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

Firenze, Italy

From $72.78

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 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
  • 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.
10,363 reviews
Total review count and overall rating based on Viator and Tripadvisor reviews
Reviews by Viator travelers.
Showing 1-10 of 10,363 reviews
Virginia_P, Jan 2023
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.
Alessandro was an excellent guide. I would highly recommend this trip.
nicholas_g, Jan 2023
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.
Siena to Pisa!
Edwin_T, Jan 2023
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.
Couples trip ❤️
Trish_L, Jan 2023
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
Skip the Meal and Save the €35
Jennifer_C, Jan 2023
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.
Great adventures in Tuscany
Rebecca_W, Jan 2023
It was an excellent tour! Good amount of time at each stop, very knowledgeable tour guide. It was much easier than trying to get around on our own and we got to see a lot!
Not enough time at each city. Need at least 2.5 hours to enjoy each city.
David_P, Jan 2023
A visit to Pisa is not worth 3.5 hours of travel time. Better to have only 2 cities and more time at each one. Also, the bus should Drop the passengers off at the closest point and then go park the bus. We should not have to walk a mile and a half before we get to our destination and a mile and a half back to the bus. I have a little they should pick us up at the drop off point near the city entrance. I have seen other buses do this. Obviously, you do not want to make it convenient for the passengers I would not take another tour nor recommend the store to anyone.
This is a must tour! 10/10 and Gloria was spectacular!
Brandon_M, Jan 2023
Highly recommend this tour!! You cover so much in one day. Siena and it's majestic cathedral, San Gimignano (a quaint and lovely town), an amazing lunch in Tuscany, and of course, Pisa! Gloria was an incredible tour guide as she is from San Gimignano. She made everyone feel welcome and kept us all entertained while explaining the history of it all. 10/10 would recommend to all with her as a guide.
Take in the sites and enjoy wine and lunch at a winery
Veronica_A, Jan 2023
This is a full packed day. Overall a wonderful experience. Here is what you should know: meeting place in front of train station is easy to find. You will however need to walk about 10 min to where the bus is parked. Tour of Siena is great. Winery food and wine is enjoyable and provides for some wonderful photo opportunities. San Gimignano is interesting to visit. Since it is winter we arrived into Pisa at sunset. Everything is illuminated well and you can still enjoy the sites. Our tour guide Angela was energetic and engaging and provided some good insights. You should know that you do get a little bit of time at each location to wonder but it’s very limited. 30-45 min tops. Bus has no restroom. Longest drive is 1.5 hours. When you return you have a 10 min walk to get to the train station meeting place. Enjoyable day
Worth it
Ashley_H, Jan 2023
It was awesome to hear the local guides viewpoint on this trip. I could not have understood the richness of history without her insights. Thanks Angela!
This was a wonderful...
vanessa66, Jan 2023
This was a wonderful tour. Our tour guide, Stefano, was charismatic and knowledgeable. The sights were beautiful and the lunch was delicious.
The tour guide, Angela...
Bindu_A, Jan 2023
The tour guide, Angela was very good, explained everything in detail and very entertaining. The driver Nicola, was very good with his smooth driving. Lunch at winery was excellent. Siena tour guide was very informative and good in explaining the details. Highly recommended this tour.
Amazing Tour, worth the cost
Shane_W, Jan 2023
The trip to Siena, the food at the winery, and the tour of San Gimignano were all amazing. Our tour guide Angel was great too and very friendly. This trip is well worth the money
Highly recommend.
Hernan_S, Jan 2023
Beautiful places. Our guide, Angela was very helpful, knowledgeable and entertaining. The bus is comfortable and lunch terrific. Great value.
Great tour of the Tuscany region
Kevin_C, Jan 2023
Very nice full day tour with Manalo and also with Donatella in Sienna. Definitely recommend getting the option for the lunch (not even sure where, if any, groups without the lunch option went during it). Four course meal with a wine accompanying each dish.
A good experience
Sloane_H, Jan 2023
Overall it was a good time with a few bumps along the way. Angelina was very energetic, knowledgeable, and fun tour guide. We had to wait to leave because our tour radios were not delivered and we had an issue with the bus during the day. But they made every effort to get us back on schedule and made sure we had time to see and do everything we were scheduled for.
Perfect day in Tuscany
Dane_V, Jan 2023
This is a must when you want to experience so many different aspects of Tuscany in a day! Angela was amazing and had a wealth of knowledge to share. She also made sure we didn't get lost as that was easy in these locations! Make sure you get the lunch and Pisa tickets!
Amazing day drip from Florence
Brittany_S, Jan 2023
We had an amazing time on this tour. Alex did a fantastic job giving us the history of Tuscany while also keeping it fun. The lunch at the vineyard was also amazing.
Tuscany Tour
Dawn_S, Jan 2023
A must do! Good to get out of the city to see more rural Tuscany Italy. Monolo was an excellent guide. Great English, so organized, brand new luxury bus, interesting information, beautiful scenery. Worth the money. Food and unlimited wine at winery was great. Tour guide in Siena was fantastic too. Starts at 8:00am and back at your stop at 7:30pm. Water available on bus for 1 euro. You can leave coat, other belongings locked on bus. Hope this review is helpful.
Long, Educational and Fun Day!
Rachel_M, Jan 2023
A worthwhile experience with a fully packed agenda, allowed us to experience so many towns in the Tuscan region! Our guide was enthusiastic but while excited about his country, at times he shared unnecessary information when the tourists wanted a break to relax on the bus. Each stop- Siena, San Gimignano, Pisa and lunch at the winery had sufficient time to learn, shop, eat and walk around. The winery was very accommodating to allergies and food sensitivities. Our guide, Alessandro, went one by one through the bus getting allergy information from each visitor, a very thoughtful touch. At the winery, we had ample time to take photos on the terrace as well as purchase wine and olive oil to ship back to the states! This tour did have a lot of walking as many of the towns did not allow the bus to enter due to being UNESCO Heritage sites. Therefore, we had to walk from a far parking lot on most occasions. The ground, however, was flat and paved in most cases. Also, a tip if you book the Tower of Pisa climb- no bags are allowed. We had to leave things on the bus and take minimal items in pockets. Overall, it was a long but educational and fun day!