Italy · UNESCO Heritage Sites

Pisa, Siena and San Gimignano Day Trip with optional Lunch & Wine Pairing

12 Hours Round trip from Florence Moderate pace

The journey

Trip highlights
  • 01 Visit Siena, San Gimignano, Pisa, and the Chianti countryside in one day
  • 02 See Piazza del Campo and Siena Cathedral square
  • 03 Enjoy free time in San Gimignano and Pisa
  • 04 Optional Tuscan lunch and wine pairing at a family-owned winery
  • 05 Travel through the scenic rolling hills of Chianti
  • 06 Admire the Leaning Tower of Pisa and the Square of Miracles
  • 07 Round-trip journey by fully-fitted GT coach from Florence

Discover some of Tuscany’s most iconic highlights in a single day on this full-day trip from Florence. Travel through the rolling Chianti countryside to Siena, San Gimignano, and Pisa, with time to explore historic streets, admire UNESCO-listed landmarks, and enjoy the region’s unforgettable scenery.

In Siena, stroll through the medieval center and see celebrated sights such as Piazza del Campo and the Cathedral square. Continue into the Chianti wine region, where selected options include a traditional three-course lunch with wine pairing at a family-owned winery, before visiting hilltop San Gimignano, famed for its medieval towers.

The day ends in Pisa, where you’ll have free time around the Square of Miracles to admire the famous Leaning Tower and surrounding monuments before returning to Florence by coach.

The view from the winery will leave you breathless, as you will be surrounded by sunny rolling hills, olive groves and vineyards, of course!

From the itinerary

At a glance

What this trip includes

Duration 12 Hours
Tour type Shared
Activity level Moderate
Accommodation Not included
Transport Not included
Wheelchair access No
Cities Florence, Pisa, Siena, Chianti, San Gimignano
Languages English, French, Japanese, Korean, Portuguese, Spanish

Day by day

The itinerary

1
Day 01

Piazzale Montelungo, Florence

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

Siena

When you arrive in the medieval gem of Siena, your guide will lead you through the picturesque streets until you reach the main piazza of the city - Piazza del Campo. Here, a professional city guide will meet the group to begin your walking tour. 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 square.

Please note that the "Semi independent option" does not include the guided tour in Siena. Clients that have chosen this option will have free time in Siena instead.

Piazza del Campo, Siena

During the included walking tour of Siena, your guide will show you an insider's view of Piazza del Campo. Not only is this piazza a popular place for locals to gather, but is is also home to an annual palio horse race, which is an epic competition between the different neighborhoods of Siena! Learn all about the history of the city, and its main square as your guide unfolds the secrets of the city to you and your group in a vivid, storytelling manner. You will spend about thirty minutes learning about Piazza del Campo. 

Siena's Cathedral (Duomo), Siena

Your guided tour will conclude in front of one of Siena’s most stunning landmarks: the Siena Cathedral. This magnificent cathedral showcases a variety of artistic styles and features works by numerous renowned Renaissance artists. If you wish, you can purchase a ticket to experience the breathtaking interior, and don’t miss the absolutely striking Piccolomini Library on your way out! Spend about twenty minutes exploring the Cathedral independently. Afterwards, enjoy a leisurely stroll through the city center before rejoining your guide to continue to your next stop.

Chianti Wine Region

After an exciting morning of exploration in Siena, it will be time to relax and refuel! We will drive about one hour through the rolling hills of Tuscany until we reach a lovely, family-owned winery in the countryside outside of San Gimignano. The view from the winery will leave you breathless, as you will be surrounded by sunny rolling hills, olive groves and vineyards, of course! Surrounded by the most beautiful Tuscan countryside, you will indulge in a wine pairing of high-level wines accompanied by a delicious three-course meal of a typical Tuscan meat and cheese plate, pasta, and dessert. 

Then, we will drive about fifteen minutes to arrive in the hilltop beauty of San Gimignano. 

San Gimignano, Province of Siena

San Gimignano is visible from close and far, with its unmistakable medieval “skyscrapers.” Sometimes called a medieval Manhattan, there are still thirteen towers intact in this perfectly preserved hilltop town. Your guide will lead you first to a famous panoramic viewpoint, where you can photograph the Tuscan countryside, and then through the ancient doors to the city. You will have an hour to explore the lovely town of San Gimignano as you please. 

Pisa

After exploring the historic beauty of San Gimignano, it will be time to depart for a great symbol of Italy - Pisa! We will drive for about an hour, as your guide shares interesting information about the city an its monuments. 

Leaning Tower of Pisa, Pisa

During your free time and if there is no queue, you can climb the Leaning Tower of Pisa to admire the incredible views of the Square of Miracles from above. The panoramic views of Pisa are truly breathtaking: from the monuments below, to the city surrounding the square, the Arno River, and the countryside in the distance... Views from the top of the tower are fascinating!

Florence

After departing from Pisa, it will take about an hour to return to Piazzale Montelungo in Florence. Enjoy your wonderful memories of a full day in the historical and artistic gems of the Tuscan Countryside as you sit back, relax, and enjoy the air conditioned coach bus

The route

Where you'll travel

Tour route map
Round trip from Florence 5 cities · 12 Hours

The fine print

Trip details

What's Included

  • Journey by fully-fitted GT Coach
  • Expert multilingual escort
  • Interactive audio guide for Chinese, Korean, and Japanese
  • Free time in Pisa and San Gimignano
  • Lunch in a typical wine farm (if option selected)
  • Siena tour with professional guide (if option selected)
  • Admission fee to Siena Cathedral (if option selected) - It will no longer be included from 1 November onwards

What's Not Included

  • Hotel pickup and drop-off
  • Food and drinks, unless specified
  • Gratuities
  • Guide in Siena and admission fee to Siena Cathedral in case you select the semi independent option
  • Admission fee to Siena Cathedral from 1 November onwards

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: Wednesday, Saturday - min 2 pax
  • PORTUGUESE: Tuesday - min 2 pax
  • ITALIAN: Sunday - min 2 pax
  • CHINESE, JAPANESE, KOREAN: If you select Chinese, Korean, or Japanese, the historical explanations and tour commentary will be provided exclusively via audio guide (via App) in your chosen language. You will not be left alone: a professional Tour Leader will accompany the group throughout the trip. The Tour Leader will manage the group and provide logistics, meeting point details, and emergency assistance in English, while the cultural insights will be delivered via the app in your native language.
  • Not wheelchair accessible
  • Not suitable for pets
  • Not recommended for people with back problems
  • Not recommended for people with heart conditions
  • Kindly note that the semi independent option does not include the local guide in Siena and entrance tickets to Siena’s Cathedral
  • Kindly note that the No Lunch Option does not include lunch, guide in Siena and Cathedral tickets
  • Please show up 20 minutes before the tour departure
  • 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 12 hours finish where they began, in Florence.

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