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Private Siena San Gimignano Tour from Florence with Winery Lunch

24 Reviews 4.92 out of 5 stars Based on 24 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.
|
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 $561.72 per person

Lowest Price Guarantee
Private Tuscany Tour
Private Tuscany Tour
Private Tuscany Tour
Private Tuscany Tour
Private Tuscany Tour
Don't miss out!
On average, this is booked 21 (0) days in advance.
10 hours (approx.)
Hotel pickup offered
Mobile ticket
Offered in: English
Instant confirmation

Overview

After leaving Florence you will travel toward San Gimignano and enjoy the views of vineyards and rolling hills as you listen to the fascinating history of this town.

On arrival your guide will walk you to the main gate and you have free time to roam the picturesque streets and squares. Maybe browse the local shops, try an award winning gelato or walk among the town’s famous medieval towers.

Next we stop at an organic, family-run wine estate. You will enjoy a traditional local lunch with plenty of wine, and soak in the idyllic location overlooking stunning views of the surrounding countryside.

After lunch, view Siena through the eyes of a local as you join a guided walking tour through the medieval city. Learn about the world’s oldest bank, see the Piazza del Campo - the site of the 600-year-old Palio horse race - and admire the interior of the Duomo, a treasure chest of artworks. Afterwards, enjoy Siena at your own pace with free time for shopping or relaxing in an open-air cafe.

What's Included

  • Winery tour and wine tasting of four varieties only for 18+ age old
  • Hearty farmhouse lunch – veggie and gluten-free options available
  • Air-conditioned vehicle
  • Gratuities
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Meeting and Pickup

Pickup point

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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Florence

After meeting your expert guide, an air-conditioned minivan will whisk you away to the first stop of the day, Siena. The drive to Siena will take about 1 hour and 15 minutes.. During the journey, your guide will explain the itinerary for the day and entertain you with interesting facts about Siena and Tuscany!!!
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15 minutes Admission Ticket Free

Siena

After lunch, a 45-minute drive will take you to Siena, 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

Oca

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'. You will visit a church and museum of one contrada. Each contrada has its own symbol, normally that of an animal including a snail, rhino and giraffe amongst others. 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!
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15 minutes Admission Ticket Included

Fattoria Poggio Alloro

After the morning exploration of Siena, a 15-minute drive will take you the the next stop: Fattoria Poggio Alloro, an organic family-run wine estate – the highlight of the day! Visit the farm, 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 meet fellow travelers while feasting on 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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2 hours Admission Ticket Included

San Gimignano

San Gimignano is a small, walled Tuscan hill town 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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2 hours 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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30 minutes Admission Ticket Free

Florence

After the visit of San Gimignano, a 1-hour drive will take you back to Florence. You will dropped off at the start point with a camera full of pictures, a stomach full of hearty Tuscan food and a host of new friends.
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15 minutes Admission Ticket Free

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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 (7)

Q: What is the cancellation policy for the Private Siena San Gimignano Tour from Florence with Winery Lunch?

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). 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?

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Activity code: C-5070P14

Traveler Photos

Reviews

4.92
24 reviews

Average 4.92 out of 5 stars based on 24 traveler reviews collected by City Sky Diving and partner sites such as Cool Destinations and TripAdvisor

5 stars
22
4 stars
2
3 stars
0
2 stars
0
1 star
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Don't miss out!
On average, this is booked 21 (0) days in advance.
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Frequently Asked Questions (7)

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 Siena San Gimignano Tour from Florence with Winery Lunch?
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).
Apr 2025
Q: What's included in the price?
A:
The following is included:
  • Winery tour and wine tasting of four varieties only for 18+ age old.
  • Hearty farmhouse lunch – veggie and gluten-free options available.
  • Air-conditioned vehicle.
  • Visit the church and the museum of one of the contrade in Siena.
  • 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.
The following is NOT included:
  • Gratuities.
Apr 2025
Q: What is the minimum age for this tour?
A:

The minimum age to participate is 8..

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 Siena San Gimignano Tour from Florence with Winery Lunch is as follows:

  • Public transportation options are available nearby
  • Not recommended for travelers with spinal injuries
  • Not recommended for pregnant travelers
  • 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 Siena San Gimignano Tour from Florence with Winery Lunch 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

  • Winery tour and wine tasting of four varieties only for 18+ age old
  • Hearty farmhouse lunch – veggie and gluten-free options available
  • Air-conditioned vehicle
  • Visit the church and the museum of one of the contrade in Siena
  • 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
  • Gratuities

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 pregnant travelers
  • 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
  • Disclaimer: Only 18 years old and above are allowed for wine tasting

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Activity name