What To Expect

What‘s Included

Reviews

• Outstanding Hiking Experience with Out of the Box Florence

  D9310EOjuanm,,Jul 14, 2025

  - Review from Tripadvisor

  5.00

  My wife and I recently took a hiking tour with Out of the Box Florence and it was a great experience. Lorenzo our guide was incredible, knowledgeable, friendly and very passionate about the area we hiked. The 3 wineries were amazing. Would highly recommend this tour it was definitely the highlight of our trip.

• Don’t hesitate to book this one!!

  Kirsten,,Apr 29, 2025

  - Review from Viator

  5.00

  This experience is incredible. Lorenzo is a true local and will guide you to 3 Chianti wineries by trekking. This is a small company and truly cares for a meaningful experience. Highly highly recommend.

• This was a well organized...

  Margaret M,,Apr 13, 2025

  - Review from Viator

  5.00

  This was a well organized and enjoyable experience. Our tour guide was knowledgeable and friendly. We loved walking through the countryside from one winery to another!

• A FANTASTIC experience in Tuscany!

  849stewartg,,Apr 1, 2025

  - Review from Tripadvisor

  5.00

  We've spent just over three weeks in Italy, and our guided Chianti Classico tour with Out of The Box Florence was undoubtedly one of the highlights of our entire trip! We began with a scenic drive through the breathtaking Tuscan countryside, then hiked between three beautiful wineries. The first two were small and intimate (just our style!), and the third was a bit larger but a wonderful private tour and tasting. We tasted a variety of delicious wines, conversed with the winemakers themselves, and also sampled their exquisite olive oils. At the second winery, we were treated to an authentic Tuscan lunch, prepared by the winemaker's mother—absolutely delicious! Our guides, Johnny and Guilia, was incredibly knowledgeable about wine, the region, and the plants we encountered along the way. It was clear that he deeply cares about the region and sustainable tourism. His passion for the area made the experience even more enriching. This was an unforgettable adventure that my wife and I will remember for years to come. I can't recommend this experience highly enough! Just a heads-up: this isn't a leisurely stroll. We covered about 5 miles of rolling hills with significant elevation changes, so be sure to wear proper footwear.

  

  

  

  

  

  

  

  

  

  

• Fantastic Experience

  Caitlin F,,Oct 27, 2024

  - Review from Viator

  5.00

  Lorenzo was a fantastic guide! we were supposed to be a group of 4 but the other couple dropped out last minute. My husband and I ended up on a private tour. We had an amazing time hiking the beautiful vines of Chianti and learned about the terrain and local vegetation along the way. We stopped at 3 wineries along the way both small and mid-sized. We had local organic meats and cheeses to pair with our wine and a homemade Italian meal. If you are even considering this experience... BOOK IT! I can not recommend this experience enough.

• A perfect day in Chianti

  lsF7969TC,,May 27, 2024

  - Review from Tripadvisor

  5.00

  Stefano began by patiently answering our questions weeks before the trip. He checked in with us as our date approached and then arrived to pick us up in Florence city center at the pre-planned time and location with his clean, spacious van. Our trek included our two adult children. Stefano was the perfect host. His English is impeccable, and he was kind to share some history of Florence, the Tuscany region, and more as we arrived in Chianti. When we realized we accidentally brought sparkling water, he stopped to be sure we had the chance to get still water. Our family of four includes a landscape architect, an ecologist, and a college minor in sustainable agriculture. He was patient to answer so many questions about the area, plants, and flowers that we saw. Our hike was exactly as expected in terms of duration and difficulty, but it was far more beautiful and peaceful than anything we could have imagined. Each winery was unique, but all welcomed us, gave us detailed information about their grapes, olives, and history, and each shared their delicious products. We had the opportunity to purchase wine and olive oil from all, but none were high-pressure situations. Our first case arrived within days of our return home! Stefano was careful to be sure we were each comfortable and he gave accurate details along the way so that we would understand how far to the next stop. While we visited the final winery, he somehow retrieved the van and had it cooled and ready to take us back to Florence. Our only regret is not staying in the area longer and having him take us to Cinque Terre too! We highly recommend Stefano, Out of the Box Florence, and look forward to returning in the future for one of his other treks! Grazie Mille!

  

  

  

  

  

  

  

  

  

  

  

  

  

  

  

• Amazing experience!

  mindyc2017,,Apr 21, 2024

  - Review from Tripadvisor

  5.00

  We booked a hiking tour of Chianti Classico with Out of The Box Florence, and it was a dream! We took a scenic drive through charming villages in the Tuscan countryside, then hiked between three wineries. We got to meet the vintners and hear their stories. Then we had some of their wine with cheese and meats of the region, along with amazing views! Our guide was very knowledgeable about wine and the area. We could tell that he cares deeply about protecting the environment and educating the public about sustainable tourism ... but he also made it fun! It was an unforgettable experience that our family will be talking about for many years.

  

  

• Florence: Tuscany & Chianti Classico Trek & Wine with Lunch

  katherinewJ6276TJ,,Apr 2, 2024

  - Review from Tripadvisor

  5.00

  Lorenzo was a fantastic tour guide. I can't say enough about how happy I am with our experience. The 3 wineries were incredible. There was heavy rainfall, so we couldn't do some of the hikes, but Lorenzo gave us many backup adventures and took us to his favorite small towns. The nature was remarkable, and it was great to meet local wine and olive oil makers. I would HIGHLY recommend this tour, as it is an amazing day. Lorenzo's flexibility and knowledge about the area and the wine was impressive. Meeting all kinds of people who have been creating wine and olive for decades was a very cool experience and I would do it many times over if I could.

• Our favorite day in Florence out of the Four Spent

  aimeeg124,,Mar 16, 2024

  - Review from Tripadvisor

  5.00

  This was our favorite day in Florence. Lorenzo met us at a cafe near our hotel. We ended up having a private tour for the day. Lorenzo was very knowledgeable about wine and plants. We enjoyed learning about foraging for mushrooms and the local flora. The countryside was so beautiful! We loved having a glimpse into two small family wineries and one mid-size winery. And, the wine was delicious!

  

  

  

  

• Incredible hike and wine by Lorenzo

  lynnerR3689FP,,Nov 21, 2023

  - Review from Tripadvisor

  5.00

  Lorenzo took our family of 3 on an unforgettable hike in Penzano (Chianti region). We couldn’t have asked for a more kind, thorough and attentive guide. He was quite knowledgeable of the region, and all the local flora. We even tasted a few herbs and berries along the way. Happening upon some olive pickers, Lorenzo explained the harvesting process and coordinated us observing on the spot. The 2 smaller wineries we visited were our favorites- so hospitable and a home cooked meal! Not to mention outstanding wine! Do yourself a favor,and book this tour! Grazie mille, Lorenzo for a fabulous day!

  

  

  
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