Out of the Box Florence

Florence, Tuscany & Cinque Terre through its trails and back roads

At a time when Tuscany is too often experienced through rushed day trips and crowded wine stops, Out of the Box Florence offers something far more immersive: outdoor adventures shaped by the people who know this landscape as home.

Their hiking routes lead travellers deep into Chianti vineyards and coastal paths, their gravel biking journeys uncover countryside roads unreachable by car, and their wine experiences bring guests to small family-run wineries far from the usual tourist circuit.

Each experience brings you beyond the postcard version of the region, into landscapes, quiet back roads and hidden corners that most visitors never reach.

Florence’s outdoor specialists

Every experience is built on genuine local knowledge. These are not standard itineraries pulled from guidebooks, but carefully designed hiking and gravel biking experiences shaped by years of firsthand exploration.

Whether climbing coastal trails above the Ligurian Sea, cycling gravel roads through Chianti or walking lesser-known vineyard paths, their itineraries are designed for travellers who want to experience Tuscany in a way that feels truly local, not from behind a bus window.

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Thoughtfully chosen local partners

What defines these experiences is not only the landscapes themselves, but the people behind each stop along the way. From biodynamic wineries and small cheesemakers to family-run trattorias and artisan producers, every partner has been personally selected for their integrity and connection to place.

Because they never accept commissions on tastings or wine sales, recommendations remain independent and genuinely based on quality. Their work supports small local producers directly while keeping tourism spending within the communities they operate in.

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Built around the things you love

No two travellers experience Tuscany in quite the same way, which is why no two days with Out of the Box Florence are alike. Some guests come for long hikes through vineyard trails, others for slower rides through the countryside or multi-day journeys that unfold at their own pace. Each route is shaped around each traveller’s preferences and interests.

Even getting from place to place feels part of the experience. With private transfers included in their own minivan, there is no rushing between stops or figuring out complicated logistics, just more time to enjoy the landscapes, stories and hidden corners along the way.

Story Behind Out of the Box Florence

At the centre of Out of the Box Florence is Stefano, whose personal relationship with these landscapes defines every experience.

Every trail, gravel road, cellar door and countryside table included in an itinerary is there because Stefano has walked it, ridden it or sat there himself, not because it is famous, but because it is worth sharing.

What began as a personal passion for exploring Tuscany outdoors evolved into a way of opening up a more intimate side of the region to others. For Stefano and his passionate local team, this has never been about showing travellers a highlights checklist. It is about inviting them into a Tuscany experienced slowly, actively and through the people who know it best.