Tuscan Hills Tour: Val d’Orcia with 2 Wine and Cheese Tastings in Florence, Italy
Florence, Italy

Tuscan Hills Tour: Val d’Orcia with 2 Wine and Cheese Tastings

Outty Ranking 70 4.6 · 55 traveler reviews11.5 hoursFrom $105
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Outty Ranking

70/100

Solid Choice. Our proprietary evaluation. How we score

Traveler rating

4.6/5

Based on 55 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.

Quick answer

Is Tuscan Hills Tour: Val d’Orcia with 2 Wine and Cheese Tastings worth booking?

Tuscan Hills Tour: Val d’Orcia with 2 Wine and Cheese Tastings is a 11.5-hour experience in Florence, Italy, from $105 per person. It scores 70 out of 100 on the Outty Ranking, which we label “Solid Choice”, based on a 4.6/5 rating across 55 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.

Outty Ranking
70 / 100
Rating
4.6/5 (55)
Duration
11.5 hours
From
$105 per person

Leave the crowds of Florence behind and journey into the heart of Tuscany with a full-day tour of the stunning Val d’Orcia, a UNESCO World Heritage Site. Discover the charming hilltop towns of Montalcino, Pienza, and Montepulciano while enjoying two wine and pecorino cheese tastings. Begin in Montalcino, home of the renowned Brunello wine, where you will visit a traditional winery and taste local flavors in an authentic setting. Take time to explore the town and admire sweeping views of vineyards, olive groves, and rolling hills. Continue to Pienza, the Renaissance “ideal city,” famous for its harmonious architecture and breathtaking panoramas over the Val d’Orcia. Stroll through its picturesque streets and discover local specialties, including pecorino cheese. End your day in Montepulciano, known for its Vino Nobile and elegant historic center. Enjoy your second tasting in a historic underground cellar before relaxing on the return journey to Florence.

What you get

    About this experience

    Leave the crowds of Florence behind and journey into the heart of Tuscany with a full-day tour of the stunning Val d’Orcia, a UNESCO World Heritage Site. Discover the charming hilltop towns of Montalcino, Pienza, and Montepulciano while enjoying two wine and pecorino cheese tastings. Begin in Montalcino, home of the renowned Brunello wine, where you will visit a traditional winery and taste local flavors in an authentic setting. Take time to explore the town and admire sweeping views of vineyards, olive groves, and rolling hills. Continue to Pienza, the Renaissance “ideal city,” famous for its harmonious architecture and breathtaking panoramas over the Val d’Orcia. Stroll through its picturesque streets and discover local specialties, including pecorino cheese. End your day in Montepulciano, known for its Vino Nobile and elegant historic center. Enjoy your second tasting in a historic underground cellar before relaxing on the return journey to Florence.

    What's included

    Included

    • Visit to a wine cellar in Montalcino with tour of the wine cellars and tasting of Brunello Wines
    • Free time in Pienza, Montalcino and Montepulciano
    • Possibility of buying wine and cheese at a very competitive price
    • Roundtrip journey by fully-fitted GT Coach
    • Expert multilingual escort
    • Visit to a winery in Montepulciano with tasting of the “Vino Nobile”
    • Pienza'pecorino cheese tasting

    What you'll see and do

    1. Florence

      Piazzale Montelungo (Departure Point): Begin your day in Florence at Piazzale Montelungo, where you will check in with our staff and meet your tour leader. As the journey starts, sit back and relax while leaving the city behind. From the comfort of your bus, you’ll enjoy views of Florence’s historic center before the scenery changes into the rolling Tuscan hills, dotted with vineyards, olive groves, and cypress trees.

      120 minutes here

    2. Val D'Orcia

      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.

      120 minutes here

    3. Montalcino

      Your first stop will be Montalcino, the Medieval town par excellence dominated by its massive fortress. In just about thirty minutes you will reach the hometown of Brunello and you will have some free time to explore the most authentic borgo of Val d’Orcia. Breathe in the peaceful atmosphere and step back to the past while taking a stroll down its steep alleys.

      120 minutes here

    4. Pienza

      Next, visit Pienza, a UNESCO World Heritage Site and a true Renaissance gem. Known as the “ideal city,” it offers breathtaking panoramic views of the Val d’Orcia. Stroll through its picturesque streets, visit the Cathedral, and discover local shops selling the famous pecorino cheese. This is the perfect place to enjoy the beauty and harmony of Tuscan architecture.

      60 minutes here

    5. Montepulciano

      You will then head the charming hilltop town of Montepulciano. Enjoy free time to explore at your own pace: wander through its narrow streets, admire elegant Renaissance palaces, and take in stunning views over the surrounding countryside. Don’t miss Piazza Grande, the heart of the town, and soak in the authentic Tuscan atmosphere.

      120 minutes here

    6. Florence

      Return to Florence: After a full day of discoveries, relax on the comfortable bus as you make your way back to Florence. Enjoy the scenic Tuscan landscapes one last time while being looked after by your tour leader, who will accompany you throughout the journey until your return.

      120 minutes here

    Where it starts and ends

    Meeting point

    Florence

    TOURS & NEWS KIOSK AT PIAZZALE MONTELUNGO BUS TERMINAL Located at 5-10 minutes walking distance from Santa Maria Novella Train Station. Look for our staff wearing a FUCHSIA CIAOFLORENCE JACKET and holding a CIAOFLORENCE CLIPBOARD!

    Hotel pickup

    No pickup: everyone meets at the start point.

    Ends at

    TOURS & NEWS KIOSK AT PIAZZALE MONTELUNGO BUS TERMINAL Located at 5-10 minutes walking distance from Santa Maria Novella Train Station. Look for our staff wearing a FUCHSIA CIAOFLORENCE JACKET and holding a CIAOFLORENCE CLIPBOARD!

    Options you can book

    • Tour in English

    • Tour in Portuguese

    • Tour in Spanish

    Before you book

    Cancellation
    For a full refund, cancel at least 24 hours before the scheduled departure time.
    Languages
    pt, en, es
    Ticket
    Mobile Only
    Runs on
    Every day
    Group size
    Up to 15 travelers per booking
    Operated by
    Ciao Florence Tours Srl

    Know before you go

    • Infants and small children can ride in a pram or stroller
    • Public transportation options are available nearby
    • Not recommended for travelers with spinal injuries
    • Not recommended for travelers with poor cardiovascular health
    • Suitable for all physical fitness levels
    • The order of the visits may change

    Photos

    Tuscan Hills Tour: Val d’Orcia with 2 Wine and Cheese Tastings in Florence, photo 2Tuscan Hills Tour: Val d’Orcia with 2 Wine and Cheese Tastings in Florence, photo 3Tuscan Hills Tour: Val d’Orcia with 2 Wine and Cheese Tastings in Florence, photo 4Tuscan Hills Tour: Val d’Orcia with 2 Wine and Cheese Tastings in Florence, photo 5Tuscan Hills Tour: Val d’Orcia with 2 Wine and Cheese Tastings in Florence, photo 6Tuscan Hills Tour: Val d’Orcia with 2 Wine and Cheese Tastings in Florence, photo 7

    What travelers are saying

    Outty’s summary of the themes that recur across 55 traveler reviews. Written by us, not quoted from reviewers.

    The guide

    7 mentions

    Travelers single out the guide as the reason the experience works.

    Food and drink

    7 mentions

    The tastings and food stops are a highlight for most reviewers.

    Knowledge and storytelling

    5 mentions

    Reviewers describe the commentary as informative rather than scripted.

    Photo opportunities

    2 mentions

    The views and photo stops come up again and again.

    Traveler reviews

    55 verified traveler reviews for Tuscan Hills Tour: Val d’Orcia with 2 Wine and Cheese Tastings. Ratings and reviews provided by Viator and Tripadvisor.

    5 star
    44
    4 star
    6
    3 star
    0
    2 star
    3
    1 star
    2
    Sort
    cris403 · May 2026

    Be wary of tour operator,...

    Be wary of tour operator, my tour was changed with knowledge, not given opportunity to cancel or change to a tour of my choosing. Several of participants became lost on tour and number given to call was not enabled as per message when calling. Tour operator did not respond to inquiries regarding change of tour nor to message sent in app about becoming lost when unable to reach by phone! Viator was of no assistance in an agreeable resolution of these issues.

    via Viator

    615aydint · October 2025

    Beautiful Tuscany

    Gratzie John. Amazing lunch and Brunello wine. Wonderful landscape. Maybe the beer tasting and the abbey to skip. 5 stars in any case.

    via Tripadvisor

    O4436QOsamf · October 2025

    Really good

    Thanks to paulo and john we had a fantastic day. The lunch was great. One of the best group tours I have ever done. Price/quality top

    via Tripadvisor

    705annemariel · October 2025

    Could have been great

    In summary, I expected this tour to be complemented by pertinent information about what we were about to see and visit. Because of a the lack of input from the guide/escort, I feel the tour did not deliver as promised and as a result was over-priced. We had high hopes for this full-day tour to the Tuscan countryside. During the two-hour bus ride to our first stop, we heard virtually nothing from our guide/escort except how long the ride would be and, much later, that we were nearly there. She did emphasize that what we would see would be very beautiful. On that count, she was right, but she provided no historical, geographical, or cultural context. That was left to audio-guides, when available. The itinerary of the tour was very good, the locations visited were interesting and worth our time. At to the Temple of Brunello we enjoyed a delicious meal and wine tasting. An excellent hostess told us about Brunello wine and used an interactive board to illustrate her comments. That was the extent of our “multi-sensory journey” at the “interactive museum” that the tour description promised. The artifacts in the building were presented in the traditional museum fashion. In Pienza, a “guide” walked us from room to room in the Piccolomini Palace telling us which number to choose on our audio-guide. She did not speak English and could not answer any questions. Once done, we were instructed by the recording to return our handsets. However, there was a second museum next door and the same handset was needed to get the commentary for that museum. Neither our local “guide” nor our tour guide told us that we should keep the handset if we planned on visiting the second museum. By the time we realized it, the museum was closing. It appears that our escort’s role was limited to leading us from point A to point B with instructions of "follow me." She was also silent on the two-hour return trip to Florence. Even after an accident near-miss, she did not even inquire if everyone was OK. I understand that our guide/escort was not the primary guide at the sites we visited, but she could have enhanced our experience with additional information, particularly with regard to the region we were visiting, wine production and history.

    via Tripadvisor

    I5844LHdavidd · September 2025

    Pleasant outing in Tuscana

    We had a lovely day out on this trip. There were 14 of us in the group so we were in a mini bus (with no toilet) but it was very pleasant. The tour guide (Julia) was very knowledgeable and helpful and made sure we were all ok. Pienza was amazing. I rate it as one of my favourite towns in Tuscana. Good tour, tour guide and bus driver.

    via Tripadvisor

    Good to know

    Duration
    11.5 hours
    Free cancellation
    Up to 24h before
    Minimum age to book
    All ages
    Availability
    Bookable today
    Runs on
    Every day
    Hotel pickup
    No pickup, meet at start point
    Booked in 30 days
    19
    Verdict
    Solid Choice

    Who runs this experience

    Operated by Ciao Florence Tours Srl, who run 68 experiences we rank across 9 cities, with an average Outty Ranking of 61.8 and 1 in the 90+ Club.

    See everything Ciao Florence Tours Srl runs

    Why this scores 70

    The Outty Ranking is a weighted composite. Here is how this experience performed on each component.

    Traveler sentiment (30% weight)73
    Review evidence (18% weight)53
    Booking momentum (14% weight)46
    Value for money (12% weight)100
    Listing quality (10% weight)85
    Local standing (8% weight)43
    Booking flexibility (8% weight)100

    Tuscan Hills Tour: Val d’Orcia with 2 Wine and Cheese Tastings: questions travelers ask

    Practical detail on this experience, plus the wider planning questions for Florence.

    How much does Tuscan Hills Tour: Val d’Orcia with 2 Wine and Cheese Tastings cost?

    +

    Prices start at $105 per person. The final price depends on the date, the time slot and the number of travelers, and peak weekends in Florence usually price higher than midweek mornings. Live pricing and remaining availability are confirmed on the booking screen before you pay.

    How long does Tuscan Hills Tour: Val d’Orcia with 2 Wine and Cheese Tastings take?

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    Plan for about 11.5 hours from start to finish, not counting travel to the meeting point. Most travelers leave another 30 minutes on either side so the rest of the day in Florence is not rushed.

    Is Tuscan Hills Tour: Val d’Orcia with 2 Wine and Cheese Tastings worth it?

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    It holds an Outty Ranking of 70 out of 100, which we label "Solid Choice". That score blends traveler sentiment (4.6/5 across 55 reviews), the depth of that review evidence, recent booking momentum, value for money against comparable last minute in Florence, and how flexible the cancellation terms are.

    Can I cancel or reschedule Tuscan Hills Tour: Val d’Orcia with 2 Wine and Cheese Tastings?

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    Yes. Cancel free up to 24 hours before the start time for a full refund. Inside that window the booking is non-refundable, and no-shows are not refunded.

    Is Tuscan Hills Tour: Val d’Orcia with 2 Wine and Cheese Tastings suitable for kids and families?

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    Yes, all ages are welcome. Families should still weigh the 11.5-hour running time, and strollers are easier on the earlier, quieter departures.

    How far in advance should I book Tuscan Hills Tour: Val d’Orcia with 2 Wine and Cheese Tastings?

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    Around 19 people booked this in the last 30 days, so popular slots go early. Two to three weeks ahead is comfortable in shoulder season, while summer weekends and holidays in Florence can sell out a month out. Same-day spots do open up when other travelers cancel, so it is worth checking if you are already in town.

    What should I bring or wear?

    +

    Bring photo ID, your booking confirmation on your phone, a refillable water bottle and comfortable shoes. Dress for the weather in Florence and add a light layer if any part of the 11.5-hour experience runs outdoors or after sunset.

    Where does Tuscan Hills Tour: Val d’Orcia with 2 Wine and Cheese Tastings start and how do I get there?

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    The exact meeting point and directions are on your voucher once you book, and they sit in central Florence within reach of public transport. Arrive 15 minutes early: late arrivals are treated as no-shows by most operators.

    What are the best things to do in Florence?

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    On Outty we rank every Florence experience on the same 0 to 100 scale, and alongside this one the highest scorers right now include The Best tour in Florence: Renaissance & Medici -by a storyteller, Small group Tuscan Wineries, Olive Oil & Gourmet Lunch or Dinner, Florence Pizza or Pasta Class with Gelato Making at a Tuscan Farm. The city page groups everything into most popular, highest reviewed, last minute and family-friendly so you can build a day around what actually delivers.

    When is the best time to visit Florence?

    +

    Booking patterns follow the same curve: prices and queues climb in peak weeks, while shoulder season gives you better availability on the top-ranked experiences and more room to change plans.

    How many days do you need in Florence?

    +

    Three full days covers the headline sights without sprinting. A workable rhythm is one anchor experience each morning, such as this one, an unhurried afternoon in a single neighborhood, then a food or nightlife booking in the evening. Five days lets you add a day trip outside the city.

    Do I book through Outty or through the operator?

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    Outty ranks and explains the experiences, then hands you to Viator to complete the booking with the operator directly. The price is the same as booking on Viator yourself, and Outty earns an affiliate commission on the referral, which is how the rankings stay free to read.

    What is included in Tuscan Hills Tour: Val d’Orcia with 2 Wine and Cheese Tastings?

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    Included: Visit to a wine cellar in Montalcino with tour of the wine cellars and tasting of Brunello; Free time in Pienza, Montalcino and Montepulciano; Possibility of buying wine and cheese at a very competitive price; Roundtrip journey by fully-fitted GT Coach; and Expert multilingual escort. Always check the voucher for the final list before you travel.

    Where is the meeting point for Tuscan Hills Tour: Val d’Orcia with 2 Wine and Cheese Tastings?

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    TOURS & NEWS KIOSK AT PIAZZALE MONTELUNGO BUS TERMINAL Located at 5-10 minutes walking distance from Santa Maria Novella Train Station. Hotel pickup is not included, so plan your own transport and arrive 15 minutes early.

    What languages is Tuscan Hills Tour: Val d’Orcia with 2 Wine and Cheese Tastings offered in?

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    It is offered in Portuguese, English and Spanish. Pick your language when choosing a date and time, as not every departure runs in every language.

    Will I get instant confirmation and a mobile ticket for Tuscan Hills Tour: Val d’Orcia with 2 Wine and Cheese Tastings?

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    Confirmation is sent by the operator after booking, usually within 48 hours; if it is not confirmed you are not charged. Mobile tickets are accepted, so you can show the voucher on your phone.

    Is Tuscan Hills Tour: Val d’Orcia with 2 Wine and Cheese Tastings wheelchair or stroller accessible?

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    The operator notes: Infants and small children can ride in a pram or stroller. If accessibility is critical, contact the operator after booking to confirm arrangements for your date.

    What happens to Tuscan Hills Tour: Val d’Orcia with 2 Wine and Cheese Tastings if the weather is bad?

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    This experience depends on good weather. If it is canceled because of poor weather, you are offered a different date or a full refund.

    What do travelers say about Tuscan Hills Tour: Val d’Orcia with 2 Wine and Cheese Tastings?

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    Across 55 reviews averaging 4.6 out of 5, recurring themes include the guide, food and drink, knowledge and storytelling. Travelers single out the guide as the reason the experience works.

    What booking options are available for Tuscan Hills Tour: Val d’Orcia with 2 Wine and Cheese Tastings?

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    There are 3 options to choose from, including Tour in English, Tour in Portuguese, Tour in Spanish. Prices and start times differ by option, so compare them on the booking screen.

    Ready to lock in your spot?

    Pick a date, choose your group, and see the exact price for Tuscan Hills Tour: Val d’Orcia with 2 Wine and Cheese Tastings.

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