Guided Tours

From Florence: Siena, San Gimignano & Chianti Day Trip with Wine Tastings

Name: From Florence: Siena, San Gimignano & Chianti Day Trip with Wine Tastings
Start: 2026-11-01T08:45:00
End: 2026-11-01T20:15:00
Location: Florence

Have a quintessential Tuscan adventure exploring Siena, San Gimignano, and Chianti while immersing yourself in the art of viticulture.

4.7/5(36)

Wolfgang W

Couple

Verified booking

2 days ago

Great tour with many highlights, very friendly staff, and lots of nice guests from every continent with whom we had pleasant conversations despite the language barrier. A very knowledgeable and witty guide – Constantino – was top, top, top. Our driver Mario drove us expertly!

Celeste P

Couple

Verified booking

Sep 2026

I liked everything. A well-organized tour, the guide was very friendly and kind. She shared many details with us. She was always very attentive to her passengers. The places we visited were beautiful, with adequate time to explore them. The wine tasting was interesting and entertaining. We enjoyed this tour, highly recommended.

Maria S

Couple

Verified booking

Aug 2026

Absolutely 10/10! ⭐⭐⭐⭐⭐ This was an amazing experience from start to finish! A special thank you to our elegant and professional driver, Mario, who made every journey comfortable and pleasant. Our lovely assistant guide, Maier (aka Maya), was incredibly kind, cheerful, and helpful throughout the entire trip. And a huge thank you to our wonderful guide, Lorenza. She speaks fluent English, Spanish, and French, and what impressed us most was that she had a well-documented, knowledgeable answer to absolutely every question we asked. Her passion, professionalism, and depth of knowledge made the tour so much more interesting. The bus was also modern, very comfortable, and equipped with excellent air conditioning, which was especially appreciated during the hot days. Overall, a fantastic team, excellent organization, great atmosphere, and an unforgettable experience. 10/10 — highly recommended! ❤️

Salil S

Solo

Verified booking

Jul 2026

Tour guide was good. Group was good. They do the best with the time available, so no qualms there. But I personally felt like there wasnt enough time to rxplore Sienna, but again as I mentioned they do the best with the time available.

Yang Z

Couple

Verified booking

Jun 2026

Alex is an incredibly warm and friendly guide! We absolutely loved this day trip to Siena, San Gimignano, and Monteriggioni. For me, visiting the actual locations from Ezio Auditore’s story was a real pilgrimage. As for the €22 lunch, it was fine, but if you prefer more freedom, feel free to choose your own restaurant—just make sure to be on time for the meeting. Finally, if you have the chance to visit a winery in Chianti, you absolutely must try Firmina. It’s a truly interesting wine to drink!

Christopher C

Couple

Verified booking

Jun 2026

Excellent tour guide in Igna and driver Luca. Both were excellent as was the tour. Highly recommended and very good value. Ciao Florence had some admin issues though

Visit Siena, San Gimignano, and Chianti in one well-paced day trip from Florence.

Enjoy a winery visit in the Chianti countryside with 3 wine tastings included.

Get free time in both Siena and San Gimignano to explore at your own pace.

Upgrade to a guided walking tour of Siena for deeper insight into its history and landmarks.

Travel comfortably with round-trip transfers and a multilingual tour leader.

Round-trip AC coach transfers from Florence

Onboard Wi-Fi access

Multilingual tour leader

Free time in Siena & San Gimignano

Chianti winery visit with 3 wine tastings

Guided tour of Siena (as per option selected)

TOTAL DURATION10 hours 30 minutes
MODE OF TRANSFERA/C Bus
Start point
Central Florence
Get direction
1 hr 11 min by a/c bus
78.3 km
1. Siena
1 attraction
At your first stop, set off on a guided tour through the main squares. Admire the architecture of Torre del Mangia (Eater's Tower) at the lively Plaza del Campo.
Highlights
Palazzo Pubblico
46 min by a/c bus
41.7 km
2. San Gimignano
1 attraction
57 min by a/c bus
45.9 km
3. Chianti Classico
1 activity
50 min by a/c bus
29.1 km
End point
Central Florence
Get direction
Your ending point would be same as your start point

You can cancel these tickets up to 48 hours before the experience begins and get a full refund.

36 reviews
How do we collect reviews?
These ratings include verified reviews from both Headout guests and our trusted partners who operate this experience locally. All reviews come from real travelers who've taken this experience.
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Guests from Canada, India, Israel and over 15 countries have loved this experience
What our guests say
Celeste P
Couple
Verified booking
Sep 2026
I liked everything. A well-organized tour, the guide was very friendly and kind. She shared many details with us. She was always very attentive to her passengers. The places we visited were beautiful, with adequate time to explore them. The wine tasting was interesting and entertaining. We enjoyed this tour, highly recommended.
Wolfgang W
Couple
Verified booking
2 days ago
Great tour with many highlights, very friendly staff, and lots of nice guests from every continent with whom we had pleasant conversations despite the language barrier. A very knowledgeable and witty guide – Constantino – was top, top, top. Our driver Mario drove us expertly!
Pierre-luc E
Couple
Verified booking
2 days ago
Unforgettable trip! Siena and its cathedral are absolute must-sees. Top-notch tour, great itinerary, and a very generous wine tasting!
Elena K
Couple
Verified booking
Last week
A wonderful and eventful trip!
Maurice B
Couple
Verified booking
Last week
Our tour guide was knowledgeable, entertaining, and did a very good job of moving a large group of people

Enjoy a flexible day exploring Siena, San Gimignano, and Chianti at your own pace.

Getting started

Begin your journey with transportation from Florence, boarding an air-conditioned coach equipped with Wi-Fi. A multilingual guide is available on board to assist you throughout the day. After departing Florence, settle in for a comfortable ride as you head towards your first stop in the Tuscan countryside.

Siena

Explore the medieval city of Siena, known for its fan-shaped Piazza del Campo and historic architecture.

Enjoy free time to wander the city’s winding streets, visit the Siena Cathedral, or relax in one of the local cafés.

If you select the guided tour option, join an expert English-speaking guide for a walking tour highlighting Siena’s history and key landmarks.

Take in the city’s unique atmosphere at your own pace or with your group.

San Gimignano

Travel next to San Gimignano, a UNESCO World Heritage Site famous for its medieval towers.

Stroll through the town’s cobbled streets and admire its well-preserved architecture.

Use your free time to sample local products, browse artisan shops, or climb one of the towers for panoramic countryside views.

Capture photos of the town’s skyline, often called the “medieval Manhattan.”

Chianti countryside and winery visit

Experience the rolling hills and vineyards of the Chianti region, renowned for its wine production.

Visit a local winery and learn about the winemaking process from the experts.

Enjoy a guided wine tasting session, sampling regional varieties.

Relax in the countryside setting, with time to appreciate the scenery and local flavors.

Wrapping up

After your visit to the Chianti winery, return to Florence by coach. The experience concludes at the original departure point, leaving you with the rest of the evening free to explore Florence at your leisure.

What to bring

Wear walking shoes as wineries are usually located on hills and visits begin with a short inclined walk.

Accessibility

This experience is not suited for wheelchair users or for prams and strollers.

Additional information

Drinks will not be served to guests under the age of 18 years.

Guests under 18 can join the tour if accompanied by at least one adult.

Your voucher will be emailed to you shortly.

Display the voucher on your mobile phone with a valid photo ID at the starting point.

Please check your final voucher for the starting point details & specific instructions.