Top Siena Tours & Vacations 2025/2026 [reviews & photos]

Siena Tours & Travel Packages 2025/2026

26 Siena trips. Compare tour itineraries from 8 tour companies. 106 reviews. 4.7/5 avg rating.

Small Group Siena Tours

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Top Siena Attractions

Siena Tours & Travel Guide

Siena Attractions & Landmarks Guide

The beautiful city has a huge history and is home to various magnificent pieces of art and historical buildings. The place is also famous for its Palio horse race that happens twice a year and attracts hundreds of spectators from all around the world. The city has a huge range of stunning architecture, museums, and galleries.  Plan your trip properly to have a taste of every important point.

Where is Siena

This lovely medieval town is worth paying a visit even if you are short on time. Located in the central Italy region of Tuscany, 30 km south of Florence, this is city was once an important commercial and banking region till the 13th century.

Best time to visit Siena

The city of Siena has a temperate climate that makes the season comfortable round the year. Summertime is hot but is more popular among tourists. Winter is low season but brings the low temperature and lots of rain.

The best time to visit is during shoulder seasons when crowds are low and the weather is pleasant. You can roam about in the city freely and explore it comfortably. You might also find some discount as well because of low people.

Weather in Siena

Summer in Siena is hot with dazzling sun and high temperatures. Despite the hot weather, this is the most popular time among tourists so every important place is crowded with visitors from June to September. Most of the restaurants, hotels, shops, etc. are closed in August as they might have gone for vacations.

During late September, the crowds start to get thin and the temperature starts dropping a bit. This makes autumn an ideal time to visit Siena. The fascinating rolling hills with changing leaves present a beautiful scene. Many vineyards also start their harvesting at this time. However, October brings showers with it and the temperature tends to become a bit colder.

Wintertime, from November to March, is the low season and you will find many restaurants and hotels closed for a month or so. But on the other side, if you book for a winter tour you might get many discounts.

Spring brings with it back the glow of the city. If you plan your trip right and get there in the springtime, you can have the opportunity to visit the region in good weather, before the arrival of the summer tourist crowd. April to May has the most pleasant weather in the city. Explore the ancient ruins, garden, piazza, cathedrals or whatever you want.

Top Things to do in Siena

Though the city of Siena is not very large it still offers a huge variety of activities for tourists. Choose those you find attractive or try to do all of them to have the true feeling of the city's culture.

1. Roman Ruins

Siena tours are incomplete without roaming about in the ancient Roman ruins. The city's origin dates back to 1st century A.D. and you can see the historical evidence throughout the city.

2. Contrada Spotting

The city of Siena is divided among 17 districts or Contrada, each having its own history, mythology, stories, and symbols. You will witness these symbols on the side of the building and you will know which district you are in. Every Contrada conducts its festivals, birth, marriages, etc. within their area. Palio race competes against each other in a highly charged and colorful manner.

3. Learn to Cook an Italian Meal

When in Italy, food is a must part of every tour. The traditional recipes passed down through generations give you the experience and taste of a lifetime. Take a cooking class to learn Tuscan typical meals and get a closer feel of the local culture.

See Italy food tours »

4. Explore Ancient Battlements

The colorful past of the Siena is filled with the tales of various fought battles against Florence and further afield armies, including the English. All these battles have left this ancient city scarred and it has been rebuilt multiple times over the years. The different styles of different rulers are reflected in the cityscape. Stroll through them all to witness the battle history of the city.

5. Stroll Around the City Walls

Take a three-hour walk around the city along these periphery walls to witness the real city life away from the tourist crowd. The ancient walls were once built to keep the residents safe from enemy armies. You will encounter some medieval house, convent or garden along the way. Just pass them through some narrow street and get back to the ancient walkways.

6. Visit Medieval Bathing Fountain

Built in the 12th century this fountain was an important meeting point of city dwellers. The Fontebranda is located below the San Domenico church and the thousands of city dwellers used it as a bathroom. The fountain had three basins; for extracting water, for washing and animals. It was once an important point of the complex underground tunnel network and supplied water to the entire city.

7. Enoteca Italiana

Seated in the bastions of Medicean Fortress, the Enoteca Italianahas an excellent wine collection from all over Italy, with more than 1600 bottles. There is a restaurant, wine bar for tasting, wine selling, wine school and much more to offer constant fun activities. Go some late afternoon to their patio and enjoy with a fantastic wine bottle.

8. Explore the Museums

The ancient city is filled with its old culture and art exhibits. If you have a taste for art and history, visit several museums in the city and get an insight into the ancient history of the region. These museums are filled with various pieces of sculptures and paintings from pre-Renaissance, Gothic and Roan times.

9. Relax In The Piazza Del Campo

The stunning square of the city is filled with various medieval buildings lined with red bricks with a fishbone pattern. This is the center of the city where tourists and locals come to sit and relax on open-air tables and enjoy their coffee. Piazza Del Campo takes you back to the true imagery of the 13th century. And it's great for people watching!

10. Admire the Architecture

There are various buildings throughout the town with amazing architecture that will leave you awestruck like the Duomo. They are the witness of the greatness and talent of those who used to rule the city. These colorful and magnificently designed buildings have a unique aspect to all of them that you will not find anywhere else.

Popular Day Tours from Siena

Many fabulous towns are surrounding Siena. Usually, Siena tours include surrounding towns to explore most of the fascinating destinations of the region.

1. Pisa

The hometown of the Leaning Tower can be reached in 1 hour and 45 minutes from Siena through the train. Plan a day trip to explore the town and take a late afternoon train to come back.

2. Florence

Stuffed with historic buildings, museums, castles and artworks, this ancient city is the true Italian masterpiece. You can take a bus or train to go there from Siena.

3. Montalcino

The beautiful medieval town is located at the top of a hill that can only be reached by 114 buses. The quaint cobbled streets and old architecture of the place makes it worth visiting.

4. Colle di Val d’Elsa

You can reach the medieval hilltop city by bus in almost 30 hours from Siena. They have an ancient tradition of crystal glass making that has been passed down through generations and is a prized skill of the locals.

5. Rapolano Terme

Escape from the bustling city life and get refuge in this ancient Roman town, nestled in the countryside. Indulge in the relaxing hot baths and spa, just like the historical Romans.

6. Monteriggioni

Nestled in the Tuscan hills of the countryside near Siena, this walled city has preserved its medieval fortification significantly. The walls and castles helped to protect Siena in many wars.

7. San Gimignano

The illustrious history of the medieval town dates back to the 3rd century B.C. The city has well-preserved its medieval tower houses throughout the centuries and the city skyline is dominated by 14 of these ancient structures standing tall above the town.

8. Lucca

Explore the beautiful walled city and its modernized outlook. People planted trees atop the original defensive walls of the city and turned them into a park circling the city.

8. Assisi

The place is home to various cathedrals, Basilicas, and churches and has played a vital role in the history of Christianity in Europe and Italy. The most important is the Basilica of Saint Francis of Assisi, which is also an important pilgrimage site.

9. Livorno

The seaside city has one of the largest ports in Italy. The stunning coast contains all types of yachts, cruise liners, and ships throughout the day. Explore the coast and then eat in any of the restaurants along the shorefront.

Top 10 Attractions in Siena

Don’t get confused by the huge list of worth visiting places in town. Following is a list of the places without which Siena tours are incomplete.

1. Piazza del Campo

Located at the heart of the city, this shell-shaped square is regarded as one of the best medieval squares in Europe and consists of various stunning architecture pieces. This central square is always filled with people and most of the people start their tour from this place.

2. Cathedral of Santa Maria Assunta

This Gothic architecture tribute has a fascinating interior with striped polychrome marble arches and beautiful fresco above the altar, as well as the ornate golden dome. The beautiful exterior has a plethora of marble and white stone design with several sublime frescos. Since the 13th century, the cathedral has stood as an icon of the city and is one of the most significant Gothic architecture pieces of Italy.

3. Santa Maria Della Scala

The complex was formerly used as a hospital, one of the very first in Europe, dedicated to caring for abandoned children, sick and poor. The hospital was supported by the rich in the region. Now the building is filled with great artworks and is home to several museums of arts and archeology.

4. Palazzo Pubblico

This amazing medieval architecture was built in the 13th century and used as the house of the Republican Government of Siena. The interior design has stunning fresco and all major rooms are covered with gorgeous paintings and ornate decorations. The building has a Gothic exterior with a plethora of pretty arched windows and double tone stone cladding.

5. Siena National Gallery

Housed inside a former palace, this fascinating building dates back to the 15th century. The gallery is located in the south of Piazza del Campo, in the historic town. The gallery consists of various amazing art collections, mostly from Sienese Artists of the 12th to 16th centuries. Besides, it also has a cartoon series by Beccafumi. If you want to learn about the history of the old city's art and culture, this is the best place.

6. Un Tubo

Visit the famous bar to enjoy the vibrant aspect of the town. The cozy ambiance, live jazz music, and huge wine variety are what make this place famous. The dimly lit interior and welcoming atmosphere will make you feel at home. There are regular exhibitions of contemporary art in the bar. This is the best place in town to have a sophisticated evening with fine drink and exhibit of art, culture, and music.

7. Fortezza Medicea

The ancient fort was built by Duke Cosimo during the 16th and 17th centuries to prevent the Sienese uprisings of the citizens who were not happy with the rule. It has a large central walled area with four triangular defensive towers. The forte is surrounded by colorful gardens that are an ideal site for a walk. This forte often holds regular festivals and concerts so make sure to check out any event going on during your visit.

8. Santuario Di Santa Caterina

Build in the honor of St. Catherine of Siena, the complex was built on the original birthplace of the lady. The arcades and loggias of the church are decorated magnificently and also have some amazing architecture. At the church of Crucified are frescoes depicting St. Catherine's life.

9. Torre del Mangia

The tall tower is one of the best points in the city. The tower was constructed simultaneously with the palace and hence, have the same double tone design and white stone crown. When constructed in the 15th century, the tower was the second tallest in Italy. Go to the top and have a scenic view of the city. But beware, you will have to climb 400 steps to reach the top.

10. Duomo di Siena

The massive church dates back to the 13th century when the fathers of the church wanted to expand it to be large enough to be bigger than Rome's St. Peter's Basilica. But the plans got destroyed due to Black Death. The half-finished walls of the new cathedral are a constant reminder of the history. The Duomo is a magnificent example of Gothic architecture with ornately decorated arcade and striped columns, as well as the decoration of the floors and artworks.

Wine tours in/from Siena

One of the specialties of Italy is the amazing wine. People from all around the world come here to taste the local specialties. You can join some wine tasting day tour to enjoy with others. Some wine classes teach you the secret recipe to have a perfect Italian wine.

These day tours take you around to various amazing sites and to specific points to taste local wine specialties. You can choose the trip as per your convenience, depending on what places you want to visit and how long do you want your trip to be.

Museums in Siena

The many museums of the town present traces of the medieval history of the area. One can easily see the connection between culture and art throughout the Siena territory. Among the huge list, the following museums are a must-see if you really want to witness the region's historical culture.

1. Complesso Museale Santa Maria Della Scala

This magnificent complex started originally as an orphanage and hostel for pilgrims. After that, it started to be utilized as a hospital facility in the 10th century for the poor, sick, abandoned children and pilgrims.

2. Museo Civico

Located in the city center, this place is one of the major highlights of the city. There is a huge amount of artwork in the museum that is preserved on its walls covered in frescoes. Even if you are on a short trip, do include this place and have a bird-eye view of the city from the tower top.

3. Museo dell'Opera Metropolitana

The huge and precious collection of the museum comprises of masterpieces like Giovanni Pisano sculptures, Stained-Glass Rose Window and Maesta altarpiece of Duccio di Buoninsegna, and much more.

4. Pinacoteca Nazionale

The museum was inaugurated in 1932 and contains a remarkable collection of numerous Renaissance and medieval paintings from various Italian artists like Duccio, Lippo Memmi, Guido da Siena, Sano di Pietro, and many more.

5. Archivio di Stato

Comparatively less popular from other Siena wonders, this place is home to a fascinating collection of ledgers with fascinating covers painted by artisans centuries ago. Build in 1858, the place has preserved the documents from ancient magistrates of Siena's provincial offices.

Siena Reviews & Ratings

4.7/5  Excellent
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Anonymous

Oct 2018

Provided byExodus Travels

Great trip, difficulty rating a bit misleading

Our second trip with Exodus. A really good group of cyclists to ride and socialize with. Leaders Becs and David did a great job supporting us and handling both t...

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Anonymous

Oct 2018

Provided byExodus Travels

Glorious Countryside

We rode through glorious towns and countryside with plenty of opportunities to take photographs. I really enjoyed the company of the other riders. I am so glad I t...

A

Anonymous

Oct 2018

Provided byExodus Travels

Amazing adventure!

This was my first cycling tour and tour with Exodus. I had an amazing experience! The trip was well planned and I feel like it had the prefect balance of cycling, ...

A

Anonymous

Oct 2018

Provided byExodus Travels

Excellent hol

Great weather. Lovely group of people. Superb tour leaders (Bex and David). Food and wine was great. Ditto scenery. Really sorry to come home. If you are reasonabl...

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Anonymous

Oct 2018

Provided byExodus Travels

Lovely Hol

Second trip with Exodus. Lovely holiday cycling through Tuscany, finishing in Florence. Lots of clmb, but not too severe. Great weather, food & wine. Group we...

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