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

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! ❤️

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!

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!

La guida era molto preparata e gentile. I luoghi che abbiamo visitato erano davvero bellissimi, ma purtroppo il tempo a disposizione non è stato sufficiente per godermeli appieno. L'unico lato negativo è che ho acquistato un tour che avrebbe dovuto portarci anche a Pisa, ma purtroppo non ci siamo andati e non abbiamo ricevuto il pranzo che era indicato nel mio voucher al momento dell'acquisto. Il personale era facilmente raggiungibile tramite messaggio, ma ho perso molto tempo a cercare di risolvere il problema; purtroppo non hanno potuto offrirmi il pranzo, ma mi hanno proposto invece uno sconto del 25%, che non credo coprisse quanto ho speso per il pranzo lì.

Great tour. All stops were amazing and tour guides friendly, knowledgeable, and personable. Unfortunately for us we were put on a Spanish speaking bus with no English. People and the guide were very helpful to try and let us know what was going on, but unfortunately a lot of the information about the tour was lost in translation. I contacted Headout to try and get at least a partial refund but was basically ignored. All they did was try and blame the tour provider and would not accept any responsibility . So in the end, great tour but Headout really disappointing.