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North Into The Val d'Elsa

Monteriggioni, 14km (8 1/2 miles) northwest of Siena along the SS2, is one of the most perfectly preserved fortified villages in all of Italy. (You've probably seen aerial photos of its stone streets at postcard stands.) The town was once a Sienese outpost; the city's soldiers patrolled the walls and kept an eye out for Florentine troops from the towers. All 14 of these vantage points have survived more or less intact since the day Dante likened them to the circle of Titans guarding the lowest level of Hell. Between April and September, you can climb up to a couple to admire the view; the ticket booth is open daily 9:30am to 1:30pm and 2 to 7:30pm, and access costs 1.50€. The tourist office is at Piazza Roma 23, 53035 Monteriggioni (tel. 0577-304-810; www.monteriggioniturismo.it).

Although more day-trippers are stopping by every year, Monteriggioni remains a sleepy little place. There's a board-rated four-star hotel (Hotel Monteriggioni; tel. 0577-305-009; www.hotelmonteriggioni.net; doubles 230€) hidden in one of the buildings, but you'll find a better value at one of the three central, characterful rooms, decorated in the Tuscan style with modern bathrooms, let by Ristorante da Remo (tel. 0577-304-370). Much of the village is taken up with quiet gardens and a few olive trees. Monteriggioni is content to offer you a lunch at one of its two restaurants, and sell you a few postcards from the shops on the central piazza.

Another 11km (7 miles) along a secondary road takes you to Colle di Val d'Elsa, the medieval birthplace of master Gothic architect Arnolfo di Cambio, who designed Florence's Palazzo Vecchio and Duomo. The tourist office is at Via Campana 43, 53034 Colle di Val d'Elsa (tel. 0577-922-791; www.comune.collevaldelsa.it). Regular buses run here from Siena and San Gimignano. Don't enter Colle's old city at the east end; instead, circle around the small center to come in the west side for the proper introduction, passing under the yawning arch of Baccio d'Agnolo's Mannerist Palazzo Campana gate (1539).

The main road of the Old Town, Via del Castello, leads to Piazza del Duomo. The cathedral contains one of the nails supposedly used to crucify Christ in a Mino da Fiesole tabernacle and a bronze Crucifix designed by Giambologna and cast by his student Pietro Tacca over the high altar. Next door is the Palazzo Pretorio, which houses a small Museo Archeologico (tel. 0577-922-954; www.museocolle.it) with a rather bland Etruscan collection and some 14th- and 15th-century frescoes. The communists jailed here in the 1920s scrawled political graffiti on some of the walls. A fine set of Sienese-school paintings resides in the nearby Museo Civico e d'Arte Sacra, Via del Castello 31 (tel. 0577-923-888), housed in the Palazzo dei Priori. If you can find time to dine, the Officina della Cucina Popolare, Via Gracco del Secco 86 (tel. 0577-921-796; www.cucina-popolare.com), serves the best seasonal Tuscan food for miles in any direction.

Asciano

The SS438 winds a gloriously scenic 26km (16 miles) from Siena to Asciano, a small town still partially girded by its 1351 walls. The town's tourist office is by the main road on Via delle Fonti, 53041 Asciano (tel. 0577-718-811). April to October hours are Tuesday through Sunday from 10:30am to 1pm, plus Tuesday, Friday, and Saturday 3 to 6pm. November to March it's Friday and Saturday only 10:30am to 1pm.

The 14th-century Museo Palazzo Corboli, Corso Matteotti 122 (tel. 0577-719-524), has charming frescoes on humanist themes and allegories, a 1410 Annunciation carved in wood by Francesco di Valdambrino, Matteo di Giovanni's altarpiece from the town's church of Sant'Agostino, and Ambrogio Lorenzetti's St. Michael altarpiece. The Etruscan collections were gleaned from tombs discovered in the area and include a couple of nicely painted 3rd- to 5th-century-B.C. vases, funerary urns, and the standard pile of pottery bits. 

At the town's Museo Cassioli, Via Fiume 8, is a collection of late-19th- and early-20th-century art by a local artist and his son (open Wed-Sun in summer, weekends only otherwise). Asciano's Romanesque and Gothic Collegiata, built of travertine between the 10th and 13th centuries, has, unusually, three apses and a 15th-century Sienese-school crucifix over the altar. You'll find the best lunch in town at La Mencia, Corso Matteotti 85 (tel. 0577-718-227; www.lamencia.it).

Asciano is surrounded by biancane, land formations where erosion has left emerald lawns, sitting like toupees atop knobby white hills. These blend to the south with the Crete Senesi, a similarly eerie landscape of eroded clay and limestone hillsides with farmhouses perched atop deep washed-out gullies and cypress crowded along sheer ridges. In the center of these weird badlands, accessible by a spectacular minor road out of Asciano, the abbey of Monte Oliveto Maggiore (tel. 0577-707-611) is hidden in its own womb of pines.

Founded in 1313 by a group of wealthy Sienese businessmen who wanted to devote themselves to the contemplative life, the red-brick monastic complex was built by the early 15th century. The Olivetans, still an active order within the Benedictines, were trying to restore some of the original simplicity and charity of the Benedictine rule, and the monks cared for victims during the 1340s Black Death. What draws most visitors today is the 36-scene fresco cycle by Luca Signorelli and Sodoma, one of the masterpieces of High Renaissance narrative painting and Sodoma's greatest work. After parking, walk under the gate tower with its small cafe and through the cool woods for about 5 minutes to the bulky brick heart of the complex. The entrance to the monastery is around to the right: A signed doorway leads into the Chiostro Grande and puts you right at the frescoes' start.

Signorelli started the job of illustrating the Life of St. Benedict here in 1497. He finished nine of the scenes before skipping town the next year to work on Orvieto's Duomo. Antonio Bazzi arrived in 1505 and finished the cycle by 1508 in his own inimitable style. Bazzi was known as "Il Sodoma," a derogatory nickname that Vasari suggests was due to Bazzi's predilection for young men. Sodoma was married at least three times, however, and may have had in the neighborhood of 30 children. To follow the cycle's narrative, start in the back-left corner as you enter. On the third, or west, wall are the Signorellis. Scene 20, Benedict Sending Mauro to France and Placido to Sicily, is an interlude by Il Riccio. Scenes 21 to 28, starting with Florenzo's Death, are by Signorelli (his last work, no. 29, was destroyed when a door was installed). Sodoma did most of the rest of the painting in this part of the monastery, including the grotesques and monotone details on the pilasters between the scenes, a self-portrait (with pet badger; panel 3), and two fine separate frescoes: a small Christ at the Column and St. Benedict Confers the Rule on the Olivetans, both in the passage leading from the church. Afterward, pop into the church to see some gorgeous intarsia choir stalls by Giovanni da Verona (1505) with scenes including cityscapes modeled in precise perspective. Monte Oliveto is open daily. Admission is free.

The SS451 leads southwest out of the Crete 9km (5 1/2 miles) to the Via Cassia SS2 and Buonconvento. Hidden within a ring of plain suburbs are Buonconvento's pretty medieval core and an excellent small museum of Sienese-school art, the Museo d'Arte Sacra della Val d'Arbia, Via Soccini 18 (tel. 0577-807-190; www.museoartesacra.it), with works by Duccio, Sano di Pietro, Andrea di Bartolo, and Matteo di Giovanni. Before leaving town, drop by the 14th-century Santi Pietro e Paolo, where you'll see a pair of 15th-century Madonna and Child paintings, one with saints by Pietro di Francesco degli Orioli and one without by Matteo di Giovanni. For more itineraries in and around the town, see www.turismobuonconvento.it.

The best hotel accommodations for miles in any direction are to be found at the Locanda del Castello, Piazza Vittorio Emanuele II 4, 53020 San Giovanni d'Asso (www.lalocandadelcastello.com; tel. 0577-502-939), set 13km (8 miles) northeast of Buonconvento in the pedestrian center of a tiny, silent little Crete village. Each of the nine rooms is decorated simply, in a refined take on the Tuscany rustic style, and the restaurant serves similarly sophisticated Tuscan flavors. 

Note: This information was accurate when it was published, but can change without notice. Please be sure to confirm all rates and details directly with the companies in question before planning your trip.