Tuscany Day Trip from Florence: Siena, San Gimignano, Pisa and Lunch at a Winery 10310 reviews
Florence, Italy

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  • Printed Voucher/E-Voucher
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What you can expect during your visit
  • Face masks required for travelers in public areas
  • Face masks required for guides in public areas
  • Hand sanitizer available to travelers and staff
  • Regularly sanitized high-traffic areas
  • Transportation vehicles regularly sanitized
To know more, please refer additional information section of this tour
Activity Highlights
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, Via di Salicotto, 76, 53100, 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! 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

Activity Details
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.
Departure & Return
Departure PointPiazza della Stazione, 50123 Firenze FI, Italy Departure Time08:00 AM
ReturnReturns to original departure point
What's Included
  • Air-conditioned vehicle
  • Professional English speaking tour guide with you for the whole day
  • Guided walking tour of Siena with entrance fee to the cathedral
  • Hearty farmhouse lunch – veggie and gluten-free options available
  • Wine tasting of four varieties
  • 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
Additional Information
  • Not wheelchair accessible
  • 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
  • Stroller accessible
  • 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
  • Near public transportation
  • Infants must sit on laps
  • 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
  • Travelers should have a moderate physical fitness level
  • 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
  • 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
  • Confirmation will be received at time of booking
Cancellation Policy
Free Cancellation - upto 24 hours in advance
Traveler Reviews

Average based on 10310 reviews.

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Traveler Photos

  • This trip was amazing. We had such a great time. Merilla was incredible, she is so knowledgeable and personable. Mosimo was a great bus driver, and the winery was delicious. Would highly recommend this trip Five stars
  • Everything was amazing. Definitely memorable. Loved all the sites, Siena being our favorite. Winery experience was also amazing. One thing of note, this is a group of 50 people. A lot of people thought reserved it thought that it was only a 30 person tour.
  • Not as expected. Transportation and bus times much longer than expected. Drop off and pickup points significant walk to/from attractions. Early morning meeting with significant walk to bus and late evening drop-off with significant walk back to taxi stand. Guide (Alice) was very friendly and tour was okay but not as expected. This was our first bus tour and I don't think I will ever book another. Not the right venue for us.
  • The trip was well organized and we had a great time exploring Tuscany. Our guide Manolo was excellent. He was very informative, patient, light hearted, and, overall great tour guide! We really enjoyed this trip and would highly recommend it!
  • Gabriel is a good tour guide. He kept our attention with his humor. All of Tuscany is worth exploring especially for a first timers like us.
  • Not as we read on the website. Tour did not end until after 9pm and the listing states 11-12hours when it was more than 13 hours. The listing also states no more that 40 people and the bus had over 53. Way to many people to keep up with the tour guide . I was on the back of the bus and by the time we got off the guide was already ahead walking so it was very hard to keep up with him between all the other tours and cars . Too many people for 1 guide. The listing does not state that the bus parks at least 1/2 mile from each stop so the time just walking from the bus to each location was a lot. The listing should state the walking tour is well over 3 miles walking from the bus to each location. The tour guide Davida was great. This your was mostly walking from the bus to the location and not enough time at each stop. One tour guide can not possibly get all 53+people thru 1/2 mile at least each to walk up and back to each location in between traffic and people. I was very disappointed in this tour. I emailed this company about the overcrowded tour 5 days ago with NO response.
  • Experiencing the medieval town of San Gimignano was breath taking. Climbing Pisa was a bucket list as well. Having the chance to visit these 3 cities in 1 day was amazing! Our guide “Alice” was great. She made the trip stress free. Highly recommend!
  • Tony and Tony were excellent! Entertaining and thorough. Brought the middle ages to life and you get a great slice of Tuscany. Beautiful! Would recommend an option to Walkabouts that they offer a Siena, San Gimignano, Lunch at Winery Option (minus Pisa). Think some people might have gone in the past, and it would make the day more reasonable.
  • It was really good, we were able to go to all the places described and the lunch was delicious, end of September is a really good time to go, a lot of people yes, but less than summer and the wineyards are ready to be harvested. Walkabout tour was perfect, great bus and guide.
  • The lunch on the Farm was wonderful. Alice was nice when she was not rushing us. The bus driver drove way too fast and we were bounced around like popcorn. The bus was uncomfortable. This 5’9” woman had her legs in her throat.
  • Although the tour ran a little long than projected, it was well worth the extra time. Our guide and driver (Giancarlo and Bruno, respectively) made the trip enjoyable and informative. As well the lunch at the organic farm was great. Overall, fabulous and if I would take the tour again I would want to be paired up with the same guide and driver.
  • Our excellent guide Manolo also our driver were amazing. For us we loved Siena best also the lunch ( wine !!). but it was all memorable
  • Tuscany day trip did not mention the great amount of walking. Sometimes it seemed quite unnecessary. Our bus was always much further from where we were going. It’s one thing to walk for an hour in Siena or San Gimignano, quite another to walk another 20 minutes to the bus
  • All in all this trip was worth it to get a glimpse of 3 different places very quickly. Honestly, I would have preferred to do just 2 places, so it wouldn't have been so rushed - St. Gimignano and Pisa. It doesn't help that bathrooms are not easily accessible, so time is wasted looking for one. The wine and cheese were good at lunch. For being in Italy, the pasta dish was not very good. Our guide Ludo was very good! She did an amazing job at keeping us all organized!
  • This was so worth the money. Our tour guide Manno was exceptional and was the bus driver. Really had good experience in all 3 cities and lunch was outstanding, way more than expected. Would recommend for sure.
  • This tour was a great way to take in several parts of Tuscany in a long day. Tour company Walkabout Tours was excellent great comfortable bus. Tour guide Anthony was very knowledgeable and kept the group organized and safe. The guide in Siena was great. She was very knowledgeable of the history of the town and present day activities like the horse races in the Piazza del Campo. The lunch at the winery Fattoria Poggia Alloro was excellent. The wines were great and the view from the restaurant terrace was spectacular. The stop at San Gimignano was perfect for a self guided tour and a must stop at Gelatera Donodoli. Best gelato. Do not let the lines deter you it moves very fast. It was then a beautiful drive down to Pisa for a short walk over to the Leaning tower. Again perfect amount of time spent there. A comfortable bus ride of just over an hour back to Florence catch a nap and end the tour. A very full day but a great way to see different areas of Tuscany in a day.
  • Great day exploring the best of the Tuscany region. Davide was a great guide and took a real interest in us all. Paulo was a great driver too. Highlights were San Gimignano, with the amazing views, and the lunch at a local Tuscan vineyard. Well organsised trip and would highly recommend to anyone visiting Florence!
  • The trip was wonderful. And a great value for what we paid. The bus was comfortable and the areas we visited were beautiful. The food at the winery was delicious and our guides David and Roberta were both informative, professional and fun.
  • Wonderful day. Favorite spots were San Gimignano & Siena. Breathtaking views. Fun lunch at the winery with excellent wines. Pisa was okay, more phenomenal if you climb to the top. Ludo was an excellent tour guide.
  • A must do tour. Our tour guide was Tony he was great. Very personable, kept us entertained with his upbeat charisma and was very knowledgeable! The lunch was excellent with plenty of wine included! Our driver also name Tony got us everywhere safely and on time! Amazing tour
  • Absolutely fantastic tour! From the iconic Leaning Tower of Pisa to the charming towns of San Gimignano and Siena, and finally, the picturesque Chianti Hills winery experience – it was a whirlwind of beauty and flavor. But what truly made it special were our guide, Davide and our driver, Carmine. Their knowledge, enthusiasm, and hospitality added an extra layer of magic to the journey. Grazie mille!
  • Marila was our guide for the day. The day started with Siena (using a local guide named Paul).Beautiful city. Lunch was at winery and the food was beautiful with the ability to buy some of the owners olive oil and wines with a gorgeous view. San Gimiginano was after lunch and then Pisa. Pay the extra and do the Pisa climb. Marila was funny, informative and a great guide.
  • Excellent tour. Well organized. Great guides. Lunch delicious and organic. We visited all the Tuscany area towns. Wonderful views. Recommended!
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10310 reviews
$91.47 USD
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