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 $72.78
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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:

See Availability.

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 : Virginia_P
We had such an amazing day. Gloria was so informative and entertaining, Nichola was the best driver we could’ve asked for to take us through those super tiny roads. It is a great way to see the best of Tuscany if you only have a few days in Florence.
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Posted On : 2023-01-31

Posted By : Somasundr
Really was an excellent trip 👌👌 The guide Mr Allessandro was very good Me and my husband enjoyed the trip
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Posted On : 2023-01-30

Posted By : Angela Z
I was a great day from start to finish! Gloria was our guide and she was fantastic, full of knowledge, energy, and humor! Nicola was our driver - he was great too, making our ride so smooth throughout! Siena was beautiful - the Cathedral was stunning! Our local Siena tour guide was so full of energy and knowledgeable, too! Lunch was good at vineyard and view was gorgeous! San Gimingano was wonderful; gelato was super good! Pisa was fun too! Would highly recommend the tour!
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Posted On : 2023-01-30

Posted By : Joandleo
The Leaning Tower of Pisa was just amazing. And the views while having the lunch was just like the photos of Tuscany i had seen in the movies. Angelo(tour guide) was amazing, bubbly, friendly and knowledgeable and so helpful. And the bus driver Fabio was brilliant. Would highly recommend this tour.
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Posted On : 2023-01-30

Posted By : Sunshine44447140379
I had a great experience with Alexandero as the leader. He is engaging and knowledgeable about the places we are going and worked extremely hard to track down everyone in this largo group so we can be on time. The views of Tuscany and the medieval towns are still beautiful and memorable in cold January.
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Posted On : 2023-01-30

Posted By : nicholas_g
This was a 12 hour excursion & recommend good walking shoes. The tour guide Alessandro & driver Danielle were excellent. We drove through Tuscany as Alessandro explained the history of the area in an entertaining way. The stop in Sienna was led by guide Roseanne? Who was excellent describing the town’s architecture, history & the Cathedral. We then drove to an organic winery & farm for a delicious lunch & wine of course, then drove onto Pisa at dusk. It was a very enjoyable day. The only negative is although the coach bus is new & large, the bathroom was locked. Otherwise I would highly recommend this trip.
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Posted On : 2023-01-29

Posted By : Edwin_T
Wonderful tour guide n good driver. Knowledgeable in all areas and super lunch n wine tasting.It was a good itinerary as expected places I wanted to see. It was worth the money of such tour.
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Posted On : 2023-01-28

Posted By : jusetravel
This was an amazing tour. Our guide was friendly and know all the detail of the places we visited. Our Lunch, the views, and overall the whole tour was very good.
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Posted On : 2023-01-25

Posted By : Trish_L
Alex the guide was amazing! The wine tasting was so good but highlight was defo the Pisa! You have to climb up even if you don’t want to, it’s an experience! Sienna was a bit boring but overall it was nice
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Posted On : 2023-01-24

Posted By : Jennifer_C
Great trip to quickly see the sites, the driver and guide were great too. Four stars because the lunch at the winery was a waste of a meal and subpar at best. Save the extra €35 they charge and either bring your own or get yourself something else to eat. The wine was passable for cooking at best and nothing more and I’m talking—ALL varietals poured. I didn’t have the courage to try the vino santo after all 3 were unpalatable; the thin slice of baked pork was dry as a bone; hard to screw up potatoes that were heated in a microwave, and they sold that same undrinkable wine at the gift shop that was tourist overpriced. Thank god for the passable, sparsely meat filled ragu pasta to help get you through the day. Save yourself money and don’t purchase the wine at their store. You won’t even have to pay this much for a good local vin de table for a local vigneron at a grocery story with much better quality. Everything else had no complaints.
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Posted On : 2023-01-24