Hiking Tuscany & Chianti Wine - 3 Organic Wineries With Lunch

I truly cannot say enough wonderful things about our experience with Out of the Box. My fiancé and I booked the hiking wine tour, which accounts for up to 7 people, but when we arrived, we were the only two booked — essentially giving us a private tour for the day. Our tour guide Alessandro was phenomenal. He was extremely knowledgable and welcoming, and by the end of the tour, it genuinely felt like we became friends because of all the time we spent together. The wineries themselves were also incredible and felt like some of the most authentic experiences we had throughout our trip. Getting to connect with all of the different owners and wine-makers was so special. The wine tour was one of the things we were most looking forward to on our trip, and it exceeded our expectations. This is a must-do, and truly a great company with good values supporting sustainable tourism. I think you have to do the hiking tour to get the best views during your day trip too!

This was our most favorite experience in our two weeks in Italy! We had a day in the Tuscan countryside with perfect weather, hiking through a stunningly beautiful and peaceful landscape meeting wonderful people and tasting wine. Our guide Manuel was amazing; knowledgeable, helpful, kind, and very charming. He made our visit feel like we were walking about with an old friend. We learned so much from him as we traveled the trail. The three wineries were all very special places, each with their own story plus lovely wine, hospitality and gracious hosts. We didn't want to leave! Thank you again to everyone we met for this memorable experience. Helpful tip, this is an actual miles long hike on gravel trails with grade changes, prepare by being well rested, wear good walking shoes and bring water.

Me and my loved one booked this activity leaving from Florence, and it was absolutely amazing! We got to meet the owners of two small size wineries and one medium-sized one, tasted over 12 different wines and also got to learn a lot about wine and Chianti in general. All that with amazing views of the region. Alexander was an great guide as well, very knowledgeable about all sorts of plants and insects of the area. We highly recommend this activity!

Manuel was a very personable and knowledgeable guide. The semi-private tour made it a more intimate experience. We learned so much about Chianti Classico! We loved the first two small family wineries and even purchase some of their wine to ship home. Loved the flow of the tour ... driving to the first winery then hiking to the 2nd winery where we enjoyed a lovely and delicious lunch with mama's homemade pasta. After lunch, we hike to the last winery ... a larger corporate environment. The pace of the hikes was appropriate for the small group and we never felt rushed. We'd recommend this tour for wine lovers that enjoy a little movement and stunning scenery.

We bought this for my Dad’s 70th birthday and I’m so glad we did! My family and I had a wonderful time and the money was well worth it! Alessandro was a very friendly and knowledgeable tour guide and went above and beyond for us. Stefano was very helpful beforehand and everything was clearly explained to us. The journey from Florence was very comfortable. The hiking was just right - not too long and easy enough terrain but still very interesting with beautiful views! The 3 wineries were each very unique which gave us a really good insight into independent Tuscan family vineyards. We enjoyed 5 different wines in each vineyard and plenty of delicious food, including an amazing Italian lunch made by Ana at Vallone Di Cecione. I would recommend to anyone looking for day out near Florence.

Our tour experience in Chianti Classico with Manuel was very intimate, sharing the tour with another couple from the USA. Manuel shared his passion and knowledge of the area and its delicious wines. The hikes from winery to winery were not too strenuous and Manuel walked at a good pace. We enjoyed tasting wines from all 3 wineries but thoroughly enjoyed the experience at the 2 smaller family wineries.

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.

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

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.

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.

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!

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.

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.

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!

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!

Stefano is absolutely wonderful! This is my 2nd time doing the wine trek and my sisters 1st time. This is the highlight of our trip! Out of the box Florence is amazing and I highly recommend people doing this tour amongst his other tours! From the views, the wineries, the people are just amazing! Stefano is also so funny and super knowledgeable of the area and makes the time so memorable! We can’t wait to come back!!

This may have been the best time we had in two weeks in Italy, and I highly recommend this for active couples that enjoy the countryside, wine, and good company. Our guide, Massi, was a charming man with excellent English, infinite patience, and a passion for the Chianti Valley. He is also an forager and historian, with knowledge of both the plants along the trail and the impacts of Rome and war to the beautiful land. The three wineries we visited were diverse, and each had a wonderful host full of stories and vision. It was a great day in Tuscany -- if you are able, contact Stefano to make it happen!

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!

If I could give Stefano more than 5 stars I would. This experience was easily the most fun that we have had in Florence! Stefano is a sommelier and a fantastic guide around the wineries, not to mention an all around fun person to be around! 11/10 experience!

I particularly enjoyed the diversity in what we saw, Stefano was an amazing host throughout the day.

Stefano is a sommelier who has deep knowledge of both wine and the Tuscany region. He took us hiking through some incredible countryside in Chianti Classico, and we stopped at 3 boutique wineries, handpicked by Stefano. We spoke at length to the winemakers, who were clearly passionate about their wines and the tradition that is Chianti Classico. We tasted some great wines, walked through the vineyards and meet some wonderful people; we also had fun and a lot of laughs with Stefano, who is a warm and engaging guide. He is passionate about sustainable tourism, and we loved this approach - so different from the mass commercialism that you see more generally in and around Florence. The walk itself is a relatively easy hike of about 10kms in total, at a very relaxed pace across an entire day, and interspersed with wine and food. Wear a decent pair of walking shoes, bring a hat and be prepared for a wonderful day!

5 stars? I would put more if I could. Our Chianti Classico trip was one of a kind, truly. Stefano is such a welcoming, knowledgeable, and unique person. He is so fun to hang out with, he really made our group feel like locals. I've done all kinds of tours in my lifetime, the hike really allowed for everyone to get to know each other and I finished this experience feeling like I had an adventure with new friends. I highly recommend it, you have to see it for yourself!

Stefano was amazing…. The wines and food was stunning…. Unique local experience . Unforgettable trip 😍

Appreciate Stefano and Chris for not only Unforgettable memory we had during this tracking, but also making to feel being a part of Chianti Classico winery! Simply Stefano organized this trip unbelievably well and in a way that we could fully feel the charm of each wine and winery. We have been to 3 wineries which they have their different characters. There we heard a very kind explanation how they take care of the product and tested various sorts of wine with local food. The other part which is tracking, We tracked most of the time next to the grape farms which were very beautiful and breath-tacking once we looked back. It was full of joy therefore i felt like it too us only a couple of hours! Definitely A MUST DO if you enjoy drinking wine! Cheers guys.

My Wife and me booked the „Great Chianti Classico Crossing“ via Amavido.de - Katrin from Amavido recomended Stefano and his tours. On the final day we met Stefano and his colleague on a free parking next to Parcheggio, the trip began quite relaxed and we even got a little breakfast. During the day we‘ve visited several very beautiful Winerys and their masters. We always felt very welcomed and we got served nice local food, and of course we tested a lot of wine, while we tested the wines, the owners told us their story and also many things about their wine! during the hiking we got many informations about the area and the wine by stefano, very interesting. We were surprised that we didnt meet even 1 single other tourist! Made the whole experience even better. I‘d recommend this trip if you stayed in Florenz and if you want to enjoy the nature afterwards. If youre interested in Wine, even better. The whole trip was very well organized by the Out of the box team. So thank you Stefano&Chris, it was an unforgettable experience for us 😃

Stefano Is amazing!!! we had an amazing tour inside the beauty of the countryside. I am a really lazy person, but Stefano is super nice and a great storyteller about Florence and the beauty of Tuscany. It is been lovely hiking with him. The real surprise is the wine tasting and the foooooddd so yummy!!! and we can't stop eating, it was too much!! if you want to relax, enjoy, eat and taste good wine, contact him!

I had an amazing experience with Stefano who definitely knows his wine, and the region : we learned a lot from him. He's really a great guy, funny and entertaining. We spent a lovely afternoon with Stefano and my friends and I strongly recommend his tours !

We had a lovely tour with Stefano through the Chianti region. Our family went into it knowing to expect great food and wine, but the guide (and owner!) Stefano made the whole experience truly special. He is so passionate and such a character :) he was full of interesting anecdotes and I found that I learned quite a bit, even though I went into it thinking I knew a good amount about the wines of the area. We did what I thought was just the right amount of walking in the day. The walking was great for the beautiful scenery, but it was also nice so that we didn't feel so guilty about all the food and wine :) I'd recommend it to one and all (that's why I'm writing the review after all). Stefano is one in a million and knowing that we were supporting a local business was a nice bonus. I look forward to my next visit to Florence (hopefully sooner rather than later) so I can see more of the region with them.

My husband, my daughter and I tried this trekking wine that we found it original, we loved it. Stefano, a nice et yong guide, was very professional and very experienced. He made us discover the hills of Chianti classico in an easy walk. We tested exceptional Italian local food and wines. We recommended this great experience : breathless landscape and amusing things to eat and drink !!!!

We had a private wine walk through the vineyards of Chianti Classico with Stefano. He was very warm and serene from the beginning and welcomed us with delicious croissants and a Prosecco. After the rocky but very nice climb we had our first wine tasting - a dream! Also at the 2 stop we were allowed to taste very delicious wines and were allowed to enjoy excellent pasta of a real Italian mom 😉 the last piece we drove the car - directly to the next tasting. All in all, a wonderful excursion, but it took a little more time than planned. But it was just wonderful 😊

Nice discovery of Chianti. The walk is a walk through the vineyards with exceptional views. A little difficult in the August heat, about 38 degrees, but it must be better the rest of the year. Excellent tastings in three small to medium-sized vineyards. Each time different wines accompanied by local products (cheese, cold cuts, olive oil,...). The producers are passionate about their work and organic production, we can only admire them and regret not being able to take more wine with us. And all this under the guidance of Stefano, cheerful, professional, very friendly guide familiar with his region and wine growing. A beautiful day. Thank you Stefano!