nowthingstodo
Saved Tours
Cart
Pienza & Montepulciano Private Wine Tour
Gallery 2
Gallery 3
Gallery 4
Gallery 5
+1

Pienza & Montepulciano Private Wine Tour

5.0(5 reviews)
8 hour(s)
English (United Kingdom)
Pienza, Italy

Free cancellation

Up to 24 hours

Instant confirmation

Mobile ticket

Modify your booking anytime

No extra fees

Best price guarantee

No hidden fees

Explore Pienza and Montepulciano on a private journey

See panoramic views from the Church of San Biagio

Discover fascinating underground attractions and historic sites

Enjoy prestigious Montepulciano wine tasting and Tuscan flavors

Discover the Hidden Underground Wonders of Pienza and Montepulciano on a Private Tour


Embark on a full-day private adventure through the stunning Val d'Orcia, a UNESCO World Heritage site celebrated for its breathtaking natural beauty and artistic heritage. Your journey begins with a convenient pickup from your accommodation, setting the stage for a day of exploration in the historic towns of Pienza and Montepulciano. These cities are not only famous for their surface-level charm but also for the mysterious and fascinating underground attractions that lie beneath their ancient cobblestone streets.


In Pienza, you will explore the hidden crypt and labyrinth, gaining a unique perspective on the architectural history of this Renaissance gem. As you stroll along charming lanes like the Via del Bacio, you will understand why this town is considered a perfect combination of harmony and beauty. The panoramic views of the surrounding valley provide a constant reminder of the natural splendor that makes this region one of the most beloved landscapes in all of Italy.


The tour continues to Montepulciano, where you will first enjoy a spectacular view from the Church of San Biagio, a masterpiece of Renaissance design. Afterward, you will descend into the underground city, a complex network that connects seven historic buildings and features the legendary Well of Love. This subterranean exploration reveals a different side of the city, showcasing the ingenuity and historical depth that have shaped the lives of its inhabitants for many centuries.


Your day concludes with a prestigious wine tasting, allowing you to sample the famous local vintages that have made Montepulciano a household name among wine enthusiasts. This private tour is fully customizable, with vegetarian options available to ensure a comfortable and personalized experience for every guest. By combining history, nature, and world-class wine, this excursion offers a complete and unforgettable immersion into the authentic spirit of the Tuscan countryside and its most iconic artistic jewels.

What's Included
  • Lunch
  • Pick up and drop off
  • English-speaking driving
  • Pienza Crypt and Underground Labyrinth access
  • Montepulciano Underground City visit with wine tasting
  • Church of San Biagio scenic stop
What's Not Included
  • Gratuities
Price start from

$ 1780.39

Contact us 24x7

Select participants and date

Excellent
star
Trustpilot
Chat now

Pickup location

Address will appear once location is loaded.

Click "Show Pickups on Map" to open the interactive map and search for your hotel or nearby location.

Click any purple pickup marker to view its connection to your searched location and find the best pickup point.

Activity Provider: My Tour in Italy

Customer Reviews

5.0
Excellent
Based on 5 reviews
C
Candy R.Google
May 25, 2025

Wow. Don’t know where to begin. I’ve done wine tasting before and tours of vineyards but this one really stood out. Our guide, Giando, really knew his stuff and was really patient with us and all our questions! It was perfectly paced and really fascinating to learn about the entire process from the farming stage, to fermenting and bottling. Our guide also kindly gave us a lot of recommendations for food and sights in the local area. We tried 5 wines in total, along with some olive oil. The views and scenery are magnificent and everything about the building’s design and its surroundings have been carefully selected by the owners (who we were told have an architect background). Do the “Great Classic” tour if you are in the area!

J
Jason Google
February 06, 2025

An elegant and modern boutique winery nestled in the Pienza countryside. We stopped in for a tasting and they welcomed us in even though they don’t usually do walk-ins. The wine, service, and overall experience was great. One of the women even left to get more bread close to closing just so we could have the cheese board! Above and beyond service.

D
David Google
June 17, 2024

Beautiful vineyard, a gem with a lovely atmosphere and friendly and knowledgeable personnel. We enjoyed a great wine tasting and relaxing time in this elegant setting.

Explore More Pienza & Montepulciano Private Wine Tour
Explore More Pienza & Montepulciano Private Wine Tour
Explore More Pienza & Montepulciano Private Wine Tour
Explore More Pienza & Montepulciano Private Wine Tour
+1
Day In a City

Explore More Pienza & Montepulciano Private Wine Tour

Discover the wonders of Pienza, Italy with this unforgettable experience. Enjoy a private full day tour of Pienza and Montepulciano in the UNESCO listed Val d'Orcia. Discover the charm of these towns, including their unique underground sites, with a morning pickup from your accommodation. Highlights of your tour include: Explore UNESCO listed Val d'OrciaVisit the crypt and labyrinthPanoramic Views at the Church of San Biagio in MontepulcianoDiscover seven historic buildings and the Well of LovePrestigious Wine Tasting of Montepulciano’s renowned winesPersonalized Experience with the option for a vegetarian menu. This tour includes: Pick up and drop off at the HotelEnglish speaking drivingVisit the Crypt of Pienza and explore two levels of the Underground LabyrinthEntrance and visit to the Underground City of Montepulciano with w. Embark on a full-day private tour through the breathtaking landscapes of Val d'Orcia, a UNESCO World Heritage site renowned for its rolling hills, picturesque villages, and rich history. Your journey begins with a convenient morning pickup from your accommodation by our driver, setting the stage for an unforgettable exploration of two of Tuscany’s most charming towns Pienza and Montepulciano. In P. Duration: 8 hours . Book your Pienza & Montepulciano Private Wine Tour today and create memories that will last a lifetime!