Small Group Tuscany Tour Montepulciano, Montalcino and Cortona in Florence, Italy
Florence, Italy

Small Group Tuscany Tour Montepulciano, Montalcino and Cortona

Outty Ranking 72 4.8 · 37 traveler reviews11 hoursFrom $177
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Outty Ranking

72/100

Strongly Recommended. Our proprietary evaluation. How we score

Traveler rating

4.8/5

Based on 37 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.

Quick answer

Is Small Group Tuscany Tour Montepulciano, Montalcino and Cortona worth booking?

Small Group Tuscany Tour Montepulciano, Montalcino and Cortona is a 11-hour experience in Florence, Italy, from $177 per person. It scores 72 out of 100 on the Outty Ranking, which we label “Strongly Recommended”, based on a 4.8/5 rating across 37 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.

Outty Ranking
72 / 100
Rating
4.8/5 (37)
Duration
11 hours
From
$177 per person

Embark on a captivating journey from Florence to discover Tuscany’s most iconic gems. Begin in Cortona, a hilltop village of Etruscan origin made famous by Under the Tuscan Sun, where you’ll explore medieval charm and visit a master ceramic artisan’s workshop (or traditional artisan shops). Continue to Montepulciano for a tasting of five fine wines, including the prestigious Nobile and Brunello di Montalcino, and enjoy a light lunch in a historic underground cellar (if option selected). Then, travel through the stunning Val d’Orcia, a UNESCO World Heritage Site, with scenic stops including filming locations from The Gladiator. End in Montalcino, a medieval town with a 14th-century fortress and breathtaking views, where you can savor the region’s rich wine culture. Return to Florence with lasting memories of Tuscany’s timeless beauty, history, and flavor. (*) if not available, it will be replaced with a visit to authentic artisan shops, with typical works Tour order may vary

What you get

    About this experience

    Embark on a captivating journey from Florence to discover Tuscany’s most iconic gems. Begin in Cortona, a hilltop village of Etruscan origin made famous by Under the Tuscan Sun, where you’ll explore medieval charm and visit a master ceramic artisan’s workshop (or traditional artisan shops). Continue to Montepulciano for a tasting of five fine wines, including the prestigious Nobile and Brunello di Montalcino, and enjoy a light lunch in a historic underground cellar (if option selected). Then, travel through the stunning Val d’Orcia, a UNESCO World Heritage Site, with scenic stops including filming locations from The Gladiator. End in Montalcino, a medieval town with a 14th-century fortress and breathtaking views, where you can savor the region’s rich wine culture. Return to Florence with lasting memories of Tuscany’s timeless beauty, history, and flavor. (*) if not available, it will be replaced with a visit to authentic artisan shops, with typical works Tour order may vary

    What's included

    Included

    • If option selected: Light Lunch in a unique and exclusive setting, an historic & underground cellar
    • Opportunity to purchase wines and local products you have enjoyed (worldwide delivery available)
    • Wine tasting including Vino Nobile di Montepulciano in a historic underground cellar
    • Ceramic decoration demonstration (*)
    • Immersive journey led by a Licensed Tour Leader
    • Dedicated Caf Tour & Travel Staff Assistance at the meeting point
    • Visit Montalcino and learn the story behind one of Italy’s most famous wine regions
    • Comfortable Mini Coach transport from Florence in a modern, air-conditioned bus

    Not included

    • Hotel pick-up and drop-off

    What you'll see and do

    1. Cortona

      Starting from Florence, the journey takes you to Cortona, one of the most ancient and charming villages in Tuscany. Perched on a hill in the Val di Chiana and made famous by the movie Under the Tuscan Sun, Cortona boasts Etruscan origins, evidenced by the imposing walls surrounding it, which date back to the 4th century BC. The village offers a perfect blend of medieval architecture, authentic atmospheres, and local culture, making it an unmissable destination for those seeking timeless beauty and authenticity.

      90 minutes here

    2. Montepulciano

      The next stop is Montepulciano: in this captivating Renaissance town, you’ll have the opportunity to taste the prestigious Nobile di Montepulciano wine in a charming and historic underground cellar, learning the secrets of its production and having the chance to purchase bottles at attractive prices. After the included tasting, you’ll have free time for lunch (not included) at a typical trattoria and to explore the beauties of the historic center, famous as the set for films like New Moon and the series Medici: Masters of Florence featuring Dustin Hoffman and Richard Madden.

      120 minutes here

    3. Val D'Orcia

      As you continue toward the Val d'Orcia, you will enter the heart of one of Tuscany’s most scenic areas, where you can admire the iconic landscapes of rolling hills dotted with cypress trees, known worldwide for their ineffable beauty and recognized as a UNESCO heritage site. Along the way to Montalcino, you will spot the settings of famous films like The Gladiator—a perfect opportunity for taking iconic photos.

      20 minutes here

    4. Montalcino

      The final stop is Montalcino, a charming hilltop town surrounded by the rolling landscapes of the Val d’Orcia. Known worldwide as the home of Brunello, one of Italy’s most prestigious wines, Montalcino offers an authentic taste of Tuscan tradition, history and beauty. Enjoy its medieval atmosphere, scenic views and deep connection to local wine culture.

      100 minutes here

    Where it starts and ends

    Meeting point

    Florence

    07:30 am , at Piazzale Montelungo (Montelungo Square), An Assistant waits for you wearing blue clothing with Caf Tour and Gray Line Logos, at the end of the ramp connecting with the railway station.

    Hotel pickup

    No pickup: everyone meets at the start point.

    Ends at

    07:30 am , at Piazzale Montelungo (Montelungo Square), An Assistant waits for you wearing blue clothing with Caf Tour and Gray Line Logos, at the end of the ramp connecting with the railway station.

    Options you can book

    • Full Tour & Tuscan Light Lunch

      Light Lunch

    • Full Day Tour

      Lunch not Included

    Before you book

    Cancellation
    For a full refund, cancel at least 24 hours before the scheduled departure time.
    Languages
    en
    Ticket
    Mobile Only
    Runs on
    Mon, Wed, Fri
    Group size
    Up to 8 travelers per booking
    Operated by
    CAF Tour and Travel - Gray Line Florence

    Know before you go

    • Public transportation options are available nearby
    • Specialized infant seats are available
    • Travelers should have at least a moderate level of physical fitness
    • The tour is confirmed with minimum 4 participants
    • (*) if not available, it will be replaced with a visit to authentic artisan shops, with traditional and typical works of the village
    • No vegetarian or gluten-free options available

    Photos

    Small Group Tuscany Tour Montepulciano, Montalcino and Cortona in Florence, photo 2Small Group Tuscany Tour Montepulciano, Montalcino and Cortona in Florence, photo 3Small Group Tuscany Tour Montepulciano, Montalcino and Cortona in Florence, photo 4Small Group Tuscany Tour Montepulciano, Montalcino and Cortona in Florence, photo 5Small Group Tuscany Tour Montepulciano, Montalcino and Cortona in Florence, photo 6Small Group Tuscany Tour Montepulciano, Montalcino and Cortona in Florence, photo 7

    What travelers are saying

    Outty’s summary of the themes that recur across 36 traveler reviews. Written by us, not quoted from reviewers.

    The guide

    6 mentions

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

    Knowledge and storytelling

    5 mentions

    Reviewers describe the commentary as informative rather than scripted.

    Food and drink

    5 mentions

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

    Small groups

    4 mentions

    The group size is repeatedly described as intimate rather than packed.

    Organization

    2 mentions

    Pickup, timing, and logistics are described as running smoothly.

    Pace and timing

    2 mentions

    Several reviewers comment on how the schedule is paced.

    Traveler reviews

    36 verified traveler reviews for Small Group Tuscany Tour Montepulciano, Montalcino and Cortona. Ratings and reviews provided by Viator and Tripadvisor.

    5 star
    34
    4 star
    0
    3 star
    1
    2 star
    0
    1 star
    1
    Sort
    barbrat2020 · October 2026

    Tuscany, Part 1

    Daniele and Samuele did an excellent job weaving us through the Tuscany countryside complete with a wine tasting ing Montepulciano. A long but thoroughly enjoyable day!

    Response from the operator: Good Morning from Caf Tour & Travel, Dear Customer, Thank you so much for your wonderful review! We are delighted to hear that Daniele and Samuele made your journey through the Tuscan countryside so enjoyable, combining great driving and guiding with a memorable wine tasting in Montepulciano. We know it was a long day, so it is especially rewarding to hear that you found it thoroughly enjoyable. We hope you took home some beautiful memories of Tuscany and its wonderful wines. We look forward to welcoming you again for another Tuscan adventure! Warm Tuscan regards, Caf Tour & Travel Team

    via Tripadvisor

    JCrip · October 2026

    Tour of Cortona, Montepulciano and Montalcino

    We had a wonderful tour with Samuele (Sam) our Tour Guide and Daniele (Dan), our driver. Very informative, on time and good communication. We did think the size of the wine portions during the tasting were unusually small (about 1 ounce, if that), for what the cost probably was charged by the store.

    Response from the operator: Good Morning from Caf Tour & Travel, Dear Customer, Thank you very much for sharing your experience with us! We are delighted to hear that you had a wonderful day with Samuele and Daniele. It is great to know that you appreciated their informative approach, punctuality, and clear communication throughout the tour. We also appreciate your comment regarding the wine tasting portions. We understand that the quantity served can influence the overall impression of a tasting experience, and we will be happy to share your feedback with our local partners. Thank you again for choosing us to discover the beautiful Tuscan countryside, and we hope to have the pleasure of welcoming you again for another memorable experience. Warm Tuscan regards, Caf Tour & Travel Team

    via Tripadvisor

    R1494IRstefand · September 2026

    Private Tour in Tuscany

    We had a wonderful private tour of Tuscany with Francesco, visiting Cortona, Montepulciano, and Montalcino. Francesco was incredibly kind, punctual, knowledgeable, and clear in his communication. He was also very accommodating and really went out of his way and made the entire day feel relaxed and enjoyable. We learned so much about the villages and the region, while still having plenty of flexibility to enjoy each place at our own pace. Francesco was a fantastic guide, and we would highly recommend taking a tour with him to anyone visiting Tuscany!

    Response from the operator: Good Morning from Caf Tour & Travel, Dear Customer, Thank you for sharing such a wonderful review! We are delighted that your private journey through Cortona, Montepulciano, and Montalcino was relaxed, enjoyable, and full of memorable moments. It is fantastic to hear that Francesco’s kindness, punctuality, knowledge, and flexibility allowed you to discover Tuscany at your own pace. We will be very happy to share your generous words with him. A Tuscan day with good company and beautiful villages is always special — we hope to welcome you again for another experience! With warm Tuscan wishes, Caf Tour & Travel Team

    via Tripadvisor

    169reeseh · September 2026

    Terrific Tuscany Tour

    Francesco was excellent. We had a great time getting to know him and learning about the history of Tuscany. He was very informed and engaging for the entire trip. The small group tour ended up being just us, which we also loved. All three spots were beautiful and we had time to enjoy each place before moving onto the next. Francesco was also flexible when we wanted to take a little more time, or when we needed to stop for a break on the first drive out of Firenze. I hope we get to take a tour with Francesco again!

    Response from the operator: Good Morning from Caf Tour & Travel, Dear Customer, Thank you for your wonderful feedback! We are thrilled that you enjoyed discovering Cortona, Montepulciano, and Montalcino and had such a great time with Francesco. It is lovely to hear that his knowledge and engaging stories brought the history of Tuscany to life, while his flexibility allowed you to enjoy each stop at your own pace. We are also glad that the small-group setting made the experience even more personal. We will be delighted to share your kind words with Francesco, and we hope you will have the chance to tour Tuscany with us again! A presto, Caf Tour & Travel Team

    via Tripadvisor

    ErinJ646 · September 2026

    Beautiful Day

    Such a beautiful way to experience Tuscany on our mother/daughter trip to Italy! We went places a big tour bus could never get to and had a much more private look into this region’s culture and heritage. Our driver Francesco was kind, engaging and extremely knowledgeable about the history of the villages we visited. It was a good combination of guided tour, free time and activities such as wine tasting and visiting a pottery shop. It was a long day, but very memorable.

    Response from the operator: Good Morning from Caf Tour & Travel, Dear Erin, Thank you for sharing such a beautiful review! We are delighted that your mother-daughter trip gave you the opportunity to discover a more intimate side of Tuscany, away from the routes accessible to larger tour buses. We are especially happy that Francesco’s knowledge, kindness and engaging personality helped bring the history and culture of the villages to life. The combination of guided visits, free time, wine tasting and the pottery experience sounds like a wonderful way to spend the day. We know it was a long day, but we are thrilled that it became such a memorable part of your Italian adventure! With warm Tuscan wishes, Caf Tour & Travel Team

    via Tripadvisor

    Good to know

    Duration
    11 hours
    Free cancellation
    Up to 24h before
    Minimum age to book
    All ages
    Availability
    Bookable today
    Runs on
    Mon, Wed, Fri
    Price range
    $177 to $185
    Hotel pickup
    No pickup, meet at start point
    Booked in 30 days
    13
    Verdict
    Strongly Recommended

    Who runs this experience

    Operated by CAF Tour and Travel - Gray Line Florence, who run 47 experiences we rank across 6 cities, with an average Outty Ranking of 55.4 and 1 in the 90+ Club.

    See everything CAF Tour and Travel - Gray Line Florence runs

    Why this scores 72

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

    Traveler sentiment (30% weight)83
    Review evidence (18% weight)48
    Booking momentum (14% weight)41
    Value for money (12% weight)100
    Listing quality (10% weight)85
    Local standing (8% weight)60
    Booking flexibility (8% weight)100

    Small Group Tuscany Tour Montepulciano, Montalcino and Cortona: questions travelers ask

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

    How much does Small Group Tuscany Tour Montepulciano, Montalcino and Cortona cost?

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    Prices start at $177 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 Small Group Tuscany Tour Montepulciano, Montalcino and Cortona take?

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    Plan for about 11 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 Small Group Tuscany Tour Montepulciano, Montalcino and Cortona worth it?

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    It holds an Outty Ranking of 72 out of 100, which we label "Strongly Recommended". That score blends traveler sentiment (4.8/5 across 37 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 Small Group Tuscany Tour Montepulciano, Montalcino and Cortona?

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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 Small Group Tuscany Tour Montepulciano, Montalcino and Cortona suitable for kids and families?

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    Yes, all ages are welcome. Families should still weigh the 11-hour running time, and strollers are easier on the earlier, quieter departures.

    How far in advance should I book Small Group Tuscany Tour Montepulciano, Montalcino and Cortona?

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    Around 13 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?

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    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-hour experience runs outdoors or after sunset.

    Where does Small Group Tuscany Tour Montepulciano, Montalcino and Cortona 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 Small Group Tuscany Tour Montepulciano, Montalcino and Cortona?

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    Included: If option selected: Light Lunch in a unique and exclusive setting, an historic & undergrou; Opportunity to purchase wines and local products you have enjoyed (worldwide delivery avai; Wine tasting including Vino Nobile di Montepulciano in a historic underground cellar; Ceramic decoration demonstration (*); and Immersive journey led by a Licensed Tour Leader. Not included: Hotel pick-up and drop-off. Always check the voucher for the final list before you travel.

    Where is the meeting point for Small Group Tuscany Tour Montepulciano, Montalcino and Cortona?

    +

    07:30 am , at Piazzale Montelungo (Montelungo Square), An Assistant waits for you wearing blue clothing with Caf Tour and Gray Line Logos, at the end of the ramp connecting with the railway station. Hotel pickup is not included, so plan your own transport and arrive 15 minutes early.

    What languages is Small Group Tuscany Tour Montepulciano, Montalcino and Cortona offered in?

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    It runs in English. 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 Small Group Tuscany Tour Montepulciano, Montalcino and Cortona?

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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 Small Group Tuscany Tour Montepulciano, Montalcino and Cortona wheelchair or stroller accessible?

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    The operator notes: Specialized infant seats are available. If accessibility is critical, contact the operator after booking to confirm arrangements for your date.

    What happens to Small Group Tuscany Tour Montepulciano, Montalcino and Cortona if the weather is bad?

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    It generally runs rain or shine, so dress for the forecast in Florence. Standard cancellation terms apply: free cancellation up to 24 hours before the start.

    What do travelers say about Small Group Tuscany Tour Montepulciano, Montalcino and Cortona?

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    Across 37 reviews averaging 4.8 out of 5, recurring themes include the guide, knowledge and storytelling, food and drink. Travelers single out the guide as the reason the experience works. One thing to know: Several reviewers comment on how the schedule is paced.

    What booking options are available for Small Group Tuscany Tour Montepulciano, Montalcino and Cortona?

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    There are 2 options to choose from, including Full Tour & Tuscan Light Lunch, Full Day Tour. 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 Small Group Tuscany Tour Montepulciano, Montalcino and Cortona.

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