Cool Destinations
Top Siena activities
Top Siena landmarks
Beyond Siena
Siena trip ideas
  • Tours by category
  • Tours by accessibility
  • Tours by feature
  • Top Siena landmark tours
  • Tours in nearby places
  • Explore Tuscany tours
  • Siena travel guides
  • Siena travel calendar
Rewards
Rewards
Wishlist
Login / Sign up
Bookings
Bookings
Cool Rewards My Rewards
$0.00
Cool Rewards My Rewards
$0.00
Wishlists
Wishlists
Profile
Help Center
Language
Log out
Start your search
Change your search
Place or activity
Select Dates

Small-Group Chianti and San Gimignano Sunset Trip from Siena

63 Reviews 4.83 out of 5 stars Based on 63 traveler reviews collected by Cool Destinations and TripAdvisor |
Recommended by 97% of reviewers
97% 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. Siena, Italy
Book online or call us
Chat now

from $230.46 per person

Lowest Price Guarantee
Chianti and San Gimignano Sunset Tour
San Gimignano at dusk
Sunset panorama
Tuscan countryside
Sunset near San Gimignano

Loading Options
Don't miss out!
On average, this is booked 18 (0) days in advance.
Add to Wishlist
8 to 9 hours (approx.)
Mobile ticket
Offered in: English

Overview

On this afternoon and evening tour from Siena to Chianti and San Gimignano, explore the beautiful Chianti region – an area rich with dense oak forests and cypress trees – and discover its famous wine by visiting a local producer, touring their cellars and tasting their wines. Then head to the UNESCO World Heritage town of San Gimignano, famous for its medieval towers. Enjoy the main sights and browse the streets and boutique stores just as the day's crowds begin to dwindle. Visit a local farm and enjoy a farm-to-table dinner of its products and wines during sunset, in a stunning location overlooking the San Gimignano towers and the rolling, vine-covered hills.

What's Included

  • Traditional dinner at farm
  • Transport by air-conditioned minivan
  • Tour of winery with wine tasting
  • Gratuities
  • Hotel pickup and drop-off
  • Entrance fees to attractions in San Gimignano
See 1 moreSee 3 more

Meeting Location

Meeting point

Piazza San Domenico
53100 Siena SI, Italy

Show on Google Maps

Detailed check-in instructions, including the exact address, are provided with your booking confirmation.

End point

This activity ends back at the meeting point.

What To Expect

Book Online

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

Safe & secure • Easy breezy • Hassle-free

Basilica Cateriniana Di S. Domenico (pass by)

Meet your tour guide at 2.30pm in front of the church of San Domenico in Siena and begin the tour with a comfortable drive through the Chianti countryside. Visit a Chianti wine estate, where you'll tour the grounds and wine cellars while learning about the wine-making process. Sit down and savor a tasting of Black Rooster Chianti Classico wine.
Read more

Cantinetta di Monteriggioni

After visiting a Chianti winery, visit a historic town that was once of fortress, Monteriggioni, to marvel at the medieval towers that are still intact. Monteriggioni is a perfectly preserved medieval town with a complete ring of walls and turrets, once Siena’s main bastion of defense against the armies of Florence. Today it is a quiet hamlet and you can enjoy leisure time exploring the charming streets and stores of local crafts.
Read more

30 minutes • Admission Ticket Free

Historic Centre of San Gimignano

In the late afternoon, arrive in San Gimignano as the crowds begin to dwindle and the many streets and squares of this medieval town of towers that flourished thanks to the via Francigena, an important trade route. Enjoy free time to enter its impressive church, the Collegiata di San Gimignano, or to explore the Civic Museum (entrance fees at own expense). Alternatively, shop the artisan boutiques for leather goods and hand-painted pottery; sample the fruits of the soil in the food shops and wine bars or discover the town’s many hidden beauties.
Read more

1 hour • Admission Ticket Free

Strada Statale 222 Chiantigiana

After your time in San Gimignano, head out of town to a nearby rustic farmhouse, where you'll be treated to a classic Tuscan dinner accompanied by wine. Enjoy the farm's products and wine over a convivial dinner with the others on tour that you can now call new friends.
Read more

2 hours • Admission Ticket Included

Show 3 more stops

Additional Info

  • Public transportation options are available nearby
  • Not recommended for travelers with poor cardiovascular health
  • Suitable for all physical fitness levels
  • Specialized infant seats are available
  • Customers who have not reached Italy's legal drinking age of 18 will not be served alcohol
  • This tour/activity will have a maximum of 8 travelers

Frequently Asked Questions

(6)

Q: What is the cancellation policy for the Small-Group Chianti and San Gimignano Sunset Trip from Siena?

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 (CEST). 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-5493CHIANTISUNSET

Traveler Photos

See more
See more

Reviews

4.83
63 reviews

Average 4.83 out of 5 stars based on 63 traveler reviews collected by Cool Destinations and partner sites such as Trustpilot, Viator, and TripAdvisor

5 stars
56
4 stars
5
3 stars
0
2 stars
2
1 star
0

Loading Options
Don't miss out!
On average, this is booked 18 (0) days in advance.
Siena Tours
Attractions
Guides
Calendar
View more

Similar Tours & Activities

Private Tour: Montalcino Wine Tasting Experience

Private Tour: Montalcino Wine Tasting Experience

8 hours • Hotel pickup offered • Free Cancellation
8 hours • Hotel pickup offered • Free Cancellation
5.0 (66)
from
$415.57
Ape Calessino Tour through Tuscan Landscapes
Likely to Sell Out
Likely to Sell Out

Ape Calessino Tour through Tuscan Landscapes

4 hours • Free Cancellation
4 hours • Free Cancellation
5.0 (1)
from
$133.81
Private Off Road Wine Tour in Chianti from Siena
Likely to Sell Out
Likely to Sell Out

Private Off Road Wine Tour in Chianti from Siena

6 hours • Hotel pickup offered • Free Cancellation
6 hours • Hotel pickup offered • Free Cancellation
5.0 (1)
from
$474.67
Let's discover Siena!

Let's discover Siena!

90 to 120 minutes • Free Cancellation
90 to 120 minutes • Free Cancellation
5.0 (4)
from
$357.61

Travelers Who Bought This Tour Also Bought

Skip the Line: Siena Duomo and City Walking Tour

Skip the Line: Siena Duomo and City Walking Tour

2 hours • Free Cancellation
2 hours • Free Cancellation
4.8 (711)
from
$48.48
Small-Group Brunello di Montalcino Wine-Tasting Trip from Siena

Small-Group Brunello di Montalcino Wine-Tasting Trip from Siena

9 hours • Free Cancellation
9 hours • Free Cancellation
4.9 (979)
from
$230.34
Siena Medieval Power Quest: Self-Guided Family Feud Game

Siena Medieval Power Quest: Self-Guided Family Feud Game

60 to 90 minutes • Free Cancellation
60 to 90 minutes • Free Cancellation
4.2 (25)
from
$9.68
Tuscan Cooking Class in Siena with Handmade Pasta, Wine & Dinner
Likely to Sell Out
Likely to Sell Out

Tuscan Cooking Class in Siena with Handmade Pasta, Wine & Dinner

4 hours • Free Cancellation
4 hours • Free Cancellation
4.9 (335)
from
$158.26

Frequently Asked Questions (6)

Activity name

The answers provided below were previously given in response to questions from Cool Destinations customers.

Filter by:

Q: What is the cancellation policy for the Small-Group Chianti and San Gimignano Sunset Trip from Siena?
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 (CEST).
Apr 2025
Q: What's included in the price?
A:
The following is included:
  • Traditional dinner at farm.
  • Transport by air-conditioned minivan.
  • Tour of winery with wine tasting.
  • Professional Guide.
The following is NOT included:
  • Gratuities.
  • Hotel pickup and drop-off.
  • Entrance fees to attractions in San Gimignano.
Apr 2025
Q: What is the minimum age for this tour?
A:

There is no minimum age for this tour, so bring your wee one along for an adventure..

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 Small-Group Chianti and San Gimignano Sunset Trip from Siena is as follows:

  • Public transportation options are available nearby
  • Not recommended for travelers with poor cardiovascular health
  • Suitable for all physical fitness levels
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 Small-Group Chianti and San Gimignano Sunset Trip from Siena will be included in your confirmation email from Cool Destinations. 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

What's Included

Activity name

  • Traditional dinner at farm
  • Transport by air-conditioned minivan
  • Tour of winery with wine tasting
  • Professional Guide
  • Gratuities
  • Hotel pickup and drop-off
  • Entrance fees to attractions in San Gimignano

Additional Info

Activity name

  • Public transportation options are available nearby
  • Not recommended for travelers with poor cardiovascular health
  • Suitable for all physical fitness levels
  • Infants and small children can ride in a pram or stroller
  • Specialized infant seats are available
  • Customers who have not reached Italy's legal drinking age of 18 will not be served alcohol
  • This tour/activity will have a maximum of 8 travelers
  • Operated by a business

Protecting you

Activity name

For your protection and stress-free bookings, use our secure platform to pay for bookings. Tuscan Escapes by Papilio SRL

Report Product Issue

Activity name

Language
Currency

Site Settings

Activity name

Currency

Activity name

Lowest Price Guarantee

Activity name

We guarantee the lowest price on all the tours available to book on our site. We'll refund the difference if you find the exact tour cheaper online until 48 hours before your tour starts.

We Make It Easy!

Gather your information

Locate your Cool Destinations Booking Number and the proof of the lower price you found.

Send it to us

Email priceguarantee@mybookings.zendesk.com with the documents, your name, and your home address.

We'll review

We'll review your materials and get in touch as soon as possible.

Receive your refund

If everything checks out, we'll refund you the price difference.

Refund Terms & Conditions

The following conditions apply to all lowest price guarantee refund requests:

  • The lowest price guarantee is available to any customer who makes a qualifying purchase through our website. The qualifying purchase must be a minimum of US$20 (or equivalent).
  • The lowest price guarantee covers retail and prepaid rates available to the general public. This does not include discounts or promotions you may receive (or be eligible for) from third-party sites or organizations such as AAA or AARP or special offers made as part of a membership program, corporate discount, daily deal, group, or rewards program.
  • Cool Destinations promotions cannot be combined with the lowest price guarantee.
  • If you find a lower retail or prepaid rate for the same tour, offered on the same date, time and priced in the same currency as your original purchase, on any other website between the time you book on Cool Destinations and 48 hours before your trip starts, we will refund the difference.
  • The lowest price guarantee does not apply where a lower overall price is found by breaking down the purchased tour into one or more parts sold separately.
  • Cool Destinations reserves the right to verify the lower price details. Examples of acceptable forms of verification include a web screenshot or a web address.
  • All refund decisions will be made at the sole discretion of Cool Destinations.
Activity name

Free Cancellation

100% refund
No refund

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 (CEST).

Sorting, ranking, and search results

Activity name

Cool Destinations wants to make your searches as relevant as possible. That's why we offer many ways to help you find the right experiences for you.

On some pages, you can select how to sort the results we display and also use filter options to see only those search results that meet your chosen preferences. You'll see explanations of what those sort options mean when you select them.

If you see a Badge of Excellence label, the award is based on average review ratings, share of bookings with a review, and number of bookings through Cool Destinations over a 12-month period.

The importance of any one factor over any other in a sort order varies, and the balance is constantly being reviewed and adjusted. We're always updating our systems and testing new ways to refine and improve your results to make them as relevant as possible to meet your needs.

Cool Support

Ask us anything!

Activity name

Cool Robot

Choose an option

Activity name

or

Cool Rewards Terms & Conditions

Activity name

Cool Rewards

  • Cool Rewards is a loyalty program operated by Cool Destinations. Rewards may be earned by any eligible person holding a Cool Destinations account, subject to the Cool Destinations customer Terms of Use.

Earning rewards

  • Rewards can be earned by making bookings on the Cool Destinations website. You will be able to see the value of the rewards you can earn during the booking process.
  • Earned rewards will be issued in a pending state and will move to a confirmed state 24 hours after the start time of the experience.
  • Earned rewards will be available to redeem once they are no longer in a pending state.
  • For bookings that are moved to a different travel date, the rewards will be redeemable after the amended travel date.
  • If a booking where rewards were issued is canceled, the earned rewards will not be redeemable and will be moved to a canceled state.

Redeeming rewards

  • To redeem rewards, you must be logged into your Cool Destinations account.
  • Any available rewards will be automatically applied the next time you make a booking, and their value will be deducted from your order at checkout, unless you choose not to apply them, which requires you to indicate this via the toggle switch. Bookings made using rewards are subject to the standard Cool Destinations Customer Terms of Use.
  • You will not be able to redeem only a portion of your available rewards at checkout. It is only possible to redeem all or none of your available rewards.
  • There is no minimum order value required to redeem your rewards. This means that you can pay for 100% of your order with rewards.
  • Rewards are non-transferable and cannot be redeemed for cash.
  • If rewards are redeemed against a booking that is canceled or refunded, the rewards will be reissued to your account.

Miscellaneous

  • You can check your Cool Destinations account to see the rewards you have collected at any time. You are responsible for ensuring that your rewards balance is correct.
  • We reserve the right to modify these Cool Rewards Terms and Conditions at any time, with or without notice, including the rules for earning and redeeming rewards. Any changes will be reflected in the updated Terms and Conditions.
  • We reserve the right to terminate the Cool Rewards program and cease issuing any further rewards on future bookings. All pending and available rewards balances will be honored.
  • By earning and redeeming rewards, you agree to these Terms and Conditions, as well as any subsequent changes made to them.