
Private tour from Florence to CORTONA & MONTEPULCIANO
Traveler rating
5.0/5
Based on 19 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 $452 per person. It scores 66 out of 100 on the Outty Ranking, which we label “Solid Choice”, based on a 5/5 rating across 19 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.
- Outty Ranking
- 66 / 100
- Rating
- 5/5 (19)
- Duration
- 8 hours
- From
- $452 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 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 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's included
Included
- Hotel pickup and drop-off
- Private tour
- Driver/guide
- Transport on comfortable Mercedes-Benz V Class with ac
- tax, tolls, parking fees
- Wifi
Not included
- lunch
- Gratuities
What you'll see and do
Duomo di Cortona
Meet our English speaking driver at your hotel on a comfortable Mercedes-Benz for start the journey to the beautiful Cortona: enclosed by stone walls dating back to Etruscan and Roman times, sits on the top of a hill about 600 meters (about 1968 feet) above sea level. This dominant position over the valley offers a spectacular view from all over the town of the surrounding valley and even Lake Trasimeno. The town has become very popular in the past decade thanks to the book by Frances Mayes, Under the Tuscan Sun (and the movie with Diane Lane) which is set in Cortona; the protagonist immediately falls in love with the town, its people, and the villa Bramasole that she purchases and fixes up. Time for relax or explore the area, the driver will suggest best things to do.
90 minutes here
Piazza Grande
Leave at 11.30am for have a delicious light lunch at a family winery. Continue then to Montepulciano on a relaxing 30 minutes drive on the hills surrounded by breathtaking landscapes....of course your driver can stop the car anytime you want if you wish to take photos. Arrival to the charming Montepulciano around 2pm. This is a medieval hill town of rare beauty full of elegant Renaissance palaces, ancient churches, charming squares and hidden corners.... Montepulciano has received great attention following the filming of the vampire saga Twilight sequel New Moon here and has seen a notable increase in visitors. A walk through Montepulciano is the best way to view the town and its beautiful landmarks as well as enjoy stunning views of the surrounding countryside covered by vineyards producing the famous Nobile which is possible to taste in the many wine shops located within the city walls.
120 minutes here
Where it starts and ends
Hotel pickup
Pickup is included for all travelers. Pickup begins about 5 minutes before departure.
Before you book
- Cancellation
- For a full refund, cancel at least 24 hours before the scheduled departure time.
- Languages
- en, it, es
- Ticket
- Mobile Only
- Runs on
- Every day
- Group size
- Up to 8 travelers per booking
- Operated by
- Tuscany In Tour
Know before you go
- Wheelchair accessible
- Infants and small children can ride in a pram or stroller
- Public transportation options are available nearby
- Specialized infant seats are available
- Transportation options are wheelchair accessible
- All areas and surfaces are wheelchair accessible
- Suitable for all physical fitness levels
- FOR WINE LOVERS: IS POSSIBLE TO ADD ON THIS TOUR THE VISIT OF A TOP RATED WINERY. PLEASE ADVISE AT THE TIME OF THE BOOKING
- Dress code is casual
- Comfortable shoes
Photos






What travelers are saying
Outty’s summary of the themes that recur across 19 traveler reviews. Written by us, not quoted from reviewers.
The guide
7 mentionsTravelers single out the guide as the reason the experience works.
Knowledge and storytelling
5 mentionsReviewers describe the commentary as informative rather than scripted.
Small groups
3 mentionsThe group size is repeatedly described as intimate rather than packed.
Organization
2 mentionsPickup, timing, and logistics are described as running smoothly.
Food and drink
2 mentionsThe tastings and food stops are a highlight for most reviewers.
Traveler reviews
19 verified traveler reviews for Private tour from Florence to CORTONA & MONTEPULCIANO. Ratings and reviews provided by Viator and Tripadvisor.
Tuscany day trip Cortona and Montepulciano and availability for wine tasting with plenty of time for shopping and lunch.
Cartons and Montepulciano were outstanding. Massimo our driver and tour guide was very social and knowledgeable and we would not hesitate to contact this company. Thank you Massimo.
Response from the operator: Hi, and thank you so much for your wonderful review! I really appreciate you taking a few minutes out of your time to share your experience and let us know how much you enjoyed it. Thank you again — it truly means a lot to us!
via Viator
A day exploring Tuscany.
Massimo made our day trip to Cortona and Montepulciano an absolute dream from start to finish. He was right on time and went above and beyond to accommodate all of our needs throughout the day. Realizing our comfort was a priority, he thoughtfully brought a spacious van that made the scenic drives between the Tuscan hills relaxing and luxurious. His deep knowledge of the area brought every historic street, hidden alley, and local tradition to life. What made the experience truly special, though, was his flexibility. Massimo let us completely set the pace, never making us feel rushed and always adapting to whatever we wanted to see or do next. By the end of the day, it didn't feel like we were on a standard guided tour at all. It felt like exploring Tuscany with a dear friend we had known for years. If you have the chance to book a private tour in this stunning region, ask for Massimo. He is a phenomenal guide who turns a simple day trip into an unforgettable memory.
Response from the operator: Wow, thank you so much! We’re truly delighted to read your enthusiasm about our service, and especially about our driver. We always do our very best to give our clients the highest level of service and make their experience truly special. I think we’re on the right track… what do you think? 😊 Thank you again for choosing to book with us. We really appreciate your trust, and we hope to welcome you back soon for more adventures together!
via Viator
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
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
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
Good to know
- Duration
- 8 hours
- Free cancellation
- Up to 24h before
- Minimum age to book
- All ages
- Availability
- Bookable today
- Runs on
- Every day
- Price range
- $452 to $720
- Hotel pickup
- Included for all travelers
- Booked in 30 days
- 7
- Verdict
- Solid Choice
Who runs this experience
Operated by Tuscany In Tour, who run 7 experiences we rank across 3 cities, with an average Outty Ranking of 47.3.
See everything Tuscany In Tour runsWhy this scores 66
The Outty Ranking is a weighted composite. Here is how this experience performed on each component.
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?
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Prices start at $452 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?
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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?
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It holds an Outty Ranking of 66 out of 100, which we label "Solid Choice". That score blends traveler sentiment (5/5 across 19 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?
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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 Private tour from Florence to CORTONA & MONTEPULCIANO suitable for kids and families?
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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?
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Around 7 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 8-hour experience runs outdoors or after sunset.
Where does Private tour from Florence to CORTONA & MONTEPULCIANO 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?
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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?
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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 Private tour from Florence to CORTONA & MONTEPULCIANO?
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Included: Hotel pickup and drop-off; Private tour; Driver/guide; Transport on comfortable Mercedes-Benz V Class with ac; and tax, tolls, parking fees. Not included: lunch; and Gratuities. Always check the voucher for the final list before you travel.
Does Private tour from Florence to CORTONA & MONTEPULCIANO include hotel pickup?
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Yes, pickup is offered for every traveler from 421 listed pickup locations in and around Florence. Be ready about 5 minutes before the start time. You can also enter a custom pickup address when booking.
What languages is Private tour from Florence to CORTONA & MONTEPULCIANO offered in?
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It is offered in English, Italian 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 Private tour from Florence to CORTONA & MONTEPULCIANO?
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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 Private tour from Florence to CORTONA & MONTEPULCIANO wheelchair or stroller accessible?
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The operator notes: Wheelchair accessible; Infants and small children can ride in a pram or stroller; Specialized infant seats are available; and Transportation options are wheelchair accessible. If accessibility is critical, contact the operator after booking to confirm arrangements for your date.
What happens to Private tour from Florence to CORTONA & MONTEPULCIANO 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 Private tour from Florence to CORTONA & MONTEPULCIANO?
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Across 19 reviews averaging 5.0 out of 5, recurring themes include the guide, knowledge and storytelling, small groups. Travelers single out the guide as the reason the experience works.
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