Siena
Neighborhood Tours

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Our most recommended Siena Neighborhood Tours

From Florence: Chianti Hills Wineries Tour with Tasting

1. From Florence: Chianti Hills Wineries Tour with Tasting

Immerse yourself in Italy's renowned winemaking culture on this guided tour by van from Florence. Leave the city behind as you head out into the Tuscan countryside, marveling at the landscape around you. Visit two local wineries and enjoy wine tastings in both of them, learning about the wine-making process from locals. Arrive in the charming town of Radda in Chianti and visit one of the town’s traditional wineries. Enjoy a tasting session of 3 regional wines, then have the opportunity to purchase them. Spend some free time exploring the narrow streets of the town. Continue towards a traditional farm and winery. Learn about the winemaking process from grape to glass. Then enjoy another tasting session of 3 Chianti wines as well as local products. Finally, sit back and relax on the return journey to Florence.

Siena: 2-Hour Food and Wine Tour

2. 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

Antinori Winery & Brolio's Castle: Private Tour

3. Antinori Winery & Brolio's Castle: Private Tour

Start your day at the office of the local partner, perfectly positioned in the city center. You will meet your personal driver with an exclusive car and your local private guide as well as wine expert. Leaving the city center, the first stop of your visit to Chianti will be Antinori's cellar in Bargino, a wonderfully innovative winery located in the green Chianti hills. Inside the cellar you can taste different types of wine, listening to stories and anecdotes about the Antinori family told by the guide who will accompany you on this wonderful journey. After this visit, you will have lunch in a typical Tuscan restaurant "La Cantinetta di Rignana", halfway between the Antinori vineyard and Brolio's Castle. Here you can taste local salami, cheeses, Tuscan crostini, extra virgin olive oil, pasta or meat dishes, accompanied by wines and local products. Ending the lunch, you can enjoy some free time inside the restaurant, which is also a farmhouse. The last stop of the visit will be the Castle of Brolio and the Barone Ricasoli vineyard. Here, you will privately visit the castle and the vineyard, discovering the cellars and the finest quality wines, tasting most of the local production, tasting every single glass, accompanied by the guide's explanation. When you're ready, you will return to Florence in your exclusive car.

Siena: Private Tour Ideal for Families with Children

4. Siena: Private Tour Ideal for Families with Children

Enjoy a private tour that takes into account children’s attention spans, not one where the young are dragged by their parents on exhausting journeys. With the help of a local guide, keep your children’s attention alive with language that is colorful and lively, and where history is mixed with art, legends, and traditions. By encouraging children to make observations, answer questions, and solve riddles, your guide will reveal the history and secrets of Siena’s monuments in a pleasant way that is sure to prevent children becoming impatient, bored, and complaining. From the meeting point in front of the Basilica Cateriniana San Domenico, you’ll learn about the traditions of the Palio di Siena horse race and admire the magnificent front of the Duomo di Siena cathedral. Next, walk the Via Banchi di Sopra — the former route of pilgrimage to Rome — that will you lead to Piazza del Campo, the principal public space of the historic center of Siena where the tour will end with a souvenir and great memories.

From Florence: Private Full-Day Jewels of Tuscany Tour

5. From Florence: Private Full-Day Jewels of Tuscany Tour

Be seduced by the eternal charm of Tuscany’s jewels on this 12-hour tour. What are Tuscany’s jewels? The beautiful cities and villages, as well as art and the historical monuments that call this unique region of Italy home. Falling in step with the more ‘human’ way of life in Tuscany, this relaxed tour begins when you want it to. You determine the pick-up time from your centrally-located Florence hotel. You will also enjoy the transportation, which is provided by a private vehicle operated by an English-speaking driver. After pick-up, you will drive through the Tuscan countryside until your first stop, Siena, is reached. Siena is a medieval city known for its artistic treasures, which have been recognized by UNESCO. In Siena you will visit the shell-shaped Piazza del Campo. Here you will find the Palazzo Comunale flanked by the Torre del Mangia. Every year the famous Palio takes place here. You will also have free time to visit the cathedral, built in the Middle Ages and admire the splendid buildings and narrow streets. From Siena, you will enjoy a drive through Chianti territory on your way to Monteriggioni. The drive boasts a panoramic view of the vineyards and olive groves. Monteriggioni is a small 13th-century town which is still surrounded with its original town walls. Here you will take a walk within the restricted perimeter of the walls, which have eleven towers with spectacular views. This is a Tuscan gem that will transport you back in time. Only a short distance away, in a pleasant country estate you will be served a typical Chianti-region lunch. You will also enjoy a guided tasting of Chianti and Vernaccia wines. After lunch you will leave the estates and go to San Gimignano, another beautiful town and UNESCO world heritage site. Famous for its signature medieval town planning, it is called the “Manhattan of the Middle Ages”. On a stroll through the town center you will discover the Piazza della Cisterna, the Dome, the Palazzo del Podestà and the Church of Saint Agostino. Your final stop will be at the famous town of Pisa, which is also a UNESCO world heritage site. In the Piassa dei Miracoli the masterpieces in marble rise from the green lawn, including the famous Leaning Tower of Pisa, the magnificent Baptistery, the stunning Cathedral and the Monumental Graveyard Tuscany is a one-of-a-kind region of boundless natural and cultural beauty. This small, personalized tour is an authentically Tuscan experience.

Florence: Pisa, Siena, San Gimignano, and Chianti Experience

6. Florence: Pisa, Siena, San Gimignano, and Chianti Experience

Your day starts in the morning with a tour of Pisa. Have time to admire the cathedral, the baptistery, the monumental cemetery, and the famous Leaning Tower. Then move on to a typical winery in the Chianti Hills on the slopes of San Gimignano. Enjoy a Tuscan lunch accompanied by a local wine tasting. Following lunch discover one of the most beautiful medieval villages of San Gimignano, or the "Medieval Manhattan, where you can explore the maze of cobbled streets, small squares and many local craft stores. Continue on with a panoramic view of the Chianti countryside before arriving in Siena, where if desired, your professional guide will take you to see the most important squares, from Piazza del Campo to the cathedral, passing through the most beautiful contrade that characterizes this city. At the end of the guided tour, choose to have some free time to enjoy a cup of coffee or a panforte (a typical local cake), and to go shopping. Your return to Florence will have a gorgeous sunset in the backdrop, making for a perfect ending to an unforgettable day spent in Tuscany.

From Rome: Siena, Chianti, Wine Tasting and Lunch

7. 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.

Siena: Market Tour and Lunch/Dinner at a Cesarina's Home

8. Siena: Market Tour and Lunch/Dinner at a Cesarina's Home

This local partner is home to Italy's first and finest network of home cooks, known as "Cesarina" (a passionate Italian cook and host whose empire is the heart of the Italian home: the kitchen). Since 2004, they have been sharing the joy of regional Italian cuisine with thousands of travelers from all over the world. Visit the local market with your Cesarina, enjoy the distinctive Italian local market and learn how to recognize the best produces from the land. Come back to your Cesarina’s home, and attend a private cooking demo where your Cesarina will share the secret of her family cookbook while finishing one of the dishes in front of you. Sit at an authentic Italian table and enjoy a 4-course seasonal menu including starter, pasta, and main course with side dish, dessert, and drinks included (water, a selection of red and white wines from regional cellars, and coffee). Feel the warmth of Italian hospitality as you connect with local people. If you want to uncover the secrets of Italian family recipes on your travels, the Cesarine are here to share their wisdom, which has been passed down in their families for generations.

Florence/Siena: 3 Wineries Experience with Lunch

9. Florence/Siena: 3 Wineries Experience with Lunch

After pickup from your accommodation in Florence or Siena, enjoy a tour and tasting session at a historic winery in the Chianti region. On the property set in the heart of vineyards, be greeted by the owners and enjoy an appetizing plate of snacks, home-produced olive oil and balsamic vinegar. Sample some of the best wines from the region, including Chianti, Riserva, and Super Tuscans. Continue with a visit to San Gimignano, known as the medieval Manhattan. The village features thirteen original 12th-century towers and is definitely the most beautiful place in the region. Visit the town center to browse the artisanal shops, and walk along the picturesque streets. Later, enjoy a delicious lunch in a boutique local winery, famous for its hospitality. Taste the traditional Tuscan food such ribollita soup, lasagna with truffle olive oil, and local almond biscuits called cantucci. All this will be paired with different wines, including Chianti, Vernaccia di San Gimignano, and Super Tuscans.

From Florence: Private Full-Day Trip to Tuscany

10. From Florence: Private Full-Day Trip to Tuscany

Discover Tuscany on this private full-day trip from Florence. Go back in time and learn about the history of Tuscany as you visit ancient sites like the stronghold of San Gimignano, the Basilica of Santa Maria Assunta, the Fortezza Medicea of Volterra, and much more. After being picked up from downtown Florence, enjoy a scenic view of the countryside as you drive to San Gimignano. This beautiful stronghold is one of the most popular attractions in Tuscany. During the trip, marvel at San Gimignano's ancient towers, visit the historic Piazza Duomo, and soak in the atmosphere at Piazza della Cisterna. Then, proceed to Volterra and stroll through the cobbled streets to reach an array of historical sites. See remarkable discoveries such as Etruscan tombs built hundreds of years before Christ, elaborate Roman baths, and an incredible theater excavated from rocks. The stop at the set of The Twilight Saga: New Moon is also worth looking forward to. Afterwards, recharge by having lunch at a local restaurant, trattoria, or farm house. Next, admire the imposing structure of the Fortezza Medicea of Volterra before heading over to Palazzo dei Priori, which is the oldest civic building in Tuscany. After your exploration, your driver will drop you off at your hotel in Florence.

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What people are saying about Siena

Overall rating

4.1 / 5

based on 5 reviews

Really great experience. We had an accident and missed the street where was the meeting point in Siena. The group was far away already when we found the spot, but tour guide Giuliano was cooperative, sent bus location and wait for us so we could catch the bus. Would be great if we had more time to stay longer in Siena.

We had a really great time and the wineries were much better than we expected. Radda is a charming town and it was a treat to be able to have some time there to wander.

Our guide Sonia was wonderful! If we were to do anther excursion like this, we’d do only 2 towns, 3 seemed too rushed.

Fab trip. Great guide Sonia. Very informative and very helpful. We'll worth the money. This trip is a must. Thank you

Excellent excursion!! Juliano was my guide and I recommend him, he was great. Go with him on tour.