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Best of Tuscany Hill Towns Private full day tour (Siena & San Gimignano)

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Firenze, Italy
Best of Tuscany Hill Towns Private full day tour (Siena & San Gimignano)

From $232.14

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icon8 hours  (approx.)
Mobile ticket
iconOffered in: English
Good for avoiding crowds

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Explore the world-class Chianti wine region on a day trip from Florence. Stop to explore Siena's sights independently, discover the hill town of San Gimignano, famous for its medieval architecture and incredible vistas. Enjoy the delights of the town of Monteriggioni. Numbers are limited to 6/7 people per van on this tour to ensure an intimate experience.
  • Small group day trip from Florence to the hill towns of Tuscany
  • Visit the medieval towns of Siena, San Gimignano, and Monteriggioni
  • Explore the hill town of Siena independently
  • Enjoy the personalized attention of a driver-tour escort (a driver-tour escort drives and guides our guests) on a small-group tour limited to six-seven people / Min 2 people for guaranteed departures
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A/C Mercedes vehicle or similar make
Local Expert English Speaking Driver-Escort
Visit Siena, San Gimignano and Monteriggioni Hill Towns
Hotel pickup and drop off
Food and drinks, unless specified
Piazza della Repubblica , Piazza della Repubblica, 50123 Firenze FI, Italy

The meeting point is in front of Cafè Paskowski in Piazza della Repubblica in Florence, 10 minutes prior the departure of the tour.

This activity will end right where it started.
Your tour will begin in central Florence, where you’ll join your your driver-tour escort and hop aboard your minivan. Head first to the Tuscan hill town of Siena, known for its Palio di Siena, a horse race held twice a year in the main square.

Continue to the medieval town of San Gimignano. Take a leisurely walk with your your driver-tour escort to admire the Gothic and Romanesque architecture, and enjoy stunning vistas from the prominent landmark of the Torre Grossa.

Make your way back to Florence along the scenic route through the Tuscan countryside, stopping in the villages of Monteriggioni before returning to your original departure point in Florence.

PLEASE NOTE: The order of the places visited might change.
Pass By:  
Piazza della Repubblica
Your Southern Tuscany semi-private tour will start at 8 am from Piazza della Repubblica in Florence where you will meet your driver-escort.
Stop At:  
With your Avventure Bellissime driver-escort you and your small tour group will leave from Florence city centre and, from there, you’ll drive through the gorgeous Chianti countryside. The first stop is at 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 time in Siena touring the city and experiencing its medieval narrow streets.
Duration: 2 hours 
Admission Ticket Free
Stop At:  
San Gimignano
After lunch we will then travel to San Gimignano, one of the most charming and picuresque Tuscan hill towns. It boasts medieval towers that were built for the richest families of that period. You can visit the cathedral, climb the ‘Torre Grossa’, take pictures of the stunning scenery which will be surrounding you and enjoy gelato in Cistern Square.
Duration: 1 hour 30 minutes
Admission Ticket Free
Stop At:  
After leaving San Gimignano, the tour returns to Florence via the Chianti area once again. We will 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 in his most famous work - the Divine Comedy.
Duration: 45 minutes
Admission Ticket Free
Pass By:  
Piazza della Repubblica
Your day tour will conclude in Piazza della Repubblica at 5 pm.
  • Confirmation will be received at time of booking
  • Children must be accompanied by an adult
  • 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.
  • It is client’s responsibility to check if the provider of the service has sent any communication up to the day prior to the tour departure – Failing in checking your email inbox might incur in extra costs involved with the excursion you have booked, and that will not be refundable.
  • Not wheelchair accessible
  • Near public transportation
  • Infant seats available
  • Operates in all weather conditions, please dress appropriately
  • All passengers pay the same rate irrespectively from their age
  • Beginning Friday 6 August 2021 and until further notice, access to museums, galleries and all related tourist venues as well as indoor bars and restaurants, will be permitted only to those in possession of a Green COVID-19 Certification (Green Pass or equivalent certificate). Please remember to also bring your ID or passport to confirm your identity. This doesn’t apply to children less than 12 years old.
  • Most travelers can participate
  • This is a private tour/activity. Only your group will participate
  • OPERATED BY Avventure Bellissime
You can cancel up to 24 hours in advance of the experience for a full refund.
  • For a full refund, you must cancel at least 24 hours before the experience’s start time.
  • If you cancel less than 24 hours before the experience’s start time, the amount you paid will not be refunded.
  • Any changes made less than 24 hours before the experience’s start time will not be accepted.
  • Cut-off times are based on the experience’s local time.
  • This experience requires a minimum number of travelers. If it’s canceled because the minimum isn’t met, you’ll be offered a different date/experience or a full refund.

Learn more about cancellations.

The answers provided below are based on answers previously given by the tour provider to customers’ questions.
What is the policy on face masks and attendee health during Best of Tuscany Hill Towns Private full day tour (Siena & San Gimignano)?
A:The policies on face masks and attendee health are:

  • Face masks required for travelers in public areas
  • Face masks required for guides in public areas
See all safety measures taken by Best of Tuscany Hill Towns Private full day tour (Siena & San Gimignano).
What is the policy on sanitization during Best of Tuscany Hill Towns Private full day tour (Siena & San Gimignano)?
A:The policies on sanitization are:

  • Hand sanitizer available to travelers and staff
  • Gear/equipment sanitized between use
  • Transportation vehicles regularly sanitized
See all safety measures taken by Best of Tuscany Hill Towns Private full day tour (Siena & San Gimignano).
What is the social distancing policy during Best of Tuscany Hill Towns Private full day tour (Siena & San Gimignano)?
A:The policy on social distancing is:

  • Social distancing enforced throughout experience
See all safety measures taken by Best of Tuscany Hill Towns Private full day tour (Siena & San Gimignano).
What measures are being taken to ensure staff health & safety during Best of Tuscany Hill Towns Private full day tour (Siena & San Gimignano)?
A:The policy on staff health & safety is:

  • Guides required to regularly wash hands
See all safety measures taken by Best of Tuscany Hill Towns Private full day tour (Siena & San Gimignano).


54 Reviews
2 stars

Reviews by Viator travelers

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Showing 1-10 of 54 reviews
Our guide Yaris was the best. He was...
anthony d
, Apr 2018
Our guide Yaris was the best. He was so knowledgeable and gave us the experience of our lives. My 16 year old daughter thought this was the highlight of our 10 day trip.
I had an excellent experience with...
, Oct 2017
I had an excellent experience with this tour, and would recommend it without reservation. We were a small group with our guide/driver Giuliano and our guide in Siena, Adele. We rode in a clean mini-van and were not crowded at all. Giuliano spoke excellent English and was an expert with wines - from grape growing, wine making, aging, bottling, distribution and even to grappa. He was able to answer all the questions in a very clear, very pleasant and helpful way. Our guide in Siena, Adele, is Sienese, and we learned a lot about the various churches and saints as well as the various contrade in Siena that compete in the famous Palio. We stopped at a family-run farm just outside of San Gimignano, where we had the various wines from the family's properties in San Gimignano and in Siena. The wines were excellent. All of the family were helping - we had Pietro, one of the sons, to help us. He explained everything in great detail, very clearly, and very thoughtfully. It was a pleasure to meet him and to taste his family's wines. We were served lunch, as part of the wine tasting. Because we were a small group, we were able to also see Monteriggioni just outside of Siena, the walled village built by the Sienese as a outpost against the Florentines in the 1200's. We also drove through Chianti on our way back and saw the Abbey of Badia a Passignano, as well as the little medieval town of Montefioralle. A very memorable trip!
Sadly, this was the one thing we did...
, Jun 2017
Sadly, this was the one thing we did during our two weeks in Italy that I actually regret. I spent hours researching tours and finally chose this one based on the towns, description, and premium price tag. However, we spent most of the day in the car! We started the day by stopping in a small town not Sienna and were told we had 10-15 minutes to explore and then to be back at the car. You can't do anything in 10-15 minutes?! We then drove to Sienna where we were dropped off by our driver and had a private 2 hour walking tour by a local guide named Isabella. Isabella was wonderful! However, the tour does not mention that you are going to a church, so I didn't have anything to cover my shoulders with. I specifically chose this tour because it doesn't mentions churches. We wanted to see and explore the town. We had no free time in Sienna to explore, shop, eat etc. The description mentions to start the day in Siena and then go to lunch - so we assumed there would be more free time to enjoy Siena and not feel rushed again. We then loaded back up and drove 30 minutes to another tiny town. Again we had 10-15 minutes to quickly explore and be back at the bus. After another 30 minute drive, we went to a vineyard in Chianti. This part of the tour was accurate and we enjoyed the quick winery tour, tasting, and lunch. We started the tour at 9am and did not eat until 2pm, so I would bring a snack! Our final stop was San Gimignano. We had about an hour to explore and hang out. The tour mentions that you will take a walk with your guide. Nope..driver stayed with the car and we were on our own. The town was a bit of a tourist trap and hard to navigate by ourselves. Many other large tour buses stop here, so it was crowded and not ideal. We then headed back to Florence. The description says Sip on more flavorful local blends before returning to your original departure point in Florence. That didn't happen at all. The only wine we had a day was at the vineyard. So, with all of that being said I would recommend getting a private tour guide and creating your own itinerary or renting a car and driving yourself! We spent more time in the car driving from place to place than we actually spent in all of the towns! I would have much rather taken the 15 minutes plus driving time from the two tiny towns and spent that time in Sienna. For 250 pp, I would have expected a much better experience. Regardless of the money, it was time we could not get back. I would have much rather spent those hours exploring than sitting in a van all day.
This was one of the best days we had...
, Jun 2017
This was one of the best days we had in Italy. An absolute MUST. The guide/driver was so friendly and knowledgeable. The vineyard was remarkable.
This trip was amazing. It was great...
Cheryl Y
, May 2017
This trip was amazing. It was great having a small group. You didn't feel lost in the crowd. Our driver/main guide was very charming and fun. Siena and San Gimignano were so beautiful and interesting. Our guide in Siena was lovely and very knowledgeable. She is from Siena and that made it even more fun. The vineyard we visited was beautiful and the tour was very informative. More importantly, the wine was wonderful and the lunch served was excellent. Be prepared to walk a lot and keep in mind that you will be doing a lot of climbing. The cities are built on hills so you have a great deal of climbing and steep inclines but the pace was slow so not too difficult. Wear good walking shoes. Also, you will be visiting a lovely church, so no shorts and no bare shoulders ladies. Carry a light shawl or scarf with you to put over your shoulders.
Our driver/guide was knowledgeable...
, Oct 2016
Our driver/guide was knowledgeable, interesting and friendly. Our local guide in Siena showed us a personal side of the city, walking through neighborhood and learning the history of this beautiful city. Our lunch and wine tour in Chianti was beautiful and delicious! Great tour!
A great tour. Our tour guide...
, Aug 2016
A great tour. Our tour guide, Jakamo, knew the areas very well and was a really valuable part of the tour. Each town was unique and really gave us a good sense of Italy that we couldn't have gotten in Florence or as part of a large group, and the winery visit was a nice addition. Definitely a fun and interesting day.
Great history lesson, and vineyard...
Amily H
, Jul 2016
Great history lesson, and vineyard experience. If your looking for more tasting, I'd recommend the all day wine tour by viator.
Our tour guide driver Jonathan ,was...
Richard S
, May 2016
Our tour guide driver Jonathan ,was a wealth of information ,pleasant, and very accommodating, a great day with him. Elizabeth ,the tour guide in sienna was also a wealth of information and showed us the nooks and crannies of Siena, what a pleasure .
Great tour despite having a relative...
Richard H
, Sep 2015
Great tour despite having a relative quiet driver and guide. Although he offered little knowledge about the area, the tour itself was great - going to wonderful wineries and shopping in Greve.
Beautiful, breathtaking...
Joseph S
, Sep 2015
Beautiful, breathtaking, countryside!! The growers of the two vineyards we visited were very hospitable. Our guide Giacomo was quite knowledgeable, a gem.
Great tour, wonderful friendly guide...
Edward K
, Jun 2015
Great tour, wonderful friendly guide. Highly recommended day trip from Florence
We had a lovely day on this tour and...
Mary H
, May 2015
We had a lovely day on this tour and enjoyed our guide, Lorenzo. He didn't rush us although we got back an hour later than scheduled, but none of us minded and was a wealth of knowledge about the area. We got to see places we'd never know about otherwise -- small towns on the outskirts of Florence. As for the wineries, we enjoyed them, and the settings were lovely, but we weren't overly impressed with the wine. Also, beware that a tasting at these is MUCH larger servings than tastings in the US. Over the course of the day we were each served almost a full bottle of wine - too much for our interest, especially on the curvy roads. But it was a relaxing day in a beautiful setting and a nice way to get away from the city.
This tour was very good. Our...
Chris A
, May 2015
This tour was very good. Our driver/guide was very informative, the terra-cotta factory tour was very nice, we went on Saturday so got to go to the city market in Greve which was very nice and the winery visits/tasting were GREAT! The only thing I would recommend would be to add one more winery visit into the tour.
Good bus, Jacamo an excellent driver...
Anne N
, May 2015
Good bus, Jacamo an excellent driver we saw the countryside and had frequent stops. Not suitable because of timings to take photos but most enjoyable wine tastings. No lunch available at a trattoria but purchased at the first vineyard meat and cheese platter for 15 e each. Very informative tasting at our second stop but unfortunately due to other visitors there was no room for us to sit outside for our tastings which would have been nice. Overall very nice to get out of the city and see the countryside.
Fantastic tour. The scenery was...
, Oct 2014
Fantastic tour. The scenery was amazing and the wineries and towns we visited were just perfect. The van was very comfortable for the drive and the length of the tour was just right. Our guide Fabrizio (forgive me if I've spelled his name wrong) was the best. He went out of his way to pick up other people on the tour who were late, took us to a few spots that weren't necessarily part of the tour (like stopping on the hill above Florence for pics, etc). One of the people on the tour left her phone behind at a previous stop, and Fabrizio called back, arranged to have someone he knew look for it and then got it back later in the day and was going to deliver it to the hotel of the person who lost it. Top notch service for sure.
Our guide was so knowledgeable and...
Sharon M
, Oct 2014
Our guide was so knowledgeable and helpful. We had a wonderful day learning about the Chianti region. What a great experience.
Great guide with a passion and lots...
Brian N
, Sep 2014
Great guide with a passion and lots of energy. Winery was reasonable and nice selection of wine. Couple of stops for pictures. Well worth the money.
Excellent. Loved the terra cotta...
Joanne T
, Jun 2014
Excellent. Loved the terra cotta factory. Nice variety. Excellent tour guide(Lorenzo)
Our Small Group Chiati Wine Region...
Helen D R
, May 2014
Our Small Group Chiati Wine Region Day Trip was outstanding! It was definitely one of the best tours I have ever taken. We had a terrific driver and guide-Tiberio. He was very informative and told us many interesting facts about Tuscany. I especially liked that this tour included a visit to a pottery factory, medieval castle and market town as well as two wineries. The only negative for me was I was expecting lunch to be on our own. Instead it was at the first winery and was a sampling of cheese,salami and prosciutto shared by two persons. I did not.know that was our lunch and we paid 15euros each for it. Still having said that, it was a fantastic trip and we thoroughly enjoyed it.

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