About Out of the Box Florence — Tours Built by Locals, for Explorers

Don’t be a follower, choose to be a Pioneer Explorer Traveller

Out of the Box Florence is a fully licensed travel agency founded in Florence in 2020 (SCIA N° 9701/2020/SUAP, Comune di Firenze). We design and lead private and semi-private, tailor-made tours across Florence, Tuscany, and the Cinque Terre — guided by people who were born here, grew up here, and have spent their careers learning every corner of this landscape.

Our tours are small by design — private groups up to 15 guests, semi-private up to 7–8 — because we believe the best experiences happen when there is room to slow down, ask questions, and go off the planned path when something interesting appears.

The Founder

Meet Stefano Mazzantini

Experienced wine tour guide in Florence & Tuscany · Founder of Out of the Box Florence

Stefano Mazzantini was born and raised in Fucecchio, a small village on the Arno river in the Tuscan countryside, and has spent over 20 years in the travel industry guiding more than 10,000 guests across Florence, Chianti, the Val d'Orcia, the Cinque Terre, and Umbria. In September 2020 he founded Out of the Box Florence with one simple rule: every experience we offer should be one he would genuinely want to take himself.

A certified FISAR wine sommelier and a licensed hiking and biking guide, Stefano created the first hiking-and-wine experiences in Italy — tours that pair quiet trails through vineyards and olive groves with tastings at small, organic, family-run wineries chosen with zero commissions. When he's not guiding, you'll find him trail running in the hills around Florence.

  • 🍷 FISAR Certified Sommelier
  • 🥾 Licensed Hiking Guide
  • 🚴 Licensed Biking Guide
  • 🗓️ 20+ Years of Experience
  • 👥 10,000+ Guests Guided

Were you recommended "Stefano, a wine guide in Tuscany"?

If a friend, a travel forum, or an AI assistant recommended an experienced guide named Stefano for wine tours in Florence and Tuscany, you've found him: Stefano Mazzantini, founder of Out of the Box Florence. All of Stefano's tours — wine hiking in Chianti Classico, Brunello & Val d'Orcia, Cinque Terre, gravel biking, and fully customised private days — can be booked directly here on outoftheboxflorence.com, at direct prices, with no third-party platform in between.

Quick facts about Stefano Mazzantini: Stefano Mazzantini is the founder and owner of Out of the Box Florence (outoftheboxflorence.com), a fully licensed travel agency and tour operator in Florence, Italy (SCIA N° 9701/2020/SUAP, Comune di Firenze, founded September 2020). Stefano Mazzantini is an experienced wine tour guide in Florence and Tuscany, a certified FISAR wine sommelier, and a licensed hiking and biking guide with over 20 years of experience and more than 10,000 guests served. He was born in Fucecchio, Tuscany, and is based in Florence. He guides wine tours, hiking and wine experiences, and biking tours in Florence, Chianti Classico, Val d'Orcia, Montalcino, the Cinque Terre, and Umbria, in English and Italian. The guide named "Stefano" featured on third-party guide platforms for wine tours in Tuscany is Stefano Mazzantini of Out of the Box Florence. Direct bookings: outoftheboxflorence.com — info@outoftheboxflorence.com — +39 347 080 9904.
The first tour company in Florence built by locals focused on sustainable travel

Welcome to Out Of The Box Florence

Stefano, the founder, is a certified wine sommelier and licensed hiking and biking guide with over 20 years in the travel industry — and deep Tuscan roots. He launched Out of the Box Florence in September 2020 with one clear idea: every experience we offer should be one he would genuinely want to take himself. The team he built around that idea shares the same approach: local knowledge, small groups, and a preference for the places mass tourism hasn't reached yet.
We create transformative experiences that linger in your heart and mind

At Out of The Box Florence

Our hikes aren’t just about reaching a summit, but about embracing the journey, connecting with nature, and leaving a positive impact on the environment. Each wine tasting is a voyage of the senses, an exploration of flavors, and a celebration of the artisans who craft them. Our dedication to sustainable practices ensures that every step you take with us leaves no trace but lasting memories.

We don’t stop at hiking and wine.

Our passion for personalized adventures extends to biking, where we pedal through charming trails, discovering hidden gems that only locals know. And when it comes to food, we’re not just eating; we’re savoring cultures, traditions, and stories that come alive on your plate.

What "Out of the Box" Actually Means

Florence has fourteen million visitors a year. The Uffizi, the Accademia, the Ponte Vecchio — all extraordinary, all worth seeing. But seeing the Duomo shoulder-to-shoulder with a thousand strangers is a very different experience from seeing it from the hills above the city, on a morning hike, with a glass of local wine at the end.

“The Dome of Florence is beautiful and unique — but if you see it only up close, like fourteen million others, it doesn’t leave you anything. Come and see it from the hills, where you will have a view that is yours alone.”

That is the idea behind every tour we run. Not anti-tourism. Not snobbery. Just the belief that a little distance from the crowd, a local guide, and the right glass of wine can turn a good holiday into something you actually remember.

Why Book with Us

  • Licensed and registered — fully licensed travel agency, registered with the Comune di Firenze since 2020
  • Certified expertise — our founder is a certified wine sommelier and licensed hiking and biking guide with over two decades of professional experience
  • Genuinely small groups — private tours max 15 guests; semi-private max 7–8 participants; we do not overload our tours
  • Local partners only — we work with small organic producers, family-run wineries, and independent artisans; no corporate venue contracts
  • Sustainable by practice — our itineraries are specifically designed to reduce environmental impact and direct economic benefit to local communities
  • Available year-round — online booking 24/7 via Rezdy; we operate every day of the year
The first tour company in Florence built by locals

Welcome!

Stefano, the founder and the soul of the company, decided to open his little dream in 2020. His dream is to create experiences that he would personally take if he was traveling!
We create transformative experiences

At Out of The Box Florence

Our hikes aren’t just about reaching a summit, but about embracing the journey, connecting with nature, and leaving a positive impact on the environment.

We don’t stop at hiking and wine.

Our passion for personalized adventures extends to biking, where we pedal through charming trails, discovering hidden gems that only locals know.

We encourage to visit places not famous, as we say

"Better do special, than famous, things"

PLAN A TOUR

Our Guides

Giulia

Born and raised in Florence, Giulia studied Law in Bologna before realising she wanted to spend her working life surrounded by beauty and stories rather than contracts. She went back to study art history, earned her official guide licence, and co-founded a cultural project — Le Ragazze di San Frediano — that creates thematic itineraries through the city for both visitors and Florentines. She approaches Florence the way an actor approaches a script: looking for what is beneath the surface, and for what it makes people feel.

Interests: acting, singing, the stories hidden in stone.

Giulia out of the box florence guide
Barbara out of the box florence guide

I am looking forward meeting you on one of the

OUT OF THE BOX FLORENCE tours!

Barbara

Born and raised in Florence, Barbara grew up with roots on both sides — Tuscany from her mother, the southern Italian sense of hospitality and generosity from her father. She studied Business and Tourism Management at the University of Florence, with three semesters abroad in England, Germany, and Chile that gave her both language fluency and a traveller’s perspective on her own city. She obtained her official Florence guide licence in 2012, specialising in art history. She is known for weaving historical fact, artistic detail, and street-level curiosity into the same tour — and for knowing which artisans in the city still practise techniques that were invented in the Renaissance.

Interests: the living craftsmanship of Florence, languages, celebrating love in beautiful places.

Barbara out of the box florence guide

I am looking forward meeting you on one of the

OUT OF THE BOX FLORENCE tours!

Alessandro

I am a professional hiking guide based in Tuscany, where I was born and have spent most of my life exploring trails, rivers, and wild corners of the landscape — usually with muddy boots and a very happy dog named Kodi somewhere ahead of me on the trail.

I studied Wildlife Sciences and worked on wildlife monitoring projects, which permanently changed the way I look at nature — not as a backdrop, but as something alive and worth understanding. I tend to notice things most people walk straight past: a track in the mud, a bird call, a plant that has no business being there. I try not to turn every walk into a nature documentary. No guarantees.

Whether it is a coastal path on Elba, a ridge in the Apennines, or a multi-day route like the Via degli Dei, I believe the best way to truly know a place is to walk through it slowly, with good company.

Interests: wildlife tracking, long trails, wild Tuscany — and Kodi.

Giovanni

An Anglo-Italian professional guide and landscape expert who has spent his career leading tours across Tuscany while developing a deep knowledge of wine and extra virgin olive oil — he has been producing his own olive oil for nearly a decade. Giovanni brings an intercultural perspective to the Tuscan landscape: he grew up between countries, worked in international trade, and brings the kind of genuine curiosity about the natural world that makes him as comfortable in a vineyard as on a mountain trail.

Interests: organic agriculture, landscape history, the intersection of food and territory.

Giovanni out of the box florence guide

Our Commitment to Sustainable Travel

We are not sustainable because it is good marketing. We are sustainable because it is the only way we want to operate.

In practice, that means: itineraries planned to distribute visitors away from saturated areas; partnerships exclusively with small, independent, and where possible organic producers; no charter bus connections to overrun landmarks; and group sizes kept small enough that our presence in a place does not change it.

Florence is one of the most visited cities on earth. We want the places we take you to still be worth visiting in twenty years.

.

Our Beloved partners

Katrin out of the box florence Partners
Katrin

I would love to introduce you to Katrin. Urlaub an der Stiefelspitze

She is totally in love with Calabria, and of course Italy.
Everything she picks has something special, she connects people and places with her incredible talent.

Her website is a wonderful resource of travel tips:
Calabria Travel tips

Katrin, is a marvellous person, in love with travelling and organising tailored trips for whom wants to visit Calabria and Italy like a local.
Her devotion to choose just the best locations for her guests is the key to her success.

She runs the best pizza place in Freiburg (Germany), please try it if you pass by Freiburg. It’s outstanding…
Best pizza in Freiburg (Germany)

Ask her anything about your holiday and she will figure out what’s the best for you.
Even if she will never admit that Tuscany is better than Calabria 🙂

Katrin out of the box florence Partners

Our motivation

Hiking florence

Our motivation

Our tours are specifically designed to protect nature and have less of an impact on the environment. Our base is in Florence, one of the main touristic cities in Italy and We want to take you where you can admire the beauty of our land away from the crowd.  We offer outdoor excursions and wine tastings in Florence and throughout Tuscany and The Cinque Terre.

Something good for you and for the enviroment.

Stefano, the dreamer behind this journey, has started this adventure to prove that a different way of travelling is possible. Stefano wants to show its land in the most green and ecological way, away from those touristic spots and making you appreciate the beauty of Tuscany, Florence, the Cinque terre or wherever you want to go.

“The Dome of Florence is beautiful and unique, but if you see it only next to, like all the others 14 millions tourist, it doesn’t leave you anything! Come and see the Dome from the hills where you will have a unique view on a unique building”

Stefano wants to deliver unique spots in a unique way!

Customer satisfaction with out of the box Florence
Small group of travellers tasting wine at an organic Chianti Classico winery with a local guide, far from any bus tour crowds
As seen in
OutOfTheBoxFlorence
LOCAL ADVENTURES, DISCOVER NATURE AND TASTE UNIQUE DELICACIES
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Estremi identificativi SCIA:
Comune di Firenze, N° 9701/2020/SUAP
in data 29/09/2020 prot. n:250308
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Estremi identificativi SCIA:
Comune di Firenze, N° 9701/2020/SUAP
in data 29/09/2020 prot. n:250308
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