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 · 1,982 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

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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
Tuscany Wine Tours from Florence: How to Choose
6 min read
Siena vs San Gimignano: Which Tuscan Town Should You Visit?
6 min read
San Gimignano Half Day Itinerary: How to Make Every Hour Count
6 min read
Reviews

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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!

Enela ROUTSI
Enela ROUTSIAugust, 21 2026

Μια πολύ ωραία εμπειρία που αξήζει να τη ζείς. Το προσωπικό πολύ ευγενικό και εξυπηρετικό. Η Λέα η ξεναγός μας ήταν γλυκήτατη ,ευγενεστατη και ξέρει πολύ καλά τη δουλειά της. Περάσαμε πολύ όμορφα και ευχαριστούμε Wolk About..😊

Brendon O'Neill
Brendon O'NeillAugust, 19 2026

You see a lot on this tour, including Siena and San Gimigignano, which I did not expect to be such highlights. Mano is a fantastic tour guide, who was incredibly informative, engaging, and did well to get to get to know everyone in a large group. Thanks for the great day Mano. While this is a long day, I think it is the best way to see highlights of Tuscany. The group sizes are large, but we were fortunate to have a good group.

Magdalena Cataldo
Magdalena CataldoJuly, 31 2026

Magdalena C

Julie De Sa
Julie De SaJuly, 18 2026

An amazing day led by the effervescent Mano. We had a fabulous day. Siena was stunning, the cathedral beautiful. Lunch was delicious and the wines were perfectly matched. San Gimignano was quaint and charming and a favourite for many of our group. We finished with a climb of Pisa, a challenge but a great view as a reward. Grazie mille to Mano and Emiliano who made our day run smoothly. It is a long day but well worth the investment. It was hot, hot, hot but beautiful.

Holly Smith
Holly SmithJuly, 14 2026

Fantastic tour from start to finish! It was the perfect way to experience Tuscany in one day. A huge thank you to our guide, Manolo, who was knowledgeable, funny, and made the day so enjoyable, and to our driver, Sergio, for getting us everywhere safely and comfortably. Highly recommend this tour!

Daniel Habib
Daniel HabibJuly, 4 2026

I did this tour yesterday with my two siblings and it was honestly the highlight of our Europe trip. It was so well organised and the time was divided perfectly, with great breaks in between everything. The real highlight however was our guide Neomi, who brought such a kind and bubble energy to the day from the beginning. It was clear she cared deeply about the safety and enjoyment of everyone on the tour, and played such a huge role in how amazing that day was. I can’t speak highly enough about the tour, and hope everyone who chooses to book this is lucky to have to have Neomi brighten their day and experience of Tuscany!

Carla Canepa Castellanos
Carla Canepa CastellanosJune, 14 2026

Loved this your!! Highly recommend the 12 hour Tuscany tour. My family if 4 with 2 teenage boys had a wonderful time with your guide, Manolo (Mano), & Elessio, our driver. They took great care of the group. Everything was well organized. Mano is just want you want in a tour guide: knowledgeable, helpful, keeps us on schedule, funny, and gives the guests space to explore and enjoy. Highly recommend this tour!

Ali Manouchehri
Ali ManouchehriJune, 14 2026

We had an absolutely incredible time on the Best of Tuscany day trip from Florence! Trying to fit Siena, San Gimignano, and Pisa all into one day felt like a tall order, but the itinerary was paced perfectly and never felt rushed. The absolute highlight of the trip, though, was our guide, Gianluca. He was incredibly knowledgeable, sharing so much fascinating history about the medieval towers and the cities, but he delivered it all with a great sense of humor that kept everyone engaged. Most impressively, he even managed to make our 11-year-old son have fun and stay entertained. From the stunning views to the beautiful winery lunch in Chianti, everything was flawless. If you want an stress-free, memorable way to see the best of Tuscany, we highly recommend booking this tour—and definitely ask for Gianluca - our new Italian cousin.

Anastacia Smoot
Anastacia SmootJune, 13 2026

My family and I had a great time with the Walk About tour. Our wonderful tour guide was Lea. She was so amazing and so nice. If I could I would give her 10 stars. Would definitely recommend booking this tour company.

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.