Private Tour Siena San Gimignano and Chianti from Cortona
Traveler rating
5.0/5
Based on 7 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.
Quick answer
Is Private Tour Siena San Gimignano and Chianti from Cortona worth booking?
Private Tour Siena San Gimignano and Chianti from Cortona is a 8-hour experience in Arezzo, Italy, from $468 per person. It scores 65 out of 100 on the Outty Ranking, which we label “Solid Choice”, based on a 5/5 rating across 7 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.
- Outty Ranking
- 65 / 100
- Rating
- 5/5 (7)
- Duration
- 8 hours
- From
- $468 per person
Kick off your day with a comfortable ride through the stunning Tuscan countryside. First, we’ll arrive in Siena, one of Tuscany’s most beautiful towns. Explore Piazza del Campo, famous for the Palio di Siena horse race, admire the breathtaking Duomo (Cathedral), and wander through the charming, narrow streets of the historic center. Wine Tasting & Light Lunch Next, we’ll head to a renowned winery for a light lunch paired with an amazing wine tasting experience. A sommelier will guide you through five exceptional wines, plus an olive oil tasting. After lunch, we’ll continue our journey with a spectacular drive through the rolling Vernaccia di San Gimignano vineyards, home to Tuscany’s most famous white wine. Stop in San Gimignano you’ll have free time to explore this medieval gem, known for its 14 towers dating back to the 13th century. The town’s atmosphere will transport you back to the Middle Ages! And of course, you can’t miss the world’s best gelato at Gelateria Dondoli.
What you get
About this experience
Kick off your day with a comfortable ride through the stunning Tuscan countryside. First, we’ll arrive in Siena, one of Tuscany’s most beautiful towns. Explore Piazza del Campo, famous for the Palio di Siena horse race, admire the breathtaking Duomo (Cathedral), and wander through the charming, narrow streets of the historic center. Wine Tasting & Light Lunch Next, we’ll head to a renowned winery for a light lunch paired with an amazing wine tasting experience. A sommelier will guide you through five exceptional wines, plus an olive oil tasting. After lunch, we’ll continue our journey with a spectacular drive through the rolling Vernaccia di San Gimignano vineyards, home to Tuscany’s most famous white wine. Stop in San Gimignano you’ll have free time to explore this medieval gem, known for its 14 towers dating back to the 13th century. The town’s atmosphere will transport you back to the Middle Ages! And of course, you can’t miss the world’s best gelato at Gelateria Dondoli.
What's included
Included
- Private transportation
- On-board WiFi
- Bottled water
- All Fees and Taxes
- In-vehicle air conditioning
- Lunch
What you'll see and do
Piazza del Campo
Piazza del Campo (or simply Il Campo) is the main square of Siena. Famous for its unique shell shape, it is known worldwide for its beauty and well-preserved architecture. It is also the site of the Palio di Siena, a horse race held twice a year. By ancient tradition, the square and the Palazzo Pubblico do not belong to any contrada.
25 minutes here · Admission included
Duomo di Siena
The Siena Cathedral, or Cattedrale di Santa Maria Assunta, is one of the masterpieces of Italian Gothic architecture. Located in the heart of the city, it stands out for its extraordinary façade of white, dark green, and red marble, as well as its interior rich in artworks. It is undoubtedly one of the most beautiful and most visited cathedrals in Italy.
20 minutes here · Admission not included
Monteriggioni
Monteriggioni is a small medieval village in Tuscany, in the province of Siena. It is famous for its spectacular walls, making it one of the best-preserved fortified villages in Italy.
Pass by without stopping
San Gimignano
San Gimignano is a charming medieval village located in Tuscany, in the province of Siena. It is famous for its medieval towers, which have earned it the nickname "Manhattan of the Middle Ages". The medieval towers: There were once over 70, today 14 remain, making the village unique in the word. They were symbols of power of the noble families. UNESCO Heritage: The historic center of San Gimignano was declared a World Heritage Site by UNESCO in 1990. San Gimignano is an unmissable destination for those visiting Tuscany, perfect for immersing yourself in the medieval atmosphere and enjoying breathtaking views.
50 minutes here
Where it starts and ends
Hotel pickup
Pickup is included for all travelers. Pickup begins about 10 minutes before departure.
Ends at
Returns to the starting point
Before you book
- Cancellation
- For a full refund, cancel at least 24 hours before the scheduled departure time.
- Languages
- en, it
- Ticket
- Mobile Only
- Runs on
- Every day
- Group size
- Up to 8 travelers per booking
- Operated by
- Tuscany Luxury Tour NCC
Know before you go
- Infants and small children can ride in a pram or stroller
- Public transportation options are available nearby
- Specialized infant seats are available
- Suitable for all physical fitness levels
Photos
What travelers are saying
Outty’s summary of the themes that recur across 7 traveler reviews. Written by us, not quoted from reviewers.
The guide
3 mentionsTravelers single out the guide as the reason the experience works.
Knowledge and storytelling
3 mentionsReviewers describe the commentary as informative rather than scripted.
Good for families
2 mentionsReviewers traveling with kids report it landed well with their group.
Pace and timing
2 mentionsSeveral reviewers comment on how the schedule is paced.
Traveler reviews
7 verified traveler reviews for Private Tour Siena San Gimignano and Chianti from Cortona. Ratings and reviews provided by Viator and Tripadvisor.
Spectacular.
This trip was incredible. Luca was a stellar driver, knows everything about the area. The winery is fantastic and worth every penny and more. This was a day we will never forget. If you do nothing else, do this!
via Viator
A Truly Personalized Tuscany Experience
Massimo made our two days in Tuscany feel completely effortless. From the planning stage onward, he was deeply involved in shaping a fully customized itinerary, patiently answering questions, refining details, and making sure the final plan suited us perfectly. Our itinerary included visits to two medieval towns, a winery tour and tasting, a truffle hunt, and a pasta-making class. It was varied, well paced, and thoughtfully arranged for the whole family—the kids especially loved the hands-on experiences. Both days were seamless, with punctual hotel pick-up and drop-off, yet the experience never felt rigid. Massimo was always flexible when we wanted to adjust the pace or spend a little more time somewhere. He is warm, knowledgeable, and genuinely informative without ever making the day feel scripted. He also very kindly helped me practice my Italian throughout the trip, which made the experience even more personal. Professional, thoughtful, reliable, and truly customer-first. I would recommend Massimo without hesitation to anyone looking for a private and genuinely personalized way to experience Tuscany.
Response from the operator: Dear Liam, Thank you so much for taking the time to write such a thoughtful and heartfelt review. Your words truly mean a lot to us. It was a real pleasure helping you plan your two days in Tuscany and, even more importantly, spending that time with you and your family. We are so happy to hear that the itinerary felt relaxed, well-paced, and enjoyable for everyone — especially the kids! The truffle hunt and pasta-making experience were certainly among the highlights, and seeing the children enjoy those hands-on experiences made it even more special. And thank you for mentioning our little Italian practice sessions! I really enjoyed that too, and I’m happy I could help you along the way. Hopefully, the next time you come back to Tuscany, your Italian will be even better! It was a pleasure getting to know your family, and we truly appreciate the trust you placed in us from the very beginning, especially while we were working together to create the itinerary. We hope to see you again in Tuscany someday. Until then, we wish you and your family all the very best! A big thank you from both of us, and a warm Tuscan hug. Massimo & Luca
via Tripadvisor
One of the best days of my life
This was seriously the most amazing experience of my entire life Max was the funnest, funniest and coolest guide. He was so knowledgeable, so attentive so caring and so positive. I will use this company 1 million times. I had the best day ever.
Response from the operator: First of all, I’m so sorry for my late reply! Things have been incredibly busy here in Tuscany, but I could never let such a wonderful review go without a proper thank you. ❤️ Reading your words honestly made my day. Knowing that this was one of the most amazing experiences of your life is the greatest compliment I could ever receive. It was such a pleasure spending the day with you, sharing Tuscany, laughing together, and creating memories along the way. I truly believe that the best experiences are not just about the places you visit, but about the people you share them with — and you made the day so much fun! Thank you for trusting us, for your wonderful energy, and for enjoying Tuscany with such enthusiasm. Your words mean more to me than you know. And if you really mean that you’ll use us “1 million times”… I’ll be waiting for you! 😂🇮🇹❤️ I hope to see you back in Tuscany someday so we can create another unforgettable day together. Grazie di cuore, and see you next time!
via Tripadvisor
From Texas to Tuscany
Max was great and helped us so much to navigate through with precise directions and enough time to enjoy a few different cities. He was such a great guide for our first time in Italy Would recommend this full day adventure to anyone wanting to leave Cortona for the day. Katrina, Meagan & Debbie *Texas*
Response from the operator: Hello Katrina, Meagan and Debbie, thank you so much for your lovely words! It was such a pleasure to share the day with you, and I really hope we can meet again to enjoy more of Tuscany together. Big hugs to all of you from Cortona! Massimo e Luca
via Tripadvisor
Wonderful trip and service!
Amazing trip with Luca. Made the trip memorable for our family of 4 and still managed to fit in a bit of time a local winery! Loved both San Gimignano and Monteriggioni and really enjoyed Luca’s knowledge of the area. Would certainly recommend Luca and would have booked for a subsequent trip but he was booked up!
via Tripadvisor
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
- 2
- Verdict
- Solid Choice
Who runs this experience
Operated by Tuscany Luxury Tour NCC, who run 4 experiences we rank across 1 city, with an average Outty Ranking of 57.8.
See everything Tuscany Luxury Tour NCC runsWhy this scores 65
The Outty Ranking is a weighted composite. Here is how this experience performed on each component.
Private Tour Siena San Gimignano and Chianti from Cortona: questions travelers ask
Practical detail on this experience, plus the wider planning questions for Arezzo.
How much does Private Tour Siena San Gimignano and Chianti from Cortona cost?
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Prices start at $468 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 Tour Siena San Gimignano and Chianti from 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 Arezzo is not rushed.
Is Private Tour Siena San Gimignano and Chianti from Cortona worth it?
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It holds an Outty Ranking of 65 out of 100, which we label "Solid Choice". That score blends traveler sentiment (5/5 across 7 reviews), the depth of that review evidence, recent booking momentum, value for money against comparable most popular in Arezzo, and how flexible the cancellation terms are.
Can I cancel or reschedule Private Tour Siena San Gimignano and Chianti from 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 Tour Siena San Gimignano and Chianti from 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 Tour Siena San Gimignano and Chianti from Cortona?
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Around 2 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 Tour Siena San Gimignano and Chianti from 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 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.
What is included in Private Tour Siena San Gimignano and Chianti from Cortona?
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Included: Private transportation; On-board WiFi; Bottled water; All Fees and Taxes; and In-vehicle air conditioning. Always check the voucher for the final list before you travel.
Does Private Tour Siena San Gimignano and Chianti from Cortona include hotel pickup?
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Yes, pickup is offered for every traveler from 126 listed pickup locations in and around Arezzo. Be ready about 10 minutes before the start time. You can also enter a custom pickup address when booking.
What languages is Private Tour Siena San Gimignano and Chianti from Cortona offered in?
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It is offered in English and Italian. 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 Siena San Gimignano and Chianti from Cortona?
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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 Siena San Gimignano and Chianti from Cortona wheelchair or stroller accessible?
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The operator notes: Infants and small children can ride in a pram or stroller; and Specialized infant seats are available. If accessibility is critical, contact the operator after booking to confirm arrangements for your date.
What happens to Private Tour Siena San Gimignano and Chianti from Cortona if the weather is bad?
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It generally runs rain or shine, so dress for the forecast in Arezzo. Standard cancellation terms apply: free cancellation up to 24 hours before the start.
What do travelers say about Private Tour Siena San Gimignano and Chianti from Cortona?
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Across 7 reviews averaging 5.0 out of 5, recurring themes include the guide, knowledge and storytelling, good for families. Travelers single out the guide as the reason the experience works. One thing to know: Several reviewers comment on how the schedule is paced.
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