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

Small Group Tuscany Tour Montepulciano, Montalcino and Cortona

Outty Ranking 72 4.8 · 31 traveler reviews11 hoursFrom $139

Pick your date

Highlighted days have spots open. Grey days are sold out or not running.

September 2026

SMTWTFS

Loading live availability

Who is going?

Adults

Age 13 and over

2

Children

Age 12 and under

0

Select a highlighted day to see live departure times and the exact price for your group.

From, per person$139
View availability on Viator

Free cancellation up to 24 hours before. Same price on Viator, Outty earns a commission.

Instant mobile ticketSpots available today

Outty Ranking

72/100

Strongly Recommended. Our proprietary evaluation. How we score

Traveler rating

4.8/5

Based on 31 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 $139 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 31 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 (31)
Duration
11 hours
From
$139 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 vi

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 31 traveler reviews. Written by us, not quoted from reviewers.

    The guide

    6 mentions

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

    Food and drink

    5 mentions

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

    Knowledge and storytelling

    4 mentions

    Reviewers describe the commentary as informative rather than scripted.

    Small groups

    3 mentions

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

    Value for money

    2 mentions

    Travelers feel they got more than they paid for.

    Good for families

    2 mentions

    Reviewers traveling with kids report it landed well with their group.

    Traveler reviews

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

    5 star
    29
    4 star
    0
    3 star
    1
    2 star
    0
    1 star
    1
    Sort
    Discover61721819959 · August 2026

    Small group Tuscany tour and wine tasting

    Francesco is a very kind person and knows history and communities that we went to very well. We very much appreciated all he shared. We also very much enjoyed the small group tour. The winery Ercolani in Montepulciano was fabulous too!

    Response from the operator: Good Morning from Caf Tour & Travel, Dear Customer, Thank you for your lovely review! We’re delighted to hear that you enjoyed the small-group experience and that Francesco made your journey even more special with his knowledge of the history and local communities. It’s wonderful to know that you also enjoyed your visit to Ercolani Winery in Montepulciano. We hope to welcome you back to discover even more of Tuscany’s beautiful towns, traditions and wines! Warm regards from Italy, Caf Tour & Travel

    via Tripadvisor

    idontwanty · August 2026

    Good

    Francesco was a very good tour guide. He was very friendly and kept us updated with the timing. Knowledgable.

    Response from the operator: Good Morning from Caf Tour & Travel, Dear Customer, Thank you for your kind words! We’re pleased to know that Francesco’s friendly approach, knowledge, and careful attention to the timing helped make your day enjoyable and smooth. Exploring Montepulciano, Montalcino, and Cortona is a wonderful way to discover a quieter side of Tuscany. We hope to see you again! Kind regards from Italy, The Caf Tour & Travel Team

    via Tripadvisor

    U2087DKchloeh · August 2026

    Fabulous experience in Italian towns!

    Francessco was a fabulous guide! Informational and personal

    Response from the operator: Good Morning from Caf Tour & Travel, Dear Chloe, Thank you for your lovely review! We’re delighted that Francesco made your journey through Tuscany’s charming towns both informative and personal. These historic places have so many stories to tell, and we’re happy you enjoyed discovering them with us. We hope to welcome you back for another beautiful Tuscan experience! Arrivederci and see you soon, The Caf Tour & Travel Team

    via Tripadvisor

    Kate_S · August 2026

    Great day visiting some...

    Great day visiting some of the lesser known places in Tuscany, perfect if you want to explore more of Tuscany outside of Sienna etc.

    Response from the operator: Good Morning from Caf Tour & Travel, Dear Kate, Thank you for sharing your experience! We’re delighted that you enjoyed discovering some of Tuscany’s lesser-known gems beyond the most famous destinations. Montepulciano, Montalcino, and Cortona offer a wonderful glimpse into the authentic beauty and character of the region. We hope to welcome you back to explore even more of Tuscany! Warmest wishes from the Tuscan countryside, The Caf Tour & Travel Team

    via Viator

    teresabT1484ZO · August 2026

    Worth the Time and Effort for a Taste of Tuscany

    Marta is a great guide. She’s kind, thoughtful and personable. Our day was extremely hot and she thought ahead about keeping us cool and in the shade. Notably, she asked if we’d like to get a shuttle up the steep hills of Montepulciano and we all agreed. It really added to the experience, eliminating the long climb to the top and saved us all the heat and exhaustion of walking. For future tours I would say it’s a must to be included in all your tours to Montepulciano. My husband and I especially enjoyed the wine tasting with a light lunch. Cortona and Montalcino were lovely and worth the stops. Rogero is a courteous and good driver. This tour was perfect to give my husband and I a brief introduction to the area so we can be prepared to return with our family.

    Response from the operator: Good Morning from Caf Tour & Travel, Dear Teresa, Thank you for your thoughtful and detailed review! We're delighted that Marta's care, attention, and thoughtful suggestions helped make your day comfortable despite the summer heat. It's wonderful to hear you enjoyed Montepulciano, Montalcino, Cortona, and the wine tasting, and we'll gladly share your appreciation with both Marta and Ruggero. We hope to welcome you and your family back to Tuscany very soon. Warm greetings from Italy, The 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
    $139 to $185
    Hotel pickup
    No pickup, meet at start point
    Booked in 30 days
    11
    Verdict
    Strongly Recommended

    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)46
    Booking momentum (14% weight)39
    Value for money (12% weight)100
    Listing quality (10% weight)85
    Local standing (8% weight)59
    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?

    +

    Prices start at $139 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?

    +

    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?

    +

    It holds an Outty Ranking of 72 out of 100, which we label "Strongly Recommended". That score blends traveler sentiment (4.8/5 across 31 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?

    +

    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?

    +

    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?

    +

    Around 11 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-hour experience runs outdoors or after sunset.

    Where does Small Group Tuscany Tour Montepulciano, Montalcino and Cortona start and how do I get there?

    +

    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?

    +

    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 Tales - guided by a STORYTELLER, Florence Pizza or Pasta Class & Gelato Making at a Tuscan Farm, Small group Tuscan Wineries, Olive Oil & Gourmet Lunch or Dinner. 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?

    +

    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.

    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.

    Pick your date