Private tour

San Gimignano and Siena Private Tour

Evocative historic Tuscan towns and a typical tasty dinner in Chianti countryside


  • Siena private tour with visit to San Gimignano
  • Discover Tuscany’s most charming historic towns
  • Leave the bustling crowds behind: set off in the afternoon! 
  • Lose yourself in the fiery Tuscan sunset
  • Luscious typical dinner and exceptional wines in the Chianti hills


EVERY DAY at 2 pm |From NOV to MAR: Mon, Wed and Fri at 1.00pm /


Approx. 8 hours






Quaint towns where time seems to have come to a halt. Mesmerizing piazzas and ancient traditions. Vineyards and rolling hills. A Siena private tour is the very best way to appreciate authentic Tuscany, and discover its heart and soul! All in full comfort, of course, with your dedicated driver and a charismatic guide for your Siena private tour.

Spend a memorable day exploring two small Tuscan gems filled with art and centuries-old historic reminiscences. Meet your private dedicated English-speaking driver and travel to Siena, one of the most enchanting medieval cities in Italy.

Meet your dedicated private guide and set off on a memorable walking visit of the town which yearly hosts the heart-stopping Palio. Siena, founded by the Romans, boasts an exciting history and striking architecture. And the local traditions are fascinating, like the famous Palio di Siena held in the town’s lovely Piazza del Campo. Here twice a year dashing horses compete in a thrilling race, the Palio di Siena, a tradition which dates back to the Middle Ages and still calls to all Sienese! Hear your guide recount fascinating legends as you wander down medieval streets, and visit the magnificent Duomo, Siena’s awe-inspiring Cathedral.

Depart Siena and enjoy the journey through the verdant Tuscan countryside: silvery olive groves, gently rolling hills dotted with golden farmhouses and quaint parish churches. 

After Siena, it will be time to visit another gem of Tuscany, delightful San Gimignano, for a leisurely stroll and a browse in the charming shops. Renowned as “the city of beautiful towers” it is certainly one of Tuscany’s most iconic and well-preserved ancient towns in the whole of Italy and has been used as a background in many movies. Roam the quaint cobblestone streets, see the graceful tall towers and browse the pretty shops lined by bottles of Vernaccia di San Gimignano, premium saffron, dainty hand-woven linens and precious hand-made Santa Fina pottery. After visiting San Gimignano set off once more, this time through the hills.

Admire the vineyards and, as the light starts changing and crimson-hued clouds come forth, stop at a charming boutique winery for a brief visit and memorable dinner. Crown your day in typical Tuscan style: a luscious typical dinner and sublime estate wines.
Our signature Siena private tour, with San Gimignano and dining is an unforgettable Tuscan lifestyle experience.


  • Private tour
  • Personalized attention
  • Transportation from/to Florence city center
  • English speaking driver/tour leader
  • Guided walking tour of Siena with professional English speaking guide
  • Surprise tasting in Siena (From 1st March 2023)
  • San Gimignano visit with free time
  • Typical dinner in a fascinating Chianti countryside location
  • Guided visit of the winery cellars
  • Wine tasting

Meeting Point

FLORENCETOWN BOOKING OFFICE - Piazza Mentana 2red - Florence - SEE ON MAP



Please inform us of any food intolerance or allergy in advance.

We regret to inform that this tour is not suitable for guests with wheelchairs or with impaired mobility.

Rain Policy

This tour runs rain or shine.

book now

from 362

from EUR 362 p.p. (price based on a party of 4 pax)

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