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A Tuscany day trip from Florence, featuring the iconic medieval tower skyline of San Gimignano, exploring this gem of the Italian countryside.
A Tuscany day trip visiting Siena's breathtaking Santa Maria Assunta Cathedral, admiring its ornate Gothic facade and bell tower, a masterpiece of medieval architecture.
Strolling through the charming medieval streets of a Tuscan town, experiencing the historic atmosphere of San Gimignano or Siena, lined with ancient brick walls and greenery.

San Gimignano, Siena & Chianti Day Tour from Florence

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Sold 400+

Duration:11 hour(s) 15 min(s)
Please present the e-voucher on-site

  • Walk through medieval streets, visit the stunning Cathedral of Santa Maria Assunta, and experience the famous Palio horse race atmosphere
  • Enjoy a wine tasting experience with locally produced delicacies while learning about the rich history of Tuscan winemaking
  • Visit the well-preserved Monteriggioni fortress and marvel at the iconic towers of San Gimignano, a true gem of the Italian countryside
[5% App discount] Code: APP5OFF , HK: APP15HK

Product Info

- What You Can Expect -

Visit Siena, the city of Palio horse-race, held twice a year, during summer season. Explore the medieval streets of its historic city center and enjoy the vibrant atmosphere of this picturesque Piazza del Campo. Admire the monumental building of its main church, the Cathedral of Santa Maria Assunta.

As a second stop, enjoy a wine tasting in the Chianti Area. Taste some excellent wines, paired with some locally produced food, and learn more about the winery's history, its wine-making process and what distinguishes it from others.

Once the winery stop is over, the tour will end with a visit to the marvelous Monteriggioni castle, a medieval fortress that is really well preserved. You may also recognize it from the Assassin's Creed video game series.

Afterward, reach the town of San Gimignano, relying on the top of a low hill at the center of Valdelsa. This wonderful landscape will seduce you with its unique skyline made of towers, built during the 14th century to demonstrate the growing power of noble families. At those times, after gaining autonomy from Volterra, more than seventy towers have been built in the S. Gimignano town center. This process was transforming a rural village into a prestigious town.

Purchase Notice

  • Stroller / pram accessible
  • Public transportation nearby
  • Infants must sit on your lap
  • Not wheelchair accessible
  • A moderate amount of walking is involved
  • Operates in all weather conditions, please dress appropriately
  • Entrance to the Siena Cathedral is not included, clients can enter at their own expenses and depending on Cathedral opening times
  • Please note that will not available on Sundays or Bank Holidays and during special event opening times can change
  • Not suitable for pets
  • Infant seats unavailable
  • Meet our staff at Villa Costanza, Florence Coach Station. How to get to Villa Costanza from Florence: take the tram T1.3*, direction 'Villa Costanza'. It will take around 20 minutes to reach the destination. Once arrived, look for our staff member(s) wearing either a green t-shirt or a white shirt with green foulard with myTour logo. *Please note that the tram ticket costs 1.50€ and you can get one at the vending machine close to the tram stop
  • For urgent communication, please contact +39 0577236330

Reminders

  • A minimum of 2 traveler(s) are required for the tour to depart. If the number of participants does not reach the minimum requirement, the tour will be canceled. An email regarding tour cancellation will be sent 1 day(s) before the departure date

  • Please refer to the voucher for actual information

  • Please carry your passport at all times for verification

  • Entrance to the Siena Cathedral is not included

  • The guests can enter at their own expenses and depending on Siena Cathedral opening times. Please note that will not be available on Sundays or Bank Holidays and during special events opening times can change

  • The tour planning can be different, but you will always do all the tour stops.

  • Participant Requirements: we recommend to bring a mask with you and wear it during all the activity

  • Please contact the local agency through the number(+39 055 07604 #1 / +39 0577 236330 #1) or WhatsApp (+39 338 3974158). The local agency offers the service from 7:00am to 10:00pm. In the event of any emergency, please contact the local agency via phone for instant assistance

Cancellation Policy

  • Once the order has been completed, it cannot be canceled, modified, or refunded
NOTE
  • Due to time zone differences, the confirmed cancellation date is based on the supplier’s local time. Please allow 2–5 business days to process your cancellation request, after which the cancellation fee will be charged according to the product’s cancellation policy. Once the cancellation is confirmed, you will receive your refund within 14 working days.

FAQ

1. What are the best months to visit Tuscany?

The best seasons to visit Tuscany are spring (April to June) and autumn (September to October). Spring offers pleasant weather with fields full of blooming flowers, creating a vibrant landscape. Autumn is characterized by grape and olive harvest festivals, with cool temperatures perfect for wine tasting and leisurely strolls. Both seasons generally have fewer tourists, allowing for a better experience of the charming medieval towns and scenic countryside.

2. What are the unique highlights of San Gimignano, Siena, and Chianti near Florence?

San Gimignano is famous for its well-preserved medieval towers, earning it the nickname 'City of Fine Towers.' You can climb a tower to enjoy panoramic views of the Tuscan countryside. Siena's highlights include its historic Piazza del Campo and the stunning Siena Cathedral, where the famous Palio horse race is held annually. The Chianti wine region is an ideal place to sample world-class wines, learn about winemaking history, and experience authentic wine culture.

3. What are the must-see attractions in San Gimignano?

The most iconic feature of San Gimignano is its cluster of well-preserved medieval towers. The 'Torre Grossa' is the only tower open for climbing, offering the highest vantage point to overlook the entire town and surrounding rural scenery. You can also wander through the winding cobblestone streets, explore Piazza della Cisterna (Well Square) and Piazza del Duomo (Cathedral Square), and indulge in local artisan gelato.

4. What historical and cultural features is Siena renowned for?

Siena is globally recognized for its unique Gothic architecture and rich history. The heart of the city is the shell-shaped Piazza del Campo, which hosts the famous 'Palio horse race' each year. The surrounding Palazzo Pubblico (Town Hall) and Torre del Mangia (Mangia Tower) are must-visit landmarks. Additionally, the magnificent Siena Cathedral (Duomo di Siena), with its intricate carvings and artworks, showcases the pinnacle of medieval art.

5. What unique wine tasting experiences does the Chianti wine region offer?

The Chianti wine region is celebrated for its high-quality Chianti Classico wines. You have the opportunity to visit local vineyards and wineries to learn firsthand about the winemaking process, from grape cultivation to bottling. Tours typically include professional wine tastings, allowing you to sample various vintages and flavors, often paired with local cheeses or olive oil, for a deep dive into Tuscan winemaking culture and cuisine.

6. What is the history and unique character of Monteriggioni Castle?

Monteriggioni is a remarkably well-preserved medieval hilltop fortress town, famous for its complete encircling walls and 14 towers. It was originally built as a military stronghold for Siena to defend against Florentine invasions, giving it significant historical importance. Walking within the ancient walls, you can immerse yourself in a strong historical atmosphere and admire the pastoral Tuscan landscape, feeling as though you've stepped back into the Middle Ages to experience its unique rustic charm.

7. What are the unmissable photo spots in San Gimignano and Siena?

In San Gimignano, the most popular photo spots include the top of the Torre Grossa, offering views of the entire medieval town's tower cluster and surrounding countryside. Piazza della Cisterna, with its unique triangular shape and ancient well, is also very photogenic. In Siena, the shell-shaped Piazza del Campo and the Palazzo Pubblico serve as classic backdrops, while the magnificent exterior and ornate interior of the Siena Cathedral are also absolute must-capture sights.

8. Besides wine, what other local specialties can be enjoyed in the Chianti region?

In addition to its premier wines, the Chianti region is also known for its abundant Tuscan cuisine. You can savor traditional dishes made with fresh local ingredients, such as the famous Ribollita (Tuscan bread soup), Bistecca alla Fiorentina (Florentine steak), or Pappardelle al ragù di cinghiale (pappardelle with wild boar ragu). Furthermore, locally produced olive oil, cheeses, and charcuterie platters are culinary delights not to be missed.

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