We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Small-Group Montepulciano and Pienza Day Trip from Siena

Select Date and Travelers
2 travelers
    What to Expect
    Begin your day trip with pickup in Siena, where you’ll hop aboard your minivan and travel toward Pienza with your guide. Pass through the Crete Senesi along the way, clay hills with a lunar-like appearance as a result of the soil’s gray coloring. 

    Arrive in the town of Pienza, the gem of the UNESCO-listed Val d’Orcia region. Enjoy some free time to explore here independently, strolling the streets or perusing the local shops.

    Head next to a dairy farm for a delicious lunch made from the farm's fresh ingredients. Treat your taste buds to a sampling of salty Pecorino cheese, a favorite in Italy, and hear about the farm’s history and production process.

    Continue to Montepulciano, a hill town overlooking the scenic Tuscany-Umbria border. Take a guided stroll around the Piazza Grande before wandering the churches, palaces or stores at your leisure. On request, make an additional stop at a winery for a tour of the cellars and tastes of Montepulciano’s celebrated vino.

    After a full day of fine food and exploration, your tour will conclude with transportation back to Siena.
    Show More
    Important Information
    Departure Point
    San Domenico Basilica
    Departure Time
    9:30 AM
    Return Details
    Returns to original departure point
    • Driver/Guide
    • Transport by air-conditioned minivan (maximum 8 passengers)
    • Cheese tasting
    • Lunch
    • Hotel pickup and drop-off
    • Gratuities
    Show More
    Additional Info
    • Confirmation will be received at time of booking, unless booked within 16 hours of travel. In this case confirmation will be received as soon as possible, subject to availability
    • Customers who have not reached Italy's legal drinking age of 18 will not be served alcohol
    • This experience requires a minimum number of travelers. If it’s canceled because the minimum isn’t met, you’ll be offered a different date/experience or a full refund
    Cancellation Policy
    For a full refund, cancel at least 24 hours in advance of the start date of the experience.
    Traveler rating
    • 15
    • 0
    • 0
    • 0
    • 0
    Traveler type
    Time of year
    • Filter
    • English
    Popular mentions
    This trip was absolutely stunningly beautiful!! Marella was our tour guide and you could tell this isn’t just a job to her....she made this tour so special and so meaningful in so many ways. She was so full of knowledge and shared so much with us, pouring her heart and soul into
    Read more
    We were picked up at the San Domenico location in Siena at 9:30 am and joined a group ( 8 in all) with tour leader Leonardo. He was wonderful and gave us a lot of iinteresting info and answered our questions as he was driving. We stopped for pictures during the beautiful Crete
    Read more
    This was a great way to get out and see a bit of the Tuscan countryside. Ambra (Amber) was an excellent guide. Very enthusiastic and knowledgeable. We had a quick stop in a tiny town famous for its artichoke festival. We had excellent coffee before we moved on to Pienza. Pienza
    Read more
    Our small group was in very capable hands with Guillermo (Will, Bill). He made sure we stopped for quality photo ops. He regaled us with history, culture, and interesting anecdotes, yet gave us plenty of time for individual exploration. There was great food and wine. Very
    Read more
    This was truly the highlight of our Italian vacation! Marella truly has a passion and is genuine and authentic with her sharing of knowledge and making this a fun and unique day for everyone. This is not a canned tour like you get anywhere else, this is off the beaten path and
    Read more
    About the operator
    By: Tuscan Escapes - Day Tours
    594 reviews
    Certificate of Excellence
    Karen H
    Spectacular walking tour MUST DO!
    Our tour guide Sylvia was wonderful. Her knowledge of Sienna provided us an in depth understanding of the history
    Read more
    Janet M
    Fort Lauderdale, Florida
    A Great Day!
    If you are in the area don’t miss this one. The tour operator could not have been more accommodating, even going
    Read more
    Darien, CT
    Siena Walking Tour Viator
    Marela was a great tour guide, clearly explaining the 3 centers of power in medieval Siena: Banks, Government, and
    Read more
    Amazing!!! 10/10
    We had a fantastic trip! Our tour guide David was both exceptionally knowledgeable and also just fun. They were
    Read more
    Houston, Texas
    Outstanding Wine Tour
    Our tour guide, Danny, was outstanding! He was extremely knowledgable about winemaking and about Montalcino wines
    Read more
    Charlotte, North Carolina
    Good day! Our tour guide, Davide, is one of the best at his job!
    We had a great day tasting Brunello's at three different wineries. Davide was our tour guide! He was very
    Read more
    Montalcino Wine Tour Far Exceeded our Expectations
    I scheduled this wine tour to celebrate my sister's birthday, and it far exceeded our expectations. From the day
    Read more
    Jim S
    Perfectly planned tour
    The tour was a perfect mix of incredible Tuscan landscape, history, wine tasting, conversation and learning a bit
    Read more
    Excellent Tour - David Made It Memorable!
    After much thought, we decided to take a full day to tour and taste Brunello wines. This tour became our most
    Read more
    A K
    Denver, Colorado
    A Perfect Day
    Our tour with Marella was fantastic. We got to visit three wineries as well as the hill town of Montalcino and
    Read more
    Wine tour Poderino winery , dinner Fattoria Poggio Alloro
    Awesome tour guides great drivers!!! David and Ambra! Wine tour Poderino winery ,sun set in San Gimignano ,dinner
    Read more
    Parksville, Canada
    Marella is a special tour guide with a big heart ❤️
    This trip was absolutely stunningly beautiful!! Marella was our tour guide and you could tell this isn’t just a
    Read more
    Atlanta, Georgia
    Superb in every way!!
    We loved every part of this tour - the wine and the wineries, the lunch , and our guide!! Double thumbs up, highly
    Read more
    Candice P
    Magical Day in Tuscan Countryside
    Elio was a passionate, knowledgeable guide who shared his love of Italy with humor. The lunch was especially
    Read more
    Groton, Connecticut
    A beautiful day
    3 vineyards, lunch with a wonderful family, gorgeous countryside. Our guide, David, was delightful and
    Read more
    Key Details
    Why Book on TripAdvisor?
    • Free Cancellation up to 24 hours in advance
    • Low Price Guarantee
    • No Booking Fees
    • Secure Payments
    • 24/7 SupportCall:+63 923-0990452