Private Tour to Siena and Montalcino from Florence in Florence
Florence, Italy

Private Tour to Siena and Montalcino from Florence

Outty Ranking 52 5.0 · 5 traveler reviews9 hoursFrom $850

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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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From, per person$850
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Outty Ranking

52/100

Worth a Look. Our proprietary evaluation. How we score

Traveler rating

5.0/5

Based on 5 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.

Quick answer

Is Private Tour to Siena and Montalcino from Florence worth booking?

Private Tour to Siena and Montalcino from Florence is a 9-hour experience in Florence, Italy, from $850 per person. It scores 52 out of 100 on the Outty Ranking, which we label “Worth a Look, based on a 5/5 rating across 5 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.

Outty Ranking
52 / 100
Rating
5/5 (5)
Duration
9 hours
From
$850 per person

• Experience for your private group. If you are looking for beautiful sceneries, medieval city and excellent wines, this tour is for you. Explore the art, culture and medieval history of Italy in this private 9-hour S

What you get

    About this experience

    • Experience for your private group. If you are looking for beautiful sceneries, medieval city and excellent wines, this tour is for you. Explore the art, culture and medieval history of Italy in this private 9-hour Siena, Montalcino countryside tour from Florence. • Starting by visiting the marvelous Gothic town of Siena with its unique Campo square (where the famous Palio is run). • Then proceed towards Montalcino, a small medieval town situated on a hill dominated by the fourteenth-century fortress, in the countryside surrounding the town the famous "Brunello" wineyards. • Stop in one of the renowned wineries and enjoy visiting their cellar and tasting their great wines. • Don't miss a Lunch and wine tasting in an Winery or Farm. Our drivers are all extremely familiar with Tuscany and with the main destinations. They will always share historical information, curiosities and traditions about the area of the sightseeing and they are available for any of your needs.

    What travelers are saying

    Outty’s summary of the themes that recur across 5 traveler reviews. Written by us, not quoted from reviewers.

    Food and drink

    4 mentions

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

    The guide

    3 mentions

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

    Knowledge and storytelling

    3 mentions

    Reviewers describe the commentary as informative rather than scripted.

    Good for families

    2 mentions

    Reviewers traveling with kids report it landed well with their group.

    Organization

    1 mention

    Pickup, timing, and logistics are described as running smoothly.

    Small groups

    1 mention

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

    Traveler reviews

    5 verified traveler reviews for Private Tour to Siena and Montalcino from Florence. Ratings and reviews provided by Viator and Tripadvisor.

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    Hector_L · January 2026

    Montalcino and Siena private tour

    Travel to Montalcino and Siena via a private driver. In my case Marco (driver) was amazing, his Italy history was unbelievable. Great driver and took us as close as you can to these locations, stop by a winery for wine tasting. Marco was very patient and great advice for restaurants at these locations. I would highly recommend this tour.

    Response from the operator: Marco is a great person befor to be a very good driver so I'm very happy to hear your review Thanks a lot

    via Viator

    DENISE_G · October 2024

    Siena

    Wonderful day exploring Siena & San G-our tour guide Luigi was very knowledgeable & made reservations at a lovely little vineyard for us for lunch

    via Viator

    Doris_G · August 2024

    Best experience in Tuscany!

    Mauro was amazing! He helped plan a wonderful trip to Siena and took great care of us during an impromptu rain storm. We highly recommend this tour!

    Response from the operator: thank you

    via Viator

    X7556HMjills · May 2023

    A day spent in Tuscany should be added to your itinerary!!!

    We were picked up at the door of our apartment right on time! Massimo was an excellent driver and tour guide. We visited Siena and Montalcino. We had plenty of time to see the sights and have a nice lunch in Siena. Massimo made sure to drop us off and pick us up in convenient locations. He also arranged a wine tasting for us at a family owned winery. It was a perfect way to see Tuscany!!

    via Tripadvisor

    Neliobb · September 2019

    Fantastic wine tour

    We took the wine tour in Podere Il Cocco and had lunch there. We were a party of 4 couples travelling through Italy, having amazing vacations. We all agreed that the day we spent in Podere Il Cocco was the best day of the trip!! Full of great wine and delicious food ! Giacomo and his family were adorable !!! Learning about wine and about their history was really inspiring. Thanks, Giacomo, we just loved it!!!

    via Tripadvisor

    Good to know

    Duration
    9 hours
    Free cancellation
    Up to 24h before
    Minimum age to book
    All ages
    Availability
    Bookable today
    Booked in 30 days
    2
    Verdict
    Worth a Look

    Why this scores 52

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

    Traveler sentiment (30% weight)82
    Review evidence (18% weight)24
    Booking momentum (14% weight)17
    Value for money (12% weight)0
    Listing quality (10% weight)85
    Local standing (8% weight)58
    Booking flexibility (8% weight)100

    Private Tour to Siena and Montalcino from Florence: questions travelers ask

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

    How much does Private Tour to Siena and Montalcino from Florence cost?

    +

    Prices start at $850 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 Tour to Siena and Montalcino from Florence take?

    +

    Plan for about 9 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 Tour to Siena and Montalcino from Florence worth it?

    +

    It holds an Outty Ranking of 52 out of 100, which we label "Worth a Look". That score blends traveler sentiment (5/5 across 5 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 Tour to Siena and Montalcino from Florence?

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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 to Siena and Montalcino from Florence suitable for kids and families?

    +

    Yes, all ages are welcome. Families should still weigh the 9-hour running time, and strollers are easier on the earlier, quieter departures.

    How far in advance should I book Private Tour to Siena and Montalcino from Florence?

    +

    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 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 9-hour experience runs outdoors or after sunset.

    Where does Private Tour to Siena and Montalcino from Florence 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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