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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.

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What our guests say

Pinelopi A

Greece
Group
Jul 2026
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

Fabrizio T

Italy
Solo
Jun 2026

+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

Zuzanna B

Belgium
Couple
Jul 2026

+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

Victoria H

Colombia
Couple
Jun 2026
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

Yang Z

China
Couple
Jun 2026

+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

Wallace Y

Brazil
Couple
May 2026
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

Dai V

Canada
Group
Jul 2026
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

Lisa S

Couple
Jul 2026
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

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