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Private Tuscany Tour: Siena, San Gimignano and Pisa from Florence

19 Reviews 5.00 out of 5 stars Based on 19 reviews collected by City Sky Diving and TripAdvisor |
Recommended by 100% of reviewers
100% of reviewers gave this experience a rating of 4 or higher.
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Badge of Excellence |Badge of Excellence This experience is highly rated by travelers and has met our top quality standards. Florence, Italy
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from $653.85 per person

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Private Tuscany Tour in One Day to Pisa, Siena and San Gimignano with Winery Lunch from Florence
Private Tuscany Tour in One Day to Pisa, Siena and San Gimignano with Winery Lunch from Florence
Private Tuscany Tour in One Day to Pisa, Siena and San Gimignano with Winery Lunch from Florence
Private Tuscany Tour in One Day to Pisa, Siena and San Gimignano with Winery Lunch from Florence
Private Tuscany Tour in One Day to Pisa, Siena and San Gimignano with Winery Lunch from Florence
Don't miss out!
On average, this is booked 24 (0) days in advance.
11 hours (approx.)
Hotel pickup offered
Mobile ticket
Offered in: English
Instant confirmation

Overview

With this personalized tour of Tuscany, you and your friends may see all the area's hidden treasures in a single day. An experience made even better with an extravagant lunch and wine sampling in Tuscany.

We're going to leave in a cozy, air-conditioned minivan in the morning for a fast-paced tour.

In Siena, as you stroll through the alleyways adorned with Renaissance and medieval architecture, your guide will give you an insider's view of the first bank in history, the exquisitely designed Duomo, and the famous Piazza del Campo.

We'll take you to a family-run Chianti estate's vineyards for a laid-back wine-tasting experience and a superlative regional culinary experience while taking in the breathtaking scenery.

Then we'll drive you to San Gimignano, one of the area's greatest treasures and one of our favorite stops on this ​private tour​.

The final stop will be Pisa, where you will have the chance to discover the Baptistery, the Cathedral, and the world-famous Leaning Tower!

What's Included

  • Scenic drive to historic Pisa to explore its hidden corners and iconic tower
  • Winery tour and wine tasting of four varieties
  • Hearty farmhouse lunch – veggie and gluten-free options available
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    Meeting and Pickup

    Pickup point
    Pickup details

    Pick up at your accommodation

    What To Expect

    Book Online

    Our secure website provides real-time availability, instant confirmation, and free, no-hassle cancellations up to 24 hours before your tour begins.
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    Siena

    Siena is a real medieval gem and in fact one of Tuscany's most famous and beautiful hill top towns. When you arrive you will join a 1 hour guided walking tour with a local city guide through Siena's most beautiful streets and sites, including the entrance to the Cathedral, a treasure chest of artworks. Afterwards, enjoy Siena at your own pace with free time for shopping or relaxing in an open-air cafe.
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    3 hours Admission Ticket Free

    Piazza Salimbeni

    The first stop on the walking tour of Siena is a bank that has its headquarters in this square - the oldest surviving bank in the world. It's called Monte dei Paschi di Siena and it has been running continuously since 1472. Your guide will explain how Siena's wealth through the centuries came from being on the pilgrim route known as the Via Francigena, a route that led pilgrims between Rome and Northern Europe. Siena prospered as a banking town by lending money and exchanging money for the merchants who were using the pilgrim route as a safe travel route. The Sienese are still wealthy from their banking past and are still famous for their banks today!
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    15 minutes Admission Ticket Free

    Contrada della Torre

    Your local guide will then walk through some of the most picturesque back streets of Siena, while telling about something very unique to Siena are the 17 districts which make up the historical centre.The name for these ancient divisions is 'contrade'. Each contrada has its own symbol, normally that of an animal including a snail, rhino and giraffe amongst others. You will visit the church and museum of one of the contrade. The sense of identity and belonging to ones 'contrada' is extremely important. They are self-contained little worlds with their own church, where newborns are baptised, and a public fountain where the newborns are baptised a second time! Needless to say there are strong rivalries between these districts, that explodes during the Palio horserace held twice a year in Piazza del Campo.
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    15 minutes Admission Ticket Free

    Piazza del Campo

    Piazza del Campo is one of the most beautiful squares you will ever see and it is also the city's gathering place, where the locals meet for a coffee and to chat and of course gossip. The unusual square (actually not a square, it's in the shape of a sea-shell, and sloping!) is the site of the famous Palio horse-race. A 600 year old tradition of Siena. The piazza gets transformed into a racing track twice a year and the contrade, or neighbourhoods of the city battle out for the highest honour possible – winning the palio. You'll hear more about this on the tour, your local guide will set the scene so that you can somehow live for a moment the vibrant atmosphere of this incredible race.
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    15 minutes Admission Ticket Free

    Duomo di Siena

    Our walking tour then ends inside the Duomo of Siena – undoubtedly the jewel of the city. If you've seen the interior of Florence's Duomo, it is nowhere near as spectacular as Siena's. The most unique part of this city's cathedral is its floor. It's an artwork on its own, made out of the world's most precious marbles – in fact, it's a combined masterpiece of over 50 images created over 2 centuries by some of Italy's most important artists. Then, enjoy walking through the city center on your own before meeting your guide again to head to your next stop!
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    15 minutes Admission Ticket Included

    Fattoria Poggio Alloro

    After the morning exploration of Siena, a 45-minute drive will take you the the next stop: Fattoria Poggio Alloro, an organic family-run wine estate – the highlight of the day! Enjoy an informal wine tasting lesson and a traditional Tuscan lunch with plenty of wine, in the most gorgeous location overlooking stunning views of the surrounding countryside. Take the opportunity to try fresh organic farm food of homemade pasta, cured meats (homemade prosciutto and salami), local cheeses, a real garden salad, and Tuscan biscotti. There is also the opportunity to buy the local products of the winery before heading to San Gimignano.
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    1 hour 30 minutes Admission Ticket Free

    San Gimignano

    After lunch, a 15-minute drive will take you to San Gimignano, that is an even smaller, walled Tuscan hill town than Siena - about 6 times smaller - and a UNESCO World Heritage Site. San Gimignano is most famous for its towers of which there were 72 though there are just 14 remaining today. From this the city gets its nickname of the little Manhattan of Tuscany. Your guide will give you a map and point out the best landmarks, so that you can roam independently the picturesque streets and squares of this enchanting hilltop town.
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    1 hour 30 minutes Admission Ticket Free

    Piazza Della Cisterna

    Your guide will lead you to the entrance city gate and that is where the main boulevard starts from, Via San Giovanni. This street will take you to Piazza della Cisterna, the heart of San Gimignano and also the setting for several films. This was the square where festivals and tournaments took place while the Piazza Duomo was the religious and political centre. This is also where the best gelato in the world is – Gelateria della Piazza 'Dondoli'. It's won many awards as the best gelato, you could try it and see what you'll think!
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    20 minutes Admission Ticket Free

    Piazza del Duomo

    From Piazza della Cisterna, the next piazza along is Piazza del Duomo – the Duomo, also known as the Collegiata, is small but is well worth visiting! The beautiful interior of the cathedral walls is filled with colorful 14th century frescoes in every space available. You could also climb up one of the medieval towers here in this piazza, next to the Duomo (the Torre Grossa) to appreciate the incredible 'BIRD'S EYE' view over San Gimignano.
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    20 minutes Admission Ticket Free

    Rocca of Montestaffoli

    Another stunning view over the towers of San Gimignano is from La Rocca. It is easily accessible behind the Duomo and It is a peaceful setting with olive trees and the wall surrounding the garden that formed part of the 14th-century fortress Medici of Florence built to protect this town from Siena. if you walk to the back of the garden and climb the steps to the top, the views over San Gimignano's skyline are absolutely breathtaking.
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    20 minutes Admission Ticket Free

    Pisa

    After the visit of San Gimignano, a 1 hour and an half scenic drive through iconic Tuscan countryside will take you to your final stop, Pisa.
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    1 hour Admission Ticket Free

    Piazza dei Miracoli

    Upon arrival, your guide will lead you straight to the famous Square of Miracles. At first sight, it is truly breathtaking - the white marble buildings glow in contrast to the perfect, green lawns. You will have about an hour to explore the Cathedral, Baptistry, Monumental Cemetery, and of course - The Leaning Tower!
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    15 minutes Admission Ticket Free

    Leaning Tower of Pisa

    During your time in Pisa, you can climb the Leaning Tower to admire the incredible views of the Square of Miracles from above. The views from the top of the Tower are truly breathtaking - from the monuments below, to the city surrounding the square, the Arno River, and the countryside in the distance... and part of the fun is also climbing the stairs inside the Leaning Tower that we will make you feel a bit dizzy at the end!
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    30 minutes Admission Ticket Included

    Florence

    After leaving Pisa, it will take about an hour to return to Florence. You will dropped off at the start point with a camera full of pictures and a stomach full of hearty Tuscan food.
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    1 hour Admission Ticket Free

    Show 13 more stops

    Additional Info

    • Confirmation is instant and will be received at time of booking
    • Public transportation options are available nearby
    • Not recommended for travelers with spinal injuries
    • Travelers should have at least a moderate level of physical fitness
    • Infants and small children can ride in a pram or stroller
    • Infants are required to sit on an adult’s lap

    Frequently Asked Questions (8)

    Q: What is the cancellation policy for the Private Tuscany Tour: Siena, San Gimignano and Pisa from Florence?

    A: You can cancel up to 24 hours in advance of the tour for a full refund. For a full refund, you must cancel at least 24 hours before the tour start time.If you cancel less than 24 hours before the tour start time, the amount you paid will not be refunded.Any changes made less than 24 hours before the tour start time will not be accepted.Cut-off times are based on the tour local time (CET).This tour requires a minimum number of travelers. If it’s canceled because the minimum isn’t met, you’ll be offered a different date/experience or a full refund. Read more Apr 2025

    Cancellation Policy

    You can cancel up to 24 hours in advance of the tour for a full refund.

    Still have questions?

    We're here to help.
    Activity code: C-5070P17

    Traveler Photos

    Reviews

    5.00
    19 reviews

    Average 5.00 out of 5 stars based on 19 traveler reviews collected by City Sky Diving and partner sites such as Cool Destinations and TripAdvisor

    5 stars
    19
    4 stars
    0
    3 stars
    0
    2 stars
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    1 star
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    Don't miss out!
    On average, this is booked 24 (0) days in advance.
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    Things To Do in Florence

    Frequently Asked Questions (8)

    Activity name

    The answers provided below were previously given in response to questions from City Sky Diving customers.

    Filter by:

    Q: What is the cancellation policy for the Private Tuscany Tour: Siena, San Gimignano and Pisa from Florence?
    A:
    You can cancel up to 24 hours in advance of the tour for a full refund.
    • For a full refund, you must cancel at least 24 hours before the tour start time.
    • If you cancel less than 24 hours before the tour start time, the amount you paid will not be refunded.
    • Any changes made less than 24 hours before the tour start time will not be accepted.
    • Cut-off times are based on the tour local time (CET).
    • This tour requires a minimum number of travelers. If it’s canceled because the minimum isn’t met, you’ll be offered a different date/experience or a full refund.
    Apr 2025
    Q: What's included in the price?
    A:
    The following is included:
    • Scenic drive to historic Pisa to explore its hidden corners and iconic tower.
    • Winery tour and wine tasting of four varieties.
    • Hearty farmhouse lunch – veggie and gluten-free options available.
    • Visit the church and the museum of one of the contrade in Siena.
    • Travel by air-conditioned luxury van.
    • Free time to explore San Gimignano at your own pace.
    • Guided walking tour of Siena with entrance fee to the cathedral.
    • Professional English speaking tour guide with you for the whole day.
    Apr 2025
    Q: What is the weather cancellation policy?
    A:

    This tour requires good weather. If it’s canceled due to poor weather, you’ll be offered a different date or a full refund.

    Apr 2025
    Q: What is the minimum age for this tour?
    A:

    The minimum age to participate is 8. This tour requires at least one adult to accompany children..

    Apr 2025
    Q: My date is not available in the calendar, I am just checking to see if it is available?
    A:

    If a date or time is not listed on the calendar, it’s sold out or unavailable for another reason. Support cannot assist further if a date or time is not on the calendar.

    If you find a date and time that works for you, book it NOW because things always sell out at this time of year.

    Apr 2025
    Q: Is this an accessible tour?
    A:

    Accessibility information for the Private Tuscany Tour: Siena, San Gimignano and Pisa from Florence is as follows:

    • Public transportation options are available nearby
    • Not recommended for travelers with spinal injuries
    • Not recommended for travelers with poor cardiovascular health
    • Travelers should have at least a moderate level of physical fitness
    Apr 2025
    Q: Where is the meeting point for this activity?
    A:

    Detailed check-in instructions – including meeting point address, Google map, and parking information – for Private Tuscany Tour: Siena, San Gimignano and Pisa from Florence will be included in your confirmation email from City Sky Diving. Please be sure to double and triple check your email address is correct at checkout so this important email makes its way to you!

     

     

    Mar 2024
    Q: How long does a refund take to reach my card, and can I get it faster?
    A:

    Once your refund is processed, it usually shows on your card statement within 5–10 business days. The exact timing depends on your bank or card issuer.

    Want it sooner? When you cancel, choose Receive a refund to my wallet instead. The credit is in your Wallet straight away and is applied automatically at checkout on your next booking when you’re signed in with the same email. You can see your balance any time in My Wallet.

    If you paid part of your booking with Wallet credit, that part always goes back to your Wallet. Trip protection isn’t refundable.

    Oct 2026

    What's Included

    Activity name

    • Scenic drive to historic Pisa to explore its hidden corners and iconic tower
    • Winery tour and wine tasting of four varieties
    • Hearty farmhouse lunch – veggie and gluten-free options available
    • Visit the church and the museum of one of the contrade in Siena
    • Travel by air-conditioned luxury van
    • Free time to explore San Gimignano at your own pace
    • Guided walking tour of Siena with entrance fee to the cathedral
    • Professional English speaking tour guide with you for the whole day

    Additional Info

    Activity name

    • Confirmation is instant and will be received at time of booking
    • Public transportation options are available nearby
    • Not recommended for travelers with spinal injuries
    • Not recommended for travelers with poor cardiovascular health
    • Travelers should have at least a moderate level of physical fitness
    • Infants and small children can ride in a pram or stroller
    • Infants are required to sit on an adult’s lap

    Report Product Issue

    Activity name