A sommelier and outdoor guide, Stefano has been leading tours all over Tuscany, Cinque Terre, and Umbria for more than 10 years. He specializes in easy walking and wine tours out in the beautiful Tuscan countryside at locally owned and operated wineries.
Stefano runs unique tours, what he refers to as “out of the box” experiences, and he focuses on bringing his guests to places where you can feel authentic Tuscany and get off the typical tourist trail.
Stefano is a driver-guide and his tours can also encompass visits to multiple towns and areas throughout Tuscany. Every tour can be fully customized to accommodate you, your interests, and travel style. If you’d like, you’ll be able to work one-on-one with Stefano to arrange the details of the tour together and to create something truly unique.
Please note: Stefano is a tour operator and has two other great guides (Gianni and Lorenzo) on his team. Even if he isn't personally available, he can usually have one of them cover for him.
Lives In
Florence
Guides In
Tuscany and Liguria
Years of Experience
13 years
Languages
English and Italian
Ciao, buongiorno! My name is Stefano, and I am a native Tuscan! I was born and grew up in Fucecchio, a small village on the Arno river in the Tuscan countryside, but for the past 13 years I have been living in Florence while working as a guide all over Tuscany, Liguria, and Umbria.
I am a fully licensed guide, with a special license in hiking, and so I love to show people special green corners of Florence and Tuscany. I like to show them a different perspective of my city and region and what better way to do it than on two feet?!
I like to help guests get out into the countryside to see unique places and so that together we can taste local regional foods and wines and also to see Tuscany in a sustainable way.
In addition to guiding, I am also a licensed Wine Sommelier from FISAR and I am passionate about wine and good craft beer. When I have some time off from all the eating and wine tasting, I like to get out into the hills and forests around Florence for trail running.
I’m looking forward to meeting you and helping you explore a side of Florence and Tuscany beyond just the most touristic highlights. My region has so much to offer beyond the main Tripadvisored things, rushed day tours, and overcrowded museums. Let me help you discover them!
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Juan M
July 14, 2025
5/5
My wife and I recently took a hiking tour with Out of the Box Florence and it was a great experience. Lorenzo our guide was incredible, knowledgeable, friendly and very passionate about the area we hiked. The 3 wineries were amazing. Would highly recommend this tour it was definitely the highlight of our trip.
Review for Stefano
Originaly posted on TripAdvisor
Journey54679003615
June 18, 2025
5/5
Traveling as 2 couples, we had a perfectly planned and guided Val D'Orcia adventure & private Brunello di Montalcino Wine tasting/tour of the property at La Magia, lunch at a local farm and a visit to Pienza, all while seeing the beautiful rolling scenery of the Tuscan countryside along with its historic landmarks. The tour was great, but it was Lorenzo - our driver and guide that made it perfect. His ability to educate with knowledge and passion for the area, the wine, the olives, cheese, families, history, towns……left us with a greater appreciation and experience! It was an unforgettable day—-we absolutely loved it! Trust that OutoftheBoxFlorence is your BEST choice for a uniquely, tailored Tuscan tour just for you. Ask for Lorenzo!
Review for Stefano
Originaly posted on TripAdvisor
Joni S
June 13, 2025
5/5
Stefano was wonderful in designing our private tour. We were based just outside of San G and were looking for a day trip that was off the beaten path where we could learn how locals lived. We challenged Stefano by giving him very short notice and the fact that we were vegan and not wine drinkers. Stefano arranged Lorenzo as our guide to Volterra and Pecciloi. Both beautiful hilltop villages with spectacular views. We loved Lorenzo’s stories and his passion about various trees and plants and their historical use. For a bespoke tour catering specifically to your interests, I highly recommend Stefano and Out of the Box Florence. We felt it was a great investment and money well spent!
Review for Stefano
Originaly posted on TripAdvisor
Terri
June 11, 2025
5/5
We went on a private hiking tour with Stefano to Pescia-San Quirico to the Rufugio USO Do Soto for lunch.Wonderful hike.Great homemade pasta lunch and fresh local cheeses and meat along with a very cold beer at the Rufugio.Wonderful host there.Stefano was fun and informative.I would recommend any of Stefanos trips
Review for Stefano
Originaly posted on TripAdvisor
Amanda K
June 4, 2025
5/5
My husband, 20 year-old son, and I did the Cinque Terre tour with Lorenzo. We had a fabulous day. Lorenzo went out of his way to make our trip special. He modified our itinerary to customize our trip (this included trying lemon juice, adding an extra walk by the ocean, and focusing on pesto for lunch!). We walked at a comfortable pace and he was always checking in to make sure we were happy. This tour was such a wonderful way to see a new place on our own schedule. I highly recommend this tour company and would absolutely book another trip with them.
Review for Stefano
Originaly posted on TripAdvisor
4.98 rating from 66 reviews
4.98 rating from 66 reviews