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

Firenze, Italy

From $81.32

Select Date and Travelers

Free cancellation
Up to 24 hours in advance.
  • 11 to 12 hours (approx.)
  • Mobile ticket
  • Offered in: English


Art, history, countryside, food. Tuscany has it all. If you only have one day free, venture into Tuscany on this day trip from Florence and discover the region's highlights with a local guide. Explore the medieval city of Siena and its cathedral before heading to the hills of Chianti for a 3-course Tuscan lunch and wine tasting. Roam the streets of San Gimignano, and travel to Pisa to admire the architectural drama of Cathedral Square—home to the UNESCO-listed Leaning Tower of Pisa. Upgrade to include skip-the-line entry, if you wish.
  • Spend a day exploring the Tuscan countryside on a tour from Florence
  • Take a guided tour through Siena, including entry to the gothic Cathedral
  • Set your own pace to explore Siena, San Gimignano and Pisa
  • Upgrade to include a hearty lunch and wine tasting at an organic vineyard in Chianti
  • Visit a UNESCO World Heritage Site—the Leaning Tower of Pisa
  • Tour is only in English to ensure maximum quality and customer service

Why Travelers Choose This Tour

The stop for lunch at the organic family-run wine estate in the Chianti area is the highlight of the day! Don't forget your camera - the view from the winery is jaw dropping

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

Meeting And Pickup

Meeting point

  • Piazza della Stazione
    Piazza della Stazione, 50123 Firenze FI, Italy

    Check-in: 7.45am - 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

Start time

08:00 AM

End point

This activity ends back at the meeting point.

What To Expect

Board your coach in Florence, and travel into the hills of Tuscany where the city of Siena awaits. Opt to take a guided tour of the city with a visit to Siena Cathedral to admire its renowned Gothic architecture. Or, make the most of some free time to set your own pace, and perhaps enjoy a coffee in the sun alongside the locals.

From Siena, return to the Tuscan countryside to explore the Chianti wine region. Stretch your legs with a stroll through a vineyard, olive grove and wine cellar, and refuel with a Tuscan winery lunch. As you sit surrounded by the grape vines, meet other visitors to the area and indulge in local treats such as cold cuts of meat, salad, pasta and fresh bread. Even better, a wine tasting takes place at the same time (not included in the tour option without lunch, guests will instead spend more time in San Gimignano)'

After lunch, journey onward to San Gimignano with its medieval towers, cobbled streets and squares. Explore the town’s historic center, cool down with a refreshing gelato and wander amid the 14 towers as you learn about their history.

Travel from San Gimignano to Pisa: your final stop of the day. Follow your guide to Cathedral Square to discover Pisa Duomo, Pisa Baptistry, the monumental cemetery (aka Camposanto) and, of course, the Leaning Tower of Pisa.

Return to Florence in the early evening, and finish your Tuscany tour with a drop-off at the start point.


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!!!

15 minutesAdmission Ticket Free


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 hours Admission Ticket Free

Additional Info

  • 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 tour/activity will have a maximum of 40 travelers

Cancellation Policy

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 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.

Traveler Photos

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Traveler Tips

Make sure to wear comfortable clothes and shoes - it's a long day but worth every minute!
Prepare for a long day, but it will be worthwhile.
Ensure to have good walking shoes, as there is a lot of walking.
10,548 reviews
Total review count and overall rating based on Viator and Tripadvisor reviews
Reviews by Viator travelers.
Showing 1-10 of 10,548 reviews
Worth the Day!
Amanda_F, Mar 2023
What a wonderful tour! I will recommend this to all my family and friends. Emiliano (bus driver) & Alex (tour guide) were fantastic! Emiliano expertly drove us through the Tuscany country. Alex has a vast knowledge of the history and made the trip so delightful! He answered all our questions and was a pleasure to spend the day with. DO TAKE THIS TRIP!
San Gimignano And Siena....
Adriana_K, Mar 2023
San Gimignano And Siena. The food at the lunch was superb as well as the four wines we tasted. The Tuscan countryside is enthralling. The bus driver, whose name I forgot, and Sara without an H , the tour guide, were both 🌟🌟🌟🌟🌟
Would not recommend
Katie_J, Mar 2023
Experience did not meet expectations. I thought the tour would be a bit smaller and more intimate, but there were literally hundreds of people on multiple large buses going to the same sites. While it was a good way to see a lot in a short time, each stop was very rushed, no restroom breaks after long drives, and the bus stopped a long way from each site and you spent most of your time walking in a sea of other tourists. Our tour guide was great though - she was friendly and helpful despite a difficult task of managing such a large group on a tight schedule.
Fun informative , lunch was awesome
Sebanti_M, Mar 2023
Though it was very good , I got lost and the bus almost left without me . ( which is not acceptable)For very large groups audio guides are a must of the guide has to wait a bit in Every corner . I have a problem in my leg and fell behind the group . However post this the guide was super careful .
Lived Siena and San...
Maria_G, Mar 2023
Lived Siena and San Gimignano and Giancarlo was great. Very organized and knowledgeable. Kathleen was also wonderful
Best experience
lisa_s, Mar 2023
Angela, was very good! She explained everything on our way to the tour and also made sure every person was happy. She was very knowledgeable. We really enjoyed Siena we’re we met another tour guide who was also very knowledgeable. We will definitely use this tour service again.
One of our best tour in Italy
Zhenyu_Z, Mar 2023
One of the best tours I had during my Italy trip. The place is amazing. The tour guide was a bit nervous because it's her first-ever tour group, but she did a good job. The only issue I have is about the toilet time. As Italy has no public toilets, the tour guide had to release everyone in a Sienna plaza and hoped everyone can find a nearby coffee shop for business. This resulted in 20 mins' delay. If she could remind people to use the toilet in the previously visited cathedral and let everyone know when the next toilet break will be, that will be better.
The best way to experience Toscany in one day
Sunny, Mar 2023
This was a wonderful trip. The tour was organized by the Walkabout Florence. Our guide Angelina was brilliant! - highly knowledgeable in history and architecture of the area. She was very pleasant and professional, and she gave us a good advice how to spend our free time (e.g. ice cream at Gelateria di Piazza in San Gimignano is a must!). Siena was beautiful, you will see Piazza del Campo with Pallazzo Pubblico and Duomo. Lunch was at Fattoria Poggio Alloro, with excellent wines. San Gimignano is a beautiful town, very pleasant to walk through. The last part is Pisa, with the Leaning Tower, Duomo of Pisa and Baptistery. Overall, a great trip, lots of walking, but the best way to experience Tuscany in one day.
Best tour of Tuscany region ever!
Guadalupe_H, Mar 2023
Really loved this tour! It was so much fun and Alessandro our guide was fantastic! He was so knowledgeable, personable and very organized! Our lunch at the winery was exceptional!! Delicious and plentiful!! One of the best tours I have ever done!
Great Tour!
Jessica_C, Mar 2023
It was an amazing trip. Our guide Alex was fantastic. Very knowledgeable and kind and energetic. I appreciated that he was very communicative and always explained what was happening and what to expect. It made the trip feel very organized. And the lunch was great and the time spent touring the towns were just enough.
Great tour
Natassha_B, Mar 2023
This trip was so great. I got to see and do so much in a single day. The tour was also well organized and punctual. Highly recommend it
10/10- would do again!
Savannah_M, Mar 2023
This was the most amazing experience we could of asked for. We were able to see so much of Tuscany in one day! Angelina was an incredible guide and extremely funny and knowledgeable! Roberto was an awesome driver as well!
Fabulous way to see Tuscany
Peggy_W, Mar 2023
We spent just the right amount of time at each location. We were lucky to have a sunny day which made the scenery come alive and was great for picture taking. Our guide Angela did a fantastic job keeping us on schedule and had a great sense of humor. Our driver Roberto was a very safe and skilled driver. Make sure to wear comfortable shoes for walking as there are a variety of surfaces as well as up and down hills to travel. The bus was comfortable and being provided extra water on the bus was appreciated.
Naomi was Amazing...
Evelyn_C, Mar 2023
Naomi was Amazing The information we were given was such a great learning experience and very informative. I lost the group and was so appreciative that the company called my phone and helped me get connected back to them !
The Best of Tuscany
christine_t, Mar 2023
This was an amazing tour! Our tour guide Gabriele was wonderful! He was so interesting and was very knowledgeable. Our guide in Siena was the best. The restaurant Fattorio Poggio Alloro is 5 star. The food and wine were delicious. Our bus drive Giancarlo was also great! I would highly recommend this tour.
Fun trip....lots to see and do
Kelli_M, Mar 2023
What an amazing day! Be prepared to go go go but it's worth it. I can't think of anything to take out to make more time so just rest on the drives between stops. The winery is superb and is actually one of my favorite meals of the entire vacation. We climbed Pisa...so amazing. This trip is a great time.
Great day trip - highly recommend!
Mikal_W, Mar 2023
This day trip through Tuscany was great! Our tour guide, Gabriel, was very nice and provided us with some interesting bits of information about the places we were visiting and some fun facts about life in Italy as a whole. We had a separate guide in Siena whose name I can’t recall, but she was very good and charismatic. Overall this was probably our favourite city of the three visited as we loved learning about the contrade and piazza del campo where the Palio takes place. Lunch at the organic vineyard was probably my favourite experience on our entire trip to Florence so far. The food and wine pairings were fantastic, and the view of the Tuscan country side from their balcony allowed for some amazing views/pictures. The final two destinations allowed for some more free time to roam. San Gimignano is well known for the Gelato (follow the guide’s recommendation) and we enjoyed sitting around the rocca for the views. Pisa is very much a destination where we went to look at the Cathedral, the Baptistry and the famous leaning bell tower of Pisa. All very neat considering it’s made out of marble but there wasn’t really much else to get too excited about. If you’re looking for an efficient way to see Tuscany’s finest outside of Florence, this is definitely for you! Side note: I can’t recall our driver’s name but he was also great and made great time getting us back to Florence ahead of schedule.
Good trip but way too long
Alina_V, Mar 2023
This tour is very packed, I would say way too much for one day. Prepare to walk very fast. Use the restroom ahead of the start of the trip because they do not wait for you if you have to stop during the tour. Pisa is the last stop, around 5 pm, by which you are already exhausted. I wish it was earlier in the itinerary. San Gimignano could be skipped, as they just want you to go to the ice cream shop at the top of the town. Pretty old city, but nothing special. Overall a good trip, just very long (got back to Florence at 8:15pm)
Jean_E, Mar 2023
It was a Great tour. We enjoyed every stop. The kids had a lot of fun. Manolo, our guide was excellent!
Excellent Tour
Daniel_J, Mar 2023
The guides made the trip very memorable. Our main guide, Sara, was very informative and she made it fun with her humor.