Private Art & Wine Tour in Cortona & Montepulciano, with lunch & 2 wine tastings
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September 2026
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Adults
Age 13 and over
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Age 12 and under
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Quick answer
Is Private Art & Wine Tour in Cortona & Montepulciano, with lunch & 2 wine tastings worth booking?
Private Art & Wine Tour in Cortona & Montepulciano, with lunch & 2 wine tastings is a 8-hour experience in Arezzo, Italy, from $308 per person. It scores 51 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
- 51 / 100
- Rating
- Not yet rated
- Duration
- 8 hours
- From
- $308 per person
Follow the trail of the film "Under the tuscan sun". We will take you to the rolling Tuscan landscape, among vineyards, art and sunflowers. We will visit the countryside and the city of Cortona, "the secret underground c
What you get
About this experience
Follow the trail of the film "Under the tuscan sun". We will take you to the rolling Tuscan landscape, among vineyards, art and sunflowers. We will visit the countryside and the city of Cortona, "the secret underground cellars" of Montepulciano. You will taste the best wines of our region and have a typical Tuscan lunch. Itineraty: • We will explore southern Tuscany and visit the medieval city of Cortona and the Monastery of San Francesco called "Le Celle" • We will stop to take photos of the landscape along the road featured in the film "Under the Tuscan Sun" • Later we will visit the "Underground Wonders" of Montepulciano (The Historic Cellars of the city) where you will find gigantic oak barrels, in which the famous Vino Nobile di Montepulciano DOCG "rests". • In Montepulciano we will have a delicious lunch and two wine tastings in two different cellars. The return is scheduled for 5pm
What's included
Included
- Private transportation
- Alcoholic beverages
- Lunch
- Bottled water
- Local expert driver and tour leader
- In-vehicle air conditioning
- All inclusive tour
Not included
- Everything not found under the heading inclusions is excluded
What you'll see and do
Cortona
Our expert driver will pick you up at your hotel or other chosen location (B&B or private apartment) and take you to discover the Tuscan countryside. The first stop will be in Cortona for a self-guided visit of the city (1 hour). Cortona is a traditional fortified Etruscan city, located approximately 600 meters above sea level, offering spectacular views of the surrounding valley and Lake Trasimeno. The main things I recommend you look for in the city center are: - Piazza della Repubblica, the historic center of Cortona - the pretty medieval streets of Cortona - Piazza Signorelli - the beautiful shops of Cortona, We will also visit the incredible Monastery of St. Francis, a peaceful place not far from the city.
90 minutes here
Strada Del Vino Nobile Di Montepulciano
After leaving Cortona, we will stop to take photos of the landscape along the road described in the film "Under the Tuscan Sun". Afterwards we will head to Montepulciano to visit the "Underground Wonders" of the city. We will visit the main square of the town (Piazza Grande), the ancient Government Palace and two historic cellars: here you will find gigantic oak barrels, in which the famous Vino Nobile di Montepulciano DOCG and Rosso di Montepulciano DOC rest.
60 minutes here
Montepulciano
In the heart of Montepulciano, you will enjoy a delicious Tuscan lunch and five wine tastings following a guided tour of a historic underground cellar located in the old town. The experience includes: • Guided tour of the historic cellar • Wine tasting of: o Rosso di Montepulciano DOC o Nobile di Montepulciano DOCG o Nobile di Montepulciano Riserva DOCG o Nobile di Montepulciano “Filai Lunghi” DOCG or IGT “Pietrose” Super Tuscan Lunch includes: • Homemade pasta (Pici, Lasagne, or Cannelloni) • Pecorino di Pienza cheese • Typical Tuscan cured meats (ham, loin, salami) The cellar is a spectacular historic site carved directly into the ancient rock beneath Montepulciano’s historic center. Its underground tunnels open into large chambers where the Nobile di Montepulciano wines are aged, offering a truly atmospheric and authentic experience.
90 minutes here
Cantina Fattoria della Talosa
The second wine tasting experience will take place in a historic underground cellar. During the Renaissance, the family who owned the estate cultivated vineyards, and by the 1700s this activity had earned widespread recognition. They are regarded as among the founding fathers of Vino Nobile di Montepulciano. Following a visit to the cellar, you will enjoy a special wine tasting of 4–5 wines. At the end of the second tasting experience, we will return to your location.
45 minutes here · Admission included
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, it, fr, es
- Ticket
- Mobile Only
- Runs on
- Every day
- Group size
- Up to 7 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
- Transportation options are wheelchair accessible
- 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
- Hotel pickup
- Included for all travelers
- Booked in 30 days
- 0
- Verdict
- Worth a Look
Why this scores 51
The Outty Ranking is a weighted composite. Here is how this experience performed on each component.
Private Art & Wine Tour in Cortona & Montepulciano, with lunch & 2 wine tastings: questions travelers ask
Practical detail on this experience, plus the wider planning questions for Arezzo.
How much does Private Art & Wine Tour in Cortona & Montepulciano, with lunch & 2 wine tastings cost?
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Prices start at $308 per person. The final price depends on the date, the time slot and the number of travelers, and peak weekends in Arezzo usually price higher than midweek mornings. Live pricing and remaining availability are confirmed on the booking screen before you pay.
How long does Private Art & Wine Tour in Cortona & Montepulciano, with lunch & 2 wine tastings 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 Arezzo is not rushed.
Is Private Art & Wine Tour in Cortona & Montepulciano, with lunch & 2 wine tastings worth it?
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It holds an Outty Ranking of 51 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 Arezzo, and how flexible the cancellation terms are.
Can I cancel or reschedule Private Art & Wine Tour in Cortona & Montepulciano, with lunch & 2 wine tastings?
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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 Art & Wine Tour in Cortona & Montepulciano, with lunch & 2 wine tastings 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 Art & Wine Tour in Cortona & Montepulciano, with lunch & 2 wine tastings?
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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 Arezzo 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 Arezzo and add a light layer if any part of the 8-hour experience runs outdoors or after sunset.
Where does Private Art & Wine Tour in Cortona & Montepulciano, with lunch & 2 wine tastings 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 Arezzo 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 Arezzo?
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On Outty we rank every Arezzo experience on the same 0 to 100 scale, and alongside this one the highest scorers right now include Tour of the vineyards and tasting of Evo wines and oil in Tuscany, Wine and olive oil tastings with the locals, Cellar Tour & Wine Tasting. 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 Arezzo?
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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 Arezzo?
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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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