Siena
Sightseeing Walking Tours

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Our most recommended Siena Sightseeing Walking Tours

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. 

Historic Siena: Guided Walking Tour

2. 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.

Total Immersion Wine Tour in Chianti

3. Total Immersion Wine Tour in Chianti

All the guests will be welcomed at the estate and brought to the roof of the cellar to see the most breathtaking views of the rolling hills at 600 meters above sea level. Here one of the passionate members of the team will provide an introduction to a history of the estate and a small general explanation of what guests will see and what they will be doing in the next one and a half hours of their time. Clients will be able to visit one of the vineyards followed by an explanation of the working process and of organic agriculture with some additional biodynamic techniqes that are often used and practised at the estate. If the weather permits, guests would be offered a glass of sparkling wine or a fresh wine of their choice at the small adjecent terrace built under an oak tree.  The tour will then take everyone to a visit through the gardens of the villa and include a visit of the vegetable garden. The cellar is the next stop, where detailed explanation follows about the harvest and selection of the grapes during the harvest, fermantation, and further aging of the wines. Each step of the viniticulture process is explained in great detail and guests would learn a lot of new and exciting things about how to make wines in the Chianti Classico area. The last stop is a tasting room, where guests will be able to try all 5 products of the estate with the selection of various local cured meats and/or cheeses with bread and olive oil. Guests will also learn particular details about the history of each wine, will learn how to smell and taste it, and what to look for when opening a new bottle of wine. The last exciting detail is the grappa, for those who would like to learn about its production and unique and delicate taste.

Siena: 2-Hour Food and Wine Tour

4. Siena: 2-Hour Food and Wine Tour

Walk around Siena and discover its best foods while meeting local vendors. Learn about the region's wine production and taste a typical white and red wine. Taste extra virgin olive oil and sample different Pecorino sheep cheeses, from fresh to seasonal, together with different local kinds of honey. As you tour the town, hear fascinating details about the rare Cinta Senese, an almost extinct pig that is unique to Siena. Then, you will learn how local truffles are found. Follow your guide and discover why the Tuscan bread is plain and how it is used in recipes. Hear the history of the recipe behind Siena's medieval cakes and bread. During the tour will taste local cold cuts and other typical Sienese products

Best of Italy: 5-Day Escorted Tour from Rome

5. Best of Italy: 5-Day Escorted Tour from Rome

Over the course of five days, visit the most enchanting locations of Italy, soaking up art, culture, cuisine and the famous Italian romance. Led by a friendly guide, depart from Rome and visit Assisi, Siena, Florence, Pisa, Bologna, Padova, Venice and Montepulciano. See masterpieces from the likes of Michelangelo, Giotto, and Cimabue. Roam ancient cobbled streets, marvel at magnificent cathedrals, and taste delightful wines. This tour aims to inform and entertain you at the same time. Staying in comfy accommodation and traveling by deluxe bus, touring Italy couldn’t be easier. With 4 meals provided for you, plus an excellent itinerary and knowledgeable guides, sit back, relax and "get Italian". Day 1 Depart from Rome at 7:15 AM heading towards Assisi. Explore this tiny town dating back to the Middle Ages. Visit the Basilica of St. Francis and see works by Giotto and Cimabue. Afterwards drive towards Siena, whose highlight is Piazza del Campo. Continue to Florence where you will check in at your hotel before enjoying dinner (included) and a well-deserved night of rest. Day 2: Florence After breakfast, spend the day exploring Florence, the cradle of the Renaissance. Visit the Duomo, the Campanile Tower, Palazzo Vecchio and the Basilica of Santa Croce. Lunch (for free) in a typical Tuscan restaurant in Piazza Santa Croce. In the afternoon, wander the cobbled streets or take a short, optional trip to Pisa where you could enjoy a tour of the Square of Miracles, the Leaning Tower and the Duomo. Dinner is at your leisure. Back in Florence rest in your hotel and recharge your batteries for the next day. Day 3 Depart for Bologna after breakfast in Florence. Wander through the city’s 38 kilometers' worth of elegant arcades, for which it is famous. From Piazza Malpighi, walk to Piazza del Nettuno and Piazza Maggiore in the heart of the city. In the afternoon, continue towards Padova, with its original Sant’Antonio Basilica. Later, you will arrive in Venice, famous for its quaint gondola boats and intricate architecture. Check in at your hotel and enjoy your first Venetian dinner (included) and overnight stay. Day 4: Venice Hit the water and board a private waterbus to enjoy a cruise through the canals of Venice. Stop off at Murano to learn about the ancient art of glass blowing. Continue on to St. Mark’s Square for an exterior visit of the splendid cathedral. See the Doge Palace and the Bridge of Sighs. Enjoy a spritz or Prosecco with your guide to cap off a day of discovery. Spend the afternoon roaming along Venice’s canals at your leisure and then return to the hotel and overnight. Day 5 After breakfast, departure from Piazzale Roma heading to Tuscany, world-known for its landscapes, its churches, castles and its delicious wines. Proceed to Val di Chiana with a stop in Montepulciano, a medieval town rich in history and art. Known for its “Noble” wine, on purchase in local wine houses, Montepulciano also hosts an annual jazz and wine festival every July. Lunch in a typical restaurant included! Spend the afternoon discovering Montepulciano at your own pace, enjoying free wine tastings in many wine shops and free time for shopping. In the evening, you will arrive in Rome, where the tour ends.

Siena: Guided City Tour with Cathedral Skip-the-Line Entry

6. Siena: Guided City Tour with Cathedral Skip-the-Line Entry

Join a small group or private walking tour to discover Siena’s famous monuments and hidden treasures with an expert guide. Enjoy skip-the-line entry to Siena Cathedral and explore tucked-away squares and gardens. Meet your guide at the San Domenico Basilica. First, follow a winding route to take in panoramic views of the city, including the Duomo and Torre del Mangia. Continue your tour with the 14th-century seashell-shaped square, Piazza del Compo, a UNESCO World Heritage site. Then, learn the history of the "contrade" (districts) that challenge each other twice a year during Siena’s Palio horse race. Walk to one of the most typical "contrada" and immerse yourself in the authentic atmosphere. Find out about Siena in the Middle Ages and the local pastry that reflects these glory days. Make sure to ask your guide where to find the best local bakery that still uses centuries-old recipes to make traditional Ricciarelli and Panforte. Next, admire the magnificent Fonte Gaia fountain with its side reliefs of "The Creation of Adam" and "The Flight from the Garden of Eden." Finally, skip the line at Siena Cathedral. Follow your guide to marvel at the magnificent marble mosaic inlay floor, stained glass, and medieval masterpieces by Duccio and Pisano. See the Renaissance highlights: several Donatello, Michelangelo, and Bernini sculptures and frescoes by Pinturicchio in the Libreria Piccolomini. Armed with a wealth of knowledge about Siena, you will say goodbye to your guide in the square in front of the cathedral.

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

7. 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

Siena: Half-day Guided Hike to Monteriggioni

8. Siena: Half-day Guided Hike to Monteriggioni

Give your mind a rest from the noise of the crowded towns, follow your expert guide on a pleasant walk along the Via Francigena, an ancient pilgrim route for the first time plotted down by the Arcbishop ‘Sigeric the serious’ of Cantebury on his return from Rome in the 9th century and considered the main artery to Rome throughout the middle ages. This route, that has for centuries been a highway of men and emotions, a spiritual pilgrimage and a wealthy trade route, has been forgotten and almost entirely relegated to history by the modern paved car roads. Only recently the route has been brought back from the grip of modernity and is today enjoyed by many pilgrims and hikers alike. Experience the beauty of the mixture between the Tuscan countryside and the glory of its medieval past, still present in it's wonderfully preserved castles, villages and ruins.  See the Tuscany you would never want to miss before returning home, pass through forests and fields, vineyards and olive groves from Siena to the imposing fortress of Monteriggioni. A medieval walled town located on a natural hillock, built by the Sienese in the thirteenth century as a bastion of defense in their wars against Florence.  Once in Monteriggioni, enjoy a guided tasting of local organic wines before saying goodbye to your guide for the end of the tour. Feel free to explore the village and the surrounding area at your own pace. You will be given a bus ticket to return to Siena.

Siena: Guided Nighttime Walking Tour

9. Siena: Guided Nighttime Walking Tour

Meet your guide after dusk, then set off on a 2 hour adventure through Siena. Walk through the city’s bustling streets and see a selection of famous landmarks including Piazza del Campo, Siena Cathedral, and the Torre del Mangia. Along the way, listen to your guide’s fascinating tales of the city’s history and culture as well as the noble families and prominent historical figures who still haunt the streets.  You’ll also discover some of the city’s hidden gems, and visit locations only the locals know about. By the end of the tour, you’ll have seen Siena from an entirely new perspective.

Siena Highlights Self-Guided Scavenger Hunt and City Tour

10. Siena Highlights Self-Guided Scavenger Hunt and City Tour

Explore the top sights in Siena with an interactive smartphone tour. Stroll through the city solving location-based riddles on this walking tour. See the rose window and elaborate façade of Siena Cathedral and view the facinating architecture in Piazza del Duomo. Solve puzzles outside of ten Siena attractions. Follow clues at each attraction to find your next destination. Enjoy the challenge of using logic, imagination, observation, and team spirit to complete the game. Feel the satisfaction of solving each riddle. Have the freedom to pause or resume the tour whenever you want. Admire the city at your own pace. Uncover interesting information and facts about the city. Snap as many pictures as you want. You can start the activity any time, the schedule is indicative. You will visit: Duomo di Siena - starting point Baptistery of St John Palazzo Piccolomini Loggia del Papa Tower of Mangia Pubblico Palace Pinacoteca Nazionale di Siena Santa Maria della Scala Facciatone Piazza del Campo - ending point and more

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What people are saying about Siena

Overall rating

4.2 / 5

based on 1,994 reviews

Our family of 5 had a great day touring Siena, San Gimignano and Pisa. Antonio has been made the day trip delightful for us, explaining the history of the places in small bites in the coach, but not overloading us with information. At the last stop, I tripped and fell. Antonio was very kind to get bandages from the pharmacy for me. Thank you again. It was a great day trip for us.

Stephen and Francesco were absolutely wonderful. This was a very immersive and intimate tour on a secluded winery. There was a lot of knowledge shared and many wines tasted. I would highly recommend this tour to anybody wanting to get the best winery tour experience.

Idania was our guide. She was amazing, engaged our kids (12 and 10yo), very entertaining. We really had a great time. Your was on time.

So informative! The depth of understand the culture and city was incredible. 10/10

Great local guide who really likes her city and is full of useful information