Private wine tour of Chianti in Siena, Italy
Siena, Italy

Private wine tour of Chianti

Outty Ranking 60 4.6 · 10 traveler reviews6 hoursFrom $457
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Outty Ranking

60/100

Solid Choice. Our proprietary evaluation. How we score

Traveler rating

4.6/5

Based on 10 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.

Quick answer

Is Private wine tour of Chianti worth booking?

Private wine tour of Chianti is a 6-hour experience in Siena, Italy, from $457 per person. It scores 60 out of 100 on the Outty Ranking, which we label “Solid Choice”, based on a 4.6/5 rating across 10 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.

Outty Ranking
60 / 100
Rating
4.6/5 (10)
Duration
6 hours
From
$457 per person

Your driver will come to your accommodation around 930 to whisk you off to your first wine tour and tasting. During the day we will escort you to three wineries to see the differences in production methods and sample each wineries products. A lunch stop will be included at a local restaurant with the tour continuing after lunch. If you have a preference for smaller, less known producers let me know at time of booking and I will concentrate the afternoons bookings with this in mind. Suitable for 1 to 8 people. We provide the driver/vehicle, winery tickets & the knowledge you need. Tour approx. 930 thru 530pm. Lunch stop included in the tour (cost of lunch not included). This is a private tour, you are not joining another group! Specific wineries are subject to availability! Tours not in the summer season may require different wineries due to opening periods. Listed wineries are for the Chianti version, the Montalcino version will includes 3 Brunello producers

What you get

    About this experience

    Your driver will come to your accommodation around 930 to whisk you off to your first wine tour and tasting. During the day we will escort you to three wineries to see the differences in production methods and sample each wineries products. A lunch stop will be included at a local restaurant with the tour continuing after lunch. If you have a preference for smaller, less known producers let me know at time of booking and I will concentrate the afternoons bookings with this in mind. Suitable for 1 to 8 people. We provide the driver/vehicle, winery tickets & the knowledge you need. Tour approx. 930 thru 530pm. Lunch stop included in the tour (cost of lunch not included). This is a private tour, you are not joining another group! Specific wineries are subject to availability! Tours not in the summer season may require different wineries due to opening periods. Listed wineries are for the Chianti version, the Montalcino version will includes 3 Brunello producers

    What's included

    Included

    • Lunch
    • Wine Tastings & Tours are included in the price

    What you'll see and do

    1. Castello di Volpaia

      Wine tour and tastinf

      60 minutes here · Admission included

    2. Castellina In Chianti

      We will be driving through the heart of the Chianti region, including possible stopping points including Castellina in Chianti, Radda, Grevein Chianti and more

      20 minutes here

    3. Rocca Della Macie

      Tour and tasting (subject to availability)

      60 minutes here · Admission included

    Where it starts and ends

    Hotel pickup

    Pickup is included for all travelers. Pickup begins about 30 minutes before departure.

    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
    Mon, Tue, Wed, Thu, Fri, Sat
    Group size
    Up to 8 travelers per booking
    Operated by
    Antony Charity

    Know before you go

    • Infants and small children can ride in a pram or stroller
    • Service animals allowed
    • Specialized infant seats are available
    • Suitable for all physical fitness levels

    Photos

    Private wine tour of Chianti in Siena, photo 2Private wine tour of Chianti in Siena, photo 3Private wine tour of Chianti in Siena, photo 4Private wine tour of Chianti in Siena, photo 5Private wine tour of Chianti in Siena, photo 6Private wine tour of Chianti in Siena, photo 7

    What travelers are saying

    Outty’s summary of the themes that recur across 10 traveler reviews. Written by us, not quoted from reviewers.

    The guide

    7 mentions

    Travelers single out the guide as the reason the experience works.

    Food and drink

    6 mentions

    The tastings and food stops are a highlight for most reviewers.

    Knowledge and storytelling

    4 mentions

    Reviewers describe the commentary as informative rather than scripted.

    Traveler reviews

    10 verified traveler reviews for Private wine tour of Chianti. Ratings and reviews provided by Viator and Tripadvisor.

    5 star
    9
    4 star
    0
    3 star
    0
    2 star
    0
    1 star
    1
    Sort
    Kerry_K · October 2025

    We had a wonderful day...

    We had a wonderful day exploring wineries in the Chianti Region of Tuscany with an amazing driver and guide, Ian. He was so knowledgeable and created a wonderful experience for us! Thank you Ian!

    via Viator

    Adam_W · October 2024

    Amazing personalized experience!

    Ian created a personalized experience that was one of a kind. We visited both smaller, lesser known wineries as well as a great tour and lunch at a famous Chianti Classico one. Ian even walked us around the ancient town of Radda.

    via Viator

    Craig_M · September 2023

    Terrific guide and experience!

    Ian was an awesome guide! He went out of his way to make sure we had a great day. He even swung by Sienna so I could pick up a piece of gear that I needed -- totally unplanned and very much appreciated!

    via Viator

    christinadK4555EO · June 2023

    Perfect wine tour

    Ian was a fantastic guide. A few days before the tour he reached out to see about any allergies, special requests, etc. My husband has Celiac and navigating that when we travel can be a bit daunting so it was very much appreciated. Ian was right on time in the morning, the vehicle spotless and comfortable. He pointed out various places of interest on our way up and down the winding roads, and even taught me a neat trick for car sickness! He picked fantastic wineries for us and made sure the lunch spot was aware of my husbands food allergies. He made sure we were well taken care of at each spot, and even brought umbrellas for us. When we found out the gelato shop we planned to go to was closed, he took us to another village for gelato and took us on a tour of the town, accompanying us into shops. He answered our endless questions about what it’s like to live in Siena as an expat, history, and wine. We could not recommend him more!!!

    Response from the operator: Hi Christina, Thank you so much for your positive feedback! We're glad to have you as our customer and to see that you enjoyed the Wine Tour experience. It makes us incredibly happy to know that we were a positive part of your trip. Do you have any recommendations for us to improve your experience? Or any tour types you would like us to offer in the future? Please share your suggestions at info@specialitytour.com P.S. If you ever need help while in Italy, or would like to book another experience, please don't hesitate to reach out; we're always here.

    via Tripadvisor

    Katie_C · October 2022

    What a great day!

    My boyfriend and I had an awesome day on this tour and got to try some fabulous wines. The lunch was also amazing! I am a picky eater and ate it all. It was so much fun!

    Response from the operator: Hi Katie, Thank you so much for your positive feedback! We're glad to have you as our customer and to see that you enjoyed the wine tour experience. It makes us incredibly happy to know that we were a positive part of your trip. Do you have any recommendations for us to improve your experience? Or any tour types you would like us to offer in the future? Please share your suggestions at info@specialitytour.com P.S. If you ever need help while in Italy, or would like to book another experience, please don't hesitate to reach out; we're always here.

    via Viator

    Good to know

    Duration
    6 hours
    Free cancellation
    Up to 24h before
    Minimum age to book
    All ages
    Availability
    Bookable today
    Runs on
    Mon, Tue, Wed, Thu, Fri, Sat
    Price range
    $457 to $675
    Hotel pickup
    Included for all travelers
    Booked in 30 days
    4
    Verdict
    Solid Choice

    Who runs this experience

    Operated by Antony Charity, who run 3 experiences we rank across 1 city, with an average Outty Ranking of 49.0.

    See everything Antony Charity runs

    Why this scores 60

    The Outty Ranking is a weighted composite. Here is how this experience performed on each component.

    Traveler sentiment (30% weight)78
    Review evidence (18% weight)41
    Booking momentum (14% weight)33
    Value for money (12% weight)37
    Listing quality (10% weight)85
    Local standing (8% weight)44
    Booking flexibility (8% weight)100

    Private wine tour of Chianti: questions travelers ask

    Practical detail on this experience, plus the wider planning questions for Siena.

    How much does Private wine tour of Chianti cost?

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    Prices start at $457 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 wine tour of Chianti take?

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    Plan for about 6 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 wine tour of Chianti worth it?

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    It holds an Outty Ranking of 60 out of 100, which we label "Solid Choice". That score blends traveler sentiment (4.6/5 across 10 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 wine tour of Chianti?

    +

    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 wine tour of Chianti suitable for kids and families?

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    Yes, all ages are welcome. Families should still weigh the 6-hour running time, and strollers are easier on the earlier, quieter departures.

    How far in advance should I book Private wine tour of Chianti?

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    Around 4 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?

    +

    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 6-hour experience runs outdoors or after sunset.

    Where does Private wine tour of Chianti 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?

    +

    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?

    +

    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 wine tour of Chianti?

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    Included: Lunch; and Wine Tastings & Tours are included in the price. Always check the voucher for the final list before you travel.

    Does Private wine tour of Chianti include hotel pickup?

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    Yes, pickup is offered for every traveler from 944 listed pickup locations in and around Siena. Be ready about 30 minutes before the start time. You can also enter a custom pickup address when booking.

    What languages is Private wine tour of Chianti 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 wine tour of Chianti?

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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 wine tour of Chianti 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 wine tour of Chianti 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.

    What do travelers say about Private wine tour of Chianti?

    +

    Across 10 reviews averaging 4.6 out of 5, recurring themes include the guide, food and drink, knowledge and storytelling. Travelers single out the guide as the reason the experience works.

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