Top experiences in Florence
17 experiences
Free cancellation
Slide 1 of 1, Piazza del Campo in Siena with Torre del Mangia and Palazzo Pubblico.

4.7(37)
Florence To Chianti Tours
from
€65Free cancellation
Slide 1 of 1, Dirt road leading to a villa surrounded by cypress trees in Chianti, Tuscany.

4.6(63)
Florence To Chianti Tours
from Original price€49
€39.2020% off
Selling out fast
Slide 1 of 1, Visitors exploring wine barrels in a Chianti cellar during a guided tour.

NEW
Florence To Chianti Tours
from Original price€99
€94.055% off
Free cancellation
Slide 1 of 1, Person walking towards Siena Cathedral in Tuscany, Italy, surrounded by greenery.

4.5(2,067)
Florence To Tuscany Tours
from
€65Free cancellation
Slide 1 of 1, Wine glasses raised in a toast during a Florence wine experience in Chianti Hills.

Free cancellation
Slide 1 of 1, Hilltop view of Montalcino, Italy, featuring historic buildings and scenic landscape.

Free cancellation
Slide 1 of 1, Aerial view of San Gimignano with medieval towers and surrounding countryside.

4.1(844)
Florence To Chianti Tours
from
€79Selling out fast
Slide 1 of 1, Tourists taking a selfie with Siena skyline in the background, featuring Torre del Mangia, Tuscany.

NEW
Florence To Tuscany Tours
from Original price€239
€179.2525% off
Selling out fast
Slide 1 of 1, Small group enjoying wine tasting on Tuscany Wine and Olive Oil Trail from Florence.

NEW
Florence To Chianti Tours
from Original price€99
€94.055% off
Free cancellation
Slide 1 of 1, Pouring red wine into a glass in a vineyard setting.

NEW
Florence To Chianti Tours
from Original price€55
€46.7515% off
Selling out fast
Slide 1 of 1, Bartender pouring red wine into a glass in a wine cellar.

NEW
Florence City Tours
€219
Free cancellation
Slide 1 of 1, Participants making fresh pasta in a cooking class, measuring ingredients into bowls.

Free cancellation
Slide 1 of 1, Friends enjoying wine in a vineyard setting.

Selling out fast
Slide 1 of 1, eBiker enjoying Chianti sunset view on a hilltop.

Selling out fast
Slide 1 of 1, Cyclists on e-bikes ride through Chianti countryside near Florence, flanked by cypress trees.

Selling out fast
Slide 1 of 1, florence chianti wine tour with tastings at 2 wineries and san gimignano visit-1

NEW
Food & Drink
from
€75Free cancellation
Slide 1 of 1, florence small-group italian wine tasting near ponte vecchio-1

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What our guests say
C
Coda S
EcuadorSolo
5/5
The guide's tips on key spots. Like the most delicious ice cream I've ever tasted in my life, in San Gimignano 🙌✨
From Florence: Siena, San Gimignano & Chianti Day Trip with Wine Tastings
Y
Yang Z
ChinaCouple
5/5
+6 more
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!
From Florence: Siena, San Gimignano & Chianti Day Trip with Wine Tastings
P
Pinelopi A
GreeceGroup
5/5
Although we lost half of the trip because we could not find the meeting point we managed to find our group and live the experience at sienna ! The girls at the meeting point were very polite and helped me book train tickets to find the other people of my group. Barbara was super guide and kind! Thanks also rachel from headout chat who gave me some credits for another trip. I am grateful.
From Florence: Tuscany, Siena, San Gimignano & Pisa Day Trip
F
Fabrizio T
ItalySolo
5/5
+4 more
An exciting experience. Highly recommended and impeccably organized from start to finish. One of the highlights was Sandro, our guide. Professional, empathetic, engaging, and tireless. You can tell he loves his job. Lucky him—and lucky are those who get to work with him. I’d also put Adele, the guide who welcomed us in Siena, on the same level. Professional, engaging, empathetic, and special. She makes you want to return to Siena tomorrow to discover the countless things this Tuscan gem has yet to reveal to a fly-by visitor—things that she, as a true Sienese, surely knows.
From Florence: Tuscany, Siena, San Gimignano & Pisa Day Trip
Z
Zuzanna B
BelgiumCouple
5/5
+2 more
We did the Chianti wine tour and it was incredible! Our guide Ms Ezgi was very enthousiast to share her knowledge of the region with us in a very professional way.The wines were very tasty. The views were breath taking. Really recommend doing this tour especially if you are a Witcher 3 Blood and Wine fan!!
From Florence: Chianti Wineries Tour with Wine Tasting
V
Victoria H
ColombiaCouple
5/5
Everything from the beginning was awesome. Logistic, samples, places. All the people was so nice and welcoming. I really enjoy this experiencie with my husband in our honeymoon trip
From Florence: Chianti Wineries Tour with Wine Tasting
I
Ian F
United KingdomGroup
5/5
Frederico was amazing. Knowledgable but not too much with ability to expand if more information was requested. Very friendly, wineries were excellent especially diameda.
Tuscany Wine and Olive Oil Trail: Small-Group Tour From Florence
D
Dai V
CanadaGroup
5/5
The tour was professionally organized from start to finish. Everything ran perfectly on schedule, with departures and arrivals right on time. Our guide was knowledgeable, engaging, and had a great sense of humor, which made the journey even more enjoyable.
A special mention goes to our driver, who demonstrated exceptional skill and experience navigating winding roads and narrow streets. We felt safe and comfortable throughout the entire trip.
The wine tasting was excellent, and the selection of vineyards was well chosen. As with our previous experiences, Headout once again delivered a fantastic tour. Thank you for providing such a memorable experience and helping make our holiday even more special.
Chianti Region Guided Tour with Local Tastings and Vineyards










