I highly recommend booking this tour. From start to finish, the guide and driver Fabio, provided an outstanding experience. After a prompt pickup at my Airbnb, he drove us south to the Pecci Celestino winery; along the way, Fabio offered numerous insights into the geography and history of the region, drawing on his years in Florence and his training as a sommelier. The visit at Celestino began with a brief tour of the vineyards and the cellar, followed by a delicious tasting of five of the winery's current offerings (including a Riserva that is one of the best wines I've tasted). From there, Fabio drove to the small town of Bagno Vignoni, where we had lunch at Osteria del Leone. Here his networking skills really shone, as he introduced me to the restaurant owner, chef, and coincidentally, the producer of the wine that was served with lunch. On our way to the second winery, we stopped in the small and beautiful hill town of Pienza, where I had 45 minutes or so to walk around, stretch my legs, and revel in the smell of various types of Parmigiano cheese wafting out of the stores. A short drive brought us to the Le Bèrne winery, where I had a chance to sample some maturing wine directly from the massive aging barrels, and then sample six different finished wines. The information provided by the winery host was detailed and fascinating, and the wines were delicious. The day finished with a 90-minute drive up the A1 back to Florence. Throughout the day, Fabio was a gracious and entertaining guide, and I strongly suggest people make a specific request for his services. I also recommend signing up for a tour with "off-road" in the description; Fabio showed up in a fairly massive truck/bus with 4x4 capability, which meant that we could travel on somewhat challenging dirt roads among the vineyards. I will not soon forget the incredible views in this gorgeous section of Italy.
About Activity
What's Included
Includes
- Traditional Tuscan lunch in the historic village of Bagno Vignoni
- Local expert guide for the duration of the tour
- Offroad transportation along Tuscany dirt roads in our customized 4x4 coach
- Visit to a family-run winery in Montalcino with cellar tour and Brunello di Montalcino wine tasting
- Visit to a family-owned winery in Montepulciano with Vino Nobile di Montepulciano wine tasting
- Free time in Pienza to explore the town, shops, and enjoy panoramic views
Excludes
Departure & Return
Departure Point
- Traveler pick up offered
Itinerary
Depart from Florence and embark on a unique wine safari through the heart of Tuscany aboard a rugged offroad vehicle, journeying along the historic Via Francigena dirt roads. This immersive experience combines the region's iconic landscapes with its most celebrated wines, artisanal traditions, and charming hill towns.
Your adventure begins in Montalcino, where you’ll visit a family-run winery nestled in the rolling hills. Explore atmospheric cellars and savor the legendary Brunello di Montalcino, one of Italy’s most prestigious wines—crafted with passion and enjoyed by locals and connoisseurs alike.
Next, head to Bagno Vignoni, a village known for its ancient thermal springs and unique piazza built around a steaming pool. Here, you’ll relax and enjoy a delicious Tuscan lunch, surrounded by the warmth and charm of this tranquil setting.
After lunch, you’ll explore the jewel of Pienza, the “Ideal City” of the Renaissance. Enjoy free time to wander its cobbled streets, visit artisan shops, sample the famous Pecorino di Pienza, and take in stunning panoramic views of the Val d’Orcia.
The final stop brings you to Montepulciano, home to the elegant Vino Nobile di Montepulciano. Visit a family-run winery where locals still come to buy their wine. Learn about their winemaking traditions and enjoy a guided tasting in a relaxed and authentic setting.
Whether you're a wine lover, culture seeker, or nature enthusiast, this wine safari offers an unforgettable way to experience the soul of Tuscany—off the beaten path, through vineyards, villages, and timeless landscapes.
Language Offered
Additional Info
Cancellation Policy
Reviews
WOW!! Sara (our guide) and Luca (our driver) were phenomenal! From the moment they picked us up at our hotel to the moment they dropped us back off they were super accommodating and mindful of creating the very best experience for us. They never made us feel rushed even though we did have an itinerary to get through and they truly navigated the day with ease. It was such a full day of fun and sun in Val d’Orcia. A year or two ago we had gone on the Chianti wine safari with Walkabout Tours and it was the highlight of our trip so we were keen to go on a wine tour with them again. Although it’s a different experience going on a private tour, I would say it was better in every way - we really got to know the wine makers and had plenty of time for diving deep into the details of wine production. The wines were sampled were truly spectacular. Our lunch stop was fantastic and the pasta dishes were truly some of the very best I’ve ever had. Getting the chance to visit Pienza and buy Pecorino was the cherry on top of it all! I personally think Val d’Orcia is incredibly underrated and everyone should consider going on this tour - especially if you enjoy Brunello and Nobile de Montepulciano!! Next time we come to Florence we are absolutely asking Walkabout Tours to take us on another wine tour! Grazie mille Sara and Luca, you’re the best!!
Fantastic experience! We really enjoyed the scenic drive down and all the stops were thoughtful. Sara and our driver were great hosts. Sara is very knowledgeable and answered all our questions. We really enjoyed the brunello wines and stopping off in Le Terme for lunch and our walk around the town of Pienza.
We absolutely loved our Walkabout Wine Safari. It was one of those perfect days where everything just clicked. The scenery, the wineries, the food, all of it. Tuscany is already beautiful on its own, but seeing it through this kind of experience just takes it to another level. Our guide, Sara, made the day even better. She was incredibly informative without ever feeling scripted, and she had this great way of making the whole group feel relaxed and taken care of. Lunch was amazing. It was one of those meals you keep talking about afterward and each stop along the way felt genuinely special. Highly recommend this tour and especially Sara. It was a day we won’t forget.
Great day out to visit 2 lovely wineries outside of the Chianti region. Visited a lovely town with a hot spring for lunch. Unfortunately it was a bit wet but still a great day.
This wonderfully fun day was So worth every penny! Our guide, Gloria was extremely knowledgable about the region, the wines, places on our route, food & just about any other question she was asked. The boutique wineries served delicious wines & foods as well as learning about the process of making the wines. Don’t miss buying some to send home! Our Tuscan lunch in the lovely town of Pienza was mouth watering. Don’t miss this tour!
We had an unfortunate rainy day but Alex, our tour guide, helped make it a memorable day and wonderful experience. The wineries we visited were enjoyable even though we couldn’t sit outside and enjoy the views with our wine tasting.
We cannot recommend this tour enough! Fabian was the perfect guide for a perfect day. He was very informative and had the best sense of humor! We met wonderful people, drank delicious wine, and ate amazing food. The tour van itself was very comfortable and pick/drop-off were as planned. It’s a full day but so worth it. We really appreciated the thoughtful choice of vineyards, towns, and the amazing lunch provided. We just received the wine we purchased and can’t wait to open a bottle!!
We visited two wineries and the city of Pienza and had lunch at Bagno Vignoni. The vehicle was a van for 8 people, not a jeep, but it was super new, clean and comfortable. The first winery was amazing in terms of taste, also the lunch was delicious and the scenery magical. Our driver was Fabian, he was extra polite, funny and well prepared to give us a great tour and many information regarding wine, food and Tuscany in general. Last but not least, we were sharing this tour with six other travelers whose mood and personalities were great and vastly contributed in the overall experience.
A fantastic wine tour we’ll never forget. The visits to the wineries were educational, and the producers were welcoming and passionate. A big thank you to our guide, who made the whole experience amazing with his knowledge and sense of humor that really resonated with us.
Sara was extremely knowledgeable, the wine was delicious, the bus was comfortable, and the group was a lot of fun! I would highly recommend this tour company.
Booking this tour was one of the best decisions my wife and I made while on our honeymoon in Italy! Gloria was an incredible host guiding us through the tour and keeping us laughing along the way. Her passion for her country and knowledge of wine kept us very engaged the whole time. Between visiting the small boutique wineries and beautiful Tuscan countryside towns, this tour was a stand out and something I would suggest to anyone visiting Florence. And the bus driver Nando got us there and back without a hitch, so glad we had him behind the wheel! Thanks again Gloria and Nando! It was a perfect day and one we will remember and talk about for many years to come!
Brilliant day with Alex. We saw so many places that we would have missed if we hadn’t done this tour. Small groups of 8 people. The bus was very comfortable and the weather was divine. This is our 3rd Tour with Walkabout and have enjoyed every one of them.
LOVED, LOVED, LOVED our guide Alex. He was AMAZING and made everything fun. The 2 wineries we went to were amazing, beautiful and fun. We did not get to go in the 4x4 vehicle in the ad (disappointing) but were in a sprinter type van which was pretty tight fit with our full tour and all adults. I did like that we got to experience a few towns in between the tastings but the tastings are exactly that....tastings. I wish we would have have more than a sample (there were 5+ samples) of each wine at each vineyard but I was expecting more wine for 11+ hour tour. At the wineries: They were amazing and I loved the detail and information that they gave about the wine and wine process. My brother did this same tour and recommended it when he was in Italy last year so we booked the same and our experiences were vastly different. Our guide Alex totally saved this tour as if we did not have him and his charm, jokes, and knowledge about wine, I would have been extremely disappointed to spend 11+ hours of my vacation on this tour.
My husband and I booked this excursion for our honeymoon and we couldn’t have had a better time! Between the thoughtfully laid out itinerary in the Val d'Orcia hills to the smooth bus ride everything was perfect. My husband and I still talk about this day! Thank you to the best guide Sara and our driver.
This was our favorite tour on our trip! Alex was very knowledgeable and gave us lots of great historical information on the areas we were touring and the wines were all delicious. The beauty of the drive was also a plus! Would recommend this tour to anyone interested in wines and Tuscany!
The wine tour was an amazing experience from start to finish. The wineries were truly authentic and Alex was a great guide. Would highly recommend!
We went on this awesome wine tour and will definitely highly recommend it. All of the places we visited were great. Gloria is super knowledgeable about the Tuscany wine region and all of the areas that we visited. She provided alot of insight as we were traveling to the different vineyard and on the bus which was very comfortable. Our driver was amazing, navigating very narrow roads in some cases. We thoroughly enjoyed the day and definitely recommend it!
My wife and I absolutely loved this wine safari in Tuscany! It was a fantastic day out. Our guide was the perfect host—incredibly knowledgeable and genuinely fun. They kept the entire experience engaging and entertaining. We especially enjoyed the two charming, family-run wineries we visited, which offered a truly authentic taste of Tuscan tradition. Highly recommended for a delightful and memorable day!
Alex was our tour guide for 2 wineries, he was very knowledgeable throughout the entire tour. The lunch was delicious, and the local vineyard wines are very very good!
We had a beautiful day driving through the Tuscan country side! We went to two different wineries, had a wonderful lunch in a small town restaurant and got to visit another town and explore. The wineries were fantastic and you could see how experienced our guide Gloria was. Our driver was also highly skilled and the bus was comfortable for the drive!
This is a great way to explore the Tuscan countryside, it's small towns—and enjoy some great wine. Fabian was an amazing guide. He's welcoming, knowledgeable and funny. After the first winery, we immediately shared his love of a good Brunello. Lunch was delicious and in a picture-perfect setting, and Pienza is a charming town. I highly recommend Fabian, this tour and the Walkabout tour group!
Fabio was a lot of fun and had knowledgeable about the area and wine. I highly suggest going on his van if given the opportunity. 5 stars all the way
We had such a wonderful experience with Gloria and the team at Walkabout Val d’Orcia Wine Tour! The entire day was very well organized and informative. We visited several beautiful wineries, enjoyed a delicious lunch, and even had time to explore the town of Pienza. It was a long day, but absolutely worth it. Highly recommend this tour to anyone looking to experience the best of Tuscany!
Alex is the perfect guide. He made sure we were comfortable, taught us about the area and the wine, was friendly and definitely made the day a memorable one. Thank you Alex!!
Our Val d’Orcia Safari Wine tour was an absolute highlight of our trip to Florence! Sarah were eexceptional guides—warm, knowledgeable, and so much fun to spend the day with. The winery visits were both educational and welcoming, with generous tastings and incredible hospitality. We learned so much about the winemaking process while enjoying delicious wines and stunning views of the Tuscan countryside. This tour exceeded our expectations and gave us memories we’ll cherish forever. We can’t recommend it highly enough—if you’re in Florence, don’t miss it! 🍷🌿🇮🇹 👉 https://www.tripadvisor.com/AttractionProductReview-g187895-d33221685-Val_d_Orcia_Safari_Pienza_Montepulciano_and_Brunello_Wine_Tour-Florence_Tuscany.html
This was a great day trip! A beautiful balance between vineyard visits and seeing the Val d’Orcia region. The off-roading allowed us to travel on the white gravel roads to reach smaller family vineyards, which felt more unique and specialized compared to other bus tours. The provided lunch was delicious and in an incredibly scenic village. Our guide, Gloria, was phenomenal both in giving us great details and information on the wines and history of the area, and also making sure we had space to explore on our own. I’d happily recommend this tour to anyone looking for a Tuscany day trip.
If Tuscany had a secret password, Fabio clearly knows it! From the moment we hopped in the van, his humor kept us laughing and his local knowledge opened doors (and wine cellars) we never would have found on our own. Because he’s a true local, we got the insider’s tour — not just the “brochure stops.” We tasted incredible wines at hidden gems that felt like visiting a friend’s family vineyard. Along the way, he entertained us with fascinating history of the region (turns out, wine tastes even better when paired with centuries-old stories and a few good jokes). And just when we thought the day couldn’t get better, he whisked us off to the most charming little town for lunch — the kind of place you’d never stumble upon without someone like him. It was the highlight of our trip. Grazie, Fabio — you didn’t just guide us, you gave us memories. 🇮🇹♥️🍇
We had a fantastic time on this tour and it was one of the highlights of our trip. Besides the beautiful vineyards, we had the opportunity to see places we otherwise would not have seen on our trip, like Pienza and Bagno Vignoni, because we did not rent a car. The small group size was great and made the whole experience feel more personal. The length of the tour was just right, not too long where you feel exhausted at the end and not too short where you feel unsatisfied; it was very well balanced. Our host Alex was charismatic, extremely knowledgeable and friendly. He answered every question we had, even if it was unrelated to the tour. He gave great restaurant recommendations and even offered us advice regarding a possible airport strike during our trip. He gave interesting context for the wine and for the region of Tuscany as a whole, with little historical facts during our ride there which was very nice. He was an excellent driver and we felt extremely safe in the vehicle during the tour (he did not drink at all). The tour alone was wonderful but Alex made it even better. If we were to return to the area, we would definitely book any tour that Alex was leading. Overall I think this tour is well worth the price, it's beautiful, fun and informative, well organized, comfortable and you get delicious food. I would recommend this tour specifically with Alex to anyone who is visiting the region. Grazie mille Alex!
Tremendous tour. Incredible wines, scenery and tour guide! We highly recommend this tour to wine lovers and nature enthusiasts. You will not be disappointed with either!!
This experience was truly amazing and Alex was a fantastic guide! My husband and I absolutely loved getting to experience the behind the scenes of wine making and meeting some amazing new people!:)
My wife and I had such a great time on this tour. Sara was a fantastic guide; she provided so much great information on the drive between locations, and brought us to some great remote spots. Our driver also crushed it. The bus was very comfortable, and we had a great group. Is it a bit pricey? Sure, but the value is 100% there, as it's a full packed day. We would absolutely go on another one of these tours of Chianti region if we are back in Florence.
My wife and I have a lovely time on our full-day wine excursion through Val d’Orcia. Sara was an excellent tour guide, continually providing some quite interesting facts and details about the wine and the surrounding regions (which were gorgeous & picturesque). We really appreciated visiting wineries that were a little more off the beaten track, getting a more intimate experience with the wine and the winemakers. Our pasta lunch was also incredible. Highly recommend!
We wanted to explore the Tuscan countryside, specifically Val d’Orcia, without having to rent a car and drive. This tour not only helped us accomplish that, but we also learned so much along the way! The tour guide, Sara, was super enthusiastic and knowledgeable about wine (in fact, she’s a certified sommelier). Even though it was a long day, she kept the energy up and gave us background on wine, the places we were visiting, history etc. Domenico was a steady driver who navigated us expertly through some tight spots. The minibus/van that had been retrofitted into a monster truck/off-road vehicle was a fun novelty, and it was comfortable and had good AC. We visited two excellent family-owned wineries and had a tour and tasting at each one. The wines were great. Though we personally don’t care much for Brunellos in general and enjoyed the second stop in Montalcino more, we learned a lot at each stop. Lunch at Bagno Vignoni was delicious and we even got some time to walk around the village. We also had some free time in Pienza, which provided great views of the valley. All in, a long but beautiful and enjoyable day out in the countryside away from the crowds in Florence. We would certainly do it again.
Fabio was entertaining, knowledgeable, and attentive to the whole group. Every stop was enjoyable and well planned. Very much enjoyable and a highlight of our trip.
Great experience on this tour. Great value for the price. Amazing tour guide! I would absolutely recommend this tour in Italy!
We had Fabian as our tour guide and he was fabulous! This tour is a drive through the Tuscan Countryside with stunning views , stops at beautiful quaint towns and a visit to 2 fantastic family wineries where you meet the families, see the wine making process and get to sample some great Italian wines. I highly recommend this tour and ask for Fabian as your tour guide !
We loved our safari wine tour and lunch. Alex was awesome and knowledgeable about the area and the wine. Our lunch was delicious as well.
The wine tour was a great experience. Our guide Alex was truly amazing. The experience left cherished memories for all the family.
Fabian was a great guide! Not only was the wine tasting experience 10/10 but it was so fun to learn about the process of wine making and how much work these families put in to what they create. Honorable mention was the lunch we had, still thinking about it!
I had the best time! Fabian was an excellent tour guide. He really loves what he does and it shows. This is the best experience I had in Italy. Highly recommend. I really loved it and would do it all over again.
We had a wonderful time on the wine Safari. Sara was a very knowledgeable and very accommodating. The van was comfortable and cool . Its a great tour
We had a fabulous time with Alex, who was an engaging and wonderful tour leader, very knowledgeable about the Tuscan wine region. It was great to visit and support the small family run wineries. Tastings were plentiful, and very very good! Lunch was amazing. Alex had a great recommendation for the group, food was excellent, and in an incredible location. Probably the best red sauce pasta I have ever had. When we return to Florence, will definitely do again. Highly recommend to any travellers considering a day tour in Tuscany.
Gloria was such a great and nice guide! My girlfriend and I had a blast on this tour and would absolutely recommend it to anyone in the area! It was so much more than a wine tour, as we truly were able to explore the region and learn about the history and culture of Val d’Orcia!
This was the best tour of our trip. The meeting place was easy to find and the group was small, as promised. I cannot say enough good things about our driver and guide, Alessandro (Alex). He was the best! He was so interactive with everyone and knowledgeable about the areas we drove through and especially about the wine. He also gave us great tips for the rest of our vacation. Even though no one knew each other beforehand, it felt like we were touring the countryside with family. The first winery that we stopped at was amazing, from the hospitality to the wine to the beautiful views. Our lunch stop was in Bagno Vignoni and served family style. The food was fabulous and I had the best Tiramisu. When they say that these wineries are off the beaten path, they are not kidding. I highly recommend this tour and if you get Alessandro as your host for the day, all the better. I'd give this tour an extra green dot if I could.
Well first of all Fabian (Aka Fabs our driver and tour guide)was a wine experts himself . He’s knowledgeable in the field was incredible. He had a fun sense of humor and kept us laughing the whole time . The family run wineries we went to were stunning and the wine was delicious. We bought a couple of cases and now I had to buy another wine fridge. Thank for creating memories for a lifetime Lou and Helen ❤️🇮🇹
The wineries were amazing! We got to drink out of the barrel! I learned so much about the wine making process! Beautiful country and amazing guide!!
We had a great day out with Fabian and the team. Truly unforgettable day out in the Tuscany hills with some great winemakers and great restaurants.
This is a must do if you’re in Florence. Probably the best wine tour I’ve done. The wines are excellent, the food delicious, and our tour guide Fabian was perfect and knowledgeable. When everyone is going to Chianti, you can have a more unique experience with the Val D’Orcia region. I highly recommend and will do this tour again when I’m back in Florence.
This wine tour from Florence was honestly one of the best days of our whole trip. The scenery all throughout Tuscany was stunning — those rolling hills, vineyards, and little villages looked like something out of a movie. We visited two wineries, both unique and special in their own way. The second one really stood out for us — it was a bit bigger, with so much character and history. The highlight was meeting the owners, an adorable couple in their 80s. They were so sweet and welcoming, and we even got to take photos with them! Our group was small, which made the whole experience feel more personal. Everyone was super nice and easy to talk to. And Gloria, our guide, was amazing — so friendly, attentive, and really knew her stuff. You could tell she genuinely loves what she does. If you’re in Florence and want a fun, relaxing day drinking wine and soaking up the beauty of Tuscany, this tour is a must. We loved every minute of it!
Monday through Friday 9 am to 7 pm EST
Reach us by phone
Reach us by email
