Top experiences in Florence
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€159
€119.2525% off
Free cancellation
Slide 1 of 1, Tourist enjoying wine and local food on a Florence food tour.
Free cancellation
Slide 1 of 1, Friends enjoying wine in a vineyard setting.
Free cancellation
Slide 1 of 1, Aerial view of San Gimignano with medieval towers and surrounding countryside.
4.1(843)
Florence To Chianti Tours
from
€79Free cancellation
Slide 1 of 1, Hilltop view of Montalcino, Italy, featuring historic buildings and scenic landscape.
Free cancellation
Slide 1 of 1, Opera singer performing at a concert in Florence with classical painting in the background.
Selling out fast
Slide 1 of 1, Bartender pouring red wine into a glass in a wine cellar.
NEW
Florence City Tours
from Original price€219
€181.7717% off
Selling out fast
Slide 1 of 1, Pouring red wine into a glass in a vineyard setting.
NEW
Florence To Chianti Tours
from Original price€55
€41.2525% off
Free cancellation
Slide 1 of 1, Couple making pasta in a small group cooking class in Florence.
4.5(425)
Mercato Centrale
€87
Selling out fast
Slide 1 of 1, Participants making fresh pasta in a cooking class, measuring ingredients into bowls.
Free cancellation
Slide 1 of 1, Person participating in a cooking class in Florence, mixing ingredients in a bowl.
4.5(426)
Mercato Centrale
from Original price€99
€84.1515% off
Free cancellation
Slide 1 of 1, Group enjoying a meal at a Florence cooking class, toasting with wine glasses.
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, eBiker enjoying Chianti sunset view on a hilltop.
Free cancellation
Slide 1 of 1, Small group making pasta in a cooking class in Florence.
Selling out fast
Slide 1 of 1, Small group enjoying wine tasting on Tuscany Wine and Olive Oil Trail from Florence.
NEW
Guided Tours
from Original price€159
€119.2525% off
Selling out fast
Slide 1 of 1, grape escape winery tour-1
Nearby cities to explore
How Headout makes choosing experiences effortless
Slide 1 of 4, We curate the best ways to experience
We curate the best ways to experience
We research and organise all unique experiences - from tickets to tours to special combos - so you get all the choices without the clutter.
We partner with the best
Every supplier is vetted for quality, reliability, and value so you only get top rated experiences. No surprises, no disappointments.
All the best options, in one place
Each experience is thoughtfully organised to give you maximum availability, great value and an easy way to choose.
Book with complete peace of mind
Free cancellations, Flexible payments, and 24/7 support - thoughtfully designed for flexibility, assurance, and total peace of mind.
1/4
Slide 1 of 4
What our guests say
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
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
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
W
Wallace Y
BrazilCouple
5/5
The class was great—taught by two instructors, both of whom were very friendly and went out of their way to make everyone feel at ease. Even the kids participated; it’s really nice to bring them along.
The food was delicious, and the wine was excellent!
Florence Pasta-Making Class With Unlimited Tuscan Wine
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
L
Lisa S
Couple
5/5
Samuel and Elvis were a very pleasant team. Samuel was always empathetic and friendly. He patiently answered every question and went out of his way to ensure the guests’ comfort. It was also very important to him that everyone received all the information in a timely manner. His fun facts about the places we visited were very entertaining. Thank you for the wonderful experience.
From Florence: Siena & San Gimignano Day Trip with Wine Tastings & Lunch