Siena, San Gimignano, Monteriggioni and Chianti Wine Tasting Tour from Florence

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From $54.57

690 reviews   (4.31)

Price varies by group size

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Pricing Info: Per Person

Duration: 10 hours

Departs: Florence, Florence

Ticket Type: Mobile or paper ticket accepted

Free cancellation

Up to 24 hours in advance.

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A full day tour, taking in the key beauties of Central Tuscany including a delicious Chianti wine tasting. You'll roll through the sweeping countryside to arrive at the jewel of Siena, with its unique Square and Gothic Town Hall. Then you'll take the road for San Gimignano, the Medieval New York, and Monteriggioni - a hilltop castle with breath taking views. But it's still not over! End your visit with a Chianti winery where you savor the best of Italian wines. This is a perfect day-out to relax and replenish your spirits.

What's Included

Expert multilingual escort

Free visit of San Gimignano and Monteriggioni

Journey by fully-fitted GT Coach

Sampling of wines, extra-virgin olive oil and regional products

Siena tour with professional guide (not included in the semi independent option)

Visit to a rustic wine estate in the Chianti area with wine tasting

What's Not Included


Hotel pickup and drop-off


Siena Cathedral tickets

Traveler Information

  • INFANT: Age: 0 - 3
  • CHILD: Age: 4 - 12
  • ADULT: Age: 13 - 99

Additional Info

  • HIGH SEASON (From April 1st until October 31st): this tour is always available in English and Spanish. Other languages are confirmed as follows: GERMAN: Monday - min 2 pax FRENCH: Tuesday - Friday, min 2 pax PORTUGUESE: Wednesday - min 2 pax ITALIAN: Satu
  • Infants are required to sit on an adult’s lap
  • LOW SEASON (From November, 1st until March, 31st): English and Spanish languages are always guaranteed. In order to confirm the excursion in French, German, Italian or Portuguese a minimum of 4 pax is required
  • Not recommended for travelers with poor cardiovascular health
  • Please note that the given order of the visits may change
  • Service animals allowed
  • Travelers should have at least a moderate level of physical fitness
  • A dress code is required to enter places of worship and selected museums. No shorts or sleeveless tops allowed. Knees and shoulders MUST be covered for both men and women. You may risk refused entry if you fail to comply with these dress requirements
  • Infants and small children can ride in a pram or stroller
  • Kindly note that the Semi independent option does not include the professional guide in Siena
  • May be operated by a multi-lingual guide
  • Please inform us of any food intolerance or allergy in advance
  • Public transportation options are available nearby
  • Specialized infant seats are available

Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

  • For a full refund, you must cancel at least 24 hours before the experience’s start time.
  • If you cancel less than 24 hours before the experience’s start time, the amount you paid will not be refunded.
  • This experience requires good weather. If it’s canceled due to poor weather, you’ll be offered a different date or a full refund.

What To Expect

There is no time to waste when exploring the stunning Tuscany hills! Meet your tour guide at Piazzale Montelungo Bus Terminal early in the morning. Piazzale Montelungo is located 5-10 minutes walking distance from the Santa Maria Novella train station. Hop on the comfortable coach bus, choose your seat, and relax before departing on your journey! The drive to Monteriggioni will take about one hour. During the journey, your guide will entertain you with plenty of interesting information about Tuscany and its sights on the way. Upon arrival, your expert guide will share some interesting information and fun stories about Monteriggioni! If you have any questions, your guide will be there to assist you.

60 minutes • Admission Ticket Free

You will have one hour of free time to explore Monteriggioni, Tuscany's hidden gem. This town is encompassed by its stunning, medieval walls. The town itself is so well preserved, you will feel as though you have travelled back in time to the Renaissance era... Explore the small cobblestone alleyways, take in the lovely views, and enjoy a cappuccino in the essence of historic Tuscany.

60 minutes • Admission Ticket Free

Next, you will head to a truly unique, medieval city in Tuscany - Siena! The drive will take about thirty minutes, and then your guide will lead you through the picturesque, ancient streets in the heart of the city until you reach Piazza del Campo. In the largest square of the city, you will meet a local and professional city guide for your included walking tour of Siena. For about an hour, the guide will share fascinating facts about this incredible city (which is listed as a UNESCO World Heritage Site), and you will visit some of the most famous points of interest. The end of the walking tour will lead you to the Siena Cathedral, where you can enter at your own expense to see the breathtaking decorations and unique architecture.

3 hours • Admission Ticket Free

Piazza del Campo
Your walking tour will begin in Piazza del Campo, a fascinating, oval-shaped piazza in the center of Siena. Not only is this a popular spot for locals to meet up with friends and relax, but it is also home to a historic palio horse race! Every year, the different neighborhoods of Siena join for the epic and exciting horse race. Your guide will share plenty of local stories as you walk throughout the Piazza and see some of the famous monuments. Your professional guide will share information in a way which brings the history of the city to life, in a vivid, storytelling manner.

15 minutes • Admission Ticket Free

Duomo di Siena
Your walking tour ends in front of the iconic Duomo of Siena. This absolutely stunning piece of architecture is equally as beautiful inside as outside; if you would like to enter the cathedral, you will have some free time to do so (ticket is not included). If you prefer to explore the city in your free time after the walking tour, there will be some time for independent sightseeing.

15 minutes • Admission Ticket Free

San Gimignano
Your journey through Tuscany will continue to San Gimignano, known as the "town of towers," because of its fascinating medieval towers still perfectly intact. The drive will take about an hour, and you will see the stunning "medieval skyscrapers" from a distance as your bus pulls into the historic town. Your guide will lead you past an incredible panoramic viewpoint of the Tuscan hills, then through the ancient city doors. You will have an hour to independently explore the town - walk the picturesque alleyways, visit the Duomo, or climb the tallest tower!

60 minutes • Admission Ticket Free

Piazza della Cisterna
As you walk through the characteristic alleyways of San Gimignano, you will inevitably make your way to Piazza della Cisterna. This is the main square of the city, and where you can find the Cathedral, Duomo, and iconic medieval architecture! Grab a homemade gelato and enjoy the lovely views of this perfectly preserved city.

30 minutes • Admission Ticket Free

Chianti Road
After exploring these medieval Tuscan cities, you will undoubtedly be ready for some Tuscan wine! Meet back with your group, and head to a nearby wine estate in the countryside outside of San Gimignano. In about fifteen minutes, you will arrive at this characteristic wine estate, where you will be seated in a modern and beautiful tasting room built into the cellar. Enjoy the delicious wine produced at the estate: during the wine tasting, the wine producer will share the secrets of Chianti wine production with your group. At the end of the wine tasting, you will have the opportunity to purchase bottles as a high-quality souvenir of your incredible day in Tuscany!

2 hours • Admission Ticket Included

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