See the Florence page for information about the capital of Tuscany.
Learn more about Montalcino and its prized wine, Brunello, on the Montalcino page.
Siena
This old rival of Florence is one of the bigger cities in Tuscany, but still retains a medieval character. Its twice-yearly Palio (horse race) in the town square re-ignites that medieval spirit. Also see Wikitravel's Siena page for good tips.
- Piazza del Campo/Palazzo Pubblico - the Piazza del Campo is the meeting point of the city and site of the Palio horse race. It is fronted by the huge Palazzo Pubblico (City Hall) with its impressive bell tower and city museum.
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Duomo/Duomo Museum - Siena's beautiful cathedral nearly rivals its arch-rival Florence's in size, and easily in beauty. Its facade alone is breathtaking, and the interior includes an embaressment of art, including statues by Michaelangelo, Donatello, and Bernini. The nearby Museo del Duomo (Cathedral Museum) includes some of the original stained glass, statues, and iconography that once graced the cathedral, as well as a breathtaking view from the ramparts that were supposed to be the cathedral's main entrance.
Chianti
The Chianti region, a large swath between Siena and Florence, is known for its wine, Chianti Classico. Colle di Val d'ElsaColle di Val d'Elsa is a beautiful Chianti-region hill town known for its crystal. The lower town is more workaday, and you can take a glass elevator to the upper, medieval town.
- Da Simone - Piazza Bartolomeo Scala 11, 057-792-6701, closed Mon, rec'd by Gambero Rosso, Espresso, and Michelin, ~€40-50.
- Dietro le Quinte - Vicolo della Misericordia 14, 057-792-0458, a great wine bar and restaurant with a beautiful garden;
Other Hill TownsFor more ideas, check out Rick Steve's Hill Towns page. The drive between Montepulciano and Montalcino, in an area called the Crete Senese ("Sienese Crests") or Val d'Orcia, is some of the most pictoresque country in Italy--just about every stock photo and postcard of "Tuscany" is taken of hills and farmhouses along this drive, dotted with hay bales and cyprus trees.
If you like hill towns, also be sure to check out nearby Umbria, which boasts such places as Orvieto, Asisi, Spello, Spoleto, and Trevi.
MontepulcianoKnown for its eponymous Vino Nobile di Montalcino wine, Montepulciano is a hill town at the eastern side of the Crete Senese. Recommended places to eat:
- Il Gambe di Gatto Cafe - Via dell'Opio nel Corso 34, 057-875-7431, closed Wed, a sampling of Chowhound and Slow Travel reviews: "one of the most charming experiences I ever had in a restaurant", 10-20 olive oils!, "magical", "best dining experience I had during my trip", "a really fun spot" run by young couple Emanuel and Laura, inexpensive
- Osteria dell'Acquacheta - via del Teatro 22, 057-871-7086 or 057-875-8443, 12:30-3, 7:30-10:30, closed Tues, rec'd by Rick Steves for pastas and salads, also good bistecca fiorentina, and other local foods like pici, rec'd by Slow Food Osterie d'Italia, ~€20-25.
- Le Logge del Vignola - via delle Erbe 6 - 057-871-7290, very nice restaurant (they even set out an amuse bouche), rec'd by Gambero Rosso, Espresso, Michelin, and TCI. ~€40-58, brunch for €20.
- Osteria del Conte - via San Donato 19, 057-875-6062, 348-814-2984, closed Wed, rec'd by Espresso, ~€25-30 not including drinks.
PienzaPerched between the wine cities of Montepulciano and Montalcino, Pienza is famous for both fresh and aged pecorino cheese. Recommended eating places:
- Trattoria Latte di Luna - via San Carlo 2, 057-874-8606 or 338-326-6791, 12:30-2:30, 7:30-9:30, closed Tues, rec'd by Rick Steves, Frommer's, and many others: "believe the hype...it was fantastic", not too expensive, truffled pasta and roast boar rec'd, Roberto and wife, wonderful pinci and maialino al latte, Slow Food, Gambero Rosso, inexpensive, reserve ahead!, ~€25-30
- Trattoria da Fiorella - via Condotti 11, 057-874-905, closed Wed, one chowhound review says it is "our favorite restaurant in Pienza...we eat here every time we visit. Very reliable, very authentic, and very good value", rec'd also by Slow travel readers.
- Osteria La Porta - via del Piano 3 (in Montechiello just SE of town), 057-875-5163, closed Thurs, €35 fixed price, with €18 lunch, rec'd by Osterie d'Italia, Espresso, Michelin, and TCI; beautiful view of Val D'Orcia.
Volterra
Famous for its alabaster, Volterra is Rick Steves' favorite Tuscan town. Volterra has beautiful views and wonderful food, and more recently has gained fame due to the Twilight novels and movies (even though one of the Twilight movies was filmed in Montepulciano, not Volterra). - Albergo Etruria - via Matteotti 32 (in historic center), 058-887-377, nice, clean rooms, free Internet, and great hosts, rec'd by Rick Steves.
- Don Beta - several of us had a nice dinner here
- Da Badò - Borgo San Lazzaro 9, 058-886-477, closed Wed, ~€40, great fresh seasonal specials; one review recommends the papparadelle di lepre (pasta with hare), rec'd by Slow Food Osterie d'Italia.
- Del Duca - via di Castello 2, 058-881-510, closed Tues, Tuscan traditions with a creative twist, fixed price between €35 and 47 or a la carte for ~€30-50, rec'd by Gambero Rosso, Esprsso, Michelin, TCI, and Rick Steves ("refined Tuscan cusine").
- Vecchia Osteria dei Poeti - via Matteotti 53, 058-886-029. Great Tuscan recipes served in a medieval palace, ~€30-40, rec'd by Alice.
San Gimingiano
One of the only towns to still retain its medieval towers, San Gimingiano is popular with tourists but still a car-free, beautiful town. It makes an easy day trip from Florence (by bus or by car); see this Rick Steves clip.
- Fattoria Poggio Alloro - a beautiful agriturismo that produces wine, olive oil, and prosciutto (especially from chianina oxen), among other specialties, run by brothers Lorenzo (Enzo) and Giancarlo Fiorini (Enzo's English is much better than his brother's), about 5 km from the town. Their terrace and pool look out onto the towers of San Gimigniano, and their Vernaccia (the local white) is quite good. 0577-950-153, 43°29.25'N 11°03.88'E. From San Gimigniano, follow signs for Certaldo, then Ulignano, and then turn right at the sign for Casaglia/Remignoli.
- Gelateria di Piazza - found in the main Piazza della Cisterna, this gelateria claims to serve the "best ice cream in the world"...which is not an idle boast, since it often wins gelato competitions.
- Il Pino - via Cellolese 8/10, 057-794-2225, closed Thurs, closed Fri lunch, rustic family restaurant, ~€30-40, rec'd by Gambero Rosso.
- Osteria del Carcere - via del Castello 13, 057-794-1905, closed Thurs lunch, Wed, near center of town, good cheese/salumi/traditional dishes, ~€30-35, rec'd by Osterie d'Italia.
CortonaFeatured in Francis Mayes' Under the Tuscan Sun, Cortona is another beautiful hill town, nestled on the Umbrian border. Apart from the town itself, the Etruscan Museum is supposed to be quite good. (Real Etruscan fans might want to go to the town of Chiusi, conveniently on A1 and train lines, which features an excellent Archaeological Museum as well as several Etruscan caves and tombs.) LucignanoVery close to the A1 highway, near the exit to Siena, Lucignano is a well-preserved medieval town with characteristic oval rings spreading out from its main piazza. - Ristorante la Rocca - via Matteotti 15/17, 057-583-6775, closed Tues, rec'd by Slow Food Osterie d'Italia, ~€30-40 with €30 fixed-price menu.
- Osteria da Toto, at Piazza del Tribunal 6, 057-583-6763, closed Tues, www.trattoriatoto.it, which offers relatively inexpensive (€15-35), hearty fixed-price meals and rooms for rent, highly rec'd by one Chowhound reader
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