Siena
Small group

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Our most recommended Siena Small group

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

1. 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.

From Siena: Pienza and Montepulciano Small-Group Tour

2. From Siena: Pienza and Montepulciano Small-Group Tour

Travel along one of the most panoramic roads in Tuscany, driving the characteristic moonscape of the Crete Senesi en route to the medieval hamlet of Pienza in the Val D’Orcia valley. One of the first towns to be entirely planned on paper by important architects and artists of the time, Pienza was commissioned by Pope Pius II - the humanist pope - to help him renovate his native town and bring it to new splendor. A wholesome lunch, based on fresh local ingredients will be waiting on a beautiful terrace (weather permitting) at a local dairy farm. Learn about the process of making Italy’s famous pecorino cheese. Continue in the afternoon to Montepulciano, one of Tuscany’s largest hill towns. Under the dominance of Siena in the Middle Ages, and Florence during the Renaissance, today it is renowned for its wine. See influences from both towns in the architecture and art of the historic center, located on a steep hill with beautiful views of the Tuscan and Umbrian border. Go to the main Piazza Grande, and tour one of the many wineries, carved out of the earth below the city. Discover some of the palaces of the noble families that once lived here. After a short walk around town with a guide, enjoy some free time to taste the fabled wines, or continue to explore the palaces, churches and streets on your own. As you follow the route of the main road downhill, imagine how hard the “Bravio delle Botti” festival must be; a competition to race wine barrels from the bottom to the top of the hill!

From Siena: Chianti Farm Cooking Class

3. From Siena: Chianti Farm Cooking Class

Add another dimension to your Siena visit and participate in a 4-hour cooking class conducted in the typical Tuscan style. Discover the secrets of preparing regional dishes from a multi-lingual chef in a professional cooking environment. You’ll learn the techniques of Tuscan cooking, the basic ingredients used in traditional dishes, and the magical way in which local cooks create their delicious meals. From bruschetta to homemade pici to a variety of types of crostini, your class will enable you to bring a bit of Tuscany to your dinner table at home. You’re sure to fall in love with Tuscany through its food!

From San Gimignano: Chianti by E-Bike with Wine Tasting

4. From San Gimignano: Chianti by E-Bike with Wine Tasting

There is no better way than by bicycle to discover the beauty and richness of this part of Italy, sharing in the passion for cycling, art, food and wine. The tour takes place in Tuscany, more specifically, in the magnificent landscapes surrounding Siena. There are, in fact, the most beautiful areas and also the most suitable for a cycling trip through Tuscany. From the seat of your electric bike, you will discover how Tuscany life flow slowly yet incessantly, creating a natural equilibrium among art, culture, and nature. Tuscany is paradise for a cycling tourist, who will be greeted by gently rolling hills embellished with winding dirt roads, curving pathways, vineyards, and shaded country roads. All of these splendors are framed by a surprisingly varied landscape where you will be able to discover abbeys, rural churches and castles. The landscape is characterized by the deep red earth, and alternates between fields of sunflowers and vineyards, and is punctuated by ancient castles and medieval hamlets. Many panoramic views allow you to see all the way to San Gimignano, overlooking forests of beautiful Italian oak and corbezzoli. The tour is crowned with a visit to the splendid medieval for tress of Monteriggioni. 

Siena: Guided Nighttime Walking Tour

5. 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.

From Siena: Small Group E-Bike Tour with Winery Lunch

6. From Siena: Small Group E-Bike Tour with Winery Lunch

Enjoy the first sights of the Chianti hills. At the starting point and before heading off on your biking route, familiarize yourself with the bike and equipment and make the necessary adjustments to fulfil your heart's desire! Then experience a closer feel for the region through a leisurely, small-group bike tour on sophisticated and easy-to-use e-bikes.  Tuscany with its historic Eroica race has rendered itself as one of the world's most famous cycling areas. E-bikes now make this area accessible to all, even those with very little biking experience. Set and modify the level of difficulty at any time, whether uphill or down the valley and give the Chianti biking experience a new flavor. The silent electric motor allows you to take in the sounds and smells that the people driving through the area inevitably miss. Enjoy the tranquility of this beautiful countryside through a route of quiet roads away from the main traffic. Enjoy an easy-paced, 20km (12mile) ride of approximately 3 hours that will allow you to explore the neat rows of vineyards, pretty olive groves, dense and shaded forests.  As well as the quaint and picturesque villages for which the Chianti has become known. Be surprised by the occasional modern art installations among the vegetation, adding a touch of quirky modernity to an otherwise traditional landscape that has otherwise remained unchanged. Take some unforgettable pictures throughout the morning, during the frequent stops to take in the sights and views, breathe in the fresh, countryside air. Explore a beautifully restored Monastery dating back to the 15 century, including its neat Renaissance gardens and silent cloisters. Admire the stunning chapel fresco, known as the "Little Sistine". Having replenished your senses, jump on your bikes for one last, short ride to the family-run winery that will welcome you to learn about the long-standing art of making wine, from the vineyards to the cellars. Then sit down to a delicious tasting of the winery's wine and olive oil, accompanied a full lunch including platters of tasty local products. 

Florence: Pisa, Siena and San Gimignano Small Group Day Trip

7. Florence: Pisa, Siena and San Gimignano Small Group Day Trip

Visit three of the most famous and fascinating towns in Tuscany. Enjoy the comfort of a small group tour and learn from your expert English-speaking tour leader. First, discover the nearby town of Siena. Its historical center is considered a UNESCO World Heritage Site. Marvel at Piazza del Campo and the majestic Siena Cathedral. After a short drive through the enchanting countryside, stop in a small, family-owned winery. Enjoy an exquisite lunch of Tuscan appetizers, pasta, and desserts paired with local wines. Next, explore San Gimignano, also known as the town of towers. Discover the fourteen medieval skyscrapers which still remain perfectly preserved. Enjoy the last stop of the day in Pisa. Visit the Square of Miracles, where you can find the iconic Leaning Tower. Spend some time snapping pictures of the famous Italian symbol. After your full-day visiting three of Tuscany’s highlights, return to Florence.

From Florence: Siena, Cortona, Montepulciano & Val D'Orcia

8. From Florence: Siena, Cortona, Montepulciano & Val D'Orcia

Meet your local tour leader and the rest of your group of like-minded young travelers for a full day to discover the unbeatable paths of Tuscany made famous by movies. From Florence, travel for 1.5 hours by private 8-seat mini-van through the beautiful Tuscan countryside enjoyed by generations on the movie screen. Learn about the Italian way of life, the local customs, cuisines, and quirks from your guide before reaching the first stop of the day, Siena. Admire this medieval town that set the backdrop of the famous movies Letters to Juliet and Stealing Beauty. Be amazed by the charming narrow streets with local artisans, red-brick squares, and gothic cathedral. Then, continue the trip towards your next destination, the famous Montepulciano, where vampires converge in the Twilight Saga's New Moon. The beautiful walled town is also the home of the Montepulciano DOCG wine, making it the perfect opportunity for a tasting of vino and other local products at a 14th-century underground cellar. Have the chance to purchase products for the perfect gift or to ship home. Here, savor a wine tasting with a light lunch made with local products. Throughout the tour, your guide will provide you with local insight and information about the specific scenes and other films set in each place, as well as free time to explore the other attractions that the towns have to offer at your leisure. After lunch, head to Cortona, the luscious hilltop town known for its olive groves and made famous by Diane Lane in Under the Tuscan Sun. Spend some free time in Cortona to explore the narrow streets, artisan stores, and other landmarks which are seen in the cinematic adaption of Frances Mayes' novel. Who knows, maybe your own Italian love story will unfold! Finally, head back to Florence for approximately 8 PM.

From Rome: Siena, Chianti, Wine Tasting and Lunch

9. From Rome: Siena, Chianti, Wine Tasting and Lunch

This tour has been designed to showcase the very best of Tuscany in just one-day and is perfect for travelers who only have a short amount of time. The day begins with departure from Rome at 6:45am on a fast speed train to Florence. Upon arrival in Florence, head to the meeting point sent to your email to meet your guide and set out on your sightseeing adventure. The first stop of the day is the historic city of Siena, which is bursting with rich architectural styles, best showcased at the cathedral and the old palace. After a brief guided walking tour of Siena, enjoy free time to explore on your own. Wander around the quaint streets of this magical town, have a traditional Italian lunch at one of the many cafés, or shop for handmade crafts and souvenirs. Continue the tour to the walled town of Monteriggioni next, which was the filming location of the blockbuster movie, Gladiator. Arrive at the UNESCO World Heritage Listed San Gimignano next, which is the most famous walled medieval town in Tuscany, and nicknamed the ‘Manhattan of Tuscany’ due to its many towers. Armed with tips and recommendations from your guide, head out on your own adventure in the town and visit the sights and attractions that interest you most. Don’t forget to stop by the store of the world-champion gelato maker, and treat yourself to a seriously sweet treat. During the day, ride through the rolling countryside of Chianti and soak up the charming scenic views on the way to an authentic Tuscan winery. Against the backdrop of luscious vineyards and olive groves, enjoy a spectacular lunch with a wine and olive oil tasting session. At the end of a truly unforgettable day, head back to Rome, arriving at approximately 8 PM.

Florence: Chianti Winery Day-Trip with Lunch

10. Florence: Chianti Winery Day-Trip with Lunch

Starting in the center of Florence, your English-speaking driver will take you on a scenic drive straight into the heart of Chianti. You will drive along the ancient Roman road “Cassia Vetus”, surrounded by rolling hills with breathtaking views over vineyards and olive groves. Your first stop will be the Medieval village of Greve, which is the birthplace of Giovanni da Verrazzano, the Florentine traveler who discovered the Hudson Bay in the 15th century. Next you will visit the superb hilltop hamlet named Montefioralle. Strolling through the narrow streets, you might be surprised to discover that this stone village has been perfectly preserved since the 12th century. You can admire breathtaking panoramas and discover anecdotes and secrets related to the “Black Rooster”, the emblem of the Chianti Classico. You will experience a genuine, family run, wine estate with medieval cellars where prestigious original oak barrels are still used for aging the wine. Learn the secrets behind the making of the regions’ extra-virgin olive oil, and find out the best way to recognize a genuine one. Your experience will end in the proper Chianti way, with a typical Tuscan meal that you will get to enjoy on the private estate. It will be prepared with organic ingredients that are grown on the property, and to top things off you’ll get to enjoy a pairing of 3 top Chianti Classico wines and taste an extra-virgin olive oil.

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What people are saying about Siena

We had a lovely time learning how to make spinach ricotta ravioli with bruschetta and tiramisu for dessert. We even had fresh herbs we helped pick from the garden. The farm where the class was held was beautiful and picturesque. I highly recommend this cooking class, our guide was wonderful and we had an amazing time.

Wonderful local tour guide (Alessandro) he was great and explained everything and answered any questions we may have. The wine tasting and lunch was perfection. Vineyard guide was extremely nice, very helpful, and explained in detail the process of how they made their wines. It is a 3-course meal.

We loved this tour!!! So much to see and learn from this experience, and great wine! Great excursion to do to get off the main cities and really see some of Italy’s countryside

Simone was so very knowledgeable, patient and fun!! We LOVED the class and learned how to make pasta and several other dishes! So so fun. Highly recommend!!

Very nice trip to Tuscany. Alex does it very well.