Private tour from Florence to CORTONA & MONTEPULCIANO in Florence
Florence, Italy

Private tour from Florence to CORTONA & MONTEPULCIANO

Outty Ranking 61 5.0 · 17 traveler reviews8 hoursFrom $466

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$466
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

61/100

Solid Choice. Our proprietary evaluation. How we score

Traveler rating

5.0/5

Based on 17 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.

Quick answer

Is Private tour from Florence to CORTONA & MONTEPULCIANO worth booking?

Private tour from Florence to CORTONA & MONTEPULCIANO is a 8-hour experience in Florence, Italy, from $466 per person. It scores 61 out of 100 on the Outty Ranking, which we label “Solid Choice, based on a 5/5 rating across 17 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.

Outty Ranking
61 / 100
Rating
5/5 (17)
Duration
8 hours
From
$466 per person

Set out on an exclusive private tour across the rolling Tuscan countryside, where golden fields, olive groves, and cypress-lined roads lead you to two of the region’s most enchanting medieval hill towns. In Cortona, a pl

What you get

    About this experience

    Set out on an exclusive private tour across the rolling Tuscan countryside, where golden fields, olive groves, and cypress-lined roads lead you to two of the region’s most enchanting medieval hill towns. In Cortona, a place of timeless charm and made famous by the film Under the Tuscan Sun, you’ll wander through narrow stone streets and soak in panoramic views that stretch endlessly across the valley. The journey continues to Montepulciano, majestically perched on a ridge, where every corner reveals stunning vistas over the Val d’Orcia and Val di Chiana — a perfect picture of Tuscany’s beauty and history combined.

    What travelers are saying

    Outty’s summary of the themes that recur across 17 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

    3 mentions

    Reviewers describe the commentary as informative rather than scripted.

    Food and drink

    2 mentions

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

    Small groups

    2 mentions

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

    Traveler reviews

    17 verified traveler reviews for Private tour from Florence to CORTONA & MONTEPULCIANO. Ratings and reviews provided by Viator and Tripadvisor.

    5 star
    17
    4 star
    0
    3 star
    0
    2 star
    0
    1 star
    0
    Sort
    lexi_e · April 2026

    Alex was extremely...

    Alex was extremely professional and helpful. He suggested sites and experiences to make our day extra special.

    Response from the operator: Thank you very much for taking the time to write your review. When our work is rewarded with positive comments like yours, it truly means a lot to us. Thanks again for choosing us, and we hope to see you back in Tuscany very soon!

    via Viator

    Arkady_S · February 2026

    Thank you very much to...

    Grazie mille to Massimo for the wonderful day trip to Cortona and Montepulciano. He was a warm and knowledgeable host and an excellent driver, always on time. The vehicle was of great quality. Massimo gave some suggestions then let us explore each town as we wanted. We had a fantastic time. Highly recommend!!

    Response from the operator: Thank you so much for your kind words—it’s truly a pleasure to read reviews like yours, and they will certainly mean a lot to our team. We’re delighted that you enjoyed your experience with us and hope to welcome you back on one of our tours again soon!

    via Viator

    Christine_M · October 2025

    Our driver, Luca, was...

    Our driver, Luca, was amazing! He shared so much history about Italy and Tuscany. His knowledge, friendliness, and politeness was beyond anything we expected. I highly recommend this tour!

    Response from the operator: Hi, and thank you so much for your wonderful review! It truly means a lot to us to hear that our clients enjoy not only our drivers but also the experiences we organize throughout our beloved Tuscany. We put a lot of care into every detail, from the tours to the local insights, and it’s incredibly rewarding to know it makes a difference. Thank you again for your kind words, and we really hope to have the pleasure of welcoming you back!...

    via Viator

    George_V · September 2025

    Alessandro the Great

    What a wonderful way to experience Tuscany. Alex went above and beyond to make our day spectacular. We had another tour cancel the day before and Alex stepped up and made a day even better with a private tour, unique wine tastings and suggestions and he was super patient with us as we constantly tasted and bought wine. What a day. Thank you Alex.

    Response from the operator: Did you ever doubt our professionalism and skills? Just kidding… thank you so much for your kind words and for appreciating our Alex! We carefully select our drivers and, as you’ve seen, we always do our best to give guests the highest experience. Well, at this point there’s only one thing left—to welcome you back to Tuscany… and you already know who to call! Many thanks again for your wonderful review and your kindness in sharing it with others...!

    via Viator

    Charles_I · September 2025

    A Charming Day in Cortona

    Our tour guide was Massimo and he was terrific in several ways, the first of which was his careful and relatively slow driving. This made the travel quite comfortable, especially for our family members who volunteered for the van’s third row. From our perspective, Cortona is the nicest Italian town we visited, and the other way Massimo excelled was by letting us stay much longer instead of traveling on to Montepulciano as the tour design called for. So as Massimo returned us to our Villa, my family agreed that we very much enjoyed the day!

    Response from the operator: We couldn’t agree more with you—Cortona is an absolute gem! At the same time, there are so many other incredible attractions in Tuscany just waiting for you to discover them: charming medieval towns, rolling vineyards, breathtaking countryside, and of course plenty of good food and wine. So, the next time you decide to come back to Tuscany, make sure to get in touch with us and we’ll be delighted to organize everything for you. Thank you again for your wonderful review!

    via Viator

    Good to know

    Duration
    8 hours
    Free cancellation
    Up to 24h before
    Minimum age to book
    All ages
    Availability
    Bookable today
    Booked in 30 days
    6
    Verdict
    Solid Choice

    Why this scores 61

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

    Traveler sentiment (30% weight)88
    Review evidence (18% weight)39
    Booking momentum (14% weight)30
    Value for money (12% weight)20
    Listing quality (10% weight)79
    Local standing (8% weight)68
    Booking flexibility (8% weight)100

    Private tour from Florence to CORTONA & MONTEPULCIANO: questions travelers ask

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

    How much does Private tour from Florence to CORTONA & MONTEPULCIANO cost?

    +

    Prices start at $466 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 Private tour from Florence to CORTONA & MONTEPULCIANO take?

    +

    Plan for about 8 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 Private tour from Florence to CORTONA & MONTEPULCIANO worth it?

    +

    It holds an Outty Ranking of 61 out of 100, which we label "Solid Choice". That score blends traveler sentiment (5/5 across 17 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 Private tour from Florence to CORTONA & MONTEPULCIANO?

    +

    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 Private tour from Florence to CORTONA & MONTEPULCIANO suitable for kids and families?

    +

    Yes, all ages are welcome. Families should still weigh the 8-hour running time, and strollers are easier on the earlier, quieter departures.

    How far in advance should I book Private tour from Florence to CORTONA & MONTEPULCIANO?

    +

    Around 6 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 8-hour experience runs outdoors or after sunset.

    Where does Private tour from Florence to CORTONA & MONTEPULCIANO 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 Private tour from Florence to CORTONA & MONTEPULCIANO.

    Pick your date