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Best of Tuscany Hilltowns Semi-Private Full Day Tour

Spend a day visiting the best of Tuscany’s hilltowns on this semi-private (max 6/7 people and min 2 people) one-day sightseeing trip from Florence. Travel by luxury minivan with an expert English-speaking driver-escort, explore the idyllic hilltowns of Siena, San Gimignano, and Monteriggioni. With a small group, personalized attention, enchanting locations and free time at all destinations, your day seeing the best of Tuscany is a fantastic experience. Return to Florence by 5pm

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Highlights and what's included

  • A/C Mercedes vehicle or similar make
  • Local Expert English speaking driver-escort
  • Pick up and drop off in Florence city centre
  • Min 2 people for guaranteed departures / Max 6-7 people
  • Personalized attention
  • Visit Siena, San Gimignano and Monteriggioni Hilltowns


Choose a personalized and in-depth experience with this one-day tour showing you the best of Tuscany, from Florence. This tour of Siena, San Gimignano and Monteriggioni starts at 8 am and runs until 5 pm. You will have all the time you need to experience the beauty of the countryside.

Since you are in a small group, your very experienced English speaking driver - escorts have far more time to interact with you and answer any questions you may have.

Let’s take a look at what your tour looks like:

With your Avventure Bellissime driver-escort, you and your small tour group will leave from Florence city center at 8 am, driving through the gorgeous Chianti countryside. The first stop is Siena – a beautiful Tuscan hill town with its famous Piazza del Campo (Campo Square), where the famous Palio, a horse race, is held twice a year. Spend some time in Siena touring and sightseeing the city and experiencing its medieval narrow streets.

San Gimignano
After lunch, travel to San Gimignano, one of the most charming and picturesque Tuscan hilltowns. It boasts medieval towers that were built for the richest families of that period. Visit the cathedral, climb the ‘Torre Grossa’, take pictures of the stunning scenery surrounding you and enjoy a gelato in Cistern Square.

San Gimignano to Florence
After leaving San Gimignano, the tour returns to Florence via the Chianti area once again. Stop at the medieval and charming village of Monteriggioni, one of the most important and preserved walled castles in the area. Such was its importance – it was mentioned in Dante Alighieri’s most famous work - the Divine Comedy.


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  • Entrance fees if applicable
  • Gratuities( Optional)
  • All it’s not specified under “inclusions”
  • Lunch

Meeting Point

Your Best of Tuscany Hilltowns Semi-Private One Day Tour starts directly outside the Cafe Paskowski in Piazza Repubblica in Florence, where you will find your guide holding a sign with Avventure Bellissime written on it

Other Information

  • This tour is not fully accessible for wheelchair users or people with walking disabilities. However, please contact us directly and we will be able to take you on alternative routes suitable for you
  • Tour operates with a minimum of 2 participants
  • The tour begins at 8am in Florence and finishes at 5pm in Florence
  • Infant seats are available on request if advised at time of booking (children who are under 36 kg/97 pounds or 150 cm/4ft 9 in must use proper child restraints). We reserve the right to refuse infants or children if we are not notified at the time of the booking and if the car seats brought do not comply with requirements by Italian law.
  • Children must be accompanied by an adult

Key Information

  • Prices from: 179.00
  • Duration: 8 hours
  • Availability: View Calendar
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100 % of reviewers liked this tour.
Oct 10 2018
Great way to get out of Florence and experience the Tuscan countryside and Chianti wine
Sep 30 2018
The wine tasting did not offer a decent quantity lunch and when we asked for ice they claimed they ran out
Jul 06 2017
Informative. Interesting. Well organized. Thank you
Jan 22 2017
Love it! Highly recommend. Great driver and tour guide

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Best of Tuscany Hilltowns Semi-Private Full Day Tour


8 hours

From 179.00
Duration 8 hours
Best of Tuscany Hilltowns Semi-Private Full Day Tour
Start Date
End Date