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

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Duration:11 hours to 12 hours (approx.)
Location: Florence, Tuscany

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Famous for a wealth of art, history, striking landscapes and outstanding produce, Tuscany really does have the best of all worlds! With only a day to spare, see the best Tuscany has to offer on this full-day guided coach trip from Florence.

WHAT'S INCLUDED

WHAT TO EXPECT

1.
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!!!
2.
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.
3.
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!
4.
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.
5.
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.
6.
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!
7.
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! 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.
8.
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.
9.
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!
10.
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.
11.
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.
12.
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.
13.
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.
14.
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.
15.
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.

ADDITIONAL INFO

• Infants and small children can ride in a pram or stroller
• Public transportation options are available nearby
• Infants are required to sit on an adult’s lap
• Travelers should have at least a moderate level of physical fitness
• Due to uneven surfaces, we cannot accept anyone with walking difficulties 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
• Full Tour option includes the visit to Pisa but not the ticket to climb the Leaning Tower
• Full Tour plus Leaning Tower Tickets option also include the tickets to climb on the Leaning Tower in Pisa.

CANCELLATION POLICY

Posted By : Lisamarie_M
This was a great way to see and learn about Tuscany! Noemi at Walkabout Tours was fantastic! The agriturismo for lunch was amazing, best meal of the trip. The towns were beautiful. Plenty of time to explore/shop on your own. It was very hot and there was a lot of walking. Long day but worth it!
Rating : full ratings
Posted On : 2024-07-02 05:18:13

Posted By : Jason_G
A great day which covered off everything we wanted to see. The best guide in Emma and awesome bus driver. Did was excellent at the winery and the scenery all round was to die for. A well organised tour and highly recommend them. Thanks for an awesome day.
Rating : full ratings
Posted On : 2024-07-02 05:04:43

Posted By : Garrett_B
Tony our guide was awesome, tour brings you to areas you would never really see because a casual traveler just won’t think about them. We did 3 tours in 7 days and saw ten times what we would have seen if we stayed in Rome. (We took train to Florence to do this)
Rating : full ratings
Posted On : 2024-07-02 04:40:00

Posted By : Kathryn_G
This was a great day trip! David was an awesome guide—he made it so much fun, while also being informative and interesting. I was very impressed by his ability to keep the large group on time and organized, so the size of the group was never an issue. Highly recommend this tour!!
Rating : full ratings
Posted On : 2024-07-02 04:38:04

Posted By : Kathy_K
Our guides were all so nice and punctual. Was a beautiful and enjoyable day with just enough free time to explore a bit t ourselves— definitely a must!!
Rating : full ratings
Posted On : 2024-07-02 03:53:18

Posted By : Sloan_Y
My family had an excellent time on this tour. The tour was well organized and our tour guide Tony was excellent. He gave good information, was personable and even took time at the end of the trip to answer any “general tourism” questions we had about Florence and Tuscany. If you do this your, I’d recommend trying to request Tony as your guide.

The three cities are beautiful, and the value of this tour versus arranging travel on one’s own cannot be overstated. The winery likewise was beautiful and the food, though not gourmet, was a welcomed addition. Lunch, though at a winery, was very thoughtful about children’s options as well.

We only had two components of the tour that could use improving. The separate Sienese tour guide was difficult to understand between her accent and her inability to use the audio technology well. Many of our group just stopped listening to her and enjoyed the scenery. The other point of improvement would be lunch which was quite hurried and left very limited time to explore the winery. If you are looking to tour a winery, this is probably not your best option.

Rating : full ratings
Posted On : 2024-07-02 03:42:24

Posted By : Sammi_W
Great tour, it’s 12hrs long but feels much shorter. We visited all the locations listed on the itinerary .Our tour guide David makes sure everyone is taken care of. He’s funny and informative.
Rating : full ratings
Posted On : 2024-07-02 03:41:34

Posted By : hazem_m
The whole trip was memorable what a great experience! From the views to the lunch and all along the guide David was amazing!
Rating : full ratings
Posted On : 2024-07-02 03:28:32

Posted By : Kevin_S
BEST tour my husband and I have had since being in Italy! Our tour guide was Davide, and the “vice president” driver was Emiliano. Davide made the tour run seamless while providing humor throughout the day. He clearly has a passion for what he does, which energizes the group for a great day. You start the day off in Siena where you have a local tour guide show you the city followed by free time. After, you head to San Gimignano. This has to be the prettiest view we have seen thus far. Our lunch at the vineyard was amazing, and then you head to town for free time. David’s recommended the world’s best gelato, and it was worth the wait! Ending the day in Pisa was incredible. Unlike other tours, this tour has ALOT of free time. Yes it is a long day, but you have more time out of the bus than on it. I would highly recommend this tour to anyone staying in Florence who wants to see Tuscany!
Rating : full ratings
Posted On : 2024-07-02 02:49:34

Posted By : trevorsZ969FI
Manila was an amazing tour guy with effortlessly and comprehensively, covering the history of our different tour sites. He worked in the history in conversation and timed his information sharing and kept everyone informed, calm, and added some humor as well. All were accounted for and comfortable and safe on the amazing tour bus with the driver Carmen (spelling unknown) who was fantastic.
Manolo is independent of the tour company and would succeed on other tours in Italy as well.
Rating : full ratings
Posted On : 2024-07-02 02:16:13