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  • Tuscany Grand Tour: Siena, San Gimignano, Chianti and Pisa from Florence

The best of Tuscany in one day: explore the fascinating Medieval towns of Siena and San Gimignano, followed by wine and lunch in Chianti and a visit to the world-renowned Leaning Tower of Pisa!


  • Semi-Private Experience: maximum 8 passengers (contact us for larger groups)
  • Discover the best of Medieval and Renaissance Tuscany in a day
  • Visit Siena, San Gimignano and the Leaning Tower of Pisa
  • Learn about Tuscan wine at a prestigious winery and sample some top Chianti wines


Centuries ago, young European and American aristocrats would set off on a cultural tour throughout Italy. The birthplace of Western history, culture and art – what better place than Italy to provide the backdrop for this quintessential voyage known as the Grand Tour. We’ve recreated this legendary journey to bring you one of our Flagship Tuscany tours!

Combining visits to the most remarkable medieval towns and the rolling Chianti hills, unforgettable views and flavorful culinary and wine experiences abound on this Semi private day trip through the heart and soul of gorgeous Tuscany.

Depart in full comfort aboard our state-of-the-art luxury van with your dedicated English-speaking driver and tour escort and arrive in Siena. Set in a beautiful landscape and surrounded by vineyards and olive groves, experience one of the most enchanting medieval cities in Italy.

Led by an expert local guide, take in the highlights of this fascinating town such as the marvelous Piazza del Campo where twice a year dashing horses compete in the highly celebrated Palio race right through the heart of Siena.

Then travel on to San Gimignano, UNESCO World Heritage Site and one of the most splendid examples of an ancient walled town. Renowned as “the city of beautiful towers” or “Tuscany’s Manhattan” it boasts an exceptional skyline, is one of the best preserved towns in all of Italy and has been featured in important Italian and Hollywood films alike.

Stroll along the cobblestone streets at leisure and admire the massive towers that once served as dwellings and now characterize this town. After taking in the characteristic local atmosphere, set off across the vineyard-clad Chianti hills for an authentic Tuscan lunch with wine tasting on the grounds of a boutique winery. Savor the authentic Tuscan flavors and enjoy a private visit to the estate’s wine cellar. After lunch we’ll stop at nearby Impruneta to learn all about the extraordinary local terracotta production, and then travel on to Pisa.

On the final leg of our journey, explore Pisa and the Piazza dei Miracoli (Miracles Square), with the world famous Leaning Tower, Romanesque Duomo, and Baptistry. The one and only Leaning Tower, created as the bell tower of the Pisa Cathedral, has been proposed as one of the seven wonders of the modern world and is truly a sight you’ll never forget. At the end of the visit travel back to Florence in full comfort, as your eyes and heart relish in the memories of your Tuscany Grand Tour.


  • Professional English speaking driver/tour leader
  • Round-trip transportation from Florence by luxury van
  • Guided walking tour of Siena with professional English speaking guide
  • San Gimignano visit with free time
  • Typical Tuscan lunch in a fascinating Chianti boutique winery
  • Winery guided tour and wine tasting learning about wine production
  • Pisa visit with focus on Miracle Square and Pisa Leaning Tower (tower tickets not included)


  • Gratuities
  • Personal extras
  • Entrance to the Leaning Tower

Know before you book

  • Confirmation is not immediate. Use the booking calendar on this page to select a date and time. No payment is required until we confirm your booking or suggest an alternative (typically within 24 hours).
  • Tour departs rain or shine
  • Due to the route covered and/or the means of transportation used, it is not possible to participate in this tour using a wheelchair, scooter, or other aid. Please contact us to inquire about customized tour options for guests with mobility challenges
  • Meet your guide on site

Know before you go

  • Bring a hat and sunblock during summer months
  • Bring water to drink
  • Wear comfortable clothes and shoes

Cancellation Policy

  • Up to 48 hours before the beginning of the activity: full refund
  • Less than 48 hours before the beginning of the activity or no-show: no refund

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