See the Florence page for information about the capital of Tuscany.
See the Pisa and Lucca page for more about these cities in western Tuscany.
Learn more about Montalcino and its prized wine, Brunello, on the Montalcino page.
This old rival of Florence is one of the bigger cities in Tuscany, but still retains a medieval character in its mostly-pedestrian streets. Its twice-yearly Palio (horse race) in the town square re-ignites that medieval spirit. Also see Wikivoyage's Siena page for good tips.
Il Palio di Siena - this horse race, which goes back to the middle ages, pits the districts (or contrade) of the city against each other twice a year; check out the Siena Palio page for more information.
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.
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 (until they ran out of money).
Contrada Fountains - Each contrada has a fountain, usually near its church and headquarters. Some are ancient, and some are modern, but finding them is a great way to explore the city and see parts of Siena that tourists usually overlook. Betsy Donnelly's site has the best description of the fountains and their locations; also check out this handy Google Map. You can also take fun pictures imitating the fountains like these folks.
Contrada Museums also might be interesting; to visit them, you typically have to contact the contrada (or the tourist office) ~2 weeks ahead of time. Locations and more at Initaly.com
***Antica Pizzicheria Chigiana de Miccoli - Via di Citta 93-95, ~€7-12 for a sandwich. Close to Piazza del Campo and the Duomo. This salumeria specializes in high-end Tuscan meats, cheeses, and wine, and their sandwiches are particularly good. Try a panino con pecorino fresco e pesto, or the porchetta. The sandwiches are often large enough for two people to share. They also have quite good biscotti di cioccolato, and the ricciarelli (traditional Sienese cookies made from almond paste) are also quite good. There is often a line, and it is significantly more expensive than your average Italian salumeria, but the quality of the food is very good.
***La Taverna di San Giuseppe - Via G.Duprè 132 (near the Onda contrada fountain), 0577 42286, €28 - €55. Traditional Sienese food in a historic, old building; known for dishes with truffles or porcini mushrooms, a bit pricey/fancy. When we went to Siena in 2014, this was our favorite stop. Rec'd Lonely Planet.
outside town in Ville di Corsano: Il Ristoro - rec'd Slow Food Osterie d'Italia 2018
Grom - an outpost is at Via Banchi di Sopra 11, Sun-Thurs 11-11 (midnight in summer), Fri/Sat 11-mid (12:30 am in summer)
La Vecchia Latteria - Via San Pietro 10, ??, rec'd Lonely Planet
Bar Il Camerlengo - Piazza Il Campo 6, ??
Caribia - via Rinaldini, ??
Bar/Pasticceria Nannini - ??
*Were* recommended but not sure anymore:
Osteria Il Carroccio - Via Casato di Sotto 32, very close to Piazza del Campo, 057-741-165, closed Wed, email@example.com, firstname.lastname@example.org, highly rec'd by various people (including Mark's friend Greg) and Osterie d'Italia (says owner/chef Renata makes great traditional dishes with a bit of "poetic license", don't miss the pici but raviolone, pasta corta, ribollita, and zuppa di cippole are also rec'd primi; great secondi too), €30 tasting menu...we went here in 2014 and thought it was good but nothing to write home about
Osteria il Campaccio - Vicolo del Campaccio 2, 057-728-4651, 057-728-4651, closed Mon in winter, popular with locals, hard to find but worth the search...raved about by Kalscheuer and the Parkers...they especially recommend the ricotta and pear pasta; also rec'd by The Independent, this slow traveller (seems especially popular with the Alma Domus convent hotel), and this Vanderbilt student...also has gluten-free pizza (??) --> but when we tried it in 2014, it was very disappointing
Grotta di Santa Caterina da Bagoga - Via della Galluzza 26, 057-728-2208, closed Sun eve, Mon, rec'd by Slow Food Osterie d'Italia (not anymore in 2018)
Osteria Le Logge - Via del Porrione 33, 057-748-013, closed Sun, focus on organic ingredients, lighter-style cooking, "revised" versions of Tuscan dishes, rec'd by Slow Food Osterie d'Italia (not anymore as of 2018)
Antica Osteria da Divo - via Franciosa 25/29, 057-728-6054, closed Sun. Traditional and creative food, was rec'd by Slow Food Osterie d'Italia but no longer in guidebook as of 2014
Antica Trattoria Papei - Piazza del Mercato 6, 057-728-0894, closed Mon. Family-run traditional place, was rec'd by Slow Food Osterie d'Italia but no longer in guidebook as of 2014, "don't miss the bistecca"
Compagnia dei Vinattieri - via delle Terme 79, 057-723-6568, closed Tues. Enoteca/restaurant was rec'd by Slow Food Osterie d'Italia but no longer in guidebook as of 2014
Il Canto - was rec'd by Slow Food Osterie d'Italia but no longer in guidebook as of 2014
Il Gratttacielo - was rec'd by Slow Food Osterie d'Italia but no longer in guidebook as of 2014, ironically named (it means "skyscraper" but the restaurant is tiny)
Trombicche - was rec'd by Slow Food Osterie d'Italia but no longer in guidebook as of 2014, nice for lunch (this Vanderbilt student especially rec's the ribollita)
San Desiderio - Piazza L. Bonelli 2, restaurant in a de-consecrated old chapel, rec'd by someone?
The Chianti region, a large swath between Siena and Florence, is known for its wine, Chianti Classico.
Colle di Val d'Elsa
Colle 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; their pear and ricotta pasta is delicious!
#Sbarbacipolla Biosteria - Via Bartolomeo Scala 11, 057-792-6701, dinner only except Sun/Mon, founded in 2010, single room featuring organic products, ever-changing menu, great cheese selection, kid's menu, recommended in Slow Food Osterie d'Italia 2014-2018
Other Chianti Towns
Gaiola in Chianti - a small town in the SE part of Chianti
Il Carlino d'Oro - rec'd by Osterie d'Italia
Al Ponte - rec'd by Osterie d'Italia
Radda in Chianti --> headquarters of the Consorzio di Chianti Classico; consider picking up a copy of Le strade del Gallo Nero map to the wineries
Le Panzanelle - rec'd by Osterie d'Italia
Panzano in Chianti
Antica Macelleria Cecchini - home to Dario Cecchini, a "celebrity butcher" (thanks in part to Netflix's Chef's Table)...he runs 3 eateries in town:
Officina della Bistecca - mostly steak
Solociccia - non steak dishes
Dario DOC - casual lunch eatery
Badia di Passignano - the Antinori winery is based here; you can see the Abbazia di San Michele Arcangelo a Passignano monastery
Val d'Orcia / Crete Senesi
The drive between Montepulciano and Montalcino, in an area called the Crete Senesi ("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 cypress trees. Especially near San Quirico d'Orcia, this area is very photogenic. This article by Slow Travel contributors describes some of the most iconic photos (such as the Belvedere Farmhouse).
Castiglione d'Orcia: beautiful castle on a hill, ~30 min SE of Montalcino (due south from San Quirico d'Orcia)
La Taverna del Pian delle Mura: rec'd by Osterie d'Italia
Monticchiello: small medieval town a little ways between Pienza and Montepulciano, a little ways off the main SP146 road, called an "overlooked gem" on this blog
La Foce - South of Monticchiello, also not far from Chianciano Terme; fancy resort, gardens, and restaurant Dopolavoro la Foce which is rec'd by Lonely Planet, TCI, and Gambero Rosso...closed from early November to late March
Hills further south: Oreade - restaurant rec'd NY Times for beautiful views and farm-to-table meals
Trequanda: Il Conte Matto - rec'd Slow Food Osterie d'Italia 2018
Montisi: Da Roberto Taverna in Montisi - rec'd Slow Food Osterie d'Italia 2018
[Laurenissima / Unlock Italy has a nice blogpost from September 2020 introducing this region]
Known for its eponymous Vino Nobile di Montalcino wine, Montepulciano is a hill town at the eastern side of the Crete Senesi. 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, does NOT accept reservations over email, big shared table, good house wine (a Rosso di Montepulciano), simple/traditional dishes change with the seasons, rec'd by Rick Steves for pastas and salads, also good bistecca fiorentina, and other local foods like pici, in centro storico, rec'd by Slow Food Osterie d'Italia (still in 2018), NY Times, review in Italian, rules warn you that the "owner is mean" and that "the only free cheese is in a mousetrap"!
Piccola Trattoria Guastini - outside town in Valiano di Montepulciano, Via Lauretana Nord 20, 057-872-4006 or 347-704-4305, rec'd Slow Food Osterie d'Italia (not anymore in 2018)
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.
La Dogana - rec'd Lonely Planet
La Grotta - rec'd Lonely Planet
Caffè Poliziano - rec'd Lonely Planet
nearby in Montefollonico: La Botte Piena - rec'd Slow Food Osterie d'Italia 2018
nearby in Torrita di Siena: Piccola Trattoria Guastini - rec'd Slow Food Osterie d'Italia 2018
Perched between the wine cities of Montepulciano and Montalcino, Pienza is famous for both fresh and aged pecorino cheese (see this NY Times article for details). 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 (not anymore in 2018), 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 Sette di Vino - rec'd Lonely Planet
Townhouse Caffè - rec'd Lonely Planet
Idyllium - rec'd Lonely Planet
La Bandita - Country house
in Montecchiello, a town just to the SE:
Osteria La Porta - via del Piano 3, 057-875-5163, closed Thurs, €35 fixed price, with €18 lunch, rec'd by NY Times, Osterie d'Italia, Espresso, Michelin, Lonely Planet, and TCI; beautiful view of Val D'Orcia.
Ristorante Daria - rec'd Lonely Planet
La Guardiola - wine bar/snack/aperitivo place rec'd Lonely Planet
(Lonely Planet also rec's La Casa di Adelina as a place to stay)
Other Hill Towns
For more ideas, check out Rick Steve's Hill Towns page.
If you like hill towns, also be sure to check out nearby Umbria, which boasts such places as Orvieto, Asisi, Spello, Spoleto, and Trevi.
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.
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 Dondoli (formerly 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 proprietor Sergio Dondoli often wins gelato competitions. Rec'd by Gambero Rosso in Gelaterie d'Italia 2020 "3 coni" (top award)...also runs gelato courses that are 3, 5, and 7 days long.
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.
Perucà - rec'd by Osterie d'Italia
Tiny town about 40 minutes west of Florence with a beautiful view
Ristorante da Delfina - where chef Craig Stoll of Delfina restaurant in San Francisco got his start, rec'd Michelin, Fodors, ...Carlo Cioni, the owner/chef, is a trip! When we went for our honeymoon in 2014, we got the "piatto di buon ricordo" ("dish of good memories") which turned out to be a tasty rabbit dish that came with a souvenir plate (!).
...also check out Dissapore's 2017 list of best Trattorias in Tuscany (mostly in smaller towns)
(Maremma/Grosseto province, Livorno Province, Massa/Carrara)
Monterchi - features the Madonna del Parto painting by Piero della Francesca
La Verna Santuario Francescano (in Chiusi della Verna) - supposedly the site where St Francis received the stigmata
Poppi - old town on a hill next to the Arno river in Casentino Valley, has a 13th-century castle
Borgo Corsignano - Lonely Planet rec's this "gorgeous country hotel"
L'Antica Cantina - rec'd Lonely Planet
Camaldoli - known for an order of monks founded here, outside town is the Eremo Di Camaldoli, a peaceful 11th-century place on the edge of the forest; monks sell various things in their 16th-century pharmacy
Sansepolcro - Lonely Planet raves about its churches an palazzi
Pasticceria Chieli - rec'd Lonely Planet
Ristorante Al Coccio - rec'd Lonely Planet
Piazza Grande and several other filming locations for Life is Beautiful
Chiesa di Santa Maria delle Pieve - oldest church, medieval art
Capella Bacci - della Francesca fresco cycle
Antica Osteria Agania - rec'd Lonely Planet
Aliciati - rec'd Lonely Planet
Featured 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.)
in Chiusi: Il Grillo è Buoncantore - rec'd by Osterie d'Italia
in Sarteano (also near A1, not far from Chiusi): Da Gagliano - rec'd by Osterie d'Italia
Eremo Francescano “Le Celle” - 8 min drive outside town, old monastery carved into a hill
Very 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