Private Day Trip Siena and Chianti Wine Experience with lunch in Florence
Florence, Italy

Private Day Trip Siena and Chianti Wine Experience with lunch

Outty Ranking 73 5.0 · 21 traveler reviews8 hoursFrom $110

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September 2026

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Outty Ranking

73/100

Strongly Recommended. Our proprietary evaluation. How we score

Traveler rating

5.0/5

Based on 21 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.

Quick answer

Is Private Day Trip Siena and Chianti Wine Experience with lunch worth booking?

Private Day Trip Siena and Chianti Wine Experience with lunch is a 8-hour experience in Florence, Italy, from $110 per person. It scores 73 out of 100 on the Outty Ranking, which we label “Strongly Recommended, based on a 5/5 rating across 21 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.

Outty Ranking
73 / 100
Rating
5/5 (21)
Duration
8 hours
From
$110 per person

• EXPERIENCE FOR YOUR PRIVATE GROUP • Leave behind the bustling city of Florence with a private full-day tour in a luxury Mercedes Minivan. Stroll through the Gothic streets of Siena and discover the black-and-white art

What you get

    About this experience

    • EXPERIENCE FOR YOUR PRIVATE GROUP • Leave behind the bustling city of Florence with a private full-day tour in a luxury Mercedes Minivan. Stroll through the Gothic streets of Siena and discover the black-and-white art and architecture of its historic center, a UNESCO heritage site. Taste renowned Chianti wines and authentic Tuscan cuisine in famous family-owned cellars of local olive oil and aged balsamic vinegar. • 8hr Full-Day private tour of Siena and Chianti from Florence • Pick-up and drop off at your selected hotel/ location (Florence Down Town) • Private transportation by minivan, Air-Conditioned • Tasting of cold cuts and cheeses from the exceptional Falorni butcher shop • English-speaking licensed driver • Learn about local history, food and culture • On request we can organize Lunch in Farm or Winery. (highly recommended)

    What travelers are saying

    Outty’s summary of the themes that recur across 21 traveler reviews. Written by us, not quoted from reviewers.

    The guide

    6 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

    5 mentions

    Reviewers describe the commentary as informative rather than scripted.

    Small groups

    2 mentions

    The group size is repeatedly described as intimate rather than packed.

    Traveler reviews

    21 verified traveler reviews for Private Day Trip Siena and Chianti Wine Experience with lunch. Ratings and reviews provided by Viator and Tripadvisor.

    5 star
    21
    4 star
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    Companion372983 · March 2026

    Fabulous Day

    What a perfect day with Alessandro. Thank you for a wonderful day. We appreciate you giving us an amazing tour of Tuscany. I would highly recommend booking this tour. Alessandro has plenty of knowledge of the area since he was born and raised here. He took us to some of his favorite hidden gems and gave us fun facts along the way. If you want a quintessential Tuscany day this is for you. You can customize it anyway you want but we let Alessandro pick for us and he delivered. Thanks again for a memorable day. Jackie & Tom

    via Tripadvisor

    L9992DDlisab · November 2025

    Siena day trip and wine tasting

    An absolutely beautiful day with Alessandro as our driver. He goes above and beyond! We highly recommend him. A perfect way to visit Siena and top it off with a winery tour and exquisite lunch on their veranda. Thank you for a lovely tour!

    via Tripadvisor

    Stay615656 · October 2025

    Sienna, wine tour and a fun personalized day of exploring Tuscany!

    Alessandro provided a five star touring day! Highly recommend! The best way to tour Sienna, wine country is with a private driver! UniqueTuscany Tours with Alessandro is a perfect choice!

    via Tripadvisor

    solorisg2025 · September 2025

    Wedding celebration for my oldest granddaughter.

    Great experience.. Alessandro was very courteous and knowledgeable about every detail in everything we wanted to know. My first time in Italy.

    via Tripadvisor

    546faithy · January 2024

    Great day in Tuscany!

    Had the best day with Alessandro. We went to the beautiful city of Siena, had lunch and a wine tasting at a boutique winery/farm and another tasting at a family winery/farm. Both made organic wine and evoo that were very high quality. Able to ship wine home. Alessandro planned the day according to our preferences and was very knowledgeable about the Tuscany area and pleasant to be with. Highly recommend!

    via Tripadvisor

    Good to know

    Duration
    8 hours
    Free cancellation
    Up to 24h before
    Minimum age to book
    All ages
    Availability
    Bookable today
    Booked in 30 days
    7
    Verdict
    Strongly Recommended

    Why this scores 73

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

    Traveler sentiment (30% weight)89
    Review evidence (18% weight)41
    Booking momentum (14% weight)32
    Value for money (12% weight)100
    Listing quality (10% weight)85
    Local standing (8% weight)70
    Booking flexibility (8% weight)100

    Private Day Trip Siena and Chianti Wine Experience with lunch: questions travelers ask

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

    How much does Private Day Trip Siena and Chianti Wine Experience with lunch cost?

    +

    Prices start at $110 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 Day Trip Siena and Chianti Wine Experience with lunch 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 Day Trip Siena and Chianti Wine Experience with lunch worth it?

    +

    It holds an Outty Ranking of 73 out of 100, which we label "Strongly Recommended". That score blends traveler sentiment (5/5 across 21 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 Day Trip Siena and Chianti Wine Experience with lunch?

    +

    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 Day Trip Siena and Chianti Wine Experience with lunch suitable for kids and families?

    +

    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 Day Trip Siena and Chianti Wine Experience with lunch?

    +

    Around 7 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?

    +

    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 Day Trip Siena and Chianti Wine Experience with lunch 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?

    +

    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?

    +

    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?

    +

    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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