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Private Tour and Wine Tasting at Castle-Wineries in Chianti from Florence

Have you ever dreamt of travelling back in time, in the era of nobles and kings? We can be your back-in-time portal and get you carried away to three of the most ancient and emblematic castles in the heart of Chianti Classico. Nowadays, these estates are not simply castles. Instead, they turned into wineries, that is why they can be regarded as castle-wineries.

Be part of a story of knights and dames, where in times of peace or war, wine was quintessential and always produced to raise the spirits or toast for better times. Apart from visiting estates erected centuries ago, you will also get to taste a wide variety of prestigious wines, that preserved their attributes from the dim and distant past. In terms of food, you will be enjoying a feast "fit for a king", as gourmet lunch is included.

Tuscany, with its enchanted landscapes, castles, fortresses, watchtowers and town walls looming from the mountains to the sea, is the perfect place to realize your desire of time travelling.

per adult from




10 hours


Hotel pickup available


Mobile ticket

Select Date and Travellers

No tour options available.

  • What's included :
    • Wine tastings
    • Lunch - Appetizers and gourmet lunch
    • Private transportation
    • Air-conditioned vehicle
    • Certified sommelier/guide with you the entire day
    • 100% Private Tour
    • Pick-up
    • Entry/Admission - Castello di Monsanto
    • Entry/Admission - Castello di Volpaia
    • Entry/Admission - Castello di Ama
    What's excluded :
    • Gratuities
  • This is a typical itinerary for this product

    Stop At: Florence, Florence, Tuscany

    Check-in and departure.

    Duration: 15 minutes

    Stop At: Castello di Monsanto, Via di Monsanto 8, 50021, Barberino Val d'Elsa Italy

    Castello di Monsanto, nowadays turned into a winery, will enable you to travel back in time. It has long been an influential producer, becoming one of the best-known and most admired wineries in the region and worldwide.

    You will tour the estate, the remnants of the old castle, the vineyards and wine cellars. One interesting element that embodies the spirit of Monsanto is its underground wine cellar. A memory of a time that has passed is also preserved by the amphitheater situated in the vast garden. After the tour, you will get to taste 4 different representative wines.

    Duration: 1 hour 30 minutes

    Stop At: Castello di Volpaia, Piazza della Cisterna Loc. Volpaia, 53017, Radda in Chianti Italy

    The second winery operates inside the walls of a medieval fortified village. Dating back to the 11th century, its 4 generations united to involve Volpaia in the intimate production o wine, olive oil and vinegar. The entire activity of the winery is undertaken in former castles and their basements, unconsecrated churches and buildings of the village, creating a systems of underground "vinoducts".

    You will have the wine tasting in the wine room inside the former castle. The visit will culminate with a gourmet lunch in a royal ambiance that preserves timeless traditions.

    Duration: 3 hours

    Stop At: Castello di Ama, Localita Ama SNC, 53013, Gaiole in Chianti Italy

    Castello di Ama is a cornerstone of the modern revival of Chianti Classico. The castle, once owned by a famous family during the Holy Roman Empire, was at some point destroyed, but from "its ashes" new dwellings were born. The vineyards around the tiny Medieval hamlet, yield a valuable production. This allowed the winemaker’s ancient craft to take new roots here. Already in the 18th century, Grand Duke Peter Leopold of Tuscany praised Ama’s wines: “around the Castello di Amma,” he wrote, “the best vines in Chianti are to be found, excellently tended.” The winery prides itself with world-awarded wines, characterized by long-lasting traditions.

    You will enjoy a tour of the estate, the vinification plant, aging cellars, the village of Ama with its villas, ancient chapels and gardens. Combined with the preserved ancient character, contemporary art collections are present on the site. The tour ends with a private wine tasting in the Enoteca.

    Duration: 1 hour 30 minutes

    Stop At: Florence, Florence, Tuscany

    Drop-off. The tour will generally end where it started.

    Duration: 5 minutes

  • Departure Point :
    Borgo Ognissanti, 70, 50123 Firenze FI, Italy
    Traveler pickup is offered
    Pickup is included and can be requested during booking or communicated before the day of the tour.
    Departure Time :
    9:00 AM
    Return Detail :
    Returns to original departure point
    Hotel Pickup :
    • Confirmation will be received at time of booking
    • Not wheelchair accessible
    • Not recommended for pregnant travelers
    • Minimum drinking age is 18
    • Children must be accompanied by an adult
    • If you have any special dietary requirements, please inform us in advance
    • Most travelers can participate
    • This experience requires good weather. If it’s canceled due to poor weather, you’ll be offered a different date or a full refund
    • This experience 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
    • This is a private tour/activity. Only your group will participate
    • Face masks required for travelers in public areas
    • Face masks required for guides in public areas
    • Hand sanitizer available to travelers and staff
    • Social distancing enforced throughout experience
    • Gear/equipment sanitized between use
    • Transportation vehicles regularly sanitized
    • Guides required to regularly wash hands
    • Regular temperature checks for staff
    • Contactless payments for gratuities and add-ons
    • We have ensured all the necessary precautions, as we highly value our travellers' safety. The experience is entirely private. We operate in accordance with governmental regulations. Safety distance will be enforced at all times. As an environmental measure, open and ventilated spaces are preferred.
  • You can present either a paper or an electronic voucher for this activity.
  • For a full refund, cancel at least 24 hours in advance of the start date of the experience.


English - Guide

Age Req.


Fitness Req.


Group Size


Organised by Enotropea Wine Tours

Activity ID: V-121337P13

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