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Private Chianti CastleWineries Experience from Florence

5 Reviews 5.00 out of 5 stars Based on 5 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.
| Florence, Italy
Book online or call us

from $619.74 per person

Lowest Price Guarantee
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Don't miss out!
On average, this is booked 26 (0) days in advance.
10 hours (approx.)
Hotel pickup offered
Mobile ticket
Offered in: English
Instant confirmation

Overview

Imagine sipping world-renowned Chianti wines in an enchanting medieval castle, surrounded by the picturesque hills of Tuscany. This dream can become a reality with a private Chianti wine tasting tour at castle wineries. Experience an intimate, luxurious journey through the heart of Italy’s most famous wine region. Whether you’re a seasoned wine connoisseur or simply curious to learn more, this exclusive tour promises an unforgettable immersion in history, culture, and, of course, exceptional wines. Follow your dream with us! Let the castles in Tuscany enchant you with their historic legacy and the array of top class-wines.

Have you ever dreamt of traveling back to the era of nobles and kings? Let us be your portal to the past, transporting you to three of the most ancient and emblematic castles in the heart of Chianti Classico. Be part of a story of knights and dames, where, in times of peace or war, wine was essential—crafted to raise the spirits or toast to better days.

What's Included

  • 100% private tour
  • Visit of 3 castle-wineries
  • Gourmet lunch
  • Gratuities
See 4 moreSee 3 more

Meeting and Pickup

Pickup point
Pickup details

Pickup is included in a radio of 3 KM and can be requested during booking or communicated before the day of the tour.

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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Safe & secure Easy breezy Hassle‑free

Florence

Pick you up from your accommodation in Florence at 9,00am. Our driver will normally be at your address at 8,45am. We will then drive to the first winery which will take approximately 1 hour.
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1 hour Admission Ticket Free

Barberino Val d'Elsa (pass by)

This Castello rises from the landscape of Chianti Classico as a place seemingly untouched by time, resting on the western slopes of the hills that overlook the Val d’Elsa. Its story began as a watchtower, a silent sentinel guarding a contested territory, around which the castle gradually took shape over the centuries. In 1260, the abandonment marked a decisive turning point: this Castello became a strategic stronghold, expanding both its structure and its role at the heart of these hills. Passing from one family to another, the castle found renewed prosperity in the sixteenth century. In 1696, the Castello pass to Marquis Carlo Riccardi Strozzi, and for centuries, the Strozzi family safeguarded the castle, until 1984, when began a new chapter under the guidance of the Albisetti family. Today, the Castello extends over 309 hectares, largely woodland, where the vineyard occupies only what nature has chosen to grant. Twenty-three hectares of vines yield around 900 hectoliters of wine
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Radda in Chianti

Step back in time as you explore this historic castle, a historic medieval fortress and guard tower located in Gaiole in Chianti. Rising from an 8th-century Longobard watchtower overlooking the Massellone stream valley, the estate evolved into a heavily fortified stronghold that stood at the center of centuries of territorial warfare between Florence and Siena. The earliest historical footprint of the estate dates back to 790 AD during the reign of Charlemagne. Throughout the 1800s, the Ricasoli Firidolfi family managed the property under a sharecropping (mezzadria) system, turning the surrounding hills into productive vineyards and olive groves. World War II took a heavy toll on the infrastructure, and the subsequent collapse of the sharecropping system led to the abandonment of the estate. By the mid-1900s, the historic castle fell into a state of near-total ruin. In 2022, the new owners fully transformed the property into a luxury boutique resort and Chianti Classico DOCG wines.
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3 hours Admission Ticket Free

Gaiole in Chianti

The Castello is a historic fortified estate and winery located on a hilltop in Castellina in Chianti, in the heart of Tuscany. The name of the estate first appears in historical documents from 1077. Due to its elevated position offering excellent visibility over the surrounding valleys, the property became a highly coveted defensive site. In 1529, during the conflicts between Siena and Florence, Sienese troops plundered and burned the complex and destroyed or spilled roughly 200 barrels of wine stored in the cellars. During the 18th century, parts of the castle were remodeled into a grand Tuscan villa style, a prosperous period during which the surrounding hamlet housed around 70 residents. Since 2018, the estate has been owned by the Swiss Sonderegger family. Today, it operates as an exclusive boutique hotel that pairs luxury agritourism with a fully organic agricultural production of Chianti Classico wine and extra virgin olive oil.
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1 hour 30 minutes Admission Ticket Free

Florence

Your guide for the day will drop you back to where you were picked up. Guides can drop clients back to other locations with prior notice.
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1 hour Admission Ticket Free

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Additional Info

  • Confirmation is instant and will be received at time of booking
  • Suitable for all physical fitness levels
  • Infants are required to sit on an adult’s lap
  • Minimum drinking age is 18
  • Children must be accompanied by an adult
  • If you have any special dietary requirements, please inform us in advance

Frequently Asked Questions (8)

Q: What is the cancellation policy for the Private Chianti CastleWineries Experience 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?

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Activity code: C-121337P13

Traveler Photos

Reviews

5.00
5 reviews

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

5 stars
5
4 stars
0
3 stars
0
2 stars
0
1 star
0
Don't miss out!
On average, this is booked 26 (0) days in advance.
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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 Chianti CastleWineries Experience 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:
  • 100% private tour.
  • Visit of 3 castle-wineries.
  • Gourmet lunch.
  • Private transportation.
  • Wine tastings.
  • Pickup from your accommodation.
  • Experienced sommelier/guide with you the entire day.
The following is NOT included:
  • Gratuities.
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 10. 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 Chianti CastleWineries Experience from Florence is as follows:

  • 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 Private Chianti CastleWineries Experience 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

  • 100% private tour
  • Visit of 3 castle-wineries
  • Gourmet lunch
  • Private transportation
  • Wine tastings
  • Pickup from your accommodation
  • Experienced sommelier/guide with you the entire day
  • Gratuities

Additional Info

Activity name

  • Confirmation is instant and will be received at time of booking
  • Suitable for all physical fitness levels
  • Infants are required to sit on an adult’s lap
  • Minimum drinking age is 18
  • Children must be accompanied by an adult
  • If you have any special dietary requirements, please inform us in advance

Report Product Issue

Activity name