Siena
Culture & History

Enter your dates to find available activities

Our most recommended Siena Culture & History

From Florence: Tuscany Day Trip with Optional Lunch and Wine

1. From Florence: Tuscany Day Trip with Optional Lunch and Wine

Begin your journey of Tuscany at Florence’s central train station, where you will be greeted by your guide who will take care of you throughout the day.  Head straight to Siena, Italy’s most picturesque medieval city, whereupon arrival your guide will take you on a walking tour. Look up to admire the lovely terracotta roofs adorning the buildings and marvel at the magnificent Gothic and Romanesque architecture of the main cathedral.   Next, head to the hilltop town of San Gimignano, a UNESCO world heritage site, famous for the tower houses built in the Middle Ages. Enjoy free time here to see its splendid squares, palaces, churches, and magnificent towers. The last stop on your Tuscan excursion is a visit to Pisa and its iconic leaning tower. Take a stroll through the Piazza dei Miracoli and see other marvelous monuments, before driving back to Florence. Best of all, choose from either a small-group or private guided experience to make your trip special. Choose the lunch option to enjoy a homemade lunch paired with an informal wine tasting at a traditional wine estate in the Chianti wine region. Savor 4 regional wines at lunch and learn about their unique production techniques. Feast on an organic, farmhouse meal while you overlook the rolling vineyards under the Tuscan sun.

Siena: Siena Cathedral Complex Pass (OPA SI Pass)

2. Siena: Siena Cathedral Complex Pass (OPA SI Pass)

See notable features of the Duomo of Siena with the OPA SI fast-track entry pass. In addition to discovering the Cathedral of Siena, visit the Baptistery, the Crypt, the Piccolomini Library, and the adjacent Museo dell'Opera, Oratory, and Facciatone viewpoint with one convenient ticket. Enter the Duomo and be amazed by its grand scale as you stroll along its stunning mosaic marble floor. Admire sculptures such as The Feast of Herod by Donatello and St. Paul by Michaelangelo, amongst many artworks which are dotted around the cathedral. Visit the Baptistery of San Giovanni within the Duomo to marvel at the splendid Baptismal Font. From here, head down into the Crypt, the underground quarters that remained hidden for more than seven centuries. Then, stroll through the Piccolomini Library and gaze up at the vibrant and colorful frescoes which adorn its walls. Admire the stunning work by Pinturicchio, which depicts ten episodes from the life of Pope Pius II. Access the Museo dell'Opera which houses a selection of archaeological fragments and artwork once part of the cathedral. See a variety of Gothic sculptures by Giovanni Pisano and paintings by Ambrogio and Pietro Lorenzetti. Head into the Oratory of San Bernardino to admire the collection of the Diocesan Museum of Religious Art, with its core at the upper oratory chapel. Discover a variety of Siennese paintings from between the 13th to the 18th century. Finish up your visit to the complex with a climb up to the Facciatone viewpoint. Be enchanted by the unforgettable view over the city of Siena and the beautiful rolling hills of the Tuscan countryside.                                                                                                                                        

Siena: Siena Cathedral & Piccolomini Library Entrance Ticket

3. Siena: Siena Cathedral & Piccolomini Library Entrance Ticket

Benefit from fast-track entry to Siena Cathedral and admire the stunning artwork and architecture of its interior. Walk along its ornate marble mosaic floor and visit the Piccolomini Library known for its collection of vibrant frescoes. Skip the line and enter the Cathedral and admire one of the foremost masterpieces of renaissance art and architecture in Italy. Gaze at elaborate altarpieces, a sculpture by Michelangelo, and all manner of ornate decorations scattered throughout its vast interior. Enter the Piccolomini Library, which contains a sprawling series of 10 frescoes by Pinturicchio chronicling the life of Pope Pius II. Gaze upwards at the domed ceiling, masterfully adorned with complex patterns and further scenes from the pope’s life.

Siena: City Walking Tour with Optional Siena Cathedral Tour

4. Siena: City Walking Tour with Optional Siena Cathedral Tour

Explore Siena's rich history, culture, and traditions with a local guide. The tour is designed to show you Siena's most intriguing sites in a short period, with plenty of stops for photos along the way. Start the tour with a visit to some of the city’s most significant sites including the Piazza del Campo, Palazzo Publicco, Palazzo Tolomei, Palazzo Salimbeni, and the ancient Banchi di Sopra. Upon exploring, learn which buildings hold UNESCO World Heritage-listed status and why. Continue the tour to the Basilica of San Domenico, which is home to Saint Catherine's relics. Next, stop by the Sanctuary of St. Catherine of Siena, where she once lived with her family. Pass by the Baptistery and the Siena Cathedral (or the Duomo di Siena), and head inside for a closer look (if the optional guided tour option is booked). Inside, admire the array of works of art from some of Italy’s most important artists. 

Siena: Educational Wine Tour & Tasting

5. Siena: Educational Wine Tour & Tasting

The Educational Wine Tour & Tasting  “Vine, Wine and Life” starts with a visit to organic vineyards where you'll go through all the main steps of the agronomic, phenolic and organic cycle, in order to understand the complexity of the “vineyard” ecosystem and of an agriculture with low environmental impact. In the historical cellar, you'll discover the chemical-physical and microbiological processes that make a quality production. You will taste the wines in a sensorial tasting room to grasp the organoleptic complexity and have a better understanding of them. The visit will end up with a light-lunch to experience the emotions the right combination of food/wine can offer your palate and spirit. All the different chapters will be discussed directly in the vineyards, cellar and tasting room in a very simple way, in order to easily understand even the most apparently complicated concepts. 

Brunello di Montalcino Full-Day Wine Tour with Tastings

6. Brunello di Montalcino Full-Day Wine Tour with Tastings

Wine lovers will enjoy this full-day tour through the beautiful Tuscan landscape with stops to visit some typical local wineries. Explore the famous wine hills of Montalcino and learn about the process and passion involved in creating Brunello di Montalcino, one of Italy's most prestigious wines. Your tour begins with a drive along the ancient Roman road from Siena to the famous wine hills of Montalcino. The first stop will be at a small, typical area winery where you’ll have a chance to walk in the vineyards, explore the cellars, and enjoy an introductory tasting of world-famous Brunello wine. Next, you’ll head to Montalcino, the hill town that gives its name to the region and its wines. Here you’ll have the opportunity to climb the fortress walls, spend some time browsing the shops and tasting the Brunello wines in wine bars, or simply enjoy the incredible views of the valleys and vineyards below. After visiting the town of Montalcino the tour continues on to the stunning ancient mystical Benedictine Abbey of Sant Antimo, a special place in a tranquil setting. You’ll enjoy a traditional Tuscan lunch at a family-run winery, accompanied by the delicious wines produced at the facility. Afterwards, you’ll have the opportunity to visit the farm. In the afternoon you’ll visit a third winery where you’ll get a detailed description of the wine-making process, and learn how the vines are cared for and about the long aging process in oak barrels. After visiting the cellars and getting to know the winemakers, you’ll sit down for a final tasting of this nectar of the gods.

From Siena: Dinner in the Chianti Vineyards

7. From Siena: Dinner in the Chianti Vineyards

A unique experience designed to give you the best of what the Chianti region has to offer: the history, the landscapes, the wine, culinary traditions, and atmosphere. Other than enjoying a delicious typical dinner of local products and dishes, you will be surrounded by the splendid and charming landscape of vineyard rows, which beautifully characterizes the Chianti region. The dishes that you will taste, all made of fresh local products, are the fruit of the hard work and care for the land that local producers have been exercising for centuries.  Upon your arrival you will be given a glass for you to carry with you on the visit of the farm’s wineries and thus enjoy a number of wine tastings on this small-scaled wine route. You will then visit the estate’s historic chapel before finally heading for dinner, the evening’s main event.  The dinner location is set to offer you maximum quality and cosiness, decorated with candles and torches. The gentle sounds of the earth and the vineyards will accompany your dinner under the stars, and a harmonious musical background, which will perfectly match the succession of dishes. You will taste pappa al pomodoro or ribollita (both typical recipes from the people’s folklore) and a barbecue of meat and fresh seasonal vegetables of the farm. Let yourself get carried away by the warmth and fragrances of the barbecue and the perfumes of the grapevines, which will enhance your dinner experience. The rural yet elegant scenery of the estate will perfectly frame and complete your evening. After the dinner you’ll be escorted back to Siena where the tour will finish.

Florence: Gimignano, Siena, Chianti Tour, Lunch & Tasting

8. Florence: Gimignano, Siena, Chianti Tour, Lunch & Tasting

Discover Tuscany on a guided day tour from Florence to the medieval cities of Siena, San Gimignano, and Monteriggioni. Enjoy views of rolling hills and vineyards, with a stop at a Chianti winery for a traditional Tuscan lunch and wine tasting. First arrive in San Gimignano, a tiny medieval town that has remained intact through the centuries. Sitting upon a hilltop, it is famous for its numerous towers, frescoes, and other art treasures. Enjoy more free time to discover this fascinating city on your own. Next, visit the charming historical hamlet of Monteriggioni, a medieval village enclosed by its famous walls, which remained standing to this day. Afterward, you will cross the Chianti rolling hills and then arrive at a small and typical winery. There, taste 4 wines, and sample balsamic vinegar and other locally produced products. Your final stop is in Siena, where you will have free time to walk along the narrow medieval streets, admiring the splendid palaces, the Cathedral, Libreria Piccolomini, and the famous shell-shaped Piazza del Campo.

Siena: Small Group Pasta and Tiramisu Class

9. Siena: Small Group Pasta and Tiramisu Class

During this private lesson, you will learn how to prepare 2 pasta recipes and the tiramisu dessert from scratch. Your Cesarina will reveal the tricks of the trade of these iconic recipes. Have fun putting your cooking skills to the test and amaze your friends and family once home with an Italian meal! This experience is suitable for families with children of all ages.

Historic Siena: Guided Walking Tour

10. Historic Siena: Guided Walking Tour

See the highlights of Siena on a walking tour as your guide tells you about the development of the city over the centuries and you enjoy the spectacular scenery and monuments. As you visit Siena’s major attractions such as the central Piazza del Campo, the Palazzo Comunale, the Cathedral, and the majestic Basilica of San Domenico you’ll learn about each of these sights in depth from your guide. You’ll also hear about the noble families that were instrumental in the history of the city, including the Piccolomini, Tolomei, and Salimbeni, and see their palazzos. You’ll learn about the great tradition of the palio and hear stories of pilgrimage and saintliness that distinguish Siena. You can decide to finish the tour with a visit to Cathedral where numerous artistic treasures are preserved. Entrance to the Cathedral is available at an additional cost. You’ll see works by artists such as Pisano, Duccio di Buoninsegna, Donatello, Pinturicchio, and Gianlorenzo Bernini. During the summer you can also see the marvelous marble floor, which is a unique work in the history of art.

Frequently asked questions about Siena Culture & History

What are other things to do than Culture & History that are worth visiting in Siena?

Other Sightseeing Options in Siena

Want to discover all there is to do in Siena? Click here for a full list.

What people are saying about Siena

Overall rating

4.5 / 5

based on 4,972 reviews

This tour was the perfect way to see the Tuscan country side in one day! It’s a long day with a lot of walking but you see so many different things in a short time. Our tour guide was very helpful when needed but also let us do our own things. The winery was amazing and would have loved to spend more time there. If you are looking to get really deep into each city and spend a lot of time looking around this tour probably isn’t for you. We had about an hour to and hour and a half in each city and lunch at the winery was about an hour as well. Would recommend this to friends or family visiting!

Enrica was a great tour guide, lots of knowledge and so friendly. Wish we would have had a little less time in Siena and a little more time at the winery perhaps touring around the grounds, but this was the itinerary and no issues with the tour we went on! You still get to see tons in just one day. Overall enjoyable and would recommend.

Great 3 hour morning hike with personable and naturalist oriented guide. Lovely lovely scenery. We would have preferred a bit more background on the Via Francigena. Winery to end with was great - we bought the winery’s artisan cheese to go along with the bread and Chianti. Overall, an excellent experience and great value!

Excellent 1-day tour to get to know the main places in Tuscany. Our guide Cristina was an excellent hostess and everything was very well organized.

Erika was an amazing guide through these beautiful cities. We enjoyed our time and discovered Tuscany. 100% recommendable.