Siena
UNESCO Sites

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Our most recommended Siena UNESCO Sites

Siena: City Walking Tour with Optional Siena Cathedral Tour

1. 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. 

From Florence: Tuscany Day Trip with Optional Lunch and Wine

2. 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.

S. Gimignano, Siena, Chianti: Escorted Tour, Lunch & Tasting

3. S. Gimignano, Siena, Chianti: Escorted Tour, Lunch & 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, stop at the charming historical hamlet of Monteriggioni, an amazing small medieval village enclosed by its famous walls, which remained standing to this day. Enjoy some free time to visit this place. Afterwards, you will cross the gently Chianti rolling hills, arrive at a small and typical winery. Taste 4 fantastic wines, then sample balsamic vinegar and other locally produced zero food miles products, to end this memorable experience in the heart of Tuscany. 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.

From Siena: Brunello di Montalcino Wine Tour by Minivan

4. From Siena: Brunello di Montalcino Wine Tour by Minivan

Brunello, considered the best wine in the world, has its ancestral roots in the passion of the inhabitants of Montalcino and in the ancient winemaking tradition, handed down from one generation to the next. The town of Montalcino, with its Sangiovese grapes the wine is produced from, stands on a charming hill that lets you relish its natural wholesomeness. The town, its ancient fortress, and some of the best wineries in the world are the focus of this specialized tour. The winemaking process which includes a long maturation in casks made from valuable wood, make Brunello the “Italian ambassador in the world of our winemaking reality.” Taste prestigious wines from some of the finest wineries in Montalcino and enjoy the wonderful surrounding area.

From Siena: San Gimignano, Montalcino & Wine Tasting

5. From Siena: San Gimignano, Montalcino & Wine Tasting

The first part of your full-day tour begins with a visit to the walled medieval town of San Gimignano, the City of Fine Towers, a UNESCO World Natural and Cultural Heritage Site. Armed with helpful information from your tour escort you’ll have free time to explore the town’s historical center and browse its artisan shops. San Gimignano is also the birthplace of Vernaccia, a white wine produced exclusively in the area. The wine is noted for its high quality and for being the first Italian DOCG wine. The tour continues on to Monteriggioni, the ancient crown-shaped fortress that appeared on Italy’s old 100-Lire currency. The 13th-century walls feature 14 towers that Dante likened to the giants in his Inferno. Afterwards, you’ll stop at a winery for a lunch of salami, cheese, and other local products, accompanied by a tasting of Chianti wines. Visit Val d’Orcia, another Tuscan jewel and a UNESCO World Heritage Site. Continue on to Montalcino, perched on a hill overlooking 1,500 hectares of Brunello vineyards that have contributed to the area’s international reputation. The final stop of the day will be a local wine cellar, where you’ll have a chance to taste the renowned Brunello of Montalcino, rated among the finest Italian DOCG wines. Sample other typical local products as well.

From Siena: Val D'Orcia Wine Tour

6. From Siena: Val D'Orcia Wine Tour

Enjoy a day of culture, wine, and food as you visit some of the most impressive towns and villages in Tuscany. Go to the picturesque town of Pienza, and taste world-famous wines produced in Montalcino and Montepulciano. Meet your guide in Siena and join the rest of the group to start your full-day tour. Depart Siena and transfer to a wine cellar in Montalcino. Cross gently rolling hills full of vineyards, and then sample local wines served with a delicious snack of the local produce. Continue to Pienza to discover the “Touchstone of Renaissance Urbanism.” Considered an artistic jewel of the landscape of Val d’Orcia, Pienza is a perfect combination of architectural beauty and harmony. Most of the lanes bearing impressive names overlook the breathtaking landscape of the Val d’Orcia. Unique smells and flavors are entwined with this natural and artistic heritage. Pienza’s most renowned tradition is pecorino cheese. End the tour at Montepulciano, where the stateliness of its Renaissance buildings and the refined beauty of the town's churches mix with the ancient tradition of wine making. Enjoy some free time before your return transfer to Siena by bus.

Historic Siena: Guided Walking Tour

7. 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.

Florence: Siena, San Gimignano, Chianti, & Pisa with Lunch

8. Florence: Siena, San Gimignano, Chianti, & Pisa with Lunch

Get lost in the beauty of Tuscany with this tour from Florence to Siena, San Gimignano, Chianti, and Pisa. Have some free time to explore San Gimignano, Siena, and Pisa at your own pace.  Meet an assistant that will help you board the comfortable coach. Relax and enjoy the countryside on the drive, or make use of the free onboard Wi-Fi. Drive through Chianti vineyards on the way to Siena. Wander through the pedestrian-friendly heart of this historic hilltop town. Stroll through the medieval brick buildings of Siena with free time to see its central square Piazza del Campo, its Gothic town hall, or its 14th-century Torre del Mangia tower. Continue through the countryside and stop at a wine estate surrounded by lush rolling hills.  Sit down for a traditional Tuscan lunch which is served with a selection of delectable regional wines. Depart for the medieval UNESCO World Heritage town of San Gimignano. Walk through its cobblestone streets and small squares to uncover charming craftsmen’s shops. Pass by hilltop hamlets and churches on the way to Pisa. Admire the Field of Miracles, a green grass area dominated by the dazzling white buildings of the Cathedral. Snap an iconic picture at the Leaning Tower. View an exquisite example of Pisan Romanesque architecture at the Baptistery. return to your meeting point in Florence.

Florence: Siena, Pisa, and San Gimignano Day Trip with Wine

9. Florence: Siena, Pisa, and San Gimignano Day Trip with Wine

Boarding your air-conditioned coach in Florence, you will meet your tour leader who will stay with your group for the duration of your day trip. As you journey through the rolling hills, vineyards and olive groves of the Chianti region, they will tell you what to look out for in each new town. Your first stop will be the medieval town of Siena, where the Palio horse race has been held twice a year since the 17th century. When you arrive in Siena you will have free time to explore the red-bricked city and admire the magnificent Duomo di Siena which stands out with its white and greenish-black marble facade. Back aboard your coach, you will spot the iconic tower houses of San Gimignano on the skyline from miles away. This Medieval walled town will be yours to explore, as you wander back in time along the narrow streets, being able to ask your tour leader where to find the best gelato. After enough free time to explore and take pictures, rejoin the group for your complimentary glass of Chianti wine and some nibbles. The coach will then return you to Florence. Hop back on your coach and enjoy a transfer to Pisa. Here you will have free time at the Piazza Dei Miracoli (Square of Miracles) to take pictures in front of the infamous Leaning Tower of Pisa. You will also have time to explore the lesser-known Duomo, a UNESCO World Heritage Site and Baptistery, before your driver returns you to Florence

Chianti and Castles Tour From San Gimignano

10. Chianti and Castles Tour From San Gimignano

Experience the region of Chianti and immerse yourself in picturesque Tuscan scenery on this guided, multi-stop trip from San Gimignano. Visit ancient churches, medieval castles, and small villages where the rhythms of traditional life remain unaltered. Stop at 2 wineries for tours and tastings. Explore the home of one of the most famous wines in the world, with its beautiful ruby-red color and characteristic violet-scented bouquet: Chianti. This wine results from a blend of Sangiovese, Canaiolo, Merlot, and Cabernet Sauvignon grapes. Get picked up directly from your accommodation in San Gimignano, then set out to discover the breathtaking landscapes that have cradled the Chianti vineyards for centuries, presenting you with a harmony of colors that can only be found in this region. After some sightseeing, the tour continues with a visit to a charming wine estate. Here, you'll have the chance to see the area close to the famous Castle of Brolio and you'll take part in a guided tour of the castle gardens. When the tour of the garden ends, enjoy a tasting of two different wines. During this tour, you'll see the characteristic Castle of Brolio from the outside as well as the inner garden of the castle. Later, move on to another winery in the middle of the Chianti Classico area, where you'll savor a second wine tasting paired with extra virgin olive oil. The tour ends with drop-off back in San Gimignano.

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What people are saying about Siena

Overall rating

4.5 / 5

based on 3,945 reviews

Experience highly recommended! Especially if you don't have a lot of time but want to discover part of Tuscany and its history through the main cities beyond Florence. The day was very pleasant and well organized; small groups well followed also in terms of languages, thanks to our fantastic guide, Luca, who satisfied all our curiosities as well as his excellent illustrations and explanations. Luca was very kind throughout the day, but above all his love for history, art and the Tuscany that he manages to convey have captivated us and made the experience even more special ...

Stefano was awesome and so was Nando. One of the most personable tour guides we’ve had in the 3 months we’ve been backpacking all over Europe and of the many tours we’ve done, he was funny and was interesting to listen to! I would recommend this tour for anyone that wants to see Tuscany! The lunch was amazing and definitely worth it! The vineyard was beautiful.

I highly recommend the tour for people, which want to see some highlights of Toscany. As I’m not eating mean I was even surprised to have some nice pasta and other dishes which made my stomach happy and Alexandro, he was a guide with a passion, always there when you have some questions

Our guide Ale from Walkabout Florence was amazing! Spent the time to talk to each of us, and was more than happy to answer questions and give us suggestions about the places we went to!

It was a long day but wonderful. So many interesting places to see. The meal at the winery was well worth the extra cost.