This trip is perfectly designed for those short on time, or simply want to see more of the region in a single day by 8-seat minivan. Lead by a seasoned team of passionate, local experts, this day tour perfectly balances fun and authenticity. Travellers will get a chance to discover some hidden treasures of Tuscany through a combination of activities and free time. So discover the best of Tuscany, and visit Siena, Monteriggioni, San Gimignano and the Chianti region!
Tour Options
From Florence: Classic Tour
Minivan : Intimate small group experience – never more than 8 guests
From Florence: Private tour
8 seat Private Minivan: Enjoy a comfortable roundtrip journey in air-conditioned minivan
Itinerary
10 min
08:45am - Meet and greet your guide and the other travellers near Porta Romana to travel by minivan to discover the best of Tuscany.
40 min
the first stop will be Monteriggioni, the most well preserved medieval village in Tuscany. This fortress city is also where “The Gladiator” was filmed, and is one of the locations for “Assassin’s Creed”. Along the journey get ready to immerse yourself in the Italian vibes and learn from your tour leader interesting facts about Tuscany & its famous cuisine.
120 min
your second stop, the dreamy town of Siena. During the orientation walk you will discover its unique architecture passing by the numerous artisan shops and finally stop at one of the most remarkable Piazzas of Italy, Piazza del Campo, site of the famous Palio race every July and August. Get some downtime to relax and explore the city at your leisure; do not miss a visit of the impressive Cathedral.
60 min
The tour will definitely pass through the Chianti Region, the heaven of Tuscan wine. A local winery will be visited and you will have a chance to merge with the Tuscan goodness: 7 different wines, extra virgin olive oils and balsamic vinegar will make your taste buds happy together with an amazing traditional Tuscan meal.
60 min
Your next destination is San Gimignano. On the way to the village, the guide will provide each traveller with a map and tips for the best places in town. Take a stroll through the cobblestone pathways, piazzas and palaces of this other UNESCO World Heritage Site known as the ‘Manhattan of Tuscany’ and explore this magical and timeless town in complete freedom.
60 min
After 1h drive, we will be back to Porta Romana at 6:00pm
Highlights
Scenic drive of the Chianti region
Wine and Extra Virgin olive oil tasting in a local winery
A short visit of Monteriggioni
Transport on a 8 seat minivan
Authentic Tuscan meal: Antipasti Toscani (bruschetta, pecorino cheese, Tuscan cured meat), Lasagna with truffle oil, traditional Ribollita Soup & Cantuccini. Veg,vegan and gluten free menu on request.
Orientation walk of Siena with our tour leader, then free time to explore independently the city
1h stop in San Gimignano and free time to discover the village at your own leisure
What's included
Included
Scenic drive of the Chianti region
Wine and Extra Virgin olive oil tasting in a local winery
A short visit of Monteriggioni
Transport on a 8 seat minivan
Authentic Tuscan meal: Antipasti Toscani (bruschetta, pecorino cheese, Tuscan cured meat), Lasagna with truffle oil, traditional Ribollita Soup & Cantuccini. Veg,vegan and gluten free menu on request.
Orientation walk of Siena with our tour leader, then free time to explore independently the city
1h stop in San Gimignano and free time to discover the village at your own leisure
Not included
Gratuities
Guided walking tours on the villages
Traveller Ratings
4.8
106 reviews
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94
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9
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2
1
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Important Information
Public transportation options are available nearby
Suitable for all physical fitness levels
The best of Tuscany in 1 day
Small groups, no bus tours, no families with crying kids and mainly only 1 language to listen to.
Please note, the tour requires a minimum of 4 participants. If not reached, a private option with a supplement will be offered.
Not recommended for travelers with walking disability
Frequently asked questions
How long does Siena, San Gimignano, Tuscany, Lunch & Wine Tasting - max 8 take?
Siena, San Gimignano, Tuscany, Lunch & Wine Tasting - max 8 lasts about 9 hours. The itinerary has 6 stops.
How much does Siena, San Gimignano, Tuscany, Lunch & Wine Tasting - max 8 cost?
Prices start at $202 per person for this Florence experience, booked through Viator with the price shown before checkout. There are 2 booking options, so the final price depends on the option you choose.
Can I cancel Siena, San Gimignano, Tuscany, Lunch & Wine Tasting - max 8 for free?
Yes. Cancel at least 1 day before the start for a full refund. Later cancellations are non-refundable.
Where does the tour start?
The meeting point is Meet us in Piazza della Calza right in front Porta Romana at the blue P ( parking ) sign at 08.45am. The tour departs at 09:00am sharp!. Hotel pickup is not part of this experience.
What languages is Siena, San Gimignano, Tuscany, Lunch & Wine Tasting - max 8 offered in?
The experience is available in EN.
Is this a private or a group tour?
It is a small-group experience with a maximum of 8 participants.
Is the tour suitable for children?
Small groups, no bus tours, no families with crying kids and mainly only 1 language to listen to.
Will my booking be confirmed immediately?
Yes, bookings are confirmed instantly.
Reviews(106)
S
Scenic22411546688
September 8, 2026
Tuscan Day Trip
Fantastic experience with Alberto! Very knowledgeable guide and found us so many hidden gems along the way! Even waited for us when our taxi was running late, thank you for a wonderful trip Alberto!
Operator response
What a great day to look back on! We’re really happy Alberto showed you some beautiful lesser-known spots and was so accommodating when your taxi was running late. It’s always lovely to hear when our guides take such good care of our guests. Maybe next time you can join us for a day trip to Pisa and Cinque Terre!
L
Lauren_P
September 3, 2026
Great way to see more of Tuscany and learn about wine
We had a great time on this tour learning about other parts of Tuscany and enjoyed getting to know the others in our small tour group. The wine tasting was fun and in a great location. Long day, but worth it if you have the time.
Operator response
Thank you for sharing your kind words, Lauren! It’s great to hear that you had such a nice time and appreciated the small-group setting. We’re also glad you enjoyed the winery visit and had the chance to try some delicious local wine and food. It’s a full day, so we really appreciate hearing that you felt it was worth it. We’d love to have you back with us for another tour in Tuscany!
J
jerodf2022
September 3, 2026
Amazing day in Tuscany!
Amazing Day in Tuscany — Ask for Ned!
One of the highlights of our trip to Italy! Ned was an amazing guide — knowledgeable, personable, and made the entire day fun. We visited Siena and San Gimignano, enjoyed incredible Tuscan scenery, and had a fantastic wine and olive oil tasting. An unforgettable day and a true taste of Tuscany. Highly recommend!
Operator response
Sounds like you really enjoyed your day with Nedas, Jerod! He’ll be very happy to hear your kind words. We’re glad you loved exploring Siena and San Gimignano, and that the Tuscan scenery made such a strong impression too. It’s also great to know the wine and olive oil tasting lived up to the rest of the day. Thank you so much for the recommendation!
Z
Z8951HHcharlesv
September 3, 2026
Lovely Tuscan Countryside
Good times, friendly and deeply knowledgeable guide. Ned was calm, friendly and responded to all questions. Well worth the cost and a great way to take in the Tuscan countryside, wine, history and sites! Siena and San Gimignano were lovely
Operator response
It’s really nice to hear that you had such a great time exploring the Tuscan countryside with Nedas! We’re glad his knowledge and calm approach made the day even better for you. It’s also lovely to hear how much you liked Siena and San Gimignano. Maybe next time you can discover another side of Tuscany with us and visit Saturnia!
T
T7096CNryanp
August 27, 2026
Luigi’s Tuscan Adventure
Luigi was the best guide to Tuscany. He knew so many interesting details for each location to elevate our experience. We really enjoyed our day visiting medieval towns in Tuscany and it was a great change of pace from our time in Florence! The winery tour as even more than we had expected!
Operator response
Thank you so much, Ryan! It’s lovely to hear how much Luigi added to your day with all the local details he shared. We’re also really happy you enjoyed exploring the medieval towns and that the winery visit exceeded your expectations. Maybe next time Tuscany brings you back, you can discover a different side of the region with us, perhaps with a visit to Saturnia!
R
Roam40682005957
July 13, 2026
Excellent tour
We had a wonderful day with Luigi! He was very informative and pleasant. Thank you so much!!!
Operator response
Thank you so much for your lovely review! We are delighted to hear that you had a wonderful day and that your tour leader Luigi made the experience both informative and enjoyable. We truly appreciate your kind words and hope to welcome you back to Tuscany in the future!
L
L9917MRbrianm
June 22, 2026
First trip to Tuscany
Great experience and enjoyed every bit of it. Tony was great! Just a fabulous time on first trip to Tuscany
Operator response
Thank you so much for your wonderful review! We’re delighted to hear that you enjoyed every moment of your first trip to Tuscany and that Tony made the experience even more special. We truly appreciate your kind words and hope to welcome you back for another unforgettable adventure!
X
X580FTjosephl
June 22, 2026
Chianti region, in a day.
Tony, our guide, was friendly and knowledgeable. We saw so many wonderful sights— Sienna, Monteriggioni, San Gimignano. The winery was excellent.
Operator response
Thank you so much for your wonderful review! We’re delighted to hear that your tour leader Antonello was friendly and knowledgeable and that you enjoyed visiting Siena, Monteriggioni, and San Gimignano. It’s also great to know that the winery was a highlight of your day. We truly appreciate your feedback and hope to welcome you back to Tuscany again!
G
G7882IUkellyl
June 16, 2026
Don’t miss experience!
What an amazing day! This tour was the perfect combination of guided and self directed exploration. All the towns are different and worth seeing, and the lunch at the winery was 10/10! Antonello was a wonderful guide.
Operator response
Thank you so much for your wonderful review! We’re delighted to hear that you had such an amazing day and enjoyed the perfect balance between guided experiences and time to explore independently. It’s lovely to know that each town offered something unique and that the winery lunch was a highlight of the day. We’re also very happy that your tour leader Antonello made the experience so enjoyable. We will be sure to share your kind words with him, and we hope to welcome you back to Tuscany again in the future!
B
bellacX3418MM
June 15, 2026
Awesome experience
Alberto was a great guide, we learned so much, explored new locations and we had a great time!! Definitely recommend!
Operator response
Thank you so much for your wonderful review! We’re delighted to hear that your tour leader Alberto made the experience so enjoyable and informative. It’s wonderful to know that you discovered new places, learned so much, and had a great time. We truly appreciate your recommendation and will be sure to share your kind words with him. We hope to welcome you back to Tuscany again in the future!
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Siena, San Gimignano, Tuscany, Lunch & Wine Tasting - max 8
