Tuscany Tours from Florence: Wine, Hiking and Gravel Bike Experiences

Out of the Box Florence runs private and semi-private wine, hiking and gravel bike tours from Florence across Tuscany and Cinque Terre. Founded in 2020 by Stefano Mazzantini, a certified sommelier and licensed hiking and cycling guide, the agency is fully licensed and never takes more than 15 guests on a tour. Over 20 day trips and multi-day itineraries are listed below.

 

Out of the Box Florence runs private and semi-private wine, hiking and gravel bike tours from Florence across Tuscany and Cinque Terre.

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Outdoor Tours

Days spent on foot or on the bike, out of the city. Vineyard trails in Chianti, the coastal paths of Cinque Terre, the hills above Florence, and gravel routes on the white roads of central Tuscany. Every route has been walked or ridden by the guide leading it, and the pace is set by the group rather than by a timetable.

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Bespoke Private Tours

Full and half days reserved for your group alone, with pick-up from your accommodation in Florence. Wine in Chianti, Montalcino and Val d’Orcia, cooking in a private farmhouse, truffle hunting tours in season, marble and lardo above Carrara, or the medieval towers of San Gimignano. Timing and stops are yours to move.


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Customised Tours

When nothing in the catalogue is quite the trip you had in mind, we build it. Single days, multi-day itineraries across Tuscany, Umbria and Cinque Terre, self-guided routes with accommodation booked and luggage moved for you, or simply a licensed private driver for the day. Tell us what you want to see and we will tell you honestly whether it fits into the time you have.

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What is the difference between a private and a semi-private tour?

The itinerary is the difference that matters. On a private tour you can change timing, stops and pace on the day itself. On a semi-private departure the route is fixed, because you are sharing it with other travellers who booked the same day.

 

Private and semi-private tours compared
Feature Private tour Semi-private tour
Group size Up to 15 guests, across two vans seating 8 and 7 Capped tour by tour, always a small group
Who you travel with Only your own party Other travellers on the same departure
How it is priced Per group, not per person Per person
Itinerary Timing, stops and pace adjustable, including on the day Fixed route and schedule
Pick-up Directly from your hotel or apartment in Florence Agreed meeting point
Free cancellation Up to 15 days before departure, less a 10% booking management fee Up to 48 hours before departure
Best for Families, groups travelling together, anyone who wants control of the day Couples and solo travellers happy to share the van

Full terms are on our FAQs page.

Which tour should you choose?

Most guests arrive with three or four days in Tuscany and one clear priority. Start from that priority rather than from the map.

If wine is the reason you came. Chianti Classico is the closest and the easiest to reach from Florence, and works as a half day or a full day tour. Brunello di Montalcino and Val d’Orcia are further south and need a full day, with a longer drive rewarded by a very different landscape. All wine days are led by a sommelier and built around small family-run estates.

If you want to walk. The hills of Fiesole give you Florence from above in half a day. The Chianti Classico wine hiking day combines trails between vineyards with three cellars. Cinque Terre is the longest day we run, on the coastal paths between the villages.

If you would rather not walk far. Several days are built without hiking, including the Cinque Terre itinerary by train and boat, San Gimignano and Certaldo, and the cooking class in Chianti.

If you ride. Our gravel itineraries follow the strade bianche of Chianti, Val d’Orcia and the Pisan hills, as single days or self-guided multi-day routes with GPX tracks and luggage transfers.

 

Who are you travelling with

A licensed travel agency

Registered in Florence under P.IVA 06155900480 and SCIA N° 9701/2020/SUAP, filed with the Comune di Firenze on 29 September 2020.

Certified guides.

Stefano is a certified wine sommelier and a licensed hiking and cycling guide. All our guides and drivers speak fluent English.

Private and semi-private only.

Maximum 15 guests, travelling in two air-conditioned vans. We do not run large shared groups.

Frequently asked questions about our tours

How many guests can join one of your tours?

Never more than 15. Private tours travel in two air-conditioned vans, one seating 8 and one seating 7, which lets us keep larger families and small groups together. Semi-private departures are capped lower, tour by tour, and the limit for each one is shown on its own page.

Which tour is best for a first trip to Tuscany?

Chianti Classico, in most cases. It is the closest wine region to Florence, the drive is short, and a single day gives you vineyards, cellars and lunch without spending hours in the van. Guests with more time usually add a full day further south, in Val d'Orcia or Montalcino.

Which of your tours involve hiking, and which do not?

The wine hiking day in Chianti, the Fiesole half day and the Cinque Terre hiking day all involve walking. Everything else is built around short walks in towns and at wineries. The Cinque Terre itinerary without hiking uses trains and boats between the villages instead of the trails.

Do you organise multi-day itineraries?

Yes. We plan multi-day trips across Tuscany, Umbria and Cinque Terre, guided or self-guided. Self-guided cycling and hiking itineraries include tested GPX tracks, accommodation booked to your budget, and daily luggage transfers between stages, so you ride or walk with a light day pack.

Can you collect us from our hotel in Florence?

On private tours, yes: we pick you up directly at your hotel or apartment and bring you back at the end of the day. Semi-private departures use an agreed meeting point in the city, confirmed by email when you book.

Can you build a tour that is not in this catalogue?

That is a large part of what we do. Tell us how many days you have, where you are staying and what you care about most, and we will draft an itinerary and say plainly if something does not fit the time available. Start from our customised tours section or contact us directly.

Are your tours suitable for children?

Many are, and families travel with us often. Some days involve walking that does not suit younger children, so under-12s are not accepted on every experience. Tell us the ages when you enquire and we will say honestly which tours work and which we would avoid.

Do you take commissions from the wineries you visit?

No, and it is deliberate. We receive no payment for bringing guests to a winery, producer or restaurant, and we take nothing on wine you buy. Every estate on our itineraries is a small family-run producer we know personally and would drink at ourselves.

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