Italy · Wine & Beer

Day Tour From Florence To Siena, San Gimignano, Monteriggioni & Chianti Wine Region With Wine Tasting

11 Hours Round trip from Florence Moderate pace

The journey

Trip highlights
  • 01 Full-day Tuscany tour from Florence by GT coach
  • 02 Explore the medieval walled village of Monteriggioni
  • 03 Enjoy a guided walking tour of Siena and Piazza del Campo
  • 04 See Siena Cathedral from the outside, with free time to enter at your own expense
  • 05 Discover San Gimignano, the famous 'town of towers'
  • 06 Travel through the scenic Chianti wine region
  • 07 Visit a Chianti winery for wine, olive oil, and regional product tasting

Spend a full day discovering some of Tuscany’s most iconic landscapes and historic towns on a journey from Florence through Monteriggioni, Siena, San Gimignano, and the Chianti wine region. Travel by coach through rolling hills and medieval scenery, with time to explore walled villages, UNESCO-listed Siena, and the famous skyline of San Gimignano.

Along the way, enjoy a guided walk in Siena, free time for independent sightseeing, and a stop at a Chianti winery for a tasting of wines, extra-virgin olive oil, and regional products. This experience combines history, architecture, countryside views, and local flavours in one memorable day.

You will have one hour of free time to explore Monteriggioni, Tuscany's hidden gem.

From the itinerary

At a glance

What this trip includes

Duration 11 Hours
Tour type Shared
Activity level Moderate
Accommodation Not included
Transport Not included
Wheelchair access No
Cities Florence, Siena, Chianti, San Gimignano
Languages Japanese, Korean

Day by day

The itinerary

1
Day 01

Florence

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. 

Monteriggioni, Province of Siena

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.

Siena

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.

Piazza del Campo, Siena

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. 

Siena's Cathedral (Duomo)

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. One of the most beautiful Gothic-style churches in Italy, with its radiant green and white marble decorations

San Gimignano, province of Siena

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! 

Chianti Wine Region

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!

Piazzale Montelungo, Florence

End your journey through Tuscany with unforgettable views of the Tuscan hills as the sunsets. The drive will take about an hour, and you will arrive in Florence in early evening. 

The route

Where you'll travel

Tour route map
Round trip from Florence 4 cities · 11 Hours

The fine print

Trip details

What's Included

  • Journey by fully-fitted GT Coach
  • Expert multilingual escort
  • Audio guide (via app) for Chinese, Korean, and Japanese
  • Siena tour with professional guide - if optional selected
  • Visit to a Chianti winery
  • Sampling of wines, extra-virgin olive oil and regional products
  • Free visit of San Gimignano and Monteriggioni

What's Not Included

  • Gratuities
  • Hotel pickup and drop-off
  • Siena Cathedral tickets
  • Low cost options do not include the Guided tour in Siena

Know before you go

  • LOW SEASON (From November, 1st until March, 31st): English and Spanish languages are always guaranteed. In order to confirm the excursion in French, Italian or Portuguese a minimum of 4 pax is required
  • HIGH SEASON (From April 1st until October 31st): this tour is always available in English and Spanish. Other languages are confirmed as follows:
  • FRENCH: Tuesday - Friday, min 2 pax
  • PORTUGUESE: Wednesday - min 2 pax
  • ITALIAN: Saturday, Sunday - min 2 pax
  • By selecting Chinese, Korean, or Japanese languages, the explanation of the monuments and the history of the tour will be provided exclusively through an audio guide (via app) in the selected language. However, you will not be alone: throughout the excursion, one of our professional Tour Leaders will always be present. The Tour Leader will coordinate the group and provide emergency assistance and logistical information (schedules and meeting points) in English.
  • Please note that services in Chinese, Japanese, and Korean are available exclusively via audio guide. If additional services are selected (such as the guided tour), these will be conducted in English by live guides. However, you will still be able to find information and insights in your native language about Siena through the app. Wine tasting will also be conducted in English.
  • Not wheelchair accessible
  • May be operated by a multi-lingual guide
  • Comfortable walking shoes are recommended   
  • The given order of the visits may change   
  • Please show up 20 minutes before the tour departure  
  • Times are subject to change due to local traffic conditions
  • Low cost options do not include the guide in Siena
  • Shared tour with other participants

Logistics

Meeting & route

Meeting point
Florence, IT
Tour start
Florence, IT
Tour ends at the same location as the start point.
End of the journey

Your 11 hours finish where they began, in Florence.

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