Hiking Chianti Classico: 3 organic wineries, 10+ wines & lunch

You walk between working vineyards and actually taste the oils pressed from the olives you pass.

A small-group hiking tour from Florence through Chianti Classico combines a 7 km walk on easy paths with visits to three organic wineries, tastings of 10+ wines and locally made oils, salami and cheese, and a Tuscan lunch. The guide is a local who knows the region by foot and keeps the group under seven people. The day is built around walking through the landscape rather than driving through it, so you move at the pace of the hills and the vines.

Step-by-step itinerary

Hiking and wine tasting in Chianti

• Drive through Chianti landscapes
• Hike 7 km through vineyards
• Visit first winery and taste wines
• Visit second winery and taste wines
• Enjoy family lunch with local food
• Visit third winery and taste wines
• Taste extra virgin olive oil
• Taste salami and cheese

The experience

The hike itself is the route: you walk 7 km on easily accessible paths through rolling hills and vineyards, moving between three organic wineries without a vehicle between stops. The terrain is gentle enough for any skill level, but you need to come in comfortable hiking shoes and bring water. The guide stays with the group the whole time, pointing out the landscape and the work that goes into the region, not narrating from a distance. Because the group maxes out at seven people, you're not moving as a cluster. The pace stays conversational.

At each winery, you taste wines made on the property, 10+ across the three stops, and at one you also taste extra virgin olive oil and local salami and cheese. These are small producers, not tourist operations, so what you're tasting is what they actually make and sell. Lunch is a proper Tuscan meal: a cold starter, pasta, and the wines you've already tasted. It happens at one of the wineries, so you eat where you've been learning.

The whole day runs eight hours from pickup in Florence. You can book this as a private tour or semi-private (shared with others), and the guide speaks English or Italian. Wear trekking shoes, bring sunscreen and a hat, and plan on being on your feet most of the day. It's hiking, not a stroll. The operator emphasizes that this is a sustainable experience: you leave no trace behind.

What’s included

• A 7 km hike on easily accessible paths through Chianti Classico.
• visits to three organic wineries with tastings of 10+ wines.
• tastings of extra virgin olive oil, locally made salami and cheese.
• a Tuscan lunch with cold starter and pasta.
• a local English or Italian-speaking guide who stays with the group the whole day.
• support for small local businesses through the wineries you visit.

Options for this experience

2 options

Semi-private optionGuide in English or Italian · 08:00Guided tour with lunch and three wine tastings, plus minivan transportation

Private Chianti Classico experienceGuide in English or Italian · 08:00Private guided wine hike with lunch and three wine tastings, minivan transport and personalised pickup

You'll see the exact price of each option when you check availability.See dates and prices

Information

Lasts 8h, runs Monday to Friday at 08:00, from € 199 per person, with a live guide in English and Italian, in groups of up to 7 and with free cancellation up to 24 h before.

Days and timesMonday to FridayDeparts at 08:00Another day? ›

GroupUp to 7

Live guideEnglish and Italian

Meeting point and pickupNo hotel pickup: you go to the meeting point. Ends back at the starting point.

Book up to2d before

AgesAdult (27 and older) · Youth (18 to 26 years) · Under 18: can't be booked

Cancellation and refundsFree cancellation up to 24 h before the start. After that, no refund.

Prices and times updated today

Good to know

Moderate physical effortPublic transport nearbyNot recommended during pregnancyNot recommended with heart problemsNot recommended with back problems

Operated by Sustainable travel Experiences and Tours - Out of the Box Florence -

Is this one for you?Choose the private option if you want to set your own pace and route through the vineyards, or the semi-private version to share costs with other wine and nature lovers on a fixed itinerary.

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Top questions

What languages is the tour guided in?

Live guide in English and Italian.

Can children come?

Yes. Ticket types: Youth (18 to 26 years). Children under 18 can't be included in the booking.

How difficult is the 7 km hike through Chianti?

The paths are easily accessible and suitable for any skill level, so you don't need hiking experience. The terrain is rolling hills and vineyard tracks, not steep or technical. You do need to be comfortable walking for several hours in hiking shoes and bring water and sun protection.

What exactly do you taste at the three wineries?

You taste 10+ wines across the three organic wineries, plus extra virgin olive oil, locally made salami and cheese at one stop. These are small producers making what they sell, not mass-market tastings. Lunch is a Tuscan meal with a cold starter and pasta, paired with the wines you've already tasted.

How many people go on this tour?

The group is capped at seven people maximum, so it stays small and conversational. You can book it private (just your group) or semi-private (shared with others up to the seven-person limit).

What's included in the price and what do I need to bring?

The hike, all three wineries, the 10+ wine tastings, oils, salami and cheese, and the Tuscan lunch are all included. You must wear comfortable trekking or trail running shoes, bring your own water, sunscreen, a hat and anything else you'd normally carry for a walk. Gratuities are not included.

Does this tour work if I'm not an experienced hiker?

Yes, the paths are easy and the guide is with you the whole time. The tour is designed for nature and wine lovers at any fitness level, though you do need moderate fitness to walk 7 km over eight hours. The operator does not recommend it for travelers with walking difficulties, spinal injuries, or poor cardiovascular health, and children must be at least 18.