San Miniato -- The most diverting Valdarno detour is a trip southwest of Empoli to San Miniato. The hilltop Old Town is famous these days mainly for its kite-flying festival (the Sunday after Easter) and the white truffles hiding under the soil of the surrounding valley -- the key market takes place on the last three weekends in November. San Miniato's long history, though, puts it as a former outpost of the Holy Roman Empire and countryside seat of emperors from Otto I to Frederick II. The latter left the town a 1240 Rocca (rebuilt after it was bombed in World War II), the taller remaining tower of which rises gracefully above the village and the shorter of which serves as the Duomo bell tower.
On Piazzetta del Castello is the Duomo, open daily from 8am to 12:30pm and 3 to 6:30pm. Few of its original 12th-century Romanesque features remain, save the facade, unusually inset with ceramic North African bowls. A few of those bowls have been removed and are kept next door in the Museo Diocesano (http://www.sanminiatopromozione.it/en/museo-diocesano), along with a Sienese school Maestà, a Neri di Bicci Madonna and Child, a Verrocchio terra-cotta bust of the Redeemer, and some baroque works. Between April and September, it's open Thursday to Sunday 10am to 6pm; October through March, it's open the same days from 10am to 5pm. The town's other worthwhile church is San Domenico, Piazza del Popolo, which contains works ranging from 14th-century Masolino-school frescoes to early-20th-century Art Deco frescoes. It's open daily from 8:30am to noon and 4 to 7pm (3-7pm in winter). However, the number one reason to visit the town is to stock up from one of Tuscany's great butchers, Sergio Falaschi, Via Augusto Conti 18-20 (tel. 0571-43-190; www.sergiofalaschi.com), where you'll find fresh and cured meats, salami made from the Cinta Senese breed of pig, homemade ragù made with veal, rabbit, and countless other animals, and much more. The shop is closed on Sunday afternoon and all-day Wednesday. If you're in town over lunch, L'Upupa, Via Augusto Conti 15 (tel. 0571-400-429), is a reliable trattoria serving tasty, yet simple, seasonal plates of pasta and plenty of truffle dishes. Primi cost 7€ to 9€, and secondi between 13€ and 18€. It's closed on Thursdays.
Empoli -- The modern market town of Empoli gave forth in 1551 a talented baroque painter christened Jacopo Chimenti but known by the name of his hometown. Although World War II bombs wreaked havoc on much of the town, the main piazza, Piazza della Propositura, is still graced with the Collegiata di Sant'Andrea, an 8th-century church with a harmonious green-and-white Romanesque facade. The facing is original 12th century in the bottom half, but the top was finished off in a seamless imitation style in the 19th century.
The inside doesn't live up to the exterior, but its Museo della Collegiata, Piazza della Propositura 3 (tel. 0571-76-284), certainly does. It was one of Tuscany's first community museums when it opened in 1859, and the collections include a detached Masolino Pietà fresco (1424-25), a tiny Filippo Lippi Madonna, and works by Lorenzo Monaco, like his 1404 Madonna dell'Umiltà with Saints. The museum is open Tuesday to Sunday from 9am to noon and 4 to 7pm.
Vinci -- Leonardo fans can take a 9km (5 1/2-mile) detour north to visit his hometown, Vinci. The village honors its original Renaissance man with the 2010-renovated Museo Leonardiano, Piazza dei Guidi (tel. 0571-933-251; www.museoleonardiano.it), in the 13th-century castle of the Guidi counts. It has no original Leonardos but does contain, in two adjacent palazzi, full-size models of some of the weird and wonderful machines he invented, faithfully reproduced from Leo's Codex Atlanticus, alongside multimedia exhibits that science-minded older children and adults will enjoy. It's open daily from 9:30am to 6pm (until 7pm in summer). You can also see the baptismal font where he was baptized in Santa Croce church and drop by the Biblioteca Leonardiana, Via Giorgio la Pira 1 (tel. 0571-933-250; www.bibliotecaleonardiana.it), which preserves copies of anything printed relating to Leonardo. The Biblioteca is open Monday through Friday from 3 to 7pm. Hike or drive 3km (2 miles) up the hill to the tiny hamlet of Anchiano to see Leonardo's modest Birth House (tel. 0571-56-519; free admission; Mar-Oct daily 9:30am-7pm, Nov-Feb until 6pm).
The Maremma stretches along Tuscany's coast from Cecina to Monte Argentario and extends inward (where it becomes the Alta Maremma), along flat, occasionally rolling land toward the mountainous interior. The Maremma was once the heartbeat of the Etruscan world and preserves scant remains of some of their most important cities and miles of the mysterious sunken roads (vie cave) they carved more than 4m (13 ft.) into the tufa. The complex canal and drainage system built by those ancient Tuscans allowed them to turn the marshy flatlands into a breadbasket -- it's still a major produce-growing province.
The conquering Romans, though, weren't as able as landscape administrators, and when the neglected drainage system broke down, marshes and bogland swamped the region and brought with them the malaria mosquito. Grand Duke Leopold I was the first to seriously attempt a large-scale reclamation of the land in 1828, and his canals still form an important part of the drainage network, but it wasn't until malaria was defeated here in the 1950s that the coastal stretches of land became livable again.
Today, the Maremma puts forth a mixed image. It's part rugged new colony, where man has reconquered the land and cowboys called butteri watch over herds of white oxen. It's also part relic of the ancient past, where centuries of relative isolation have allowed Etruscan ruins and towns to decay romantically. You'll encounter very few other tourists as you explore archaic hill towns and grassy, mounded Etruscan tombs.
Pitigliano and the Alta Maremma -- It's a substantial diversion from the coast to Pitigliano -- turn inland on the SS74 at Albinia and drive northeast on a slow road for 51km (31 1/2 miles) -- but even hill-town veterans won't be prepared for the almost Transylvanian sight of the town seemingly growing from living tufa rock. It's an unforgettable sight.
Pitigliano's twisted alleys and gnarled stone staircases make for pleasant strolling, especially along Via Roma, which you can follow all the way to the town's oldest church, San Rocco, whose Romanesque interior sports a handsome nave and aisles supported by travertine columns. It is the town's Jewish community, banished here under the Medici grand dukes, that have left the most interesting historical mark, and gave the town its nickname, Piccola Gerusalemme ("Little Jerusalem"). The mazelike Jewish Museum and Synagogue, Vicolo Marghera (off Via Zuccarelli; tel. 0564-616-006; www.lapiccolagerusalemme.it), is built into the former ghetto. The ritual baths, matzo oven (last used for Passover in 1939), and kosher wine cellars are carved into the tufa that underpins the town. The synagogue was built in 1598, shortly after Jews were banished from Rome. This fascinating area is open Sunday through Friday 10am to 12:10pm and 3:30-6:10pm (shorter afternoon hours off season). If you're in town over lunchtime, Il Grillo, Via Cavour 18 (tel. 0564-615-202), serves good value, rustic Maremman dishes in a traditional dining room. It's closed Tuesday.
Pitigliano also sits at the center of a network of Etruscan "sunken roads" (vie cave) hollowed out of the volcanic rock upon which the Alta Maremma sits. Nobody is quite sure what the vie cave were for -- processional walkways or livestock droving paths are two theories -- but these days they are free and open to anyone armed with a decent local map. Even in summer, you'll likely have the routes to yourself. The best of them is the Via Cava di San Giuseppe, 1km (under 1 mile) out of Pitigliano on the road to Sovana. Just west of Sovana is the Tomba Ildebranda (Hildebrand's Tomb; tel. 0564-614-074; www.leviecave.it), the most extensive and important Etruscan burial site in the Maremma, which (in its 3rd-century B.C. heyday) was decorated with vivid pictures of vegetables. Leave an hour at least to explore the network, including the Via Cava di Poggio which originates here. It's open daily March through September 10am to 7pm (plus weekends only until 5pm Oct). There are more Etruscan remains at Saturnia, but it's the thermal springs that have put the town on the map. The cascade of swirling, steaming, slightly stinky sulfur water at a constant temperature of 37°C (97°F) is a surreal place for a dip. On a sunny day the cataract cascade reflects an intense cobalt blue, looks like nothing so much as an oversized ornamental water feature, and makes for a great photo. It's just outside of Saturnia by the road to Montemerano, is completely free, but gets busy on weekends, even way out of high season.
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.