Siena is the capital of the province of Siena in Tuscany, Italy. People visit Siena from all over the world to see the historic center, which is a UNESCO World Heritage Site. The city retains a medieval cityscape full of art, museums, and some of the best cuisine in the world. Siena dates back to between 900-400 BC when the Etruscans settled there and is part of Roman mythology. Siena is found in the central part of Tuscany amidst the Chianti Hills, beautiful valleys, and the Crete Senesi. The Mediterranean climate offers gorgeous weather and visitors to the city can enjoy sites around Siena such as the Siena Cathedral, Piazza del Campo, Palazzo Salimbeni, and the city gardens. Siena is also near many other nearby historic cities.


1.Arezzo

Arezzo
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Arezzo is a city with ancient origins centered at the meeting place of four valleys in southeastern Tuscany. Known for being the site where Man of the Elm, a body that dates to the Paleolithic era, was discovered, Arezzo is also home to many other ancient places that visitors can see and explore. Some of the best sites to see in Arezzo include fortresses, the remnants of a Roman amphitheater, ancient cathedrals, and prolific artworks at the museums. Spend the day in Arezzo for wine tastings, take a drive down the Route of the Setteponti, or take a walking tour of the city and visit The Medici Fortress which was built in the 16th century.

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2.Asciano

Asciano
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25 km southeast of Siena is the quiet little town of Asciano nestled in the Ombrone River Valley. Many people love to travel to Asciano and the Crete Senesi Region to explore the picturesque landscapes and visit the medieval center. One of the most popular attractions in Asciano is the Saint Agatha Collegial Church which was first built in the 12th century. Much of the original structure remains, though some parts of the church have been updated. Visitors can stop by the Museum Cassioli next to the church to view local Sienese art and the Corboli Museum just down the road to explore archaeology and artifacts from the Etruscan tombs. Spend the day and drive out to Monte Oliveto Maggiore monastery 10 km south of town.

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3.Bologna

Bologna
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Bologna is found in Northern Italy and is the capital city of the Emilia-Romagna region. The bustling metropolitan city has been one of the great urban centers of Tuscany for centuries and is known for its historic architecture and a well-preserved city center with long porticoes that have been meticulously restored. Bologna is also where the world-famous University of Bologna is. The university is the oldest in the world and was declared a European Capital of Culture in 2000, UNESCO City of Music in 2006, and was inducted into the Creative Cities Network. The best places to visit in Bologna include Piazza Maggiore with Basilica of St. Petronius, St. Stephen Basilica, the leaning towers—Torre Garisenda and Torre degli Asinelli, and the university campus. Visitors should also make sure to stop at a local café for authentic Bolognese food.

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4.Buonconvento

Buonconvento
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Buonconvento is known to be one of Italy’s most beautiful villages. Visitors driving into Buonconvento are greeted by medieval walls and architecture. The small village is found at the convergence point of the Arbia and Ombrone Rivers and features museums housing art from some of Italy’s finest artists and the Sienese school of art, and ancient cathedrals dating back to 1100. The best time to visit Buonconvento is during the Sagra Della Val d’Arbia in September. The popular event celebrates art, food, sports, and music. This annual festival started in 1805 and drew hundreds of visitors to the small medieval town.

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5.Chianti

Chianti
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Known for Chianti Wine, this area of Tuscany is visited by people from all over the world who want to experience wine country. The Chianti Region covers the provinces of Florence and Siena but isn’t clearly defined on any map. The territory is perfect for spending the day wine tasting and driving through the picturesque countryside to visit small stone villages, olive groves, castles, fortresses, and ancient church parishes. Most people visiting the Chianti region will spend the day in Siena or Florence, where there are many tourist attractions such as museums and historic sites. There are many different types of guided tours and walking tours that offer visitors a taste of the Chianti regions, depending on their preferences.

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6.Colle di Val d'Elsa

Colle di Val d'Elsa
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Stop by Colle di Val d’Elsa on your way from Siena to Florence to enjoy this charming town known for crystal glass making, exquisite restaurants, and a medieval ambiance. During summer months there are monthly first Sunday markets and glass making shows that visitors can explore. There are also museums, the old historical center, and Volterra—an ancient fortress with walkable roads, that tourists can enjoy exploring all day long. Colle di Val d’Elsa is only thirty minutes from Siena and is easily accessible by car or bus. Some of the best sites to visit are the Civic and Diocesan Museum, Archeological Museum, and Via Della Misericordia, where visitors can watch glass blowing presentations.

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7.Cortona

Cortona
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Visitors wishing to explore hillside towns in Tuscany will love spending the day at Cortona. Marked by steep vertical streets, there are many historic and cultural sites to visit in Cortona such as Cortona Etruscan Museum and the Cortona Diocesan Museum set against Renaissance architecture. The Piazza Della Republica is one of the most popular attractions and is the focal point of the city. The Medicean Fort is another great place to visit for sweeping views of the city and the Val di Chiana. Some great times to consider coming to Cortona are during the bric-a-brac market that happens monthly, the crossbow competition, or Cortona Mediaeval Week that happens in the middle of summer annually. There are also many performing arts events happening all year round.

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8.Fiesole

Fiesole
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The charming town of Fiesole is one of the least touristy hillside towns near Florence. The town overlooks the valley and features numerous Tuscan villas with the most famous being Lorenzo di Medici’s Villa Fiesole. The streets in Fiesole are very narrow, and the town is best visited via city bus though personal vehicles are allowed. There are also many excellent restaurants in Fiesole such as Le Reggia Degli Etruschi and Trattoria Tullio. You’ll need reservations to dine at both of these highly sought-after restaurants. Tours of the Cathedral of Fiesole and other historic churches are available as well as the Roman baths and theatre at Fiesole are available.

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9.Florence

Florence
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When people think of the Italian Renaissance, Florence is one of the most iconic places that comes to mind. Some of the most significant artworks in history are found in the museums, castles, and churches in Florence. Tourists to Florence can spend several days exploring historic sites such as the Cathedral, Baptistery, Accademia, Uffizi, the Bargello, and many art galleries and libraries. One of the most famous libraries, San Lorenzo, was designed by Michelangelo. Visitors who want to explore the Oltrarno, the newer part of Florence, can enjoy a walk through the Boboli Gardens, Pitti Palace, and climb the hill up to the San Miniato al Monte. There are many different tours of Florence offered by travel and tourism companies that visitors can tailor to their own interests.

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10.Greve

Greve
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Greve is known as the gateway to the Chianti region, and the world-famous vineyards are visible before you leave the city limits. Greve offers a tranquil ambiance with a quaint small-town atmosphere and is the headquarters for a local comune between Florence and Siena. There are many villa rentals, bed & breakfasts, and other accommodations for people who want to spend a few days visiting Tuscan wine country. A farmer’s market occurs every Saturday, and the town sits just below the Castle of Montefioralle and is at the crossroads of three historic roads once used for pilgrimages. The Main Square is the perfect place to visit for boutique shopping, local restaurants, and artisan workshops.

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11.Livorno

Livorno
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The Mediterranean is not better explored than in a port city. Livorno is located on the Tyrrhenian Sea and is a stop on many cruise ship itineraries and has a ferry station that can transport visitors to the surrounding islands. Livorno was built in the 16th century as a mercantile port city, but visitors can spend the day exploring the 17th century New Venice District which is surrounded by canals and features boutiques, restaurants, and bars. Many locals in Livorno port their boats in the waterways surrounding the district. Visitors wanting to spend the entire day in Livorno should visit during the Effetto Venezia Festival.

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12.Lucca

Lucca
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Found at the base of the Apuan Alps, Lucca is one of the most visited cities in Tuscany. The village is less than thirty minutes from the Versilia coast and is a great place to visit for visitors who are sick of climbing and steep roads since it isn’t on the hillside. Visitors can come to Lucca by car or train with trains leaving from Florence and Pisa. The attractions in Lucca are centered around the town’s ancient history including Piazza dell ‘Anfiteatro, and archeological remains housed beneath the 12th-century churches and villas. The walls around the fortress are now used as a pedestrian promenade and are one of the main attractions in the city now.

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13.Montalcino

Montalcino
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Montalcino is a 14th-century medieval village that features a military layout and steep streets that wind up the hills. There are many historic churches including the Church of Sant’ Agostino which was also constructed in the 14th century, A neoclassical Cathedral, and several others. The town hall, however, dates even further back, to the 13th century, and is known for the towering bell tower. Visitors driving around the countryside of Montalcino can see one of the most notable examples of French Romanesque architecture found any more in Italy at the Abbey of saint’ Antimo. Montalcino is surrounded by forests, olive groves, and vineyards and was declared part of a UNESCO World Heritage Site in 2004. Spend the day wine tasting and sampling honey or exploring the ancient sites and monuments.

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14.Montepulciano

Montepulciano
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Montepulciano is a medieval town full of renaissance palaces, in the south of Tuscany surrounded by gorgeous valleys. The town is also where scenes from the vampire movie Twilight was filmed, which has increased tourism in the historic town. Nobile wine is produced in Montepulciano, and the countryside is covered in vineyards and wineries. The Piazza Grande is the center of town often showcases special events such as the annual barrel racing contest each August. Several other villages surround Montepulciano including Pienza and Bagno Vignoni, a thermal village.

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15.Monteriggioni

Monteriggioni
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A historic walled city dominates the hilly landscape of Monteriggioni. The town is found in the province of Siena, and the castle was built in the early 13th century to overlook Cassia Road and control Val d’Elsa and defend from enemy armies. There were initially fourteen towers total and two gates, one facing Rome and the other, Florence. The perfectly circular wall houses a village inside that is for the most part still original. When visiting Monteriggioni, visitors should park in the lot at the base of the bill then climb the short ascent to the village. The Church of Santa Maria Assunta is part of the original construction and faces the Piazza di’ Roma. The best time to visit is in July during the Medieval Festival of Monteriggioni where people dress in Medieval clothing with live performances, acrobats, bards, and theater.

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16.Monteroni d'Arbia

Monteroni d'Arbia
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Monteroni d’Arbia is the very heart of Tuscany just a few miles from Siena on the famous road to Rome, Via Francigena. The city is surrounded by rolling hills, vineyards, olive groves, and poppy fields, making for a very scenic trip through the Tuscany countryside. Monteroni d’Arbia is home to a medieval mill complex dating back to the early 14th century, and the mill pond is even still intact. Visitors should stop by Cuna, a fortified farm that was established in 1224, and The Castle of San Fabiano which was constructed around 1100. The formal gardens at the castle are still maintained, and there are often special exhibits that can be toured and events.

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17.Pienza

Pienza
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Pienza is in the south of Tuscany and means “the city of Pius” after Pope Pius II who was born there when it was named Corsignano. The Pope hired architect Bernardo Rossellino to transform the village into a Renaissance town using humanist urban planning design concepts. The construction on the town started in 1459 and took four years to complete. Pienza remains mostly unchanged today. Visitors to Pienza can visit several important buildings, including Pizza Pio II, and Rossellino’s masterpiece, Palazzo Piccolomini. The entire town is a UNESCO World Heritage Site and hosts an annual cheese festival on the first Sunday in September.

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18.Pisa

Pisa
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Pisa is famous for more than just the Leaning Tower, though the tower is one of the most famous attractions in the world. Visitors to Pisa can spend an entire day exploring the Square of Miracles, Cathedral, Baptistery, and several museums. Just a short walk away is the Clock Palace and Piazza Dei Cavalieri, as well as the Knight of St. Stephens headquarters. Pisa is also known for cecina, a gluten-free bread made of chickpea flour and a few other basic ingredients. Many people eat cecina with a flatbread called schiacciatina. Visit in June to participate in a series of annual events is held that celebrates the patron saint of Pisa, San Ranieri. Other great attractions in Pisa include Luminara and the Battle of the Bridge.

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19.Pistoia

Pistoia
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Pistoia is located between Florence and Lucca in the northern region of Tuscany. The Pistoia Mountains are an excellent location for skiing, and the area is known for the plants and flowers that are exported to countries around the world. Many of the nurseries have been owned by the same families for generations. Pistoia is also famous for its thermal baths that royalty has used for health benefits and spa treatments. Visitors who love outdoor sports will enjoy exploring the mountains, and just outside the city is the Zoo of Pistoia and Pinocchio Park. For some of the world’s finest artisan chocolates, explore the Tuscan chocolate valley, which comprises Pisa, Prato, and Pistoia.

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20.Portovenere

Portovenere
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The medieval town of Portovenere is a UNESCO World Heritage site on the Gulf of Poets in Liguria Italy. Many visitors stop in the town on their way to Cinque Terre, which is close. Most people arrive in the coastal town by boat and spend time in the harbor exploring the shops and cafes where they can watch boats pass down the channel. Just behind the harbor are the old town and the old city gate, which both date back to the 12th century. The town is full of narrow streets, artisanal shops, and boutiques. At the top of the hill, visitors will find Doria Castle which overlooks the Bay of Poets and ancient gardens. Other notable attractions in Portovenere include Church of San Lorenzo, Church of Saint Peter, and Lord Byron’s Grotto where the famous poet would stay and write and swim with other poets. Outdoor explorers can also spend time at Porto Venere Natural Park. The surrounding islands are also great for cave exploration and sailing.

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21.Prato

Prato
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Prato is full of contemporary avant-garde spaces, a culture steeped in Renaissance history, a vibrant nightlife, and is known around the world for the fantastic luxury textiles manufactured there. One of the most iconic parts of Prato is the pulpit designed by Donatello and Michelozzo at Cathedral of Santo Stefano. Pope Francis once spoke from the pulpit, and the church holds a religious relic that once belonged to the Virgin Mary. The interior of the church is decorated with historic frescoes created by Filippo Lippi. Other great attractions to see when visiting Prato include Palazzo Pretorio which is the Prato Civic Museum, the Castello dell’ Imperatore built in the 13th century, and check out the place where the world-famous biscotti di Prato is made.

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22.Rapolano Terme

Rapolano Terme
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The rugged landscape of Rapolano Terme is known for the therapeutic thermal springs that have been used in traditional Roman baths for centuries. The spas offer hydro-massage, mud baths, and many other relaxing skin treatments. The region is also famous for its production of travertine stone which has been mined from waterfalls, limestone basins, and springs since the 16th century. This stone is what many of the most famous Italian monuments are built from including Church of San Biagio, and Church of Provenzano in Siena. Visitors to Rapolano Terme can also enjoy touring the olive groves, visiting the Grange Museum, and The Imperial Palace and Ancient Serre Grange.

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23.San Gimignano

San Gimignano
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The origins of San Gimignano, according to local legend, date back to 63 B.C. when two brothers each built a castle for themselves when they escaped from Rome. The first settlements in the area go back to the Etruscan period, and traces of these ancient settlements are still being discovered. Visitors to San Gimignano can visit the remaining 13 of the original 72 towers built in the 14th century to represent the wealthiest families in the region. Other great attractions to visit in San Gimignano include Museum of Sacred Art, Ornithological Museum, more than ten historic churches, The Ruins of Castelvecchio and the Natural Reserve of Castelvecchio. Guided tours of the town are also available.

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24.Val d'Orcia

Val d'Orcia
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Beautiful fields of sunflowers and rolling hills surround Val d’ Orcia. The territory is a protected UNESCO World Heritage Site and is crisscrossed by vineyards that produce the wines of Brunello. Pienza is known as the ideal city and features the world-famous Palazzo Piccolomini. Other great places to visit in Val d’ Orcia are the fortress at Castiglion d’ Orcia or Radicofani, a hilltop town with ancient towers, and Montalcino which is still surrounded by a medieval wall. Visitors interested in religious history or medieval architecture should check out the Abbey of Sant’ Antimo. There are also many thermal baths to relax at or museums to explore.

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25.Volterra

Volterra
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Volterra is close to both Siena and Florence in the province of Pisa. The origins of the town go back to Etruscan times and was one of the main towns of the Etruscan confederation during the end of the fourth century. Volterra is best known for its urban layout and the preserved 4th-century gates that lead into the city. Visitors can still walk parts of the 4th-century perimeter walls and visit the Acropolis where there are two ancient temples and several ancient buildings. Several other historic Roman buildings can also still be visited including the remnants of the Roman Theater, and places where the Twilight Movie was filmed.

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25 Best Best Best Weekend Getaways and Day Trips from Siena, Italy


  • Arezzo, Photo: e55evu/stock.adobe.com
  • Asciano, Photo: anghifoto/stock.adobe.com
  • Bologna, Photo: bbsferrari/stock.adobe.com
  • Buonconvento, Photo: LianeM/stock.adobe.com
  • Chianti, Photo: janoka82/stock.adobe.com
  • Colle di Val d'Elsa, Photo: TwilightArtPictures/stock.adobe.com
  • Cortona, Photo: marcociannarel/stock.adobe.com
  • Fiesole, Photo: sansa55/stock.adobe.com
  • Florence, Photo: JFL Photography/stock.adobe.com
  • Greve, Photo: stepmar/stock.adobe.com
  • Livorno, Photo: ArTo/stock.adobe.com
  • Lucca, Photo: stepmar/stock.adobe.com
  • Montalcino, Photo: stevanzz/stock.adobe.com
  • Montepulciano, Photo: Ekaterina Pokrovsky/stock.adobe.com
  • Monteriggioni, Photo: Zechal/stock.adobe.com
  • Monteroni d'Arbia, Photo: Maurizio Sartoretto/stock.adobe.com
  • Pienza, Photo: stevanzz/stock.adobe.com
  • Pisa, Photo: emperorcosar/stock.adobe.com
  • Pistoia, Photo: Alberto Masnovo/stock.adobe.com
  • Portovenere, Photo: wildman/stock.adobe.com
  • Prato, Photo: sansa55/stock.adobe.com
  • Rapolano Terme, Photo: Silvia Crisman/stock.adobe.com
  • San Gimignano, Photo: kmiragaya/stock.adobe.com
  • Val d'Orcia, Photo: christiane65/stock.adobe.com
  • Volterra, Photo: rolandbarat/stock.adobe.com
  • Cover Photo: Alberto Masnovo/stock.adobe.com