Tuscany Day Trip from Florence: Siena, San Gimignano, Pisa and Lunch at a Winery

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  • Duration: 11 to 12 hours (approx.)
  • Location: Firenze, Italy
  • Product code: 5070TUSCANY
From USD $70.39
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Adult (Age : 18 to 99)
Child (Age : 0 to 7)

This is a typical itinerary for this product

Stop At: Florence, Florence, Tuscany

We will meet at the front of Santa Maria Novella train station at 7:45am, ready for an 8.00am start. Your guide will be holding a WALKABOUT TOURS sign, right by the taxi stand at Santa Maria Novella train station across from the outside McDonald's. After meeting your expert guide, an air-conditioned coach will whisk you away to the first stop of the day, Siena. The drive to Siena will take about 1 hours 15 minutes. During the journey, your guide will explain the itinerary for the day and entertain you with interesting facts about Siena and Tuscany!!!

Duration: 15 minutes

Stop At: Siena, Siena, Tuscany

Siena is a real medieval gem and in fact one of Tuscany's most famous and beautiful hill top towns. When you arrive you will join a 1 hour guided walking tour with a local city guide through Siena's most beautiful streets and sites, including the entrance to the Cathedral, a treasure chest of artworks. Afterwards, enjoy Siena at your own pace with free time for shopping or relaxing in an open-air cafe.

Duration: 3 hours

Stop At: Piazza Salimbeni, 53100, Siena Italy

The first stop on the walking tour of Siena is a bank that has its headquarters in this square - the oldest surviving bank in the world. It's called Monte dei Paschi di Siena and it has been running continuously since 1472. Your guide will explain how Siena's wealth through the centuries came from being on the pilgrim route known as the Via Francigena, a route that led pilgrims between Rome and Northern Europe. Siena prospered as a banking town by lending money and exchanging money for the merchants who were using the pilgrim route as a safe travel route. The Sienese are still wealthy from their banking past and are still famous for their banks today!

Duration: 15 minutes

Stop At: Contrada della Torre, Siena Italy

Your local guide will then walk through some of the most picturesque back streets of Siena, while telling about something very unique to Siena are the 17 districts which make up the historical centre.The name for these ancient divisions is 'contrade'. Each contrada has its
own symbol, normally that of an animal including a snail, rhino and giraffe amongst others. The sense of identity and belonging to ones 'contrada' is extremely important. They are self-contained little worlds with their own church, where newborns are baptised, and a public fountain where the newborns are baptised a second time! Needless to say there are strong rivalries between these districts, that explodes during the Palio horserace held twice a year in Piazza del Campo.

Duration: 15 minutes

Stop At: Piazza del Campo, 53100, Siena Italy

Piazza del Campo is one of the most beautiful squares you will ever see and it is also the city's gathering place, where the locals meet for a coffee and to chat and of course gossip. The unusual square (actually not a square, it's in the shape of a sea-shell, and sloping!) is the site of the famous Palio horse-race. A 600 year old tradition of Siena. The piazza gets transformed into a racing track twice a year and the contrade, or neighbourhoods of the city battle out for the highest honour possible – winning the palio. You'll hear more about this on the tour, your local guide will set the scene so that you can somehow live for a moment the vibrant atmosphere of this incredible race.

Duration: 15 minutes

Stop At: Duomo di Siena, Piazza del Duomo 8, 53100, Siena Italy

Our walking tour then ends inside the Duomo of Siena – undoubtedly the jewel of the city. If you've seen the interior of Florence's Duomo, it is nowhere near as spectacular as Siena's. The most unique part of this city's cathedral is its floor. It's an artwork on its own, made out of the world's most precious marbles – in fact, it's a combined masterpiece of over 50 images created over 2 centuries by some of Italy's most important artists. Then, enjoy walking through the city center on your own before meeting your guide again to head to your next stop!

Duration: 15 minutes

Stop At: Fattoria Poggio Alloro, Localita Montefalconi SNC, 53037, San Gimignano Italy

After the morning exploration of Siena, a 45-minute drive will take you the the next stop: Fattoria Poggio Alloro, an organic family-run wine estate – the highlight of the day! Visit the farm, enjoy an informal wine tasting lesson and a traditional Tuscan lunch with plenty of wine, in the most gorgeous location overlooking stunning views of the surrounding countryside. Take the opportunity to meet fellow travelers while feasting on fresh organic farm food of homemade pasta, cured meats (homemade prosciutto and salami), local cheeses, a real garden salad, and Tuscan biscotti. There is also the opportunity to buy the local products of the winery before heading to San Gimignano.

Duration: 1 hour 30 minutes

Stop At: San Gimignano, San Gimignano, Tuscany

After lunch, a 15-minute drive will take you to San Gimignano, that is an even smaller, walled Tuscan hill town than Siena - about 6 times smaller - and a UNESCO World Heritage Site. San Gimignano is most famous for its towers of which there were 72 though there are just 14 remaining today. From this the city gets its nickname of the little Manhattan of Tuscany. Your guide will give you a map and point out the best landmarks, so that you can roam independently the picturesque streets and squares of this enchanting hilltop town.

Duration: 1 hour 30 minutes

Stop At: Piazza della Cisterna, Piazza Della Cisterna, San Gimignano Italy

Your guide will lead you to the entrance city gate and that is where the main boulevard starts from, Via San Giovanni. This street will take you to Piazza della Cisterna, the heart of San Gimignano and also the setting for several films. This was the square where festivals and tournaments took place while the Piazza Duomo was the religious and political centre. This is also where the best gelato in the world is – Gelateria della Piazza 'Dondoli'. It's won many awards as the best gelato, you could try it and see what you'll think!

Duration: 20 minutes

Stop At: Piazza del Duomo, San Gimignano Italy

From Piazza della Cisterna, the next piazza along is Piazza del Duomo – the Duomo, also known as the Collegiata, is small but is well worth visiting! The beautiful interior of the cathedral walls is filled with colorful 14th century frescoes in every space available. You could also climb up one of the medieval towers here in this piazza, next to the Duomo (the Torre Grossa) to appreciate the incredible 'BIRD'S EYE' view over San Gimignano.

Duration: 20 minutes

Stop At: Rocca of Montestaffoli, Via della Rocca 6, 53037, San Gimignano Italy

Another stunning view over the towers of San Gimignano is from La Rocca. It is easily accessible behind the Duomo and It is a peaceful setting with olive trees and the wall surrounding the garden that formed part of the 14th-century fortress Medici of Florence built to protect this town from Siena. if you walk to the back of the garden and climb the steps to the top, the views over San Gimignano's skyline are absolutely breathtaking.

Duration: 20 minutes

Stop At: Pisa, Pisa, Province of Pisa, Tuscany

After the visit of San Gimignano, a 1 hour and an half scenic drive through iconic Tuscan countryside will take you to your final stop, Pisa.

Duration: 1 hour

Stop At: Piazza dei Miracoli, Piazza del Duomo, 56126, Pisa Italy

Upon arrival, your guide will lead you straight to the famous Square of Miracles. At first sight, it is truly breathtaking - the white marble buildings glow in contrast to the perfect, green lawns. You will have about an hour to explore the Cathedral, Baptistry, Monumental Cemetery, and of course - The Leaning Tower! Upgrade to include skip-the-line entry, if you wish.

Duration: 15 minutes

Stop At: Leaning Tower of Pisa, Piazza del Duomo Piazza dei Miracoli, 56126, Pisa Italy

During your time in Pisa, you can climb the Leaning Tower to admire the incredible views of the Square of Miracles from above. The views from the top of the Tower are truly breathtaking - from the monuments below, to the city surrounding the square, the Arno River, and the countryside in the distance... and part of the fun is also climbing the stairs inside the Leaning Tower that we will make you feel a bit dizzy at the end! To avoid disappointment, we suggest to upgrade to include the pre-booked tickets since the entrance to climb the Leaning Tower is according to time slots.

Duration: 30 minutes

Stop At: Florence, Florence, Tuscany

After leaving Pisa, it will take about an hour to return to Florence. You will dropped off at the start point with a camera full of pictures, a stomach full of hearty Tuscan food and a host of new friends.

Duration: 1 hour


  • Air-conditioned vehicle
  • Professional guide
  • Detailed maps of all destinations visited
  • 3-course lunch at a wine estate
  • Wine tasting
  • Free time to explore the towns at your own pace
  • Entry/Admission - Duomo di Siena


  • Gratuities
  • Hotel pickup and drop-off
  • Food and drinks, unless specified

Schedule Details

Departure Dates:

March 1 - November 30
December 1 - February 28
Monday, Wednesday, Friday and Saturday

Departure Point:

Piazza della Stazione, 50123 Firenze FI, Italy

Departure time

08:00 AM


11 to 12 hours(approx.)

Return details

Returns to original departure point

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Additional Information

Confirmation will be received at time of booking

Due to uneven surfaces, we cannot accept anyone with walking disabilities or using a wheelchair

Vegetarian option is available, please advise at time of booking if required

It is recommended to book any rail travel from Florence after 9pm to allow time for any traffic delays on your return journey

When the Duomo of Siena is closed for religious services, Santa Maria della Scala museum will be visited instead

Operates in all weather conditions, please dress appropriately

Please note: For the Leaning Tower of Pisa children under the age of 8 are not admitted. Children between 8 and 12 years old must be accompanied by an adult and held by the hand at all times while you are in the Leaning Tower of Pisa. Teenagers between 13 and 18 years old must be accompanied by an adult while you are in the Leaning Tower of Pisa

Not wheelchair accessible

Stroller accessible

Near public transportation

Infants must sit on laps

Travelers should have a moderate physical fitness level

This experience requires good weather. If it’s canceled due to poor weather, you’ll be offered a different date or a full refund

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

This tour/activity will have a maximum of 40 travelers

Hand sanitizer available to travelers and staff

Gear/equipment sanitized between use

Transportation vehicles regularly sanitized

Guides required to regularly wash hands

Paid stay-at-home policy for staff with symptoms

Posted By : Daydream17806815140
This trip was fantastic! Well planned at every step. Our guide Mano was incredibly knowledgeable, funny and truly did a superb job! He gave great background on Florence on the bus ride to Siena then handed off to the local tour guide Donatella for the walking tour. Donatella was a very cute extremely friendly lady who was a walking encyclopedia of everything Siena. She told us about the famous Pailo horse race and took us inside the gorgeous cathedral. Afterwards Mano had us watch a short documentary on the bus ride to lunch. Lunchtime at the organic winery was delicious! We had pasta, pork, vegetables and got to taste 4 amazing wines. In San Gimignano Mano gave us an amazing tip to try the world champion winning gelato. I got the blueberry ricotta and taste of Italy flavors. Yummm! Our last stop was in Pisa at sunset! We got to take lots of photos with the leaning tower and even went up to top to see the sunset over the cathedral and surrounding city. It was a busy day but amazing way to see Tuscany in a short amount of time.
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Posted On : 2022-12-06

Posted By : Angelina K
The trip was educational and fun. I would recommend the tour to anyone as it was family friendly as well. As well as telling us the historical importance of the buildings we visited, tour guide Sara and the bus driver Antonio were friendly and knowledgeable. The view of San Gimignano was beautiful and breathtaking. Pisa looked elegant and beautiful. The lunch was amazing and the wine was excellent. The sheer educational value and the scenic views are once in a lifetime experience. 11/10 would recommend.
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Posted On : 2022-12-06

Posted By : jackc1232020
Sara was the best travel guide ever with friendly vibes and immense knowledge about Tuscany ! The tour was filled with fantastic views coupled with great food and wine! Book it already :)
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Posted On : 2022-12-05

Posted By : sholl789
This is truly a TASTE of Tuscany. Be prepared to hoof it, a lot. This was a precisely measured tour. Time schedule was of utmost importance. Got a lot of information, took in beautiful sites and covered exactly what tour advertised. Best part was experienced guide Mano and Nickoli the bus driver. No worries just gotta follow direction.
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Posted On : 2022-12-05

Posted By : Jason_D
We covered a lot in one day with Mano. 3 towns and one winery lunch. Mano was a great guide and was very informative. We now know that we will definitely be back. I would highly recommend this trip, including the winery lunch.
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Posted On : 2022-12-04

Posted By : Sabine_R
If you have very little time it’s a great tour to take. However, be ready to climb stairs and up hill. It is a little rushed as there is a lot to see in a short time. It was dark by the time we reached Pisa. Make sure to carry change with you as u are required to pay for the use of restrooms. No restrooms on the bus.
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Posted On : 2022-12-03

Posted By : Swati_A
plus points 1. Sara (without an H) was the perfect guide for us. She kept us entertained all the time. 2. Perfect driving throughout 3. everything was well planned and ran on time. 4. plenty of time given to explore the towns even though we were on tight schedule.
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Posted On : 2022-12-03

Posted By : Anita_E
Everything about the trip was great from the incredible bus driver to the knowledgeable but funny tour guide, Stephan. They did everything they could to accommodate everyone's needs, even getting taxis for a few couples that needed them for the end of the tour.
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Posted On : 2022-12-03

Posted By : Tina_L
Stephen was amazing. At first I was shocked by the number of people and thought this would be a bad tour but wow - he worked his ass off and made it an amazing day for all of us.
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Posted On : 2022-12-03

Posted By : Sunshine22983212296
Even though it was a cold rain all day, the trip was great. Our guide kept things upbeat and fun. Angela had so much great info and was super friendly. I highly recommend to everyone.
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Posted On : 2022-12-03