21st-century traffic seriously dilutes Siena's charm.

There are two required sightseeing stops in town. First is the Duomo (cathedral), surely one of the loveliest in Europe. Of note are the inlaid marble and mosaic floor, carved pulpit, and lushly frescoed Piccolomini Library.

Then cross the street and visit the Ospedale di Santa Maria della Scala. A hospital since the 800s, it opened to the public as an exhibition space in the 1990s, and is well worth a visit for its medieval interior and frescoes.

The other required stop is the museum in the Palazzo Pubblico, especially the Sala del Mappamondo frescoed by the Sienese master Simone Martini, and the next room, decorated with scenes of good and bad government according to Sienese philosophy.

Art lovers will also want to see the work of artists of the Sienese school in the Pinacoteca Nazionale.

After dark, students from Siena's ancient university (founded in 1241) lounge on the pavement of the illuminated Campo, while tourists eat slightly overpriced food in the Campo's sidewalk cafes.

The show here is worth the price, but a better meal can be had around the corner at Le Logge.

For nightlife, the best choice is another stroll before retiring to a hotel room with a view of the surrounding hillsides.

Siena's Palio has been characterized as a cross between a medieval pageant and a horse race. It's 90 seconds of wild bareback riding that has been taking place each summer for about 700 years.

The origins of the Palio have been lost in the mists of time. Official city records from the year 1310 say only that it was to be run on Aug. 16 "in honor of the Blessed Virgin." It appears the race took place even before that time. In 1656, a second Palio was initiated on July 2 to honor the Madonna of Provenzano.

Today's spectacle starts with a lavishly costumed procession featuring flag-throwing routines choreographed to drumbeats. Set in the 14th-century Piazza del Campo, it time-trips the 21st-century traveler back into a scene from the Middle Ages.

The race is a contest among 10 of the 17 neighborhoods (contrade) within the walls of Siena. But only 10 districts participate in each race. Seven are automatically entered because they didn't compete the previous July. The remaining three are chosen by lot. The same selection process is used for the August Palio.

In the week before the Palio, the town is filled with anticipation and preparation. In each contrada, flag-waving rehearsals are held in the neighborhood's square. Each district has flags decorated with its own emblem and chooses young bearers to twirl the flags in an elaborate display during the historical procession leading up to the race. Why flags? No one knows for certain. But some note that in medieval Tuscany, colored flags were used as signals to armies.

The night before the Palio, drums and singing echo in the streets, and huge dinners are held in the contrade.

As the day of the Palio dawns, the bell in the Palazzo Pubblico begins its day-long ringing, audible far beyond the city gates. Each horse is blessed in the church of its contrada; flags fly from every street corner.

Late in the afternoon the pageantry of the Palio procession begins: Representatives of each district parade in elaborate 15th-century costumes that cost thousands of dollars. They're accompanied by drummers and the flag bearers.

Then the cart carrying the palio (banner), drawn by four oxen, enters the Campo to the fanfare of the Town Hall's silver trumpet.

Before the horses take their places at the starting line, there is much strategizing. Instead of just racing to win, one contrada might conspire with another to block or interfere with a common "enemy." Or jockeys may give out misinformation about their horses or strategies. This is considered an essential part of the Palio.

Finally, at 7:30 p.m., the race begins - three loops around the Piazza del Campo, less than two minutes of mayhem accompanied by constant shouting from the crowd. After all, the banner and the neighborhood's honor are at stake.

All night the winners and their allies parade through the streets showing off the silk palio, beating drums, shouting, and waving flags, while contrada leaders make plans for the next Palio.

It's difficult to find a hotel room in Siena during Palio time. Try to make reservations at least four months ahead. Grandstand seats are quite expensive ($350 or more), but there is free standing room in the piazza. Unless you line up very early, you'll mostly see other spectators.

For more information, see www.sienanet.it and www.initaly.com.

• The best time to visit Siena is May through September, which is also high tourist season. Hotel reservations are essential during this time.

• The Palio is held July 2 and Aug. 16.

• For more information, call the Italian Tourist Board at (212-245-4822).

• Contact the Siena tourist office by phone at 011-39-0577-280551, e-mail at aptsiena@siena.turismo. toscana.it, or visit the website at www.siena.turismo.toscana.it.

• Another website: www.comune. siena.it/turismo/webasp/home.asp.

• Siena hosts two important summer music festivals each year. The town's Academy Chigiana, one of Italy's most important music schools, holds a festival each July or August. Siena Jazz, an event that takes place in July and August, is an international jazz festival.