Private Day Trip

Siena & San Gimignano private day trip from Florence

Key Details

  • Duration: 8 hours
  • Departure Time: Customizable
  • Language: English
  • Service Type: Private Day Trip
  • Departure Location: Florence & Tuscany
  • Availability:View Calendar

Do This Because

  • Explore the beautiful medieval city of Siena
  • See the magnificent Cathedral, the shell-shaped Piazza del Campo and much more
  • Stop in Monteriggioni for a picture of a 13th century hilltop fortress
  • Fall in love with the unique Tuscan landscape, driving through marvelous postcard views
  • Option to stop for lunch in a typical place to relax and enjoy a proper Tuscan menu
  • Stroll around the picturesque Town of San Gimignano famous for its Medieval Towers

What To Expect

Enjoy the top quality of this private tour from Florence to Siena and San Gimignano; the perfect experience to visit two of the most famous cities in Tuscany.
See the highlights of Siena, take a picture of the hilltop fortress in Monteriggioni, walk through the narrow streets of San Gimignano and admire the beautiful Tuscan countryside. All of this at your own pace and with the maximum comfort you can get only with a private door to door service


Full Description

The first stop of this private day trip from Florence to Siena and San Gimignano, after a scenic one hour drive through the Tuscan countryside, is Siena, the birthplace of the beloved Italian Saint Catherine.
This beautiful city made of brown Siena-colored bricks (so that’s how they named the color!), its jumble of narrow streets and delightful squares, the medieval towers that make such a spectacular skyline, its spectacular cathedral, the tall and trim Torre del Mangia, all together create an enticing atmosphere almost like stepping back in time.
Siena is built on three hills and is home to one of the most authentic and important Gothic cathedrals south of the Alps. Despite the city’s architectural masterpieces, it is the unusual shell-shaped Piazza del Campo that receives the most consideration having been seen in numerous films and photographs.
This brick covered square is used twice a year for the famous “Palio” horserace, an event that involves the entire population and is considered one of the most important events in the life of the Senese people. This reckless bareback race is run on July 2nd and August 16th, has Roman origins but has first been officially recorded in 1283. A kind of happy frenzy rules over Siena during the time leading up to the Palio and visitors can get the chance to observe the locals during the many ceremonies that are involved in the “Palio” race. Almost anything will be done to win this extremely competitive race and bring home the “Palio” a silk banner that will proudly displayed in the “contrada” or neighborhood it represents.
During your private excursion to Siena and San Gimignano from Florence, you will have the chance to stop in Monteriggioni a 13th century hilltop fortress.
Whilst travelling between Siena and San Gimignano you’ll be able to admire the typical Tuscan landscape (vineyards, olive trees, rolling hills, old stone buildings, etc.).
Your private day trip to Siena and San Gimignano will continue, with the stop in San Gimignano; a small medieval town in Tuscany, famous for its splendid skyline made up of 13 towers.
This 11th century town rises 334 meters above the Elsa Valley along the ancient “Via Francigena” on which traders and pilgrims going to Rome traveled. San Gimignano prospered considerably during this period thanks to this route and all the inns that were built along its way to accommodate these travelers. With prosperity, many patrons in San Gimignano were able to hire the best craftsmen and artists to magnificently decorate the churches and monasteries here. Dante Alighieri came to San Gimignano on May 8, 1300 as the Ambassador of the Guelph League in Tuscany.
Today, San Gimignano’s important cultural and natural heritage have been recognized by UNESCO. As in all of Italy, the Black Plague of 1348 greatly reduced the population of San Gimignano and led the city into a grave economic depression and caused the town to submit to Florence’s rule in 1353. Later in the centuries though, San Gimignano rediscovered its cultural importance and beauty together with its agriculture and eventually overcame its decline becoming the beautifully restored town it is today. In spite of its rather small size there is plenty to admire in San Gimignano.
Besides its 13 remaining towers (there were once about 40!), you can also see the “Duomo” or Collegiate Church and its magnificent frescoes, the “Palazzo del Popolo”, the “Palazzo Nuovo del Podestà” which is now the town hall. Other interesting places to see are church dedicated to Saint Augustine with its famous fresco cycle of this Saint’s life painted by Benozzo Gozzoli, the Museum of Holy Relics, and the infamous Museum of Torture and its macabre displays of early torture instruments.
You will love just wandering up and down the main street in San Gimignano and going in and out of the numerous specialty shops. The ceramics are beautiful here but there are also places for buying leather goods and linens.
For food and wine lovers there are many shops that sell delicious local products including San Gimignano’s “Vernaccia” white wine. You will be able to taste this wine in several of the wine stores in the town.
You private tour from Florence to Siena and San Gimignano will end with a relaxing drive back to your accommodation.


    Prices below are per party (not per person), vary depending on your party size, and are valid with pick up/drop off in Florence. For different pick up/drop off locations, large parties (9 or more people) or customized itineraries, please contact us
    - Party of 1-2 people - Euro 450.00
    - Party of 3-4 people - Euro 500.00
    - Party of 5-6 people - Euro 550.00
    - Party of 7-8 people - Euro 600.00

What's Included

  • Door to door service with pick up - drop off at your accommodation in Florence
  • Private knowledgeable English speaking driver to lead you through the experience (max flexibility, comfort and privacy)
  • Transport with fully equipped Mercedes vehicle
  • Free wifi and fresh bottled water on board
  • All taxes, tolls and gasoline
  • No hidden costs

What's Not Included

  • Entrance fees (if applicable)
  • Lunch (if interested)
  • Gratuities (optional and entirely at the client's discretion)

Things To Note

  • The above description is just an example of itinerary departing from Florence. For custom itineraries, different pick up/drop off location, we invite our clients to contact one of our tour coordinators to help them design their own itinerary
  • Although our past clients, on their reviews, prefer to name our drivers “guides or driver-guides” for their wealth of information, for the Italian law, all off the drivers (not just ours), are not allowed to leave their vehicle and walk/enter with clients, museums/churches/attractions.
    If you are interested in very detailed explanation about what you will see, or you prefer to have a guide walk around with you, or enter a museum/attraction, we can reserve this optional service, for an additional cost.
    How much a guide can enrich your experience, depends by the itinerary/attractions you are inetersted in and your level of interest, so if you are in doubt, ask us, and we will give our sincere opinion.

Siena & San Gimignano private day trip from Florence

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