
Private Art & Wine Tour in Cortona & Montepulciano, with lunch & 2 wine tastings
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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 Siena, Italy, from $297 per person. It scores 55 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
- 55 / 100
- Rating
- Not yet rated
- Duration
- 8 hours
- From
- $297 per person
Follow us inside the rolling Tuscan landscape, amidst wine, art, Middle Ages, Renaissance and history visiting Cortona and "the secret underground cellars" of Montepulciano. You will taste the best wines of our Region and meal with a typical tuscan lunch. The beautiful and untouched landscape is the absolute protagonist in Val d' Orcia. This area of Tuscany boasts of endless rolling hills covered with grain or sunflowers, a rich green valley which encompasses the Orcia river. First we will explore the South of Tuscany and visit the Medieval town of Cortona. Later we'll 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 “rest”. In Montepulciano we'll have also a first and a second wine tasting experience in two differerent cellars, with a delicious tuscan lunch. (Pecorino cheese, bruschettas, ham, cold cuts, always with the best wines of our Region).
What you get
About this experience
Follow us inside the rolling Tuscan landscape, amidst wine, art, Middle Ages, Renaissance and history visiting Cortona and "the secret underground cellars" of Montepulciano. You will taste the best wines of our Region and meal with a typical tuscan lunch. The beautiful and untouched landscape is the absolute protagonist in Val d' Orcia. This area of Tuscany boasts of endless rolling hills covered with grain or sunflowers, a rich green valley which encompasses the Orcia river. First we will explore the South of Tuscany and visit the Medieval town of Cortona. Later we'll 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 “rest”. In Montepulciano we'll have also a first and a second wine tasting experience in two differerent cellars, with a delicious tuscan lunch. (Pecorino cheese, bruschettas, ham, cold cuts, always with the best wines of our Region).
What's included
Included
- Private transportation
- Alcoholic beverages
- Bottled water
- Lunch
- In-vehicle air conditioning
- Local expert driver & tour leader
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
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
Cantina Fattoria della Talosa
Also in the heart of Montepulciano you will have a delicious Tuscan lunch and 5 wine tastings after a guided tour inside the Talosa Historic Winery. Take up again: - Guided tour of the Historic Cellar - Tasting of Rosso di Montepulciano Doc, Nobile di Montepulciano Docg wines; - Nobile di Montepulciano Riserva Docg; - Nobile di Montepulciano “Filai Lunghi” Docg or IGT “Pietrose” Super Tuscan; - Lunch with: Homemade pasta (Pici, Lasagne or Cannelloni) - Pecorino di Pienza; - Typical Tuscan cured meats (ham, loin, salami). Talosa is a historic and spectacular winery in the heart of Montepulciano, carved into the historic center. Its tunnels dug into the ancient rock both open onto the large rooms where the Nobile wine rests.
90 minutes here · Admission included
Azienda Agricola Ercolani
The second wine tasting experience will be in the historic cellar of Cantina Ercolani. During the Renaissance the Ercolani family cultivated vines and in 1700 this activity was highly appreciated. In fact they were one of the "founding fathers" of Vino Nobile. After the guided tour of the cellar we will have a special wine tasting (7/8 wines) accompanied by appetizers. At the end of the second tasting 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
- Suitable for all physical fitness levels
- Transportation options are wheelchair accessible
- 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
Who runs this experience
Operated by Pek Tuscany in Limo, who run 48 experiences we rank across 9 cities, with an average Outty Ranking of 51.1.
See everything Pek Tuscany in Limo runsWhy this scores 55
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 Siena.
How much does Private Art & Wine Tour in Cortona & Montepulciano, with lunch & 2 wine tastings cost?
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Prices start at $297 per person. The final price depends on the date, the time slot and the number of travelers, and peak weekends in Siena 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 Siena 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 55 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 Siena, 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 Siena 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 Siena 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 Siena 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 Siena?
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On Outty we rank every Siena experience on the same 0 to 100 scale, and alongside this one the highest scorers right now include Small-Group Brunello di Montalcino Wine-Tasting Trip from Siena, Siena: A Wine Tour and Tasting Experience, Small-Group Montepulciano and Pienza Day Trip from Siena. 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 Siena?
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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 Siena?
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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 Art & Wine Tour in Cortona & Montepulciano, with lunch & 2 wine tastings?
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Included: Private transportation; Alcoholic beverages; Bottled water; Lunch; and In-vehicle air conditioning. Not included: Everything not found under the heading inclusions is excluded. Always check the voucher for the final list before you travel.
Does Private Art & Wine Tour in Cortona & Montepulciano, with lunch & 2 wine tastings include hotel pickup?
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Yes, pickup is offered for every traveler from 95 listed pickup locations in and around Siena. You can also enter a custom pickup address when booking.
What languages is Private Art & Wine Tour in Cortona & Montepulciano, with lunch & 2 wine tastings offered in?
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It is offered in English, Italian, French 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 Art & Wine Tour in Cortona & Montepulciano, with lunch & 2 wine tastings?
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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 Art & Wine Tour in Cortona & Montepulciano, with lunch & 2 wine tastings wheelchair or stroller accessible?
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The operator notes: Specialized infant seats are available; Infants and small children can ride in a pram or stroller; Transportation options are wheelchair accessible; and Wheelchair accessible. If accessibility is critical, contact the operator after booking to confirm arrangements for your date.
What happens to Private Art & Wine Tour in Cortona & Montepulciano, with lunch & 2 wine tastings if the weather is bad?
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It generally runs rain or shine, so dress for the forecast in Siena. Standard cancellation terms apply: free cancellation up to 24 hours before the start.
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