Tuscan Wine & Cheese Tour
From€78.2
8 hours
Florence, Italy
About this activity
Experience the best of Tuscany's wine and cheese culture on this guided tour through the picturesque Val d'Orcia region, including visits to Pienza and Montepulciano.
Highlights
- Explore Val d'Orcia's scenic landscapes
- Visit historic Pienza town
- Taste renowned Tuscan wines
- Sample traditional Pecorino cheese
- Discover ancient Roman ruins
Full description
Indulge in a delightful journey through Tuscany's renowned Val d'Orcia region, celebrated for its rolling hills and vineyards. This full-day tour offers a unique opportunity to visit historic towns like Pienza and Montepulciano, where you'll savor exquisite local wines and traditional Pecorino cheese. Immerse yourself in the rich history and culture of the area, with stops at ancient Roman ruins and charming local farms. Whether you're a wine connoisseur or a cheese enthusiast, this tour promises an unforgettable taste of Tuscany's culinary heritage.
Included / Excluded
- Guided tour of Val d'Orcia region
- Wine tasting at local vineyards
- Cheese tasting at traditional farms
- Meals not specified in the itinerary
Itinerary
1
Discover the postcard views of the green, rolling hills in Val d’Orcia. Meet your friendly, local tour guide at Piazzale Montelungo Bus Terminal. Piazzale Montelungo is located 5-10 minutes walking distance from Santa Maria Novella train station. Grab a seat on the comfortable coach bus, and you will shortly depart for the scenic beauty of Val d’Orcia! During the picturesque drive, your guide will dive into some interesting information about the towns and lush land of the Valley. The drive to Val d’Orcia will take about two hours.
Duration: 2 hoursAdmission: NOT_APPLICABLE
2
After driving through the spellbinding, Tuscan hills, you will be itching to explore one of the fairytale towns! Your first stop will be Montalcino, the land of world-renowned Brunello wine. Follow your guide uphill into the town, as you stroll through labyrinths of cobblestone, medieval streets. Your guide will lead you to a famous Brunello winery. A local producer will lead you through the winery, as he or she explains the secrets of Brunello production. Then, indulge in some samples of some of the finest wines in Italy! Cheers!
Duration: 1 hourAdmission: NOT_APPLICABLE
3
You will have some free time after the wine tasting to independently explore Montalcino and enjoy a pleasant, Tuscan lunch on your own. Montalcino is a hidden gem of Tuscany, encompassing the medieval essence of the region. We recommend you walk uphill through the town, until you reach the town's majestic Fortress. Here, you can find breathtaking views of the surrounding rolling hills, ancient oak trees, scenic roads, and perfect vineyards! . The medieval stronghold's impressive stone walls and towers will transport you back in time, evoking its strategic significance in ancient battles. The fortress is not only a historic gem but also a prominent cultural landmark, showcasing the rich heritage of this region. Don't forget your camera to capture the breathtaking landscapes!
Duration: 1 hourAdmission: NOT_APPLICABLE
4
After your journey through the rolling hills, you will arrive in Pienza, standing upon a hill and dominating the Orcia Valley with extraordinary views! Your guide will explain that Pienza is different from other towns in Tuscany, as it was rebuilt to be an idealist-Renaissance town by order of Pope Pius II. Enjoy exploring Pienza at your leisure - admire the atmosphere of harmony and peace that surrounds you.
Duration: 1 hourAdmission: NOT_APPLICABLE
5
As you walk along the narrow and charming streets of Pienza, you will be captivated by the breathtaking Pienza Cathedral. Located in the town's charming historic center, the cathedral is a masterpiece of Renaissance architecture. You'll be enachanted by the cathedral's elegant facade adorned with intricate sculptures and delicate details. Pienza's relaxed atmosphere and charming ambiance make it a perfect spot to unwind and enjoy the beauty of Tuscany. Immerse yourself in the historical richness and artistic splendor of Pienza and create lasting memories in this timeless Tuscan town.
Duration: 10 minAdmission: NO
6
Val d’Orcia stands out in Tuscany as being home to some of the most stunning landscapes in the region. If you have ever seen a postcard from Tuscany, it most likely was a photo from Val d’Orcia! Your bus driver will bring you by some of the famous landscapes, so be sure to have your camera ready! Your guide will point out the Chapel of the Madonna di Vitaleta, one of the most photographed spots in Tuscany. This small chapel contrasts magically with the bright, green rolling hills, and it is perfectly framed with a line of cyprus trees. Legend has it that this was the exact spot where Virgin Mary appeared to the shepherds. The bus will also drive by the gladiator’s home in Ridley Scott’s Academy Award-winning “Gladiator.” Although the film primarily focuses on Rome, the gladiator character (played by Russel Crowe) heads home in a serene paradise surrounded by rolling, green hills and cyprus trees. Your guide will explain that this tiny slice of heaven was filmed in Val d'Orcia!
Duration: 10 minAdmission: NOT_APPLICABLE
7
The last stop of your tour in Val d’Orcia will bring you to Montepulciano, home to the exquisite Vino Nobile vineyards. More recently, the town also became a popular destination, as it is where the vampire movie, "New Moon,'' was filmed. Spend an hour discovering the most elegant village in Val D'Orcia - full of magnificent palaces, Renaissance buildings, and imposing churches. There is no better way to finish a tour of Tuscany than with a wine tasting! Meet back with your group, and follow your guide to a wonderful winery in the historical heart of Montalcino. Follow a local producer into the fragrant wine cellar, and learn all about the Nobile wine making process. Then, savor the flavors of the famous Nobile wine! This tasting will be accompanied by some light snacks, made from fresh, local ingredients. Then, purchase any last-minute souvenirs before heading back to Florence.
Duration: 2 hoursAdmission: NOT_APPLICABLE
8
The bus will take you back to Florence, and you will arrive back in the early evening. Don’t miss out on this magical opportunity to explore the postcard scenery and picturesque, hilltop towns of Val d’Orcia!
Duration: 2 hoursAdmission: NOT_APPLICABLE
Meeting point
Start Location
Unknown location
Important information
Know before you book
- Tour operates rain or shine; dress appropriately for the weather.
- Confirm your booking at least 24 hours in advance.
- Check the meeting point and time provided in your booking confirmation.
Know before you go
- Wear comfortable walking shoes for uneven terrain.
- Bring a camera to capture the stunning landscapes.
- Carry a water bottle to stay hydrated during the tour.
Cancellation policy
Free cancellation up to 1 days before the activity starts
For a full refund, cancel at least 24 hours before the scheduled departure time.
Accessibility
- Stroller Accessible
- Easy Public Transport
- Infants Required On Laps
- Infant Seats Available
Good to know
- Minimum drinking age is 18 years
- May be operated by a multi-lingual guide
- Please advise any specific dietary requirements at time of booking
- Vegetarian option is available, please advise at time of booking if required
- Please show up 20 minutes before the tour departure
- English and Spanish are always guaranteed. In order to confirm the excursion in Italian, German, Portuguese or French a minimum of 4 pax is required
- The order of the visits may change and Montepulciano could be the first stop
- If you select Chinese, Korean, or Japanese, the historical explanations and tour commentary will be provided exclusively via audio guide (via App) in your chosen language. You will not be left alone: a professional Tour Leader will accompany the group throughout the trip. The Tour Leader will manage the group and provide logistics, meeting point details, and emergency assistance in English, while the cultural insights will be delivered via the app in your language. The wine tastings will be conducted in English. However, the app will provide additional information about the local wine in the selected native language.
Traveler reviews
4.71,281 reviews
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Must do tour of Val d’Orcia!
A fantastic day tour of the Val d’Orcia with a very knowledgeable guide. As wine tasting novices, we so much enjoyed sampling three Tuscan wines at both of the two wineries. With free time to explore Montalcino, Pienza and Montepulciano, this full day tour gave us a truly unforgettable experience during our week’s stay in Florence. Leon was a very friendly and efficient guide, who made sure the day went smoothly without feeling rushed. 100% recommend!
markpH6472SZMay 24, 2026TRIPADVISOR
Ex elect day in Tuscany
Very enjoyable day - I especially liked we had free time in each town. The views are spectacular and the towns are very special. Not a lot of tourists which was nice! The tour includes 2 wine tastings at 2 different wineries. Lots of great information and I didn’t feel like we were being “moved through”’the tastings.
NorthStar00355188927May 24, 2026TRIPADVISOR
Wonderful winery tour
The tour is wonderful. The cities are beautiful and the two winery we visited are fantastic. Our tour guide Leo is so nice and informative. He takes care of all of us during the tour. This is the best tour I have ever joined.
joanlkmleeMay 24, 2026TRIPADVISOR
Wine tour in Tuscany, really good.
It was a great day out exploring wine regions in Tuscany. Leon was very attentive and shared alot of knowledge He also took us to really historical wine houses which was a treat. Thank you also to Roberto for driving us safely everywhere. Thank you so much
Global48733859752May 24, 2026TRIPADVISOR
Wonderful. Not to miss
It was a pleasure to have this tour with our Guide Leon. He's a poliglot so he speaks many languages making everyone to feel comfortable. Thank you for the experience!
Laurentiu-Crist... SMay 24, 2026TRIPADVISOR
Additional information
Minimum drinking age is 18 years
May be operated by a multi-lingual guide
Please advise any specific dietary requirements at time of booking
Vegetarian option is available, please advise at time of booking if required
Please show up 20 minutes before the tour departure
English and Spanish are always guaranteed. In order to confirm the excursion in Italian, German, Portuguese or French a minimum of 4 pax is required
The order of the visits may change and Montepulciano could be the first stop