
PRIVATE TRANSFER: from Florence to Assisi with stops in Montepulciano & Cortona
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September 2026
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Adults
Age 13 and over
Children
Age 12 and under
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Free cancellation up to 24 hours before. Same price on Viator, Outty earns a commission.
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Quick answer
Is PRIVATE TRANSFER: from Florence to Assisi with stops in Montepulciano & Cortona worth booking?
PRIVATE TRANSFER: from Florence to Assisi with stops in Montepulciano & Cortona is a 8-hour experience in Florence, Italy, from $80 per person. It scores 56 out of 100 on the Outty Ranking, which we label “Worth a Look”. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.
- Outty Ranking
- 56 / 100
- Rating
- Not yet rated
- Duration
- 8 hours
- From
- $80 per person
Embark on a scenic journey from Florence to Assisi with our expert driver, stopping in two iconic Tuscan towns: Montepulciano and Cortona. Discover the region’s hidden gems, from breathtaking landscapes to charming villa
What you get
About this experience
Embark on a scenic journey from Florence to Assisi with our expert driver, stopping in two iconic Tuscan towns: Montepulciano and Cortona. Discover the region’s hidden gems, from breathtaking landscapes to charming villages, fine wines, and deep history. Begin in Montepulciano, a medieval hilltop town famous for its cobblestone streets and the grand Piazza Grande. Visit two historic wineries, where an expert oenologist will guide you through a tasting of five local wines. For lunch, your driver will recommend authentic local restaurants to enjoy true Tuscan flavors. Continue to Cortona, an ancient Etruscan city known for its local boutiques and artisan workshops. Stroll through the historic center, explore its traditional crafts, and discover the charm of the town featured in Under the Tuscan Sun. Finally, travel onward to Assisi, enjoying a scenic ascent to this spiritual city, surrounded by magnificent views and a rich cultural heritage.
What's included
Included
- Private transportation
- Bottled water
- In-vehicle air conditioning
- Local expert driver-Tour leader
- Alcoholic beverages
Not included
- Lunch
- Everything not found under the heading inclusions is excluded
What you'll see and do
Montepulciano
Our driver will pick you up in Florence and drive you through the scenic hills of Umbria and Tuscany to Montepulciano. Explore the main square of Montepulciano, visit the Temple of San Biagio, and enjoy lunch at your choice or our driver's recommendation. Montepulciano is renowned for its excellent red wines—Nobile and Rosso di Montepulciano. Our driver, well-versed in the area, will guide you through captivating underground cellars for an incredible wine tasting experience, showcasing the best wines and their unique characteristics.
120 minutes here
Cortona
After Montepulciano, our next stop is the captivating town of Cortona. Enjoy a self-guided tour of the historical center, a cultural and artistic hub in the Val di Chiana after Arezzo. Founded by the Etruscans, Cortona, or 'Curtun,' preserves its Etruscan origins and tells tales of Renaissance artists like Luca Signorelli and Beato Angelico, along with Baroque artist Pietro di Cortona. Immerse yourself in the charm that inspired the film 'Under the Tuscan Sun.' Just beyond the city, explore the Hermitage of San Francesco, known as 'Le Celle.' This monastery, with its mystical atmosphere, served as inspiration for San Francesco, who composed 'The Canticle of Creatures' here.
90 minutes here
Lake Trasimeno
After exploring Cortona, our journey continues towards Assisi, passing the scenic Trasimeno Lake with an optional stop on request. Nestled in the green heart of Umbria, Lake Trasimeno boasts picturesque beds of reeds and enchanting white water lilies, creating a natural paradise for wild ducks, cormorants, kites, and kingfishers. The transfer concludes in Assisi (or Perugia), where our driver will drop you off at your specified location—be it a hotel, private flat address, B&B, or your desired destination.
Pass by without stopping
Where it starts and ends
Hotel pickup
Pickup is included for all travelers.
Before you book
- Cancellation
- For a full refund, cancel at least 24 hours before the scheduled departure time.
- Languages
- en, fr, es
- Ticket
- Mobile Only
- Runs on
- Every day
- Group size
- Up to 6 travelers per booking
- Operated by
- Pek Tuscany in Limo
Know before you go
- Specialized infant seats are available
- Infants and small children can ride in a pram or stroller
- Suitable for all physical fitness levels
- Wheelchair accessible
Photos






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
- $80 to $250
- Hotel pickup
- Included for all travelers
- Booked in 30 days
- 0
- Verdict
- Worth a Look
Why this scores 56
The Outty Ranking is a weighted composite. Here is how this experience performed on each component.
PRIVATE TRANSFER: from Florence to Assisi with stops in Montepulciano & Cortona: questions travelers ask
Practical detail on this experience, plus the wider planning questions for Florence.
How much does PRIVATE TRANSFER: from Florence to Assisi with stops in Montepulciano & Cortona cost?
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Prices start at $80 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 TRANSFER: from Florence to Assisi with stops in Montepulciano & Cortona 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 TRANSFER: from Florence to Assisi with stops in Montepulciano & Cortona worth it?
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It holds an Outty Ranking of 56 out of 100, which we label "Worth a Look". That score blends traveler sentiment (0/5 across 0 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 TRANSFER: from Florence to Assisi with stops in Montepulciano & 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 PRIVATE TRANSFER: from Florence to Assisi with stops in Montepulciano & Cortona 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 TRANSFER: from Florence to Assisi with stops in Montepulciano & Cortona?
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Around 0 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 TRANSFER: from Florence to Assisi with stops in Montepulciano & 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 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?
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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.
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