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Siena CathedralWine tasting & winery tours

Our most recommended Siena Cathedral Wine tasting & winery tours

From Florence: Day Trip Pisa, Siena & San Gimignano w/Lunch

1. From Florence: Day Trip Pisa, Siena & San Gimignano w/Lunch

Experience the wonders of Tuscany on one memorable day. Leave Florence for a 12-hour excursion and see the beautiful landscapes, architecture, and artworks of the region. Treat yourself to some local cuisine, and choose a guided tour in your language to learn even more about the historic area. Begin with Pisa and visit its stunning Piazza dei Miracoli. Admire the Baptistery, the Cathedral of Santa Maria Assunta, and, of course, the famous Leaning Tower of Pisa. After your free time in Pisa, head to a typical Tuscan winery in the Chianti Area and enjoy a delicious lunch with some local wine. Explore the city of Siena and visit to Piazza del Campo, where the Palio di Siena horse race is run, and Piazza del Duomo, where you will see the exterior of the magnificent cathedral. Enjoy your last stop in San Gimignano, a UNESCO medieval town, world-known for its Vernaccia di San Gimignano. The system of towers of San Gimignano tells the glories of the powerful families. Between saffron fields and typical indigenous vineyards, the city knows how to offer postcard views.

From Florence: Tuscany Day Trip with Lunch at Chianti winery

2. From Florence: Tuscany Day Trip with Lunch at Chianti winery

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.

Tuscany: Siena, San Gimignano, Chianti, and Pisa Day Tour

3. Tuscany: Siena, San Gimignano, Chianti, and Pisa Day Tour

Spend the day discovering many of the main highlights of the Tuscan countryside on this guided tour with a traditional Italian lunch included. Make your way through the rolling hills as you discover the charm of Pisa, San Gimignano, and Siena. Your first stop will be Pisa and the Square of Miracles. See the cathedral, baptistery, and, of course, the famous Leaning Tower. The Leaning Tower is almost 56 meters tall, about 183 feet, and leans at about 4 degrees, making it one of the most famous and iconic buildings in the world.  From Pisa, drive past hilltop hamlets scattered across some of the most beautiful and enchanting areas of the countryside. Arrive at San Gimignano where a traditional Tuscan lunch with wine tasting will be served, if the option is selected. Continue to the preserved medieval village of San Gimignano, a UNESCO World Heritage site often nicknamed the “Manhattan of the Middle Ages” because of its famous tall, narrow towers. Explore the town center and the charming craftsmen shops along the cobbled stone streets and small squares. End the tour in Siena, a hilltop town rich in art and traditions. Stroll the pedestrian historical center and visit the beautiful local cathedral. Take a guided walking tour along the small medieval streets and squares, passing the oldest bank in the world, and the Piazza del Campo. Sample Lunch Menu - Appetizer: cold cuts ( prosciutto, finocchiona, salami ) bruschetta olive oil and truffle oil pecorino cheese with balsamic vinegar and green salad - Main Course: penne with meat ragout and parmesan cheese - Dessert: homemade tart with jam and vinsanto - Tasting of 3 different wines

From Florence: San Gimignano & Siena Tour with Wine Tastings

4. From Florence: San Gimignano & Siena Tour with Wine Tastings

Explore the heart of beautiful Tuscany on a full-day tour of the towns of San Gimignano and Siena, then discover the bucolic wine region of Chianti. Depart from Florence by an air-conditioned bus to your first stop, the UNESCO World Heritage Site of San Gimignano. Discover one of the most splendid examples of an Italian medieval town. Distinguished by its famous towering skyline, San Gimignano stands along the Via Francigena on the hills of the Upper Val D’Elsa. Get acquainted with the Tuscan environment with the town’s Vernaccia di San Gimignano wine, saffron, and Santa Fina pottery. Enjoy some free time to stroll through the town on your own and see its beautiful squares, architecture, churches, and side streets. Afterward, head out to a unique location in the Chianti countryside to enjoy a wine tasting. Once you hop off the bus, be guided around a splendid winery. Get introduced to the estate's fascinating history and background. Head inside the cellars to learn the secrets of Chianti winemaking together with the local host. Then enjoy a delicious wine tasting of Chianti Classico. Continue to Siena for a guided tour of its enchanting architectural styles, including the Cathedral (exterior only) and Palazzo Comunale (Municipal Building, exterior only) in Piazza del Campo. The famous shell-shaped square provides the stage for the thrilling Palio horse race, run twice every summer.

Siena: Walking Food Tour with Tastings

5. Siena: Walking Food Tour with Tastings

Enjoy a rich meal (lunch or dinner) within the city of Siena on a guided food tour. Learn about each dish you taste as you visit local restaurants, cafes, and historic eateries. Discover what the local cuisine has to offer. Try some of the best food in Siena and learn a little bit about the local culture along the way. Here's a list of possible tastings: Charcuterie and cheese board - Taste the best charcuterie and cheeses from the area accompanied by a good glass of local wine. Pici cacio e pepe or with wine - Pici senesi are made in a way that respects ancient processes, such as bronze wire-drawing. You can taste them seasoned with cacio e pepe or with wine. Pappa senese - of peasant origin, the recipe has been handed down from generation to generation. With a small detail that differentiates it from the traditional Tuscan pappa al pomodoro. Ribollita - the typical soup made of bread and vegetables, delicious! Tonno del chianti - an ancient Tuscan recipe made with pork, purged for days in coarse salt and then cooked 5 hours in white wine and herbs. Ricciarelli - Marzipan biscuits in the shape of a grain of rice with a crunchy, wrinkled and cracked surface coated in sugar and a grainy interior that is soft to the bite... delicious!

From Florence: Pisa and Siena with Wine Tasting in Chianti

6. From Florence: Pisa and Siena with Wine Tasting in Chianti

Spend a day surrounded by the Renaissance beauty and rolling hills of Chianti, visiting Pisa and Siena with our private driver. A wonderful experience between art, wine, Tuscan legends and local food to discover vineyards, leaning towers, sunflowers and typical Tuscan farms. Meet your driver at your hotel, B&B or private apartment in Florence and set off on a discovery tour of Tuscany with stops in Pisa, a rural Tuscan farmhouse, and in the afternoon in Siena. First stop in Pisa to admire "Piazza dei Miracoli" and the famous Leaning Tower. Visit the other buildings that surround the area, including the Baptistery and the Cathedral. Depart from Pisa, driving through one of the most beautiful Tuscan wine roads. You can also request an extra stop at the famous village of San Gimignano. Stop for lunch in a Tuscan farm: visit, 3-course lunch and wine tasting. This farm promotes genuine Italian food and wine culture all over the world. A beautiful Italian experience to learn the best pairings between wine and food, the etiquette of the glass, the secrets of Italian cuisine, Tuscan winemaking techniques and more. Three-course lunch, with homemade pasta, bruschetta, salami, pecorino cheese, ham, salami and more. Wine tastings with: Chianti, Chianti Riserva, Sangiovese, Vernaccia and Super Tuscan, and also Extra Virgin Olive Oil Tasting Pepper Olive Oil Tasting Balsamic vinegar tasting Truffle Olive Oil Tasting After lunch, the tour continues with the visit of Siena to the historic center of this city, declared a World Heritage Site by Unesco, known for its splendid architecture and the beautiful main square, Piazza del Campo. Furthermore, Siena is also known for its legendary Palio horse race, which takes place twice a year and attracts hundreds of spectators. The most interesting things to see in Siena are: the famous Piazza del Campo, the Duomo, the Baptistery, the Church of San Domenico and the wonderful narrow streets of the historic center such as the "Via di città". At the end of the visit, we will return to your location/address in Florence.

From Rome: San Gimignano, Siena, Chianti Wine and Lunch

7. From Rome: San Gimignano, Siena, Chianti Wine and Lunch

Start your tour early in the morning from Rome, where we'll head to our first destination, the iconic San Gimignano. There you will have the opportunity to discover its medieval architecture and its walled streets. In addition, you can walk through its iconic Piazza della Cisterna and visit its representative Torre Grossa. The next stop will be a wine cellar, a great symbol of Tuscany culture. Along with a guided tour, you will learn how this precious delicatessen is made and you will have the opportunity to taste it. You can delight yourself with the aroma of the prestigious Chianti. You will be lucky to taste 15 varieties of wine and oil from the region, besides appetizers like Tuscany cheeses, salami, and the famous bruschetta! You will enjoy a traditional lunch, tasting the best dishes in the area, if you select the option. After this gastronomic visit, we will head to Siena, known for its traditions, and cultural heritage. There you can enter its historic center and stroll through Piazza il Campo. With its peculiar shell shape, it is considered one of the best medieval squares in Europe. Nor can you miss its characteristic Duomo di Siena and its ancient Tower of Mangia. Finally, with a full stomach and a backpack loaded with beautiful landscapes and picturesque cities, we will return to Rome through the serene Val d'Orcia.

From Florence: Private GUIDED tour, Siena & San Gimignano

8. From Florence: Private GUIDED tour, Siena & San Gimignano

• Stop At: Siena, Tuscany. Experience Siena through the expert and knowledgeable lens of a professional tour guide! Siena is one of the most popular and visited places in Tuscany. It is known throughout Italy for its distinguished medieval architecture. Upon arrival, explore with your guide Siena’s rich history and art, through its notable local monuments such as the famous seashell-shaped Piazza del Campo and the outstanding Siena Cathedral. Many local shops fill the historic streets of Siena, a great opportunity for you to taste local food or buy some gifts! Duration: 3 hours • Stop At: Castello di Monteriggioni, Tuscany. Make a lovely stop in the small, fortified village, which is still surrounded by its original medieval walls. Located not far from Siena, Monteriggioni is a great spot for a short walk after lunch at one of the local restaurants. Duration: 2 hours • Pass By: Village of Fonterutoli, Siena. Fonterutoli has been an important village ever since the Roman times. The Via Romea passes here, and is still today traveled by pilgrims from all over the world. Location of the historic Mazzei family since 1435 (for 24 generations), the village of Fonterutoli maintains its medieval appearance intact. Stroll in the village to stretch your legs and take some beautiful photos. Duration: 30 minutes •Stop At: Organic Farm/Winery Tenuta Casanova, Tuscany. (*optional) *OPTIONAL lunch at the Farm or Winery. Have lunch in a wonderful organic farm. While the owner will show you around the property, his wife will prepare a delicious and unforgettable lunch for your private group. The owner will show you to his cellar to admire his Super Tuscans and Chianti Classico wines -Craft Wine- and to the nearby Acetaia, a vinegar cellar, with old vinegar. Afterwards, experience a unique dining setting while taking in an amazing Tuscan panorama. You will taste organic specialties, such as the typical Lasagna with traditional sauces, crostini, local meats and cold cuts, legumes, seasonal vegetables, honey, and cheeses seasoned with an incredible aged balsamic vinegar. Wine will accompany this lunch every step of the way. Each of the four main courses and desserts will be paired with a different and distinctive glass of wine. We will conclude with ice cream and balsamic vinegar or other desserts. (This option will slightly reduce your time to visit the cities of Siena and San Gimignano, and exclude the possibility to visit the fortress of Monteriggioni). Duration: 2 hours •Stop At: Historic Center of San Gimignano, Tuscany. The beautiful stronghold of San Gimignano is one of the most popular tourist attractions in Tuscany. San Gimignano is a treasure of medieval architecture, frozen in time at 1300 AD. Above all, it is famous for its ancient towers, which still stand out from its skyline, earning it the nickname Manhattan of the Middle Ages. This is the last destination of the day, before returning to Florence. Duration: 1h30m

From Livorno: Siena and Chianti Day Trip with Wine Tasting

9. From Livorno: Siena and Chianti Day Trip with Wine Tasting

Immerse in a day of exploring rolling hills, medieval art, grapevines, and Tuscan flavors. Visit the main square and Gothic cathedral in Siena. Explore the breathtaking landscapes of Chianti. Visit a winery and have a tasting of different wines. Start your private day tour from the port of Livorno. Discover Siena's artistic and cultural heritage. Learn about the annual Palio horse race held there that attracts huge crowds. This medieval city is also home to architectural masterpieces including the Palazzo Pubblico, located in Piazza del Campo, with its Torre del Mangia. Explore the stunning Siena Cathedral, one of the few remaining examples of Italian Gothic architecture. Then, travel through the stunning hills of Chianti, a region famous for its scenery and vineyards. Arrive at a local winery to taste some Chianti and learn about how their grapes are produced. After a guided tour, indulge in a rich sampling of wines and delicious local produce, followed by the opportunity to purchase these local products. After a full day in Tuscany, be taken back to the port by your driver, in time to board your ship.

Siena food tour and Chianti wine

10. Siena food tour and Chianti wine

Welcome to the Gem of Tuscany, Siena. I will take you for a wonderful walk and show you the gems that this city has offer. During our tour we will see the "the oldest bank of the world" and the beautiful medieval square of Piazza del Campo considered Unesco world heritage. The main attraction you will see are: - The lookout where you will see entire Médiéval town - Piazza Salimbeni - Piazza del Campo - Piazza Tolomei - The Cathedral of Siena (outside) - Traditional shops with food tasting & Chianti wine. - Medieval Alley During our tour you will try some local food and wine like the famous Chianti, Pecorino cheese, Salame toscano, Finocchiona, handmade focaccia, bruschetta, prosciutto and typical sweets made in Siena like Ricciarelli or cantuccini paired with holy wine. Vegetarian and Gluten free options available. We will discover together the myths, legends, and secrets of this medieval town and we will have the occasion to see very iconic neighborhoods and street where normally locals spend their time with friends and family. This will be your occasion to live the city like a local.

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What people are saying about Siena Cathedral

Overall rating

4.4 / 5

based on 1,531 reviews

Stefono was an amazing tour guide: great knowledge of the area, just the right amount of wit, and he cared about us having a good experience! We also had a local guide in Sienna, who was amazing in her own right. The lunch was absolutely delicious with a variety of wines, good food, and a great view! The whole day was a whirlwind and left you ready for a nap on the drive back to Florence, but it was a fantastic experience well worth the price!

Our tour guide Alex was very enthusiastic and knowledgeable and shared lots of great information throughout the tour. The food and wine were great and overall it was a time well spent. I highly recommend. San Gimignano is a must see!!!

Lorenzo did a great job, this tour was truly special thanks to him. Would definitely recommend going for the lunch included option, some of the best food I’ve had in all of Italy.

Alex was such an amazing tour guide. He was friendly and really made the experience the best of tuscany. the tour was beautiful and so informative

It was a great way to see Tuscany in a short amount of time. The lunch at the winery was excellent!