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Siena and San Gimignano - medieval streets, art and the Campo

Siena and San Gimignano make the essential medieval heart of a Tuscan route. Siena rewards a full day and an evening, while San Gimignano is compact enough for a focused visit built around its towers, frescoes and hilltop views.

In brief: Siena is the larger, living medieval city, with the Duomo, civic art, contrade and Piazza del Campo. San Gimignano is the dramatic hill town of the towers. They can be combined by road or bus, but each deserves time beyond a quick photograph.

Siena

Siena lies about 76 km south of Florence and 27 km southeast of Colle di Val d'Elsa. Narrow streets, steep alleys, a Gothic cathedral, early Renaissance painting and the Palazzo Pubblico over Piazza del Campo make it one of Europe's most complete medieval cityscapes. It is not a museum: shops, local neighborhoods and the evening passeggiata remain part of daily life.

Siena's golden age began after the victory over Florence at Montaperti in 1260. The city built its major monuments, created an influential government led by Nine and flourished in art, textiles and trade. The Black Death devastated the population in 1348, and Siena later fell under Florentine rule after a 16th-century siege. The long period of decline helped preserve the medieval fabric that visitors see today.

The historic 17 contrade remain active neighborhoods. Their animals and emblems appear on banners and walls, and residents retain strong loyalties to the district where they grew up. The twice-yearly Palio makes that identity most visible in Piazza del Campo on July 2 and August 16, but contrada culture is present throughout the year.

Getting to Siena and getting around

From Florence, the quickest road is the Florence-Siena superstrada. The Via Cassia, or SR2, is a more scenic alternative. Drivers coming from Rome should exit the A1 at Valdichiana, then use the Siena-Bettolle superstrada. Autolinee Toscane runs frequent direct buses from Florence; they are usually faster and simpler than trains, which can require a change at Empoli.

Leave a car in a perimeter parking lot because driving is difficult or impossible through much of the center. The medieval city follows a Y-shaped plan over several hills and is divided into terzi, so even a short map distance can involve a steep climb. The Siena Tourism Office is at Il Campo 1; the listed phone number is 0577/292222.

How long to stay

A brisk walk can cover Siena's main sights in one day, but staying longer makes the city more rewarding. Allow time for the churches, museums and street scenes, then join the evening passeggiata through the three main streets: Via di Citta, Banchi di Sopra and Banchi di Sotto. Many sights reduce their hours on Sunday afternoon and Monday, so check the calendar before choosing museum days.

The cathedral complex

  • Battistero - the 14th-century Gothic baptistery sits below the cathedral and contains a large bronze font designed by Jacopo della Quercia. Reliefs include Lorenzo Ghiberti's Baptism of Christ and Donatello's Feast of Herod. A combined ticket covering the Duomo, Cripta and Museo dell'Opera starts at €14; the baptistery is at Piazza San Giovanni and the listed phone is 0577/286300.
  • Cripta - discovered during excavation and opened to visitors in 2003, this hidden space retains unusually vivid late-13th-century frescoes. A €16 combined ticket covers the Duomo, baptistery, roof terrace and museum. The entrance is down the steps to the right of the cathedral at Scale di San Giovanni.
  • Duomo - the facade combines multicolored marble with sculpture by Nicola and Giovanni Pisano, while the interior uses green-and-white striping, a gilded dome and inlaid floors. More than 40 artists worked on 56 marble compositions over nearly 200 years. The floor is uncovered from late June to late July and again from mid-August to mid-October. Look for the carousel pulpit by Nicola Pisano and Pinturicchio's frescoes in the Biblioteca Piccolomini. The €16 ticket includes the crypt, baptistery, roof terrace and museum.
  • Museo dell'Opera - housed in the unfinished extension of the cathedral, the museum protects Giovanni Pisano's sculptures, a tondo attributed to Donatello and the Duomo treasury. Duccio's Maesta, painted between 1308 and 1311, is the central masterpiece. Admission is included in the €16 combined ticket, and a view from the museum tower completes the visit.

Campo, civic art and churches

  • Palazzo Pubblico and Torre del Mangia - Siena's Gothic town hall has served as the civic center since the 1300s. The Museo Civico contains Ambrogio Lorenzetti's Allegories of Good and Bad Government in the Sala della Pace. The Torre del Mangia climb is long and steep but gives a broad view over the city. Museum admission is €6; museum plus tower is €15. The address is Piazza del Campo 1 and the phone is 0577/292368.
  • Piazza del Campo - the fan-shaped main square is divided into nine brick sectors, recalling the medieval Council of Nine. The Fonte Gaia at the upper end is a copy of Jacopo della Quercia's fountain; the original reliefs are in the Santa Maria della Scala complex. On the two Palio dates, July 2 and August 16, the square becomes the center of the horse race and its surrounding crowds.
  • Pinacoteca Nazionale - five centuries of Sienese painting show how much Renaissance art developed outside Florence. The collection includes the early Master of Tressa, Guido da Siena, Duccio, Ambrogio Lorenzetti and studies by Domenico Beccafumi. Admission is €6; on Sunday and Monday the museum closes after 1:30 pm. It is at Via San Pietro 29; phone 0577/281161.
  • San Domenico - this large brick church is closely associated with Saint Catherine of Siena. Her chapel contains a contemporary portrait, and the apse-side terrace looks toward the Duomo and the center. Admission is free; the church is at Piazza San Domenico and the phone is 0577/286848.
  • Santa Maria della Scala - the former hospital opposite the Duomo now houses Sienese art, archaeological collections and the restored Pellegrinaio frescoes, which recount the hospital's charitable work. The underground museum contains the original reliefs from the Fonte Gaia. Admission is €9; it closes Tuesday from November to mid-March. Address: Piazza del Duomo 2; phone 0577/292615.

Where to eat and sleep in Siena

  • Antica Trattoria Papei - three generations of the Papei family serve straightforward Sienese specialties behind the Palazzo Pubblico at Piazza del Mercato 6. Outdoor seating works in every season, and the average main is €15. Phone 0577/280894.
  • Osteria Il Grattacielo - a small, inexpensive lunch stop at Via Pontani 8, popular for verdure sott'olio, affettati misti, pasta and affordable house wine. The average main is €12; phone 331/7422835; no dinner Sunday. The listed website is a Google Sites page, so confirm current details locally.
  • Grand Hotel Continental - a historic palace on Banchi di Sopra 85 with an elegant entrance, polished public spaces and a central location. Rooms start at €420, breakfast costs extra and there are 51 rooms. Phone 0577/56011; the hotel is listed through Starhotels.
  • Hotel Santa Caterina - outside the walls at Via Piccolomini 7, this welcoming property is an easy walk from the center and serves breakfast in its garden. Rooms start at €200, there are 22 rooms and breakfast is included. Phone 0577/221105.
  • Palazzo Ravizza - a historic palazzo at Pian dei Mantellini 34, about 10 minutes from the center, with antique furnishings, high ceilings and a garden beyond the walls. Rooms start at €150, there are 41 rooms and breakfast is included. Phone 0577/280462.

San Gimignano

San Gimignano stands 14 km northwest of Colle di Val d'Elsa, 38 km northwest of Siena and 54 km southwest of Florence. Its tall walls, narrow lanes and cluster of medieval towers create the classic Tuscan hill-town image. Fourteen towers remain today; during the Guelph-Ghibelline conflicts, more than 70 once filled the skyline and rooftops offered an alternative route across town.

The main street is touristy and lined with souvenir shops, but the town remains worth the effort because important Renaissance painting survives inside its churches and civic buildings. Visit the main sights, then step away from the busiest route for the quieter walls, lanes and countryside views.

Getting to San Gimignano

By car, leave the Florence-Siena superstrada at Poggibonsi Nord and follow the signs. From Florence, the bus requires a change at Poggibonsi but is a workable public-transport option. Siena has several direct buses each day. Every listed bus service is operated by Autolinee Toscane, and San Gimignano has no train station. The San Gimignano Tourism Office is at Piazza Duomo 1; the listed phone is 0577/940008.

The essential sights

  • Collegiata - San Gimignano's main church is not formally a cathedral because the town has no bishop. Almost every wall inside carries frescoes, including Bartolo di Fredi's 14th-century Old Testament cycle and the later Life of Christ scenes attributed to Lippo Memmi. Admission is €5. The church is at Piazza Pecori 1-2; entrance is on the left side and the phone is 0577/286300.
  • Museo Civico - the civic museum occupies the former Palazzo del Popolo beside the Torre Grossa. Paintings by Pinturicchio and Benozzo Gozzoli, along with two large tondi by Filippino Lippi, show the wealth of medieval and Renaissance San Gimignano. A cumulative museum ticket is €9; the San Gimignano Pass for museums and the church is €13. Address: Piazza Duomo 2; phone 0577/286300.
  • Sant'Agostino - the free church contains Benozzo Gozzoli's 15th-century cycle on the life of Saint Augustine, with 17 scenes along the choir wall, and a 15th-century altarpiece by Piero del Pollaiolo. It is at Piazza Sant'Agostino 10; phone 0577/904313.

Restaurants and hotels in San Gimignano

  • Cum Quibus - an intimate, creative restaurant at Via San Martino 17, with Tuscan foundations, non-Tuscan ingredients, a strong wine list and courtyard seating in warm weather. The average main is €26; phone 0577/943199; closed Wednesday and Thursday and January-February. Confirm the current website and reservation details locally.
  • Enoteca Gustavo - a wine bar at Via San Matteo 7 for Vernaccia di San Gimignano by the glass, cheese plates and crostini. The average main is €15; phone 0577/940057.Check current opening details locally.
  • Osteria del Carcere - a former jail at Via del Castello 13 that now resembles a wine bar, with pates, seasonal soups and salads and a goat-cheese sampler. The average main is €20; phone 0577/941905; closed Wednesday and from early January through March, with no Thursday lunch.
  • Hotel La Collegiata - a former Franciscan convent and later noble residence north of town, with terrace views and elegant rooms. Rooms start at €241, there are 20 rooms and breakfast is included. It closes November-March; address Localita Strada 27; phone 0577/943201.
  • Hotel Pescille - a farmhouse hotel 4 km south of San Gimignano, with quiet views and a 10-minute walk to town from the property. Rooms start at €250, there are 38 rooms and breakfast is included. A vehicle is necessary; it closes from mid-October to mid-April. Phone 0577/940186.
  • Torraccia di Chiusi - an 11-room family agriturismo about 5 km from town, with simple rooms, walking possibilities and countryside views. Rooms start at €200 and breakfast is included. The final approach is a winding gravel road, so a car is necessary. Address: Localita Montauto 16; phone 0577/941972.
Siena or San Gimignano
Choose Siena when...Choose San Gimignano when...
You want a full day of museums, churches, civic art and evening streetsYou want a compact hill town centered on towers, frescoes and views
You are interested in contrade life and the Palio dates of July 2 or August 16You are building a Chianti route from Poggibonsi or the Florence-Siena road
You prefer frequent direct buses from Florence and a larger range of restaurantsYou are happy to use a bus connection or a car because there is no train

Give Siena the time to become a city rather than a checklist, then let San Gimignano's towers close the route with a view across the Tuscan hills.