Award-winning Tuscany day trip from Florence

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

Siena, San Gimignano, Pisa and a Chianti winery in one seamless day, with local guides, scenic countryside and authentic Tuscan flavors.

4.5 · 1,991 reviews
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12 hours Multiple departure times Florence departure 24-hour Free Cancellation
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Why travelers love this tour

A full Tuscan day, beautifully organized

Explore iconic medieval towns, taste world-class wines, enjoy a traditional Tuscan lunch and soak in breathtaking countryside views without worrying about logistics.

Iconic destinations

Guided walking tour through the medieval city of Siena

Authentic experiences

Traditional Tuscan lunch and informal wine tasting at a Chianti vineyard (not included in the tour option without lunch)

Free Time in San Gimignano

Free time to explore the medieval hilltop town of San Gimignano

Scenic Drive to Pisa

Scenic drive to historic Pisa to discover its iconic Leaning Tower and hidden corners

Ready to book?

Tour at a Glance

Prices, times and meeting point — all in one place.

From€ 75,00
Free CancellationUp to 24 hours before departure
Duration12 hours
DepartureMultiple departure times
Meeting pointThe meeting point is in Piazza Stazione. 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.Open in Google Maps
Itinerary

Your day in Tuscany

A carefully paced route through Tuscany's most loved landscapes, towns and flavors..

Depart FlorenceWe'll gather at the front of Santa Maria Novella train station, and after meeting your expert guide, an air-conditioned coach will whisk off to the first stop on our jam-packed itinerary.
View SienaView Siena through the eyes of a local as you join a guided walking tour through the medieval city made up of yellow-ochre buildings, terracotta rooftops and green shutters. Learn about the world’s oldest bank, see the Piazza del Campo - the site of the 600-year-old Palio horse race - and admire the interior of the Duomo, a treasure chest of artworks. Afterwards, enjoy Siena at your own pace with free time for shopping or relaxing in an open-air cafe.
A Tuscan Lunch at a Chianti VineyardNext we stop at an organic, family-run wine estate – the highlight of our Tuscany tours! You will take part in an informal wine tasting lesson, trying Chianti, Vernaccia and Tuscan dessert wine, Vin Santo. Next enjoy traditional local lunch with plenty of wine, and soak in the idyllic location overlooking stunning views of the surrounding countryside. Take the opportunity to meet fellow travellers while feasting on fresh, organic farm food, including homemade pasta, cured meats (homemade prosciutto and salami), local cheeses, a real garden salad and Tuscan biscotti (if the tour option without lunch is chosen, this part of the tour is not included but there will be more time spent in San Gimignano).
Don't forget your camera - the view from the winery is jaw dropping!
San GimignanoAfter lunch we visit the enchanting hilltop town of San Gimignano where you have free time to roam the picturesque streets and squares. Maybe browse the local shops, try an award winning gelato or walk among the town’s famous medieval towers.
Scenic Country Drive & PisaA scenic drive through iconic Tuscan countryside will take you to your final stop, Pisa. Here, take a closer look at the iconic Leaning Tower, the Cathedral and the Baptistery. A brief tour of the historic heart of Pisa will show you another side of the city.
Upgrade to include skip-the-line entry to the Leaning Tower
Return to FlorenceYou will be dropped off in Florence at around 8.30pm with a camera full of pictures, a stomach full of hearty Tuscan food and a host of new friends.
Highlights

What's included

  • Air-conditioned coach travel
  • 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
  • Maps of and information about all the towns visited
Duration12 hours
DepartureMultiple departure times
Free cancellationUp to 24 hours before departure
Know before you go

Helpful details before booking

A few practical notes to help you choose the right Tuscany day trip and arrive prepared.

  • Mobility RestrictionsDue to uneven and steep surfaces, we are unable to accept wheelchair users or those with walking difficulties on our Tuscany tours.
  • Tower Climb Age LimitChildren under the age of 8 years are not permitted to climb the leaning tower of Pisa.
  • Alternative Visit NoticeWhen the Duomo of Siena is closed for religious services, Santa Maria della Scala museum will be visited instead.
  • Dietary Requirements NoticeVegetarian option is available, but we regret that gluten free or other alternative dietary requirements cannot be catered for
Plan your Tuscany trip

Travel guides before you go

View all guides
San Gimignano Local Crafts
6 min read
Vineyard to Bottle Process in Chianti
6 min read
Organic Wineries in Tuscany
6 min read
Reviews

Loved by travelers

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Yvonne Kanak
Yvonne KanakOctober, 6 2026

This tour was recommended to us and did not disappoint! Every stop was perfect and lunch was delicious. Our tour guide Mano was awesome. The right blend of knowledgeable, friendly and funny! Thanks to Mano and Sergei for a wonderful day in Tuscany. We’d recommend this tour.

Jacobus Smith
Jacobus SmithOctober, 5 2026

Thank you so much, Miri, for such a wonderful day in Tuscany! We really enjoyed the tour, the beautiful places, and all the interesting stories and information you shared with us. You made the whole experience very enjoyable and memorable for our family. Thank you again for everything!

Saurav Ghosh
Saurav GhoshSeptember, 21 2026

Manolo and Sergei are excellent. Tour was very good

Anna Thomas
Anna ThomasSeptember, 19 2026

Most amazing trip! Thank you to our Tour Guide Lea and driver Alessie for making this trip all about us, showing us Tuscany, in a super organized yet relaxing day!!! Memories are irreplaceable. Definitely a recommendation. ask for Lea!

Genevieve Rouleau
Genevieve RouleauSeptember, 18 2026

What a wonderful day! Yes, we walked a lot — more than 20,000 steps — but every step was worth it. We discovered Siena, San Gimignano and Pisa, learned about their fascinating history and their centuries of rivalry with Florence, and took impressive photos all along the way. Noemi was truly the highlight of this tour. She seems to be an infinite source of knowledge about Tuscany, its history and culture, yet she presents everything in such an engaging way that we were never bored listening to her. From the power struggles between Florence and its neighboring cities to the story of Pisa’s salt embargo and the tradition of unsalted Florentine bread, she brought Tuscany’s history to life. She is also exceptionally organized. We particularly appreciated the maps of the ancient towns with clear meeting points — such a simple detail, but incredibly helpful for exploring independently without getting lost. Noemi was very vigilant about keeping the group together and clearly explained why everyone needed to cooperate and return on time, especially on such a long and full day. We came back tired, but with wonderful memories, beautiful photos and the feeling that we had learned so much about Tuscany. Noemi is an outstanding guide and a tremendous asset to this tour. We would happily travel with her again!

Daniela Munoz Gallardo
Daniela Munoz GallardoSeptember, 18 2026

Manolo was our tour guide, he was knowledgeable, personable and enthusiastic throughout the tour. We had an amazing time. The sites we visited were BEAUTIFUL. The lunch at the winery was delicious! Highly recommend! Thank you Manolo!

Rotem Porat
Rotem PoratSeptember, 15 2026

We had a great time with Manolo going to Sienna, having wine tasting and lunch at a vineyard, visiting San Gimignano and finally Pisa. In each stop he explained everything (including bathroom options), took care of special requests for lunch, and was funny and friendly from start to finish. In my opinion there was enough time in each stop to appreciate the place. Pickup from near the SMN train station was convenient. Recommended.

Nikoleta Toulatos
Nikoleta ToulatosSeptember, 9 2026

Manolo did a wonderful job keeping everyone happy, safe, educated and fed! My family and I had the most amazing day that exceeded all expectations!!

Yara Sanchez
Yara SanchezSeptember, 7 2026

Amazing tour, worth every second, definitely recommend to anyone that wants to get a true experience of the Tuscan countryside. Giano and Luca were great tour leaders, so helpful and made the experience unforgettable and educational

Janaina Artem Ataide
Janaina Artem AtaideAugust, 21 2026

We had such a great day, wonderfully guided by Manolo! Domenico was an excellent driver, skillfully navigating even the tiniest streets! It was incredible to discover Siena and San Gimignano, learn about their history, and see all their highlights. The food was also amazing, and I really appreciated that gluten-free options were available. Thank you so much, Manolo, Domenico, and Walkabout Tours, for making this such a memorable experience! Highly recommended!

Good to know

Frequently Asked Questions

We do not organise hotel pick-ups for difficulties with parking and scheduling, but our meeting point at Florence's main train station is very central and should be easy to get to. Many hotels are located within easy walking distance of the train station, otherwise a taxi (you could ask your hotel to book it for you) would be the fastest option, dropping you off right at our meeting point.

When you make a reservation you will have the chance to upgrade your tour to include entry to the Leaning Tower before you proceed to the payment stage. Remember that children under the age of eight are not permitted to climb the tower.

There is quite a lot of walking during the day, so comfortable shoes are recommended! The ancient cities of Siena and San Gimignano are built on hilltops and are mostly closed to traffic, so we have some walking to do (including steps and uneven surfaces) from the bus to the centre. Participants must be able to keep up with the group for the guided sections of the tour but there is plenty of free time for relaxing. We are unable to accept anyone with walking difficulties or wheelchair users.

We suggest comfortable clothing and above all, comfortable shoes for walking. In the summer months please remember that you are expected to cover your shoulders to visit inside churches, but if you are dressed for a hot day don't worry, you will be given a disposable paper cape for the Cathedral in Siena.

We have arranged an itinerary so that you will cover as much of Tuscany as possible but without spending too long on the bus. The longest ride of the day is through beautiful Tuscan scenery and lasts about an hour and a half.

Our bus does not have a washroom. However the day is very well divided that you are never too far from washrooms. In the morning it takes just over an hour from Florence to Siena, then just forty minutes from Siena to the wine estate. After lunch we go to San Gimignano (only ten minutes drive) and from there to Pisa which takes one and a half hours. After Pisa it's just over an hour to Florence, depending on traffic.

Definitely! If you would prefer an alternative to the menu we have chosen, please tell your tour leader and he/she will telephone ahead to arrange it.

The thing to remember is that it is a long day (12 hours) and the city visits can be tiring for children. We have had occasional problems in the past when tired children have become fractious and noisy during the bus rides and disturbed the other passengers. So the decision has to be yours because you know your children! We reserve the right to ask you to leave the tour if in the tour leader's opinion your child disrupts the tour. We suggest to parents of very young ones that they use a back pack type of baby carrier rather than a stroller/pram because of the many steps, steep slopes and uneven surfaces in the medieval towns that we visit. It's also much quicker getting on and off the bus!

If you have plans to stay in Pisa, you can bring your luggage with you (there is plenty of space on the coach) and collect it at the end of the tour, before the rest of us head back to Florence.

If you have to get to the airport at Pisa, it's about fifteen minutes by taxi – the tour leader can help organise a taxi for you. If you are traveling by train, Pisa Centrale station is a ten minute taxi ride or bus ride away.

Our tours leave from and return to the main railway station in Florence, so if you are travelling on by train, bring your luggage with you in the morning and take the train in the evening directly after the tour. You will save both time and money by not having to use the luggage deposit! We recommend that you book any rail travel from Florence after 9pm to allow time for any traffic delays. We cannot be held responsible for any loss or extra expense incurred in the unlikely case of delays due to unforeseen circumstances beyond our control.
Pricing starting from:€ 75,00
24-hour free cancellation
Passionate expert guidesLocal guides who love what they do.
Excellent valueTop experiences at fair prices.
Easy, secure bookingBook online in minutes.
Flexible paymentsMajor cards accepted.
24-hour cancellationPlans change? Cancel up to 24h before.