Siena & San Gimignano: Exclusive Tuscany Day Trip from Florence in Florence
Florence, Italy

Siena & San Gimignano: Exclusive Tuscany Day Trip from Florence

Outty Ranking 74 5.0 · 33 traveler reviews8 hoursFrom $149

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September 2026

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Outty Ranking

74/100

Strongly Recommended. Our proprietary evaluation. How we score

Traveler rating

5.0/5

Based on 33 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.

Quick answer

Is Siena & San Gimignano: Exclusive Tuscany Day Trip from Florence worth booking?

Siena & San Gimignano: Exclusive Tuscany Day Trip from Florence is a 8-hour experience in Florence, Italy, from $149 per person. It scores 74 out of 100 on the Outty Ranking, which we label “Strongly Recommended, based on a 5/5 rating across 33 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.

Outty Ranking
74 / 100
Rating
5/5 (33)
Duration
8 hours
From
$149 per person

Have you been dreaming of Tuscany? Then this tour is for you. Wake up in Florence, where your private driver will meet you at your hotel and whisk you to the lush green hills of Tuscany. Your first stop will be San Gimig

What you get

    About this experience

    Have you been dreaming of Tuscany? Then this tour is for you. Wake up in Florence, where your private driver will meet you at your hotel and whisk you to the lush green hills of Tuscany. Your first stop will be San Gimignano, a beautiful and picturesque medieval town known for its many towers and gorgeous views. Then, stop at a marvelous local winery nestled in the Tuscan countryside. Enjoy a light lunch with a selection of locally produced wines, followed by a tour of the vineyard. With your taste buds still in heaven from the delicious wine and food you enjoyed, hop back on your private luxury drive to Siena. Here, your private driver will share a few stories and anecdotes and give you time to explore on your own. If you are looking for a bit more in depth knowledge about Siena and San Gimignano, upgrade your tour by choosing the option with Private Tour Guide, who will accompany you throughout the entire day. The day will end with a relaxing drive back to your hotel in Florence.

    What's included

    Included

    • Enjoy an exclusive and luxurious car ride through the Tuscan Hills
    • Option to add-on a Full-Day Private Guide on board (choose the option with private guide)
    • Non-alcoholic beverages available during the lunch
    • Visit San Gimignano & Siena, both UNESCO world heritage sites
    • Delight in Lunch and Wine Tasting in the Tuscan hills, near San Gimignano
    • Round trip All-day Private Chaffeur from and back to your hotel in Florence

    Not included

    • Gratuities

    What you'll see and do

    1. San Gimignano

      Wake up in Florence and get ready for your day of exploration to begin. Your first stop will be San Gimignano, so sit back and enjoy a 90 minute private drive in a comfortable luxury vehicle. Your driver will add to the scenery by sharing stories, gossip and anecdotes about the estates and villas you pass along the way. The marvelous Medieval hill town of San Gimignano, located in the province of Siena, is currently on the list of UNESCO world heritage sites. San Gimignano or “Town of Towers” is famous for its unique and outstanding architecture. As you enter the fortified walls of the city you will learn about the famous towers and delight in the history of this picturesque town. Once there, you will be dropped off so to allow you free time to walk around the village and explore on your own. Your visit will be enhanced by the fun facts and stories your driver will share before dropping you off.

      150 minutes here

    2. Siena

      Your driver will take you across the valley to a typical Tuscan winery. Originally an ancient convent, this stunning property has been transformed into an outstanding winery and farm, where you will enjoy a nice glass of wine and some traditional food. You will then get a personal tour of the winery. Your Tuscany Day Trip continues to Siena, another highlight of Tuscany. In Siena, your private driver will guide you from site to site while sharing the elaborate history and intriguing stories of the city, and giving you free time to explore each site on the tour. Siena too is a Unesco heritage site. Every building and every corner of this quaint yet bustling town tells stories of bygone eras. And of course, you will also stop at the world-famous Piazza del Campo. Hear fantastical stories of the history of Piazza del Campo and then hop off to take delight in this shell shaped square, imagining the crowds that gather to watch Il Palio, the famous horse race that take place twice a year.

      210 minutes here

    Where it starts and ends

    Hotel pickup

    Pickup is included for all travelers. Pickup begins about 15 minutes before departure.

    Options you can book

    • Option Without Guide

      Private Chaffeur without guide: This option includes the private chaffeur but it does NOT include a Full Day Private Tour Guide. Pickup included

    • Option with Private Guide

      Full Day Private Guide: This option includes a Private Tour Guide on board who will be with you the entire day. Pickup included

    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 15 travelers per booking
    Operated by
    LivTours

    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

    Siena & San Gimignano: Exclusive Tuscany Day Trip from Florence in Florence, photo 2Siena & San Gimignano: Exclusive Tuscany Day Trip from Florence in Florence, photo 3Siena & San Gimignano: Exclusive Tuscany Day Trip from Florence in Florence, photo 4Siena & San Gimignano: Exclusive Tuscany Day Trip from Florence in Florence, photo 5Siena & San Gimignano: Exclusive Tuscany Day Trip from Florence in Florence, photo 6Siena & San Gimignano: Exclusive Tuscany Day Trip from Florence in Florence, photo 7

    What travelers are saying

    Outty’s summary of the themes that recur across 33 traveler reviews. Written by us, not quoted from reviewers.

    The guide

    6 mentions

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

    Knowledge and storytelling

    5 mentions

    Reviewers describe the commentary as informative rather than scripted.

    Food and drink

    3 mentions

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

    Good for families

    2 mentions

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

    Traveler reviews

    33 verified traveler reviews for Siena & San Gimignano: Exclusive Tuscany Day Trip from Florence. Ratings and reviews provided by Viator and Tripadvisor.

    5 star
    33
    4 star
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    3 star
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    ankonag · August 2026

    Off to the Races in Siena

    Emanuela was excellent. She was kind and knowledgeable. We really enjoyed our laid back day seeing Siena, Tuscan countryside (with winery), and San Gimignano. The weekend we went was the horse race event and it was even more special to see the set-up and festivities for that tradition!

    via Tripadvisor

    133marcyh · June 2026

    Tuscany

    Driver spoke excellent English. He gave great advice on where to go in each stop. Very accommodating.

    via Tripadvisor

    Resort677955 · April 2026

    Favorite Day of Our Entire Italy Trip

    This was our favorite day of our entire Italy trip. The Siena and San Gimignano tour was outstanding, and Gabrielle made it even better. He is such a kind and genuine person, and you can tell he truly cares about the experience his guests have. One thing that really stood out was how easy he was to understand. His English pronunciation was excellent, which made a big difference in being able to fully enjoy and follow everything throughout the day. The day itself was perfectly structured. We started with exploring and shopping in Siena, then moved into a private wine tasting with a great lunch, and finished in San Gimignano with more time to walk around and enjoy the town. It never felt rushed and flowed really well from start to finish. If you are considering a day trip from Florence, this is a must. It was a true highlight of our trip.

    via Tripadvisor

    K8157UTryanp · March 2026

    Beautiful day

    Great guide and tour! Lovely day!

    via Tripadvisor

    Sherry H · March 2026

    Tour in Tuscany

    Where to even begin? We spent the entire day driving from Florence to the Tuscany area with stops in Siena and San Gimignano. Mattio was our fabulous driver and Rafaella was our fearless leader. The weather was cool but beautiful. Not enough words to describe the Tuscan region but I can chat about our tour. Rafaella’s knowledge of landmark’s, history of the region and descriptions of building is second to none. She has an outsized personality and is always smiling and happy. She manages an excellent team in Florence. Her local knowledge and ability to explain the customs of the region was phenomenal. She made us feel like part of her family.

    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
    Price range
    $149 to $797
    Hotel pickup
    Included for all travelers
    Booked in 30 days
    12
    Verdict
    Strongly Recommended

    Why this scores 74

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

    Traveler sentiment (30% weight)92
    Review evidence (18% weight)47
    Booking momentum (14% weight)40
    Value for money (12% weight)86
    Listing quality (10% weight)85
    Local standing (8% weight)74
    Booking flexibility (8% weight)100

    Siena & San Gimignano: Exclusive Tuscany Day Trip from Florence: questions travelers ask

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

    How much does Siena & San Gimignano: Exclusive Tuscany Day Trip from Florence cost?

    +

    Prices start at $149 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 Siena & San Gimignano: Exclusive Tuscany Day Trip from Florence take?

    +

    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 Siena & San Gimignano: Exclusive Tuscany Day Trip from Florence worth it?

    +

    It holds an Outty Ranking of 74 out of 100, which we label "Strongly Recommended". That score blends traveler sentiment (5/5 across 33 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 Siena & San Gimignano: Exclusive Tuscany Day Trip from Florence?

    +

    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 Siena & San Gimignano: Exclusive Tuscany Day Trip from Florence 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 Siena & San Gimignano: Exclusive Tuscany Day Trip from Florence?

    +

    Around 12 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 Siena & San Gimignano: Exclusive Tuscany Day Trip 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?

    +

    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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