The inland hills of southern Tuscany display the region at its best, an infinite gradation of trees and vineyards that encompasses the depopulated crete before climbing into the hills around Monte Amiata. Southwest of Siena towards the sea, the memorable but little-visited hill-town of Massa Maríttima presides over a marshy coastal plain. Magnificent monastic architecture survives in the tranquil settings of San Galgano and, further east, Monte Oliveto Maggiore, which also boasts some marvellous frescoes. The finest of the hill-towns to the south of Siena is Montepulciano, with its superb wines and an ensemble of Renaissance architecture that rivals neighbouring Pienza.
Further south, the tourist crush is noticeably eased in smaller towns and villages that are often overlooked by visitors gorged on Florentine art and Sienese countryside. Wild Monte Amiata offers scenic mountain walks, Saturnia has some remarkable sulphur springs, and the isolated, dramatic medieval town of Pitigliano nurtures the amazing story – and scant remains – of what was once Tuscany’s strongest Jewish community.
The road south from Volterra over the mountains to MASSA MARÍTTIMA is scenically magnificent yet little explored: classic Tuscan countryside which is given an added surreal quality around Larderello by the presence of soffioni (hot steam geysers), huge silver pipes snaking across the fields, and sulphurous smoke rising from chimneys amid the foliage.
Like Volterra, Massa has been a wealthy mining town since Etruscan times. In 1225, it passed Europe’s first-ever charter for the protection of miners; in the century afterwards, before Siena took over in 1335, its exquisite Duomo went up and the population doubled. The trend was reversed in the sixteenth century, and by 1737, after bouts of plague and malaria, it was a virtual ghost town. Massa gained its “Maríttima” suffix in the Middle Ages when it became the leading hill-town of this coastal region, even though the sea is 20km distant across a silty plain. Its recovery began with the draining of coastal marshes in the 1830s. Today, it’s a quiet but well-off town, where the effects of mining are less evident than agriculture and low-profile tourism. While visitor numbers are much lower than, say, San Gimignano, Massa is the closest hill-town to several coastal resorts, and on summer evenings it fills up with beach-based day-trippers.
The outskirts of Massa have been marred by modern development, but the medieval town itself at the top of the hill, divided between two very distinct levels, remains a splendid ensemble. Piazza Garibaldi, the main square of the lower section, is a perfect example of Tuscan town planning. Its thirteenth-century Duomo, set on broad steps at a dramatically oblique angle to the square, is dedicated to the sixth-century St Cerbone, whose claim to fame was to persuade a flock of geese to follow him when summoned to Rome on heresy charges. Behind the altar in its airy interior (daily 8am–noon & 3–7pm; free), the Arca di San Cerbone is a marble “ark” carved with bas-reliefs depicting the life of the saint. A modest Museo Archeologico occupies the Palazzo del Podestà opposite (Tues–Sun 10am–1pm & 3–6pm; Nov–March closes at 5pm; €5) – worth visiting for the town’s undisputed masterpiece, a superb Maestà altarpiece by Ambrogio Lorenzetti, coloured in vivid pink, green and tangerine, with Cerbone and his geese lurking in the corner.
A picturesque lane, Via Moncini, climbs steeply from the northern end of the square up to the quiet Gothic upper town, known as the Città Nuova. Passing through a gateway, you emerge beneath a slender and very spectacular – albeit militarily useless – arch that connects the high town walls to the Torre del Candeliere. Set in the centre of Piazza Matteotti, and part of the thirteenth-century Fortilizio Senese, the tower is open to visitors, who can enjoy a stupendous panorama from the top (April–Oct daily 10.30am–1.30pm & 4–7pm; Nov–March 11am–1pm & 2.30–4.30pm; €2.50).
Buses connect Massa with Volterra (change at Larderello) and Siena. The helpful tourist office is just below Piazza Garibaldi at Via Todini 3/5 (daily except Tues 9.30am–1pm & 4–7pm; April, May & Nov closed Sun pm; Dec–March closed all Sun; 0566.902.756, www.altamaremmaturismo.it). Massa’s only central hotel is the comfortable Il Sole, Corso della Libertà 43 (0566.901.971, www.ilsolehotel.it; €91–120); otherwise go for the pleasant, slightly motel-like Duca del Mare, immediately below the old town at Piazza Dante Alighieri 1 (0566.902.284, www.ducadelmare.it; €61–90), which has cheery rooms and a nice pool. There’s also a good hostel, Ostello Sant’Anna, in the higher part of town, converted from a school at Via Gramsci 3 (0566.901.115, digilander.libero.it/leclarisse; dorm beds €15; 9am–noon & 5pm–midnight).
While bars and cafés line Piazza Garibaldi, the best restaurants are in the lanes and alleyways nearby. La Tana del Brillo Parlante, Vicolo del Ciambellano 4 (0566.901.274; closed Wed), a lovely little place with a couple of outdoor tables, serves good pasta and meat dishes, while Osteria da Tronca at Vicolo Porte 5 (0566.901.991; dinner only, closed Wed) offers inexpensive osteria-style food.
The classic Tuscan countryside that stretches south of Siena is known as the crete. This tranquil, sparsely populated region of pale clay hillsides, dotted with sheep, cypresses and the odd monumental-looking farmhouse, was a heartland of medieval monasticism in Tuscany. The Vallombrosan order maintained their main house at Torri just south of Siena; the Benedictine order had theirs at Sant’Antimo near Montalcino; and the Cistercians founded the convent and abbey of San Galgano. Now ruined, this is one of the most alluring sights in Tuscany, complete with its hilltop chapel housing a “sword in the stone”. The finest monastery of all lies southeast of Siena, at Monte Oliveto Maggiore.
The Abbazia di San Galgano, surrounded by majestic fields of sunflowers in a peaceful rural setting 26km northeast of Massa Maríttima, is perhaps the most evocative Gothic building in all Italy – roofless, with grass for a floor in the nave, nebulous patches of fresco amid the vegetation, and panoramas of the sky, clouds and hills through a rose window. During the twelfth and thirteenth centuries, local Cistercian monks were the leading power in Tuscany. The abbots exercised powers of arbitration in city disputes, while the monks in Siena served as the city’s accountants. Through them, the ideas of Gothic building were imported to Italy. The order began a hilltop church and monastic buildings here in 1218, but their project to build a grand abbey on the fertile land below was doomed to failure. Building work took seventy years up to 1288, but then famine struck in 1329, the Black Death in 1348, and mercenaries ran amok in subsequent decades. By 1500, all the monks had moved to the security of Siena. The buildings mouldered until 1786, when the bell tower was struck by lightning and collapsed. Three years later, the church was deconsecrated, and the complex was abandoned for good.
These days, the main appeal of the abbey (unrestricted 24hr access; free) is its general state of ruin, although the basic structure has been stabilized. In summer, it makes a wonderful open-air venue for opera performances, staged on various evenings between late June and the end of July; see www.sangalgano.org for schedules.
Atop the solitary hill nearby, the unusual round Romanesque church of Monte Siepi commemorates the spot where Galgano – a local twelfth-century knight – renounced his violent past by thrusting his sword into a stone. Amazingly enough, Galgano’s sword in the stone has survived, protected under glass as an object of veneration. A side chapel preserves the decaying remains of a man’s hands: local legend has it that two wolves – companions of Galgano – tore them from a robber who had broken into the saint’s tomb.
By far the easiest way to reach the abbey is to drive, though two or three buses daily between Massa Maríttima and Siena can drop passengers on the main road nearby. The abbey’s vaulted scriptorium holds a small tourist office (April–Oct Mon–Fri 10am–1pm & 3–6pm, Sat & Sun 10am–1pm & 2.30–6.30pm; 0577.756.738, www.prolocochiusdino.it). A nice little café faces the abbey from the far end of its entrance avenue, attached to the Fattoria le Planaie (0577.799.018, www.sangalgano.org; €61–90), with comfortable en-suite rooms if you fancy spending a night or two in this isolated spot.
Tuscany’s grandest monastery – the Abbazia di Monte Oliveto Maggiore, renowned for its absorbing Renaissance frescoes – stands 26km southeast of Siena, or roughly 50km east of San Galgano, in a secluded but exceptionally beautiful tract of countryside. By car, you can approach from the crossroads town of Buonconvento, climbing quickly into forests of pine, oak and cypress, and then into the olive groves that enclose the monastery. One afternoon bus daily from Siena’s train station goes to the village of Chiusure, 2km east of the abbey.
When Pius II visited in 1463, it was the overall scene that impressed him: the architecture, in honey-coloured Sienese brick, merging into the woods and gardens that the Olivetan or White Benedictine monks had created from the eroded hills of the crete. The pope recognized the order within six years, and over the following two centuries this, their principal house, was transformed into one of the most powerful monasteries in the land. Only in 1810, when the monastery was suppressed by Napoleon, did it fall from influence. Today it’s maintained by a small group of Olivetan monks, who supplement their state income with a high-tech centre for the restoration of ancient books. From the gatehouse, an avenue of cypresses leads to the abbey. Signs at the bottom of the slope direct you along a walk to Blessed Bernardo’s grotto – a chapel built on the site where the founder lived as a hermit.
The abbey (daily 9.15am–noon & 3.15–6pm; winter closes 5pm) is a huge complex, though much of it remains off-limits to visitors. The entrance leads to the Chiostro Grande, where the cloister walls are covered by frescoes that depict the Life of St Benedict, the founder of Christian monasticism. The fresco cycle, which begins on the east wall, immediately to the left of worshippers emerging from the church itself, was started in 1497 by Luca Signorelli, who painted nine panels in the middle of the series that start with the depiction of a collapsing house. The colourful Antonio Bazzi, known as Il Sodoma, painted the remaining 27 scenes between 1505 and 1508. He was by all accounts a lively presence, bringing with him part of his menagerie of pets, which included badgers, depicted at his feet in a self-portrait in the third panel. There’s a sensuality in many of the secular figures, especially the young men – as befits the artist’s nickname – but also the “evil women” (originally nudes, until the abbot protested). The church was given a Baroque remodelling in the eighteenth century and some superb stained glass in the twentieth. Its main treasure is the choir stalls, inlaid by Giovanni di Verona and others with architectural, landscape and domestic scenes (including a nod to Sodoma’s pets with a cat in a window). Stairs lead from the cloister up to the library, again with carving by Giovanni; sadly, it has had to be viewed from the door since the theft of sixteen of its twenty codices in 1975.
Highest of all the major Tuscan hill-towns, at more than 600m, the ravishing, self-contained community of MONTEPULCIANO stretches atop a long, narrow ridge 65km southeast of Siena. Its main street, the Corso, coils its way between scores of crumbling Renaissance palazzi and churches, here clustered around perfect little squares, there towering over tiny alleyways. Wherever stairways or mysterious passages drop down the hillside, you get sudden, stunning glimpses of the quintessential wine-growing countryside rolling off to the horizon; occasionally terraced gardens allow you to contemplate the whole stunning prospect at leisure.
Henry James, who compared Montepulciano to a ship, spent most of his time here drinking – a sound policy, in view of the much-celebrated Vino Nobile, production of which dates back well over a thousand years. More recent visitors have been enticed by the drinking of blood rather than wine; Montepulciano’s ancient squares made an ideal location for the 2009 teen vampire movie New Moon.
Montepulciano is served by regular buses between Siena and Chiusi, and also welcomes one daily direct from Florence. The local train station is also on the Siena–Chiusi line, but it’s 10km northeast of town, and more frequent services call at the main-line station of Chiusi itself, 22km southeast; connecting buses run from both. If you’re driving, only enter the town if you have a hotel reservation; failing that, you’ll have to park outside the walls, perhaps in the free spaces to the east.
The main tourist office is outside the walls at the lower end of town, at Piazza Don Minzoni 1 (April–Sept Mon–Sat 9am–12.30pm & 3–8pm, Sun 9am–12.30pm; Oct–March Mon–Sat 9.30am–12.30pm & 3–6pm, Sun 9.30am–12.30pm; 0578.757.341, www.prolocomontepulciano.it), though you can also pick up information in the Museo Civico higher up.
Montepulciano doesn’t hold nearly enough hotels to meet summer demand, though private rooms are also available. Reserve well ahead, and visit the website www.montepulcianohotels.it. On summer nights, the town’s cool hilltop breezes offer a welcome relief from the heat at lower elevations.
Albergo Duomo Via San Donato 14 0578.757.473, www.albergoduomo.it. A short distance from Piazza Grande, the three-star Duomo has excellent facilities and smart clean rooms, plus free private parking. €91–120
Bellavista Via Ricci 25 0578.716.341, www.cretedisiena.com/camerebellavista. Six great-value rooms near the main square, five have en-suite bathrooms, and four superb countryside views. Cash only; free parking. No one lives here; ring an intercom, and the owner will arrive shortly. €61–90
La Terrazza Via Piè al Sasso 16 0578.757.440, www.laterrazzadimontepulciano.it. Peaceful, well-equipped little hotel, in an old house just below the Duomo; breakfast is served on the leafy roof terrace in summer. €91–120
Meuble Il Riccio Via Talosa 21 0578.757.713, www.ilriccio.net. Lovely little B&B in a stunning medieval building just off Piazza Grande, with five very comfortable rooms and a mosaic-floored courtyard. €91–120
The steep climb from the lowest point in Montepulciano – its northern gate, the Porta al Prato – up to the highest, the main Piazza Grande, takes around twenty minutes. It’s a delightful walk, passing a superb and unusually consistent array of Renaissance architectural treasures, as well as the town’s southern gate, the Porta delle Farine.
Montepulciano’s rise to eminence began in 1511, when the town finally threw in its lot with Florence rather than Siena. The Florentines thereupon sent Antonio Sangallo the Elder to rebuild the town’s gates and walls, which he did so impressively that the council took him on to work on the town hall and a series of churches. The local nobles meanwhile hired Sangallo, his nephew Antonio Sangallo the Younger, and later the Modena-born Vignola, a founding figure of Baroque, to work on their own palazzi. Totally assured in conception and execution, this trio’s work makes a fascinating comparison with Rossellino’s Pienza.
Sangallo’s first commission was the Porta al Prato itself. Inside the gate at the first square, Piazza Savonarola, a stone column bears the heraldic lion (marzocco) of Florence. The church of Sant’Agostino, just beyond, was designed by the earlier Medici protégé, Michelozzo, who also carved the relief above the door. Its interior holds fine Sienese paintings by Lorenzo di Credi and Giovanni di Paolo.
The street forks about 100m further along, where the Renaissance Loggia di Mercato overlooks Piazza dell’Erbe. Turning right off the Corso will lead you steeply up to a beautiful little piazza fronting the church of Santa Lucia, where a chapel on the right contains a fabulous Madonna by Signorelli. Just below Santa Lucia, Via del Poggiolo runs down to the church of San Francesco and continues – as the imposing Via Ricci – up to the Piazza Grande past the Sienese-Gothic Palazzo Neri-Orselli, home to the Museo Civico (Tues–Fri & Sun 10am–8pm, Sat 10am–10pm; €7). Besides an extensive collection of small-town Gothic and Renaissance works, including glazed terracottas by Andrea della Robbia, this hosts substantial temporary exhibitions each year.
Piazza Grande, Montepulciano’s theatrical flourish of a main square, is built on the highest point of the ridge. Its most distinctive building is the Palazzo Comunale, a thirteenth-century Gothic mansion that continues to serve as the town hall. Michelozzo added its clocktower and rustication in imitation of Florence’s Palazzo Vecchio; an upstairs ticket-office grants access to the tower itself, though disappointingly you can’t climb all the way to the top, just to the castellated terrace immediately below the clock (April–Oct Mon–Sat 10am–6pm; €2).
Two of the palazzi on the square were designed by Sangallo. The highly innovative Palazzo Tarugi, alongside the lion and griffin fountain, has a public loggia cut through one corner. Headier pleasures await at the Palazzo Contucci, one of the many buildings scattered about Montepulciano that serve as cantine for the wine trade, offering free degustazione (tastings) and sale of the Vino Nobile. Sangallo and his contemporaries never got around to building a facade for the plain brick Duomo across the square (daily 9am–1pm & 3.30–7pm; free). Its interior is an elegant Renaissance design, scattered with superb sculptures by Michelozzo, while the finest of its paintings is the Sienese Taddeo di Bartolo’s iridescent 1401 altarpiece of the Assumption, a favourite subject for Sienese artists.
Sangallo’s greatest commission came in 1518, when he was invited to design the pilgrimage church of San Biagio just below the town. Set amid lush, pristine lawns, at the end of a long rural avenue, it makes a wonderful fifteen-minute walk down from the centre. This was the second-largest church project of its time after St Peter’s in Rome, and exercised Antonio until his death in 1534. The result is one of the most serene Renaissance creations in Italy, constructed from a porous travertine whose soft honey-coloured stone blends perfectly into its niche in the landscape. Its major architectural novelty was the use of freestanding towers to flank the facade (only one was completed). While the interior is somewhat spoiled by Baroque trompe l’oeil decoration, it remains supremely harmonious. The nearby Canonica (rectory), endowed by Sangallo with a graceful portico and double-tiered loggia, is scarcely less perfect.
Acclaimed since the medieval era, Vino Nobile di Montepulciano today boasts a top-rated DOCG mark; something the townspeople have not been shy in exploiting. Wine shops along the streets of Montepulciano sell gift sets, while local vineyards often offer in-town tastings (usually free, but requiring advance notice). Every restaurant can provide a range of vintages, the very cheapest of which will still set you back at least €20. The tourist office can organize wine-tasting rambles for visitors. Among the many places to check out are the venerable Contucci at Via San Donato 15 and also in the Palazzo Contucci on the Piazza Grande (0578.757.006, www.contucci.it) – the family line in Montepulciano goes back a thousand years – and the Cantina Del Redi, Via di Collazi 5 (0578.716.092, www.cantinadelredi.com).
Abundant restaurants line the streets and squares of Montepulciano, and you’ll also find several small cafés, as well as plenty of places to sample the region’s Vino Nobile wine.
Otherwise, nightlife and entertainment opportunities tend to be sparse, though things liven up in July during the three-week Cantiere Internazionale d’Arte (0578.716.368, www.cantiere.toscana.nu or www.fondazionecantiere.it), which presents exhibitions and concerts around town. The last Sunday in August sees the Bravìo delle Botti, a barrel-race in medieval costume. In early September, the five-night, irresistibly named Live Rock Festival of Beer (www.liverockfestivalofbeer.it) is celebrated in the tiny village of Acquaviva, 10km northeast near Montepulciano’s train station.
Acquacheta Via del Teatro 22 0578.717.086, www.acquacheta.eu. Small traditional osteria, just down from the Duomo, that’s always busy with locals. Lots of cheese and truffle, a changing menu of the day, and home-made pasta dishes from €5.50; you can get a truly memorable meal for under €20. Closed Tues.
A Gambe di Gatto Via dell’Oppio nel Corso 34 0578.757.431. Tiny, hugely friendly bistro, with an emphasis on organic wine and olive oils, and a devotion to “slow food”. Only come if you’ve plenty of time; if you do, you’re in for a treat, with daily menus of simple but imaginative cuisine at very reasonable prices.
Caffè Poliziano Via di Voltaia nel Corso 27. This glorious wood-panelled 1868 tearoom, restored to a classic Art Nouveau design, serves tea, coffee and pastries, with free wi-fi, and offers great views from a small terrace at the back. Its adjoining restaurant, Il Grifin d’Oro, serves full meals at around €25, including specialities like pici (fat spaghetti) with wild boar ragù. Daily 7am–midnight.
La Briciola Via delle Cantine 23. Friendly restaurant with outdoor tables on a quiet alley just inside the Porta al Prato, serving quality wood-fired pizza, as well as a range of flavourful Tuscan primi (€8) and secondi (€12–18). Closed Wed.
La Grotta Via di San Biagio 0578.757.607. Opposite San Biagio church, about 1km outside the city walls, this brick-vaulted sixteenth-century restaurant serves classic Tuscan cuisine and has its own garden. Typical mains cost over €20. Closed Wed.
Trattoria di Cagnano Via dell Opio nel Corso 30 0578.758.757. Popular and bustling, this offers a wide range of pizzas, from the simple €5 margherita to the €7.50 estate (mozzarella, tomatoes, rocket, prosciutto and parmesan), as well as outside seating. Closed Mon.
The tiny, perfectly preserved village of PIENZA, 11km west of Montepulciano, is as complete a Renaissance creation as any in Italy, established as a Utopian “New Town”, in an act of considerable vanity, by Pope Pius II. A scion of the leading family of what was formerly Cortignano, he set about transforming his birthplace in 1459, under the architect Bernardo Rossellino. The cost was astronomical, but the cathedral, papal and bishop’s palaces, and the core of a town (renamed in Pius’s honour), were completed in just three years. Pius lived just two more years, and of his successors only his nephew paid Pienza any regard: intended to spread across the hill, the planned city remained village-sized. Today, despite the large number of visitors, it still has an air of emptiness and folly: a natural stage-set, where Zeffirelli filmed Romeo and Juliet.
Traffic converges on Piazza Dante, just outside the main gate, Porta al Murello. From there the Corso leads straight to Rossellino’s centrepiece, Piazza Pio II, which deliberately juxtaposes civic and religious buildings – the Duomo, Palazzo Piccolomini (papal palace), Bishop’s Palace and Palazzo Pubblico – to underline the balance between church and town. While making the usual medieval nod to Florence in its town hall, the square is otherwise entirely Renaissance in conception.
The Duomo boasts one of the earliest Renaissance facades in Tuscany; the interior, on Pius’s orders, took inspiration from the German hall-churches he had seen on his travels, and remains essentially Gothic. The chapels house an outstanding series of Sienese altarpieces, commissioned from the major painters of the age – Giovanni di Paolo, Matteo di Giovanni, Vecchietta and Sano di Pietro. How long the building itself will remain standing is uncertain though. Even before completion a crack appeared, and since an earthquake in the nineteenth century it has required much buttressing – the nave currently dips crazily towards the back of the church.
Pius’s residence, the Palazzo Piccolomini (Tues–Sun: mid-March to mid-Oct 10am–1pm & 2–6.30pm; mid-Oct to mid-March 10am–1pm & 2–4pm, but closed early Jan to mid-Feb and last 2 weeks of Nov; open Mon on public hols; €7; www.palazzopiccolominipienza.it) sits alongside the Duomo. Visitors are free to walk into the courtyard and through to the original “hanging garden” behind to the left, where a triple-tiered loggia offers a superb view over the valley. To see the apartments above, however, which include Pius II’s bedroom, library and other rooms filled with collections of weapons and medals, you have to join one of the frequent half-hour guided tours, for no extra charge.
Further mementoes of the pope – notably his English-made embroidered cope – are cherished in the excellent Museo Diocesano across the piazza (Wed–Mon 10am–1pm & 3–6pm; €4.10). The true highlights there however are some stunning tapestries and, especially, paintings, including a wonderful anonymous depiction of the life of Christ in 48 tiny panels, one of which shows Jesus meeting a black devil, complete with wings and horns.
Buses between Montepulciano and Buonconvento stop at both Pienza and San Quírico d’Orcia. Drivers, as ever, should park outside the city walls. The very helpful, central tourist office is at no. 30 on the Corso (daily 10am–1pm & 3–6pm; 0578.749.305, www.comunepienza.it). In the heart of the village, the small Giardino Segreto, Via Condotti 13 (0578.748.539, www.ilgiardinosegretopienza.it; €91–120), offers pleasant rooms and self-catering apartments, while there’s also a beautiful, much more upscale hotel, the Relais Il Chiostro di Pienza, in a converted Franciscan monastery at Corso Rossellino 26 (0578.748.400, www.relaisilchiostrodipienza.com; €151–200).
As a popular day-trip destination, Pienze holds several good restaurants. Among the best are the friendly Latte di Luna, just inside the walls at Via San Carlo 6 (0578.748.606; closed Tues & all July), where the nice outside seating area is screened by flowers, and maialino arrosto, roast suckling pig, is the house speciality; Sperone Nudo, with several tables on the delightful little Piazza di Spagna just off the main square (0578.748.641, www.speronenudo.it); and the good-value Buca delle Fate, a simple trattoria serving Tuscan country food, at Corso Rossellino 38/A (0578.748.272; closed Mon and parts of Jan & June). Pienza is centre of a region producing pecorino sheep’s cheese, and has gone overboard on natural food shops: cheesy smells await around every corner.
The rambling old village of SAN QUÍRICO D’ORCIA stands at a crossroads 8km west of Pienza. Its old town is quiet and rather decayed, but holds an exceptionally pretty Romanesque Collegiata church. For drivers, the stunning but inaccessible Castello Ripa d’Orcia, an isolated castle hotel-restaurant down a gravel road 5km southwest of town (0577.897.376, www.castelloripadorcia.com; minimum stay two nights; closed Nov to mid-March; €151–200), makes a wonderfully peaceful place to stay.
The extraordinary ancient site of BAGNO VIGNONI is tucked away 6km southeast of San Quírico. Its central square is entirely taken up by an arcaded Roman piscina, or open pool; the springs still bubble up at a steamy 51°C, and the old, flooded piazza with its backdrop of the Tuscan hills and Renaissance loggia – built by the Medici, who, like St Catherine of Siena, took the sulphur cure here – made a memorable scene in Tarkovsky’s film Nostalgia. Bathing in the piscina itself is forbidden, but you can enjoy the sulphur springs at the Piscina Val di Sole alongside, a modern spa complex that forms part of the characterful Posta Marcuccihotel (0577.887.112, www.hotelpostamarcucci.it; €201–250; pool free to guests, €15 per day to others). Also facing the piscina, Pius II’s fifteenth-century summer retreat is now the romantic Albergo Le Terme (0577.887.150, www.albergoleterme.it; €91–120). Several appealing restaurants are scattered on the adjacent lanes and squares, including the excellent Antica Osteria del Leone, Via dei Mulini 3 (0577.877.300; closed Mon), and the self-service Bottega di Cacio, Piazza del Moretto (0577.887.477), where shaded gardens make a great spot for an inexpensive lunch.
Another classic Tuscan hill-town, MONTALCINO, perches 20km west of Pienza. Set within a full circuit of walls and watched over by a rocca, it looks tremendous from below – and similarly, from up in the town, the surrounding countryside strewn with vineyards, orchards and olive groves is equally impressive. A quiet place, affluent in an unshowy way from its tourist trade, Montalcino produces a top-notch DOCG wine, Brunello di Montalcino, that’s reckoned by many to be the finest in Italy. For a spell during the fifteenth century, the town acquired great symbolic importance: this was the last of the Sienese comune to hold out against the Medici, the French and the Spanish, after Siena itself had capitulated. That role is acknowledged at the Siena Palio, where the Montalcino contingent – under its medieval banner proclaiming “The Republic of Siena in Montalcino” – takes pride of place.
For once, Montalcino’s streets are not too narrow to admit cars, but if you don’t have a hotel booking it’s still best to park outside the centre. Regular buses arrive in Piazza Cavour at the north end of town from Buonconvento and Siena; most pass first through Torrenieri, from where connections head to Pienza and Montepulciano. The tourist office is just up from the central Piazza del Popolo at Costa del Municipio 1 (daily 10am–1pm & 2–5.50pm; 0577.849.331, www.prolocomontalcino.it).
As accommodation is severely limited, it’s wise to book ahead at any time of year. Besides a handful of hotels and private rooms, numerous agriturismi can be found in the countryside immediately around town.
Albergo Giardino Piazza Cavour 4 0577.848.257, albergogiardino@virgilio.it. There’s really nothing special about Montalcino’s cheapest hotel rooms, but there’s no arguing with the prices, you get a friendly welcome – and some face right onto a verdant square. €61–90
Albergo Il Giglio Via Soccorso Saloni 5 0577.848.167, www.gigliohotel.com. Stylish and appealing hotel in a central, sixteenth-century townhouse, where the pleasant air-conditioned rooms have good bathrooms and great views; some have frescoed ceilings and terraces, too. Rates include a good breakfast. €121–150
Castello di Velona Località Castello di Velona, Castelnuovo dell’Abate 0577.800.101, www.castellodivelona.it. Superb twenty-room, four-star hotel, isolated in lovely open countryside on its own hill and ringed by cypress, close to Castelnuovo dell’Abate, about 10km south of Montalcino. Expensive, but rates drop in low season and there are often web deals. €401 and over
Vecchia Oliviera Via Landi 1 0577.846.028, www.vecchiaoliviera.com. Three-star hotel on the edge of town, where the eleven fine rooms form part of a well-restored former olive mill close to Porta Cerbaia and the walls, but do get some traffic noise. There’s also a pool, and the patio has excellent views. €91–120
Montalcino’s main street, Via Mazzini, leads from Piazza Cavour at the north end of town to the Piazza del Popolo, an odd little square set beneath the elongated tower of the town hall, based in all but its dimensions on that of Siena. An elegant double loggia occupies another side with, opposite, a wonderful and rather Germanic nineteenth-century café, the Fiaschetteria Italiana, which is very much the heart of town life.
Steps (Scale di Via Bandi) near the café lead up to the excellent, thoroughly modernized Museo di Montalcino e Raccolta Archeologica Mediovale e Moderna (Tues–Sun 10am–1pm & 2–5.50pm; €4.50 or €6 joint ticket with the Rocca fortress). The quality of the art on show is out of all proportion to the size of the town, and takes in a wealth of Sienese painting and early sculpture, including a fabulous twelfth-century Crucifixion. Separate basement galleries cover the early archeological history of this site, with a Neolithic burial chamber and some Bronze Age artifacts. The neighbouring church of Sant’Agostino has recently been incorporated into the complex, and can now only be entered via the museum; it’s slowly being restored, to reveal some stunning frescoes, and also host temporary exhibitions.
Following Via Ricasoli south brings you to the hilltop, fourteenth-century Rocca fortress. The open space enclosed within its impressively intact walls makes a great venue for summer concerts. At the foot of one of its towers, a spacious enoteca (0577.849.211, www.enotecalafortezza.it) sells the famed Brunello wine, along with bread, cheese and salami, and provides access to the ramparts (April–Oct daily 9am–8pm; Nov–March Tues–Sun 9am–6pm; €4, or €6 joint ticket with Museo Civico). The panorama that unfolds from up there is said to have inspired Leonardo’s drawing of a bird’s-eye view of the earth; on a clear day you can even see Siena.
Montalcino is filled with good restaurants, and also holds a row of fine enotecas along via Matteotti, all of which sell local wines by the glass or bottle and have pavement seating on the town side with huge views from the back.
Al Giardino Piazza Cavour 1 0577.849.076, www.ristorantealgiardino.it. Fine local cooking, just outside the walls that has won the approval of the Slow Food movement: the chef is the owner. Pleasant interior, while the “garden” in the name refers to its tables in the square opposite. Mains €18–20. Closed Wed.
Osteria Les Barriques Piazza del Popolo 20–22 0577.848.411. Far and away the best food in town, in a tiny dining room out of sight of the main street; great pasta for under €10, and fabulous steaks.
Trattoria L’Angolo Via Ricasoli 9 0577.848.017. Informal little bar-trattoria just down from the Rocca, serving snack lunches, pasta dishes for around €8, specials at €6–15, and totally divine Fiorentine beef. Closed Tues.
Osteria di Porte Al Cassero Via Ricasoli 32 0577.847.196. Indoor and outdoor seating near the Rocca, very reasonable prices, and top-notch food, from the wild boar to the tiramisù. Closed Wed.
Taverna Grappolo Blu Via Scale di Moglio 1 0577.847.150. Located in a little alley off Via Mazzini. The old stone-walled interior is cool and appealing, and the pastas are excellent.
At 1738m, the extinct volcano of Monte Amiata is the highest point in southern Tuscany. Rising in a succession of hills forested in chestnut and fir, it’s visible for miles around. A circle of towns rings its lower slopes, but the only one worth visiting for its own sake is Abbadia San Salvatore; nonetheless, old castles and bucolic countryside make the area a good detour. Towns such as Abbadia are refreshingly cool for summer walking, and in winter are the nearest ski resorts to Rome.
The village of ABBADIA SAN SALVATORE, the main focus for visitors to Monte Amiata, shelters at its heart a perfect, self-contained medieval quarter. The Benedictine abbey around which it developed was founded under the Lombards and rebuilt in 1036. A mere fraction now remains of the original, and most remnants date from the Middle Ages; the highlight is a large and beautiful eighth-century crypt, its 35 columns decorated with Lombard motifs. Summer visitors arrive in droves, lured by the landscape, cool breezes and some good easy walking paths. The best, the 29km Anello della Montagna, circles the mountain between 900m and 1300m – a long day’s walk, or easily manageable in sections round to Arcidosso. In July and August, buses shuttle up to the summit, offering a panorama that stretches to the sea.
Buses serve Abbadia San Salvatore from Siena, Buonconvento, Chiusi and Montepulciano; those from Rome and Grosseto to Abbadia pass first through Arcidosso. Avoid the Monte Amiata train station – it’s 45km away. The tourist office, Via Adua 25 (Mon–Sat 9am–1pm & 4–6pm, Sun 9am–1pm; 0577.775.811, www.amiataturismo.it), is headquarters for the Amiata region. Among the best value of the numerous hotels are the Cesaretti, Via Trento 37–43 (0577.778.198; €60 and under), and the central San Marco, Via Matteotti 19 (0577.778.089; €61–90).
Tuscany’s deep south, on the Lazio border, is its least visited corner. PITIGLIANO, the area’s largest town, is best approached along the road from Manciano, 15km west. As you draw close, the town soars above you on a spectacular outcrop of tufa, its quarters linked by the arches of an immense aqueduct. Etruscan tombs honeycomb the cliffs, but the town was known for centuries for its flourishing Jewish community. Today it has a slightly grim grandeur, owing to its mighty fortress and the tall and largely unaltered alleys of the old Jewish ghetto.
Immediately through the main city gate, Piazza Garibaldi is flanked by the fortress (1459–62) and aqueduct (1543), with views across houses wedged against the cliffside. Within the fortress, the lovely interiors of the Renaissance Palazzo Orsini (April–July & Sept Tues–Sun 10am–1pm & 3–7pm; Aug daily 10am–7pm; Oct–March Tues–Sun 10am–1pm & 3–6pm; €3) are filled with jewellery and ecclesiastical ephemera. Opposite it, the Museo Archeologico (same hours; €2.50) holds an interesting collection of Etruscan vases and trinkets.
The fortress backs onto Piazza della Repubblica, Pitigliano’s elongated main square. Beyond that lies the old town proper, a tight huddle of arches and medieval alleys. This is where you’ll find the old Jewish Quarter, centred on the Via Zuccarelli, which has been turned into a sort of outdoor museum known as La Piccolo Gerusalemme (Little Jerusalem), with a kosher baker, butcher, a synagogue and a small attached Jewish museum, the Mostra Ebraico (daily except Sat: April–Sept 10am–1.30pm & 2.30–6.30pm; Oct–March 10am–12.30pm & 3–5.30pm; €3). Pitigliano’s eighteenth-century synagogue part-collapsed in the 1960s, and lay derelict until renovation in 1995. Only the grand stone arch and the stairs leading up to the women’s gallery survive from the old building, along with plaques commemorating visits made by grand dukes Ferdinand III in 1823 and Leopold II in 1829. Although the Jewish community is virtually gone, many Italian and foreign Jews still choose to tie the knot here. Staff are happy to show you around the old ghetto, which includes a bakery on Via Marghera. A few minutes’ walk beyond, at the western end of town, you can see traces of the Etruscan wall below the Porta Capisotto.
Three RAMA buses daily from Manciano and Grosseto, two from Orbetello and one from Siena drop off on Piazza Petruccioli just outside the city gate. The helpful tourist office at Piazza Garibaldi 51 (Tues–Sun 10.30am–12.30pm & 3–7pm; 0564.617.111, www.comune.pitigliano.gr.it) has maps of the Vie Cave, ancient Etruscan paths that weave between tombs (some free, some with admission) and cliffside caves all around the town. The only hotel, the Guastini, Piazza Petruccioli 16 (0564.616.065, www.albergoguastini.it; €61–90), also has a good restaurant. Alternatively, try the award-winning, mid-priced Osteria Il Tufo Allegro, carved into the cliffs at Vicolo della Costituzione 5 (0564.616.192; closed all Tues & Wed lunch).
The Valdarno (Arno valley) upstream from Florence is a heavily industrialized tract, with no compelling stop before you reach the provincial capital, Arezzo, which is visited by foreigners in their thousands for its Piero della Francesca frescoes, and by Italians in even greater numbers for its antiques trade. South of Arezzo is the ancient hill-town of Cortona, whose picturesquely steep streets and sense of hilltop isolation make it an irresistible place for a stopover.
Piero della Francesca’s frescoes – which belong in the same company as Masaccio’s cycle in Florence and Michelangelo’s in Rome – are what makes AREZZO a tourist destination, but in Italy the city is equally well known for its jewellers, its goldsmiths, and its trade in antiques: in the vicinity of the Piazza Grande there are shops filled with museum-quality furniture, and once a month the Fiera Antiquaria turns the piazza into a vast showroom.
Arezzo has been one of Tuscany’s most prosperous towns for a very long time. Occupying a site that controls the major passes of the central Apennines, it was a key settlement of the Etruscan federation, and grew to be an independent republic in the Middle Ages. In 1289, however, its Ghibelline allegiances led to a catastrophic clash with the Guelph Florentines at Campaldino; though Arezzo temporarily recovered under the leadership of the bellicose Bishop Guido Tarlati, it finally came under the control of Florence in 1384. Nowadays, while Florence’s economy has become over-reliant on tourist traffic, well-heeled Arezzo goes its own way, though in recent years it has started to market itself more seriously as a place to visit.
Arezzo’s premier folkloric event is the Giostra del Saracino, which was first recorded in 1535 and is nowadays held in the Piazza Grande on the first Sunday in September. The day starts off with various costumed parades; at 5pm the action switches to the jousting arena in the piazza, with a procession of some 350 participants leading the way. Each quarter of the city is represented by a pair of knights on horseback, who do battle with a wooden effigy of a Saracen king. In one hand it holds a shield marked with point scores; in the other it has a cat-o’-three-tails which swings round when the shield is hit, necessitating nifty evasive action from the rider. A golden lance is awarded to the highest-scoring rider. In the days immediately preceding the joust you’ll see rehearsals taking place, and in recent years the event has become so popular that a reduced version of the show is now held on the penultimate Saturday of June, with parades at around 8pm, followed by the main event at 9pm; to book tickets, call 0575.377.462 or see www.giostradelsaracino.arezzo.it (Italian only).
The musical tradition that began with Guido d’Arezzo (widely regarded as the inventor of modern notation) is kept alive chiefly through the international choral competition that bears his name: the Concorso Polifonico Guido d’Arezzo, held in the last week of August. The less ambitious Pomeriggi Musicali is a season of free concerts held in various churches, museums and libraries; on average there’s one concert a week from mid-January to June.
The antiques fair (fiera antiquaria) takes over the Piazza Grande on the first Sunday of each month and the preceding Saturday. The most expensive stuff is laid out by the Vasari loggia, with cheaper pieces lower down the square and in the side streets.
Arezzo is a major stop for trains between Florence and Rome, and is also served by a branch line from Perugia. Buses arrive just north of the station, across Viale P. Francesca. The tourist office is outside the station, at Piazza della Repubblica 28 (mid-March to mid-Nov daily 9am–7pm; mid-Nov to mid-March Mon–Sat and 1st Sun of month 10am–6pm; 0575.377.678, www.apt.arezzo.it).
Accommodation can be hard to come by, especially when the antiques fair is on. In addition, the town is booked solid at the end of August and beginning of September, when the Concorso Polifonico Guido d’Arezzo and the Giostra del Saracino follow in quick succession. There are some attractive and good-value B&Bs in town; the tourist office has details on these and on the local hostel, the Ostello Villa Severi (some way north of the centre at Via Francesco Redi 13), which is currently closed for rebuilding.
Antiche Mura Piaggia di Murello 35 0575.20.410, www.antichemura.info. This cosy six-room B&B has an excellent location, just a two-minute walk from the Duomo, with wood-beamed ceilings and stone walls giving it an appealingly rustic feel. The rooms overlooking the internal courtyard are quieter. Breakfast is taken in a nearby bar. €61–90
Foresteria San Pier Piccolo Via Bicchieraia 32 0575.370.474, www.foresteriasanpierpiccolo.it. The nicest budget accommodation in central Arezzo, the Foresteria comprises a dozen rooms, mostly with rustic frescoes and en-suite bath, in a former convent. No credit cards. €61–90
Graziella Patio Via Cavour 23 0575.401.962, www.hotelpatio.it. This small, welcoming four-star is located a minute’s stroll from San Francesco. The rooms’ decor is inspired by the journeys of Bruce Chatwin: the elegant, colonial-style suite #101 is on two levels, with a bed and a roll-top bath on the mezzanine, while other rooms are decked out in an array of exotic colours. €151–200
Vogue Hotel Via Guido Monaco 54 0575.24.361, www.voguehotel.it. The common areas of the four-star Vogue are looking a little tired, but its 26 rooms, all with a traditional feel, have been carefully refurbished. Several boast frescoed ceilings, and many have bathtubs in the room. Avoid the overpriced “Queen” and “Vogue” rooms; the “Trend” rooms are spacious and fairly priced. €151–200
There are two distinct parts to Arezzo: the older quarter, at the top of the hill, and the businesslike lower town, much of which remains hidden from day-trippers, as it spreads behind the train station and the adjacent bus terminal. From the station forecourt, go straight ahead for Via Guido Monaco, the traffic axis between the upper and lower town. The parallel Corso Italia, now pedestrianized, is the route to walk up the hill.
In the heart of the old town, west of the main Corso Italia, stands the Basilica di San Francesco (Mon–Fri 9am–6.30pm, Sat 9am–5.30pm, Sun 1–5.30pm; Nov–March closes Mon–Fri 5.30pm, Sat & Sun 5pm), home to Piero della Francesca’s magnificent fresco cycle.
The frescoes are in the choir and can be seen from the nave, but you need to get closer to really appreciate them, and you’re not allowed beyond the altar steps unless you’ve bought a ticket (€6, or joint ticket): visits are limited to 25 people at a time (same hours as the church), and to thirty minutes per group. You are encouraged to book tickets in advance by phone (0575.352.727) or online (www.apt.arezzo.it). However, you can make a reservation in person at the ticket office beside the church, and you may not have to wait long before getting in; in winter there’s rarely any wait at all.
Built in the 1320s, the plain basilica earned its renown in the early 1450s, when the Bacci family commissioned Piero della Francesca to depict The Legend of the True Cross, a story in which the wood of the Cross forms the link in the cycle of redemption that begins with humanity’s original sin. Starting with the Death of Adam on the right wall, Piero painted the series in narrative sequence, working continuously until about 1457. However, the episodes are not arranged in narrative sequence, as the artist preferred to paint them according to the precepts of symmetry: thus the two battle scenes face each other across the chapel, rather than coming where the story dictates.
The literary source for the cycle, the Golden Legend by Jacopo de Voragine, is a very convoluted story, but the outline of the tale is as follows: a sprig from the Tree of Knowledge is planted in Adam’s mouth; Solomon orders a bridge to be built from wood taken from the tree that grew from Adam’s grave (below the Death of Adam, to the left); the visiting Queen of Sheba kneels, sensing the holiness of the wood, and then later (to the right) tells Solomon of her prophecy that the same wood will be used to crucify a man; Solomon then orders the beam to be buried (back wall, middle right); the Emperor Constantine (back wall, lower right) has a vision of victory under the sign of the Cross; Constantine defeats his rival Maxentius (lower right wall); under torture, Judas the Levite (back wall, middle left) reveals to St Helena, mother of Constantine, the burial places of the crosses from Golgotha, which are then excavated (middle left wall); the True Cross is recognized when it brings about a man’s resurrection; and the Persian king Chosroes, who had stolen the Cross, is defeated by Emperor Heraclius (lower left wall), who returns the Cross to Jerusalem (upper left wall).
A €10 joint ticket (biglietto unico) gives you a single admission to the following monuments and museums in Arezzo: the Museo Archeologico, the Museo Statale d’Arte Medievale e Moderna, the Casa Vasari and the della Francesca frescoes in San Francesco. The ticket can be bought at any of these four locations, but bear in mind that immediate admission to San Francesco may not be possible.
Further up the Corso from San Francesco stands one of the finest Romanesque structures in Tuscany, the twelfth-century Pieve di Santa Maria (daily: May–Sept 9am–1pm & 3–7pm; Oct–April 9am–noon & 3–6pm). Its arcaded facade, elaborate yet severe, is unusual in presenting its front to a fairly narrow street rather than to the town’s main square. Dating from the 1210s, the carvings of the months over the portal are an especially lively group. Known locally as “the tower of the hundred holes”, the campanile was added in the fourteenth century. The oldest section of the chalky grey interior is the raised sanctuary, where the altarpiece is Pietro Lorenzetti’s Madonna and Saints polyptych, painted in 1320. The unfamiliar saint on the far left, accompanying Matthew, the Baptist and John the Evangelist, is St Donatus, the second bishop of Arezzo, who was martyred in 304. His relics are in the crypt, encased in a beautiful gold and silver bust made in 1346.
On the other side of the Pieve, the steeply sloping Piazza Grande has an unusual assortment of buildings, with the wooden balconied apartments on the east side facing the apse of the Pieve, the Baroque Palazzo dei Tribunali and the Palazzetto della Fraternità dei Laici, which has a Renaissance upper storey and a Gothic lower. The piazza’s northern edge is formed by the arcades of the Loggia di Vasari, occupied by restaurants and shops that in some instances still retain their original sixteenth-century stone counters.
At the highest point of town looms the large and unfussy Duomo (daily 7am–12.30pm & 3–6.30pm). Inside, just beyond the organ, is the tomb of Bishop Guido Tarlati, head of the comune of Arezzo during its resurgence in the early fourteenth century; the monument, plated with reliefs showing scenes from the militaristic bishop’s career, was possibly designed by Giotto. The small fresco nestled against the right side of the tomb is Piero della Francesca’s Magdalene, his only work in Arezzo outside San Francesco.
A short distance north of the Duomo you’ll come across the basilica of San Domenico (daily 8am–7pm), where, above the high altar, hangs a dolorous Crucifix by Cimabue (1260), painted when the artist was about 20. Signs point the way to the nearby Casa Vasari, Via XX Settembre 55 (Mon & Wed–Sat 8.30am–7.30pm, Sun 8.30am–1.30pm; €2), designed and decorated luridly by the celebrated biographer-architect-painter for himself. Down the slope, at Via San Lorentino 8, the fifteenth-century Palazzo Bruni-Ciocchi houses the Museo Statale d’Arte Medievale e Moderna (Tues–Sun 8.30am–7pm; €4), with a collection of minor paintings by local artists and majolica work dating from the thirteenth to the eighteenth centuries.
All the principal sights are in the upper part of town, with two exceptions. The Museo Archeologico (daily 8.30am–7.30pm; €4), which occupies part of a monastery built into the wall of the town’s Roman amphitheatre, is impressive chiefly for the marvellously coloured coralline vases produced here in the first century BC – the skill of Arezzo’s glassblowers achieved a reputation throughout the Roman world. A ten-minute walk away, south of the city centre at the end of Viale Mecenate, stands Arezzo’s most exquisite church, Santa Maria delle Grazie (daily 8am–7pm). Built at the instigation of St Bernardino, the church is fronted by a tiny pine-ringed meadow that’s flanked by a pair of arcades, and is entered through a delicate portico built by Benedetto da Maiano in the 1470s. The church is essentially a single room, containing little more than a few seats and an altarpiece by Parri Spinello, painted on the instructions of St Bernardino; the beautiful marble-and-terracotta altar that encases it was created by Andrea della Robbia.
Arezzo’s restaurants are of a generally high standard, and you’ll find some nice cafés around piazzas Guido Monaco, Grande and San Francesco. For picnic provisions you can’t do better than Sbarbacipolle, at Via Garibaldi 120.
Antica Osteria L’Agania Via Mazzini 10 0575.29.381. A very good and informal trattoria with welcoming atmosphere and local dishes (special emphasis on truffles and mushrooms in season) at around €25 per head; it draws much of its clientele from the antiques dealers. The Antica Vineria next door serves soups, salads, and cheese and meat plates at even lower prices in a bustling dining room. Tues–Sun noon–3.30pm & 6.30–11pm.
Fiaschetteria de’ Redi Via de’ Redi 10. Busy little osteria with a superb range of vintages and decent simple meals, such as big salads and bruschette (€6–7). Daily 11.30am–3pm & 7pm–midnight; closed Mon in winter
Il Cantuccio Via Madonna del Prato 76 0575.26.830. Good-value food served in a pleasant vaulted cellar. The home-made pasta dishes are particularly delicious. Expect to pay in the region of €25 per person. Thurs–Tues noon–2.30pm & 7–10.30pm.
Il Gelato Via de’ Cenci 24. This gelateria off Corso Italia serves Arezzo’s best ice cream; the speciality is the pane e nutella flavour, a calorific concoction of hazelnut, chocolate and brioche. Thurs–Tues 11am–midnight, closes 8pm in winter months; closed Jan & Dec.
Il Saraceno Via Mazzini 6 0575.27.644. Family-run trattoria, founded in 1946, with a good wine cellar and traditional Aretine specialities (notably duck) at around €30 per head; good wood-oven pizzas too. Thurs–Tues noon–3.30pm & 7–11pm; closed two weeks in Jan.
Miseria e Nobiltà Via Piaggia di San Bartolomeo 2 0575.21.245. With its enticing creative Italian menu and medieval vaulted dining room, this stylish (but not expensive) place makes a refreshing change from the town’s more traditional restaurants. It’s busiest (and more atmospheric) at dinner. Tues 6pm–12.30am, Wed–Sun 12.30–2.30pm & 6pm–12.30am.
Arezzo is the springboard for the Piero della Francesca art itinerary, which extends eastwards to Urbino and Rimini via the village of MONTERCHI, famous as the home of the Madonna del Parto, a rare depiction of the pregnant Madonna. The painting is now the focal point of a museum (daily 9am–1pm & 2–7pm; Nov–March closes 5pm; €3.50), with displays on the history of the fresco and the story of its restoration, as well as a 40-minute video on the life of the artist.
SANSEPOLCRO, 25km northeast of Arezzo (served by SITA and Baschetti buses and by trains from Perugia and Città di Castello), is where Piero della Francesca was born in the 1410s, and where he spent much of his life. The Museo Civico, at Via Niccolò Aggiunti 65 (daily: June 15–Sept 15 9.30am–1.30pm & 2.30–7pm; rest of year 9.30am–1pm & 2.30–6pm; €6), houses a sizeable collection of pictures, including work by Pontormo and Santi di Tito, but the primary focus of attention is della Francesca’s Resurrection. Painted for the adjoining town hall in the 1450s and moved here in the sixteenth century, it’s one of the most overpowering images of the event ever created, with a muscular Christ stepping onto the edge of the tomb – banner in hand – as if it were the rampart of a conquered city. Elsewhere in the museum, an early della Francesca masterpiece, the Madonna della Misericordia polyptych, epitomizes the graceful solemnity of his work.
The best place to stay is the welcoming Albergo Fiorentino at Via Luca Pacioli 56 (0575.740350, www.albergofiorentino.com; €61–90), which has been in business since 1807. On the same premises is a very good restaurant, the Fiorentino (closed Wed), where you can expect to pay around €30 a head, as well as a small B&B, La Locanda del Giglio (0575.742.033, www.ristorantefiorentino.it; €61–90). Another very good restaurant in the same price range is the family-run Da Ventura, Via Niccolò Aggiunti 30 (0575.742.560; closed Sun eve & Mon).
Travelling south from Arezzo you enter the Valdichiana, reclaimed swampland that is now prosperous farming country. From the valley floor, a 5km road winds up through terraces of vines and olives to the hill-town of CORTONA, whose heights survey a vast domain: the Valdichiana stretching westwards, with Lago Trasimeno visible over the low hills to the south. The steep streets of Cortona are more or less untouched by modern building: limitations of space have confined almost all later development to the lower suburb of Camucia, which is where the approach road begins.
Even without its monuments and art treasures, this would be a good place to rest up, with decent hotels and excellent restaurants. In recent years, though, Cortona’s tourist traffic has increased markedly, in the wake of Frances Mayes’ Under the Tuscan Sun and Bella Tuscany, books that continue to entice coachloads of her readers to the town. Accordingly, you’d be well advised to book accommodation well in advance between Easter and late September, especially during the Tuscan Sun Festival (www.tuscansunfestival.com), in late July or early August, which features everything from opera and ballet to cooking demonstrations and visits to local vineyards.
Cortona is easily visited as a day-trip from Arezzo, but in many ways it’s the more pleasant of the two in which to spend the night. There are hourly LFI buses between the two towns, and stopping trains from Arezzo call at Camucia-Cortona station, from where a bus (roughly every 30min) takes ten minutes to run up to the old town; buy tickets at the station bar. Florence–Rome trains stop at Teróntola, 10km south, which is also served by a bus every one to two hours (25min to Cortona’s Piazza Garibaldi); Teróntola is the station to get off at if you are approaching from Umbria. The centre is closed to all but essential traffic, so if you’re driving you should use one of the free car parks on the periphery.
The tourist office is at Via Nazionale 42 (mid-May to Sept Mon–Fri 9am–1pm & 3–6pm, Sun 9am–1pm; Oct to mid-May Mon–Fri 9am–1pm & 3–6pm, Sat 9am–1pm; 0575.630.352, www.cortonaweb.net).
Sabrina Via Roma 37 0575.630.397, www.cortonastorica.com. A cosy and inexpensive eight-room three-star; the breakfasts are excellent and it has a nice family atmosphere. €61–90
San Michele Via Guelfa 15 0575.604.348, www.hotelsanmichele.net. The most luxurious central choice, this handsome 43-room four-star has been converted from a rambling medieval townhouse. The rooms are a generous size, even if the decor is rather routine; the suites, though much pricier at around €250, are worth splashing out on, especially no. 214, which offers marvellous views from its private terrace. €91–120
Villa Marsili Via Cesare Battisti 13 0575.605.252, www.villamarsili.net. Situated a short distance down the slope from Piazza Garibaldi, this friendly four-star – occupying an eighteenth-century villa – has airy rooms nicely furnished with antiques: most command photogenic views of the Valdichiana. The breakfast is excellent, and thoughtful touches such as free early-evening aperitivi and post-dinner cantuccini are a bonus. €151–200
Ostello San Marco Via G. Maffei 57 0575.601.392, www.cortonahostel.com. Clean and spacious 80-bed HI hostel in the heart of the town in an old monastery, with fantastic views from the second-floor dorms. The management is friendly, a simple breakfast is included and bikes are available free of charge. Open mid-March to mid-Oct; reception daily 7–10am & 3.30–10pm. Dorm beds €16; doubles and family rooms available (€20 per person; bunk beds only).
From Piazza Garibaldi Via Nazionale, the only level street in town, connects to Piazza della Repubblica, which is overlooked by the grandstand staircase of the squat Palazzo del Comune. Just behind is Piazza Signorelli, named after Luca Signorelli (1441–1523), Cortona’s most famous son, and site of the Museo dell’Accademia Etrusca e della Città di Cortona – or MAEC, for short (April–Oct daily 10am–7pm; Nov–March Tues–Sun 10am–5pm; €8, or €10 combined ticket with Museo Diocesano). On the lowest floor, which charts the development of Cortona from the earliest recorded settlements to Roman times, some spectacular specimens of Etruscan gold, turquoise and crystal jewellery catch the eye. Upstairs there’s a good deal more Etruscan material on show, most notably a bronze lamp from the fourth century BC, which is honoured with a room all to itself. Etruscan and later bronze figurines fill an avenue of cabinets in the middle of the main hall, surrounded by some fairly undistinguished pictures, though Pietro da Cortona, Signorelli and Pinturicchio provide a few highlights.
Piazza Signorelli links with Piazza Duomo, where the Duomo (daily 8am–12.30pm & 3–6.30pm) sits hard up against the city walls. The interior is rather chilly, but there’s a Pietro da Cortona Nativity on the third altar on the left, and a possible Andrea del Sarto (an Assumption) to the left of the high altar. Across the little piazza, a couple of churches have been knocked together to form the Museo Diocesano (same hours as MAEC; €5, or €10 combined ticket), where the highlight of the small collection of Renaissance art is an exquisite Annunciation, painted by Fra’ Angelico when he was based at Cortona’s monastery of San Domenico.
In the upper town, the most engaging building is San Niccolò (daily 10am–noon & 5–7pm), a frail little church with a gravel forecourt, a delicate portico and a fine wooden ceiling that’s sagging with age. Signorelli’s high altarpiece is a standard which he painted on both sides – ring the bell and the caretaker will take you to see it. Near the summit of the town stands Santa Margherita (daily 9am–noon & 3.30–7pm), resting place of St Margaret of Cortona, the town’s patron saint. Her tomb, with marble angels lifting the lid of her sarcophagus, was created in the mid-fourteenth century, and is now mounted on the wall to the left of the chancel, while her remains are on display in a glass coffin directly behind the chancel.
For a town of its size, Cortona has an abundance of good restaurants, most within a very short distance of Piazza della Repubblica.
Dardano Via Dardano 24 0575.601.944. This excellent, unpretentious and inexpensive trattoria is full to bursting most nights. With its appealing menu of local dishes, it’s a good place for a hearty meal, followed by the house digestivo, made from laurel leaves. Thurs–Tues noon–2.45pm & 7–10pm.
Fufluns Via Ghibellina 1–3 0575.604.140. There’s a full menu of Tuscan dishes on offer, but this spacious and bustling place is best known for its generous pizzas. Booking advised at weekends. Wed–Mon 12.15–2.30pm & 7.15–10.30pm.
La Bucaccia Via Ghibellina 17 0575.606.039. Husband-and-wife team Romano and Agostina are at the helm of this refined restaurant, with an atmospheric stone-walled dining room and 500-bottle wine cellar. Jovial Romano is a certified cheese expert, Agostina is the chef and teenage daughter Francesca is the sommelier. You can eat very well for €40. Daily noon–4pm & 7–11.30pm; closed Mon in winter.
Osteria del Teatro Via Maffei 5 0575.630.556. Occupying the whole lower floor of a rambling old mansion, this is a good-naturedly busy (sometimes frantic) place, featuring delicious home-made pastas on a meat-heavy menu; portions are generous and the prices more than fair – the bill should be around €35 per person. Thurs–Tues noon–2.30pm & 7–10pm; closed three weeks in Nov.
Route 66 Via Nazionale 78. This self-styled “music bar” with DJs at weekends attracts the youngest crowd in town. It does food too, but it’s not the nosh that makes it popular. Daily 11am–2am; closed Mon in winter.
Arezzo to: Assisi (12 daily; 1hr 35min); Bolzano (3 daily; 5–7hr); Camucia-Cortona (hourly; 20min); Chiusi (hourly; 1hr); Florence (hourly; 1hr); Foligno (every 2hr; 1hr 45min); Orvieto (hourly; 50min–1hr 20min); Perugia (8 daily; 1hr 10min); Rome (hourly; 1hr 40min); Teróntola-Cortona (hourly; 25min); Venice (5 daily; 5hr); Verona (3 daily; 3hr 30min–4hr 45min).
Empoli to: Florence (every 30min; 35min); Pisa (every 30min; 30–55min); Siena (every 30min; 55min–1hr 10min).
Florence to: Arezzo (hourly; 1hr); Assisi (8 daily; 2hr–2hr 30min); Bari (15 daily; 7hr–9hr 30min, change at Bologna or Rome); Bologna (every 30min; 1hr–1hr 40min); Bolzano (5 daily; 4hr–4hr 30min); Empoli (every 20min; 30min); Genoa (2 daily; 3hr 10min); Lecce (13 daily; 9hr 10min–15hr, change at Bologna or Rome); Livorno (12 daily; 1hr 30min); Lucca (every 30min; 1hr 15min–1hr 45min); Milan (hourly; 2hr 45min–3hr 30min); Naples (hourly; 3hr 30min–5hr); Perugia (8 daily; 1hr 35min–2hr 10min); Pisa airport (6 daily; 70–1hr 30min); Pisa central (every 30min; 60–1hr 20min); Pistoia (every 20–30min; 40–55min); Prato (every 20–30min; 20–30min); Reggio Calabria (from Campo Marte 5 direct trains daily; 9hr 15min–11hr; from Santa Maria Novella, changing at Rome 6 daily; 8hr 10min–10hr); Rimini (hourly; 2hr 20min–3hr 30min, change at Bologna); Rome (every 20min; 1hr 45min–3hr 40min); Siena (hourly; 1hr 30min–2hr); Trieste (3 daily; 4hr 40min–6hr 20min); Udine (3 daily; 4hr 20min–6hr); Venice (9 daily; 2hr 50min–3hr 45min); Verona (6 daily; 2hr 20min–2hr 45min); Viareggio (14 daily; 1hr 20min–1hr 55min).
Grosseto to: Cécina (17 daily; 45min–1hr 20min); Florence (6 daily; 3hr); Livorno (hourly; 1hr 10min–2hr); Orbetello (16 daily; 20–30min); Pisa (hourly; 1hr 20min–2hr 20min); Rome (hourly; 1hr 40min–2hr 20min).
Livorno to: Florence (12 daily; 1hr 25min); La Spezia (hourly; 1hr–1hr 30min); Pisa (every 20min; 20min); Rome (19 daily; 2hr 30min–3hr 45min).
Lucca to: Florence (every 30min; 1hr 20min–1hr 45min); Pisa (every 30min; 30min); Pistoia (every 30min; 40min–1hr); Rome (15 daily; 3hr 15min); Viareggio (every 30min; 20–30min).
Pisa to: Empoli (every 30min; 30–55min); Florence (every 30min; 1hr–1hr 30min); Livorno (every 20min; 15min); Lucca (every 30min; 30min); Viareggio (every 30min; 15–20min).
Prato to: Pistoia (every 20–30min; 15min).
Siena to: Asciano (15 daily; 30min); Buonconvento (hourly; 25min); Chiusi (hourly; 1hr 20min); Empoli (every 30min; 1hr); Grosseto (10 daily; 1hr 30min).
Arezzo to: Città di Castello (14–17 daily; 1hr 30min); Cortona (hourly; 1hr 10min); Monterchi (2–6 daily; 40min); Sansepolcro (20 daily; 1hr).
Cortona to: Chianciano (4 daily; 1hr), changing for Montepulciano.
Florence to: Castellina in Chianti (3 daily; 1hr 35min); Greve in Chianti (3 daily; 1hr 5min); Radda in Chianti (2–3 daily Mon–Sat; 1hr 35min); Siena (30 daily; 1hr 20min–3hr); Volterra (6 daily; 2hr 25min). In addition to these state-owned SITA services, numerous independent bus companies operate from Florence to most Tuscan towns, including Arezzo, Grosseto, Lucca, Pisa, Sansepolcro and Viareggio.
Livorno to: Piombino (8 daily; 2hr).
Lucca to: Florence (30 daily; 1hr 15min); La Spezia (7 daily; 2hr 20min); Livorno (3 daily; 1hr 20min); Pisa (35 daily; 40min); Pisa airport (3 daily; 1hr); Viareggio (30 daily; 40min).
Massa Maríttima to: Piombino (2 daily; 25min); San Galgano (2 daily; 1hr).
Montalcino to: Buonconvento (hourly; 35min); Monte Amiata (2 daily; 1hr).
Montepulciano to: Buonconvento (7 daily; 1hr); Chiusi (every 30min; 50min); Pienza (7 daily; 20min); San Quírico (7 daily; 40min).
Pisa to: Florence (hourly; 1hr 10min); La Spezia (7 daily; 1hr 20min); Livorno (every 30min; 45min); Viareggio (hourly; 20min).
San Gimignano to: Poggibonsi (hourly; 35min).
Siena to: Abbadia San Salvatore (3 daily; 1hr 20min); Arezzo (4 daily; 2hr); Buonconvento (8 daily; 30min); Florence (30 daily; 1hr 20min–3hr); Massa Maríttima (3 daily; 1hr 20min); Montalcino (6 daily; 1hr); Montepulciano (5 daily; 1hr 20min); Pisa (1 daily; 2hr 20min); Poggibonsi (half-hourly; 30min–1hr); Rome (8 daily; 3hr); San Galgano (3 daily; 40min); San Gimignano (12 daily; 1hr 15min); Volterra (4 daily; 2hr).
Volterra to: Colle Val d’Elsa (for connections to Florence & Siena; 6 daily; 45min); Pisa (1 daily; 1hr 10min).
Livorno to: Capraia (1–2 daily; 3hr).
Piombino to: Portoferraio (10–22 daily; 50min).