Classic Tuscany Itinerary

Here's a sample itinerary for a quintessential few days in Tuscany.

DAY 1: Murlo, Montalcino, Sant’Angelo in Colle


Set off to Murlo, a tiny Etruscan hilltop town with ringed stone walls and expansive views all the way to Siena. On a hill just behind the town is Poggio Civitate, the most extensively excavated Etruscan site, including a villa. A modern museum shows Murlo as it may have during the Etruscan era, and the villa holds treasures like tiny gemstone sphinxes and black-pottery plates. For a Tuscan souvenir, on your way out stop at Apicoltura Quercioli Sonia (Piazza Morviducci; 39-57-781-4255), in Vescovado, to buy delicious artisanal honey. From there take the SP45 south through wooded hills to the Brunello-Rosso capital, Montalcino, a mecca for oenophiles. Park outside the fortress walls and head up the steep hill to the central piazza and the wine bar Enoteca La Fortezza (39-57-784-9211), which offers a huge selection of Brunello vintages. Be sure to try its wild-boar salami and local pecorino too. Afterward, climb the fortress tower and walk along the walls (the Enoteca waives the fee for customers). On a clear day, you can see all the way to Montepulciano, over the Val d’Orcia. For a dash of history, go to Caffe Fiaschetteria Italiana (6 Piazza del Popolo). Founded in 1888 by Ferruccio Biondi Santi, the father of Brunello wine, the café serves coffee, snacks and a full lunch.

Indagare Tip: If you can’t visit all the vineyards you want to, look for the bottles you missed at the Enoteca and have it ship them home for you. The service is pricey but extremely reliable. Market day in Montalcino is Friday.

LUNCH Trattoria Il Pozzo (2 Piazza del Pozzo; 39-0577-844015), in nearby Sant’Angelo in Colle, offers traditional fare, including the area’s best pici pasta (Tuscan pinched noodles) and bistecca, according to the locals. For something a bit more upscale, try Boccon di Vino (39-57-784-8233), located just outside Montalcino en route to Buonconvento, or Taverna dei Barbi (170 Localita Podernovi), at the nearby Fattoria dei Barbi vineyard.

AFTERNOON Indulge your Brunello fantasy and reserve a walking tour (light hike) of the rolling vineyards at Tenuta Il Poggione (, producer of highly lauded wines, together with an afternoon tasting. If you prefer a more organized tasting, plus better shipping rates back to the States, visit the Castello Banfi, whose Taverna serves both lunch and dinner daily in season. Although owned by Americans, the estate is 100 percent Italian, from its 13th-century fortress to the 2,400 hectares of planted vineyards, as are its superb wines and balsameria, where it brews and ages its fine balsamic vinegar.

Indagare Tip: In July and August, Montalcino holds a month of jazz and theater festivals; the first week of September is Honey Week, when local producers set up along the fortress walls. If you’re lucky enough to be there on either the second Sunday in August or the last weekend in October, the opening and closing of the hunting season, respectively, you’ll witness lavish ceremonies, complete with medieval costumes, parades, competitions and feasting in the evening.

DINNER Even if you think you’ve had enough Brunello and Rosso for one day, you should cap it off with an evening at the celebrated wine estate Poggio Antico (39-0577-848044; The estate’s terrace restaurant offers a menu that changes with the seasons and availability of local produce, but the views of the vineyards and of Monte Amiata, Italy’s second-highest volcano, are constant. Alternatively, if you missed the tasting at Castello Banfi, make up for it with a wine-paired menu at the estate’s Taverna, housed in the building’s vaulted cellars. And if driving home afterward seems problematic, the Castello’s nearby Borgo has fourteen exceptional rooms.

DAY 2: San Quirico, Bagno Vignoni, Pienza, Montecchiello, Montepulciano


Begin the day by driving to lovely San Quirico, a prominent stage on the pilgrimage route to Rome, where popes, emperors and saints stopped off. Don’t miss the charming Horti Leonini sculpture gardens. Continue toward Ripa d’Orcia e Vignoni, following the scenic white-gravel road’s scenic, which passes the beautiful, crumbling Castello di Vignoni as it descends to Bagno Vignoni. This quaint old village features a large thermal bath in the center, with a public spa right behind it. Stop for coffee at Osteria del Leone (Via dei Molini 3), overlooking the baths. Journey on to the Val d’Orcia’s largest town, Pienza, where you can tour the impressive cathedral and hanging gardens of the Palazzo Piccolomini. Don’t miss the fantastic photo opportunities on the panoramic lanes (passegiatas): Via del Bacio (Street of the Kiss) and Via dell’Amore (Street of Love). Pienza is also known for its artisanal shops and fresh pecorino cheese.

Visit Fratelli Biagiotti (Via I Maggio) for wrought iron, Bottega Artigiana del Cuoio di Valerio Truffelli (Corso Il Rossellino 58) for leather goods; and for fresh cheese and other products, go to the small family farm at Il Casale (64–53026 Pienza), on the road to Montepulciano, just as you leave Pienza.

LUNCH If you are hungry enough to lunch in Pienza, sit on the sunny patio at Latte di Luna (2–4 Via San Carlo; 39-57-874-8606), at the end of Corso Rossellino, and order its specialty, maialino arrosto (roast suckling pig), which draws a local crowd. If you can wait, make the fifteen-minute drive to the small, picturesque medieval town of Monticchiello and snag a table on the elevated, ivy-covered terrace or in front of Osteria La Porta (1 Via del Piano, 39-0578-755163), located right at the entrance to the city. Order local dishes like wild-boar carpaccio and ribollita (Tuscan soup). Don’t be fooled by the quaint vibe here: reservations are recommended.

AFTERNOON Take a quick stroll through Monticchiello to walk off lunch. Although there’s not much to do, the town is one of the prettiest in the Val d’Orcia. Spend the rest of the afternoon in the vino nobile capital, Montepulciano, sampling the wines and perusing the small shops. Park your car below, and enter through the Porta al Prato. Don’t miss the 14th-century Church of Sant’Agnese, just outside the gate. Within the walls, the beautiful Renaissance palazzos and quaint streets lead to Piazza Grande, the main square, where you’ll find the Palazzo Comunale (town hall). Climb the tower for the sweeping view. For a more organized survey, complete with wine tasting, check out the historical-cellars tour at Strada del Vino Nobile di Montepulciano (Piazza Grande 7), which takes you to the city’s underground cellars, still filled with oak barrels. On your way out, visit the Bottega del Rame (Via dell’Opio nel Corso 64), where you can watch the centuries-old technique of copper beating. For a bottle of the local olive oil, stop at Il Frantoio di Montepulciano (Piazzale Pasquino; 39-57-875-8732). Don’t miss the renowned Caffè Poliziano (Via Voltaia del Corso 27/29), with its strong coffee and array of sweets.

Indagare Tip: Cheese lovers should stop along the road from Pienza to Montepulciano, at Caseificio Cugusi (Via della Boccia 8; 39-0578-757558) for the Sardinian family’s fresh pecorino, ricotta and ravigiolo.

DINNER For an authentic Tuscan meal, try the cozy A Gambe di Gatto (34 Via dell’Opio nel Corso; 39-57-875-7431), run by a friendly young couple eager to indulge their diners with multiple olive-oil options and complimentary wine tastings. If you crave a two-inch-thick steak plus handmade pasta, bread and desserts, visit Osteria dell’Acquacheta (Via del Teatro 22).

Indagare Tip: If you’re in Montepulciano on the last Sunday in August, don’t miss the traditional Bravio delle Botti (Battle of the Wine Barrels). Eight competitors vie for a cloth painted with the image of the town’s patron saint, San Giovanni Decollato, whom the race honors, by rolling wine barrels along a challenging course. Ceremonies celebrating each team are held during the day and through the evening once the winner is pronounced.

DAY 3: Cortona & Arezzo


Spend the morning exploring the fortified Etruscan town of Cortona—immortalized in Frances Mayes’s novel Under the Tuscan Sun—which overlooks the valley. Once inside the walls, leave the car behind and visit the 13th-century town hall in Piazza Repubblica and the Duomo, whose plain façade belies its ornate interior. After a cappuccino at Caffè Vannelli (Via Regina Elena), continue along the Via Nazionale, which is lined with small antiques and ceramic shops. Check out the vast selection of fresh pastas and sauces at the Bottega della Pasta Fresca (29 Via Dardano, Cortona; 39-57-560-4211), just inside the Porta Colonia. This is one of Italy’s important art centers, so be sure to visit the Museo Diocesano, where Fra Angelico’s Annunciazione hangs alongside works by the Berrettini brothers and Luca Signorelli.

Indagare Tip: The Tuscan Sun Festival (, held in Cortona every August, features internationally acclaimed talents in film, music, literature and wine/cuisine. Reserve tickets in advance.

LUNCH Head back down the hill for a memorable culinary experience at Il Falconiere, a charming property with a kitchen that offers painstakingly prepared dishes, including magnificent breads. Seated either in the limonaia or on the terrace, you can complement your meal with wines from Barracchi’s own vineyard, which lies right below the restaurant. Try the Ardito, a nice blend of Syrah and Cabernet. For something a bit lighter, there’s Cortona’s Taverna Pane e Vino (27 Piazza Signorelli; 39-57-563-1010), a brick-walled cantina in a 14th-century palazzo.

Indagare Tip: Il Falconiere also hosts an excellent cooking school, with courses lasting from an afternoon to a week.

AFTERNOON A haven for art and antiques lovers, Arezzo is perhaps best-known for its frescoes by local artist Piero della Francesca. To view his Legend of the True Cross cycle, visit the small 14th-century church in the Piazza San Francesco; you will need to buy tickets if you want to see them close-up. Next, tour the gorgeous 12th-century Santa Maria della Pieve (7 Corso Italia), with its Lombard Romanesque architecture and medieval reliefs. Tucked among antiques stores and jewelry shops—Arezzo is known for its gold-chain jewelry—is the early 19th-century Caffé dei Costani (Piazza San Francesco), perfect for an afternoon espresso; for a sweet treat, Pasticcerria de’ Cenci (Via de’ Cenci) is your spot.

Indagare Tip: On the first Sunday of each month and the preceding Saturday, hundreds of dealers and artists bring their antiques, reproductions, and original pieces to Via Cavour and Piazza Grande, in the town’s historic center, for Fiera Antiquaria di Arezzo.

DINNER If you bypassed Il Falconiere for lunch, go there for dinner, which lasts an average of five hours in the breathtaking terrace setting. If you prefer to stay in Arezzo, check out Buca di San Francesco (1 Via San Francesco, 39-57-523-271), where 14th-century frescoes line the walls and guests enjoy simple Tuscan fare.

Tuscany Itinerary Driving Times

  • Siena to Murlo: 30 mins.
  • Murlo to Montalcino: 30 mins.
  • Montalcino to Sant’Angelo in Colle: 15 mins.
  • Montalcino to San Quirico: 20 mins.
  • San Quirico to Pienza: 15 mins.
  • Pienza to Monticchiello: 15 mins.
  • Montichiello to Montepulciano: 20 mins.
  • Montepulciano to Cortona: 45 mins.
  • Cortona to Arezzo: 40 mins.

Published onJuly 22, 2018

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