Day trip

Florence: Tuscany & Chianti Classico Trek & Wine with Lunch

Activity provider: Out of the box Florence
Day trip

Florence: Tuscany & Chianti Classico Trek & Wine with Lunch

Activity provider: Out of the box Florence

From US$ 270.87 per person

Join this 8-hour tour through Tuscan vineyards, olive groves and rolling hills. Take short treks in Chianti Classico wine region, stopping at 3 wineries.

About this activity

Free cancellation
Cancel up to 24 hours in advance for a full refund
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Covid-19 precautions
Special health and safety measures are in place. Check your activity voucher once you book for full details.
Duration 8 hours
Check availability to see starting times.
Live tour guide
English, Italian, Spanish
Pickup optional
- Please wait in the hotel lobby 10 minutes before your scheduled pickup time - Guide will hold a sign "Out of the box Florence"
Private or small groups available


  • Discover Chianti Classico wine region by foot
  • Taste delicious local wines and food
  • Meet great local organic producers
  • Explore Tuscany in a small group
  • Be a part of sustainable tourism and get a chance to support a local business
Full description
Spend a day walking in nature where local wines and food are combined to have a marvelous day out in Tuscany through natural beauties, historical small wineries, and little villages nestled in the heart of the Chianti wine region. Understand the process of wine-making and olive oil production. Hop on a minivan and be driven along unique little roads in the Chianti Classico wine region. Reach the starting point located in Panzano in Chianti. The exact drop-off point is a secret. Start the day with a little walk through the Conca d'oro, a magnificent natural Amphitheater where the best Chianti Classico wines are produced. Walk through vineyards leading you to the first winery stop. from the 12th century, run by a local family. At this family-run winery from the 12th century, visit the wine cellar. This is the second oldest building in Panzano in Chianti, used as a medieval post. Enjoy marvelous wines and food tasting in a stunning historical location. Say goodbye to this unique wine cellar and continue walking through olive groves and vineyards toward the second winery. Savor lunch and another wine tasting (sometimes the lunch is postponed to the next stop). The marvelous wine here is produced by 3 generations of local farmers. Tuck into a tasty Tuscan lunch with a selection of their wines, perfect to recharge for another hike towards the last winery. The last Winery is a modern winery created by Italian artists. Settled right at the top of the hills overlooking Montefioralle, an enchanting castle nested in a great position. In the last winery, all modern techniques are combined with old, time-tested knowledge. Enjoy the last wine tasting here. For those who want to hike more, there is the final stretch downhill to reach Montefioralle. Get on the minivan back to Florence.
  • Transportation by air-conditioned minivan
  • Easily-accessible paths, suitable for any skill levels
  • Extra virgin olive oil tasting
  • Expert guide and wine sommelier
  • Lunch in a family organic winery, with starter and pasta
  • 3 wine tastings, including cheese, salami, ham, olive oil and saffron tasting
  • Visiting to 3 organic small family wineries, with 11 wines
  • Sustainable local tourism experience
  • Hotel pickup and drop-off
  • Gratuities
Not suitable for
  • Pregnant women
  • People with back problems
  • People with mobility impairments
  • People with heart problems
  • Wheelchair users
  • Children under 18 years
  • People with pre-existing medical conditions

Select participants and date



Meeting point

- Arrive 15 minutes before the activity starts. - Look for the sign "Out of the box Florence" - Meeting point is right at the corner with the bar Cafè lietta

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Important information

What to bring

  • Sunglasses
  • Sun hat
  • Hiking shoes
  • Water
  • Biodegradable sunscreen
  • Comfortable clothes
  • Sports shoes
  • Weather-appropriate clothing

Not allowed

  • Luggage or large bags
  • Backpacks

Know before you go

  • This tour takes place rain or shine
  • Around 12 km of walking is involved on the day tour
  • The terrain is uneven with ups and downs. Designed to have more downs than ups
  • Sometimes due to winery's supplies, all products are not available
  • Alternatives routes may need to be taken at times to avoid winery closures
Customer reviews

Overall rating

5 /5

based on 2 reviews

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Absolutely the best day of our trip. Stefano is a wonderful guide and he has composed such a nice experience for guests. The trekking was definitely reasonable for any fitness level (I was very out of shape for this trip) and really added to the experience, being able to see the beautiful countryside and historical architecture in the region. It was so special meeting the vineyard owners and hearing them talk about their wine with such pride. Lunch made by one of the wine maker’s mothers was out of this world good. Just remarkably charming. Stefano is knowledgeable in all sorts of things so kept the walking portions of the tour engaging and fun. He’s just a fun person to be around. I wish we could take him to Rome to lead the rest of our excursions on our tour of Italy! Book this experience - you will love it!

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September 21, 2022

Stefano is a highly knowledgeable and friendly guide who is passionate about sustainable tourism. He is a sommelier and handpicked three wonderful wineries in Chianti Classico for us to visit. We did a gentle hike through the incredible countryside (about 10kms total over the whole day) which was interspersed with wine tasting and lovely food. We met some wonderful winemakers, who are clearly passionate about Chianti Classico and their wines. Wear good walking shoes, bring a hat and be prepared to have fun; it was an unforgettable experience.

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June 6, 2022

Product ID: 401516