Private Tour of Siena, San Gimignano and Chianti, Departing from Florence

8 h
Day Trips & Excursions
difficulty Easy
Wheelchair Not Accessible
Best reviews

We could not have asked for a more pleasant experience

Polo C
Pick up included

Private Tour of Siena, San Gimignano and Chianti, Departing from Florence

Join our exclusive tour of Siena, San Gimignano and the Chianti countryside from Florence. Discover the best of Tuscany with our unique activity from Florence, including a tour of San Gimignano and Siena, but also the pleasure of admiring the Chianti countryside.

Explore the amazing landmarks and landscapes of Tuscany
Visit the superb medieval city of San Gimignano and its heritage
Discover the unique heritage of Siena
Learn more about the famous Palio horserace in Siena
Admire the unique sights of Chianti countryside

Fall in love with Tuscany with this inspiring experience from Florence, a tour that will reveal the inner beauty of the Tuscan countryside and its most magnificent highlights. You will have the chance to see and learn more about Tuscany and Italy, with our private tour of Siena, San Gimignano and the Chianti countryside, an area that is so rich in natural and cultural heritage, creating one of the most beautiful regions in the world.

A private tour to discover Siena, San Gimignano and the Chianti

The first stop of this tour of Tuscany from Florence is the spectacular town of San Gimignano, famous for the 13 tall towers that give the town skyline a special charm. Located along the ancient Via Francigena, popular in the past for travelers going to Rome, San Gimignano has prospered and along dozens of high towers, the town also preserves a beautiful cathedral and other treasures.
The tour of San Gimignano will reveal all of its heritage and atmosphere, so you will discover some of the more interesting towers, the “Duomo”, the “Palazzo del Popolo” and the “Palazzo Nuovo del Podesta”, serving as a town hall today. One of the most pleasant experiences in San Gimignano is exploring its authentic streets and discovering the small traditional shops that may have been there for centuries.

Admire the Chianti and its gems

Following the road to Siena, the tour of Tuscany will stop in Monteriggioni, a spectacular village built on a hill to survey an ancient Roman road, preserving its impressive medieval walls. Built by the people of Siena to control the road against their enemies from Florence, Monteriggioni is today one of the most authentic destinations in Tuscany.
The amazing activity from Florence will continue with the beautiful city of Siena, birthplace of Saint Catherine and one of the most enticing Italian cities. With its Siena red colored bricks and narrow streets, lovely piazzas and beautiful churches, Siena makes for a perfect destination.

Visit Siena and its amazing attractions

The tour of Siena will certainly include its most interesting highlights, like the tall Torre del Mangia, or the impressive cathedral. But probably the most famous landmark of Siena is Piaza del Campo, where the popular “Palio” horse race takes place two time a year. Considered the symbol of Siena, the race involves the whole population and has a history of many centuries where the neighborhoods of Siena battle for the pride to win the Palio banner.
These and many others will be revealed during your tour of Siena. Driving back to Florence, we will take time to admire the stunning landscapes of Chianti region, following the famous Chianti Wine Road. You will have the chance to admire several of the traditional villages and towns of Chianti.

  • San Gimignano
  • Monteriggioni
  • Siena
  • Chianti
  • Professional English-speaking driver
  • Transfer by car or minivan with air conditioning
  • 8-hours tour
  • Pick-up and drop-off in Florence
  • Tour guide (available on request)
  • Lunch
  • Tips (optional)
Meeting point: 

Meeting point information and local telephone numbers at your destination are included on your Confirmation Voucher.


As this is a private tour, you can customize the itinerary as you prefer, adding stops or spending more time in one place instead of another.
We suggest you wearing comfortable clothes and shoes.

Confirmation will be received within 48 hours of booking, subject to availability. Once your booking is confirmed we will email you a voucher. This is your ticket and proof of purchase.

Reviews of Private Tour of Siena, San Gimignano and...

Reviewed by Polo C from Stati Uniti

Tutto bene

My wife and I had ourselves a wonderful day traveling through Tuscany with Stefano as our punctual, friendly, amusing, and knowledgeable guide. We not only enjoyed the tour but his company. From beginning to end we had an ongoing conversation on just about everything. Stefano recommended a place for lunch in Siena that was perfect. He also gave us some recommendations for places to eat in Florence including a fantastic restaurant for pizza. We could not have asked for a more pleasant experience.
Reviewed by PeggyKaz from Stati Uniti

Full day Tuscan countryside tour

We did the full day tour of the Tuscan countryside (Sienna, San Gimignano, Monteregione, lunch and winery visit/tasting) with Francesco. Everything about it was excellent. Francesco even went beyond the scope of the tour by taking us up to Piazza Michelangelo for a view over the city. I highly recommend this day trip.