Guided Tours

From Florence: Siena, San Gimignano & Chianti Day Trip with Local Flavors Experience

Name: From Florence: Siena, San Gimignano & Chianti Day Trip with Local Flavors Experience
Start: 2025-10-10T08:45:00
End: 2025-10-10T20:15:00
Location: Florence

Streets of San Gimignano with historic stone buildings and tourists exploring.

Vineyards and olive groves in Chianti region, Tuscany, Italy.

Hand holding a glass of rosé wine in a Chianti vineyard during an e-bike tour.

Wine barrels in a cellar during Chianti wine tasting tour from Florence.

Duration

11 hr 30 min

Free cancellation

Free cancellation up to 24 hours before the start of your experience

Book now, pay later

Book now without paying anything. Cancel for free if your plans change.

Guided tour

Transfers included

Meals included

Indulge in a sumptuous meal as a part of your experience

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

Travel in style with round-trip transfers from Florence by GT coach, complete with seamless multilingual support.

Experience Siena’s rich history on a guided tour, from the stunning Palazzo Pubblico to the iconic Torre del Mangia in the lively Piazza del Campo.

Wander amidst the medieval towers of San Gimignano, a UNESCO World Heritage Site, and let your curiosity lead the way through its historic streets.

Delight in the world of Chianti as you stroll through a local estate, uncovering the secrets of wine making. Cap your experience with a hearty 3-course Tuscan lunch.

Full-day trip around Siena, San Gimignano, and Chianti

Multilingual assistance on board

Pick up from Florence

Round-trip AC coach transfer

Expert English-speaking guide in Siena

Vineyard visit, lunch, and wine tasting in Chianti

TOTAL DURATION10 hours 30 minutes
MODE OF TRANSFERA/C Bus
FIRST DEPARTURESiena
LAST DEPARTURESiena
Start point
Central Florence
Get direction
71 min by A/C Bus
78.3 km
1. Siena
1 attraction
Highlights
Palazzo Pubblico
Get direction
46 min by A/C Bus
41.7 km
2. San Gimignano
1 attraction
Highlights
Piazza della Cisterna
Get direction
57 min by A/C Bus
45.9 km
3. Chianti Classico
1 activity
Things to do
Vineyard tour & wine tasting
Included in price
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 24 hours before the experience begins and get a full refund.

4.6
11 ratings
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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4
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What our guests say
Richard
Aug 2025
Verified booking
4/5
Great experience. Our guide Lori was very friendly. The small group was great, we had a lot of fun. The organized tour was great. The only downside was that there was no French translation.
Luc
Aug 2025
Verified booking
5/5
Sanjay
Jul 2025
Verified booking
5/5
Jean
May 2025
Verified booking
5/5
Professional beautiful cities interesting
Bruno
Apr 2025
Verified booking
4/5

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

Florence to Siena

Ready to step into medieval culture with a modern flair? From central Florence, you will be transported in a fully-fitted GT coach to the luscious hills of Tuscany. Your professional multilingual guide will assist you through the tour.

Venture into Siena where history comes alive amidst architectural marvels and famous Palio games. Here, witness the Piazza del Campo and its stunning Palazzo Pubblico and Torre del Mangia with your guide in the heart of the city. Next, visit the Piazza del Duomo, the Cathedral, one of the finest examples of Italian Gothic architecture.

San Gimignano and Chianti wines

Next, step into the picture-perfect hilltop town of San Gimignano. Encounter the ancient skyscrapers, giving it the apt moniker 'Manhattan of the Middle Ages'. Feel free to tour the town’s cobblestone streets and artisanal shops, independently. Don’t forget to take every opportunity for a snapshot of the mesmerizing scenery.

Finally, visit a rustic estate in Chianti, where a wine producer welcomes you. In the lap of the Classico region, tour the grape-filled vineyards and cellars while gathering insights into the wine-making process. Experience a few local favorites and regional samples with a traditional 3-course meal. Return to Florence in your coach after a day of true Tuscan adventure.

What to bring

Wear walking shoes for vineries are usually located on the top of the hill and you start the visit with a short inclined walk.

Accessibility

This experience isn’t suited for wheelchair users or 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 they are each accompanied by at least one adult.

Your voucher will be emailed to you instantly.

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

Please arrive at the meeting point 15 minutes before the scheduled time of your visit to avoid any delays.

Meeting Point

Please check your final voucher for meeting point details and specific information. The meeting point details will be given on the final voucher which will se sent.