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Discover a 900-year-old castle’s secret cellars with a guided tasting of three wines, bread, and EVO oil—perfect for lovers of history, wine, and authentic Tuscany.

If you’re looking for an experience that combines history, wine, and Tuscany’s culinary delights, this tour of Castello del Trebbio offers just that. Priced at $46.10 per person, it’s a well-balanced mix of storytelling, tasting, and sightseeing that appeals to both wine lovers and those curious about Italian heritage. What makes this tour particularly appealing is its unique setting: a fortress and winery that’s been around for nearly a millennium. Plus, with glowing reviews and a 5-star rating, it’s clear that many travelers find it worth every euro.
One thing we especially appreciate is the incredible authenticity of the experience — walking through ancient cellars, tasting premium wines, and savoring fresh bread with extra virgin olive oil (EVOO) in a private castle setting. However, a potential consideration is that the tour doesn’t include transportation from Florence, so travelers will need to arrange their own way there. But for those who enjoy a scenic drive or want to start their day with a bit of adventure, this is a small hurdle.
This tour is best suited for history buffs, wine enthusiasts, families, or anyone eager to experience Tuscany’s heritage firsthand. If you love discovering hidden gems away from crowded tourist spots, this intimate and informative experience will hit the right notes.

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Starting at Castello del Trebbio in Pontassieve, the tour begins at 10:30 am. The meeting point is conveniently located on Via di Santa Brigida, making it accessible for those staying in Florence or nearby. Keep in mind that the tour does not include transportation, so a short drive or arranged pickup from Florence is necessary. Many visitors comment on the ease of finding the location and the beautiful surroundings, which provide a perfect backdrop for the experience.
Once inside, you’ll be taken on a walk through the castle’s historic architecture and private cellars, which have been used for centuries to age wine. According to reviews, the property’s views are “amazing,” and the tour guide is praised for being knowledgeable and engaging. You’ll learn about the castle’s history, its role in regional winemaking, and the significance of its ancient cellars, which have been preserved remarkably well.
The highlight for many is the tasting session, where you sample three different wines. Reviewers mention that the wines were “fabulous,” and the selection is curated to showcase the best of the estate’s offerings. These wines are paired with fresh bread, slices of cheese, and salami — all of which add to the sensory experience. The guide usually provides insights into the wine’s characteristics, what makes each one special, and how they are crafted.
One reviewer, Heather, described the tasting as “wonderful,” noting that she left with a few bottles of wine and olive oil, eager to enjoy them back home. The tasting is relaxed but informative, allowing guests to savor the flavors and learn about the art of wine and olive oil production.
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Beyond wine, you’ll also get to taste premium extra virgin olive oil (EVOO), which is considered a treasure in Tuscany. The oil is served alongside bread for dipping, and reviewers highlight the rich, fresh flavors that stand out compared to mass-produced options. This part of the tour offers a real taste of Tuscan culinary tradition, emphasizing the importance of quality ingredients.
Throughout your visit, you’ll be surrounded by rolling Tuscan hills and scenic landscapes, making it an ideal spot for photography and quiet reflection. The property’s stunning views are frequently praised and serve as a perfect setting for enjoying your tastings.
The entire experience lasts approximately 1 hour and 30 minutes, with a maximum group size of 16 travelers. This small-group format ensures personalized attention and a more intimate atmosphere, which many reviews commend.

At just over $46 per person, this tour offers excellent value considering the depth of experience, quality of tastings, and the historic venue. It’s not just a tasting — it’s a chance to step back in time, learn about traditional winemaking, and savor authentic Tuscan flavors in a setting that’s both beautiful and meaningful.

This experience is ideal for visitors who appreciate history, scenic landscapes, and authentic food and drink. It’s perfect for those wanting a break from city sightseeing and craving a more intimate, cultural experience. Families with older children can enjoy the guided tour and tastings, especially since vegetarian options are available. And of course, wine lovers will find the selection and storytelling particularly compelling.

Is transportation from Florence included?
No, the tour does not include transportation. Guests need to arrange their own travel to Castello del Trebbio, though many find the location easily accessible and enjoy the scenic drive.
Can I visit the castle if I’m not a wine drinker?
Absolutely. While the tour involves wine tasting, the historical and scenic aspects of the castle are interesting even without participating in the tastings.
Are dietary restrictions accommodated?
Vegetarian options are available if advised at the time of booking. Other dietary needs are not specified but can be addressed upon request.
How long does the tour last?
The entire experience takes about 1 hour and 30 minutes — perfect for fitting into a day of exploring Tuscany.
Is the tour suitable for children?
Most travelers can participate, and children are welcome, especially since the setting is safe and scenic. However, since the tasting involves alcohol, it’s better suited for older children or teenagers.
What should I wear?
Smart casual attire is recommended — comfortable but neat clothing suitable for strolling through historic sites and scenic grounds.
What happens if I need to cancel?
The experience is non-refundable and cannot be changed once booked, so be sure of your plans before confirming.

This tour of Castello del Trebbio stands out as a wonderful blend of history, flavor, and scenery. It offers a rare chance to explore a nearly 900-year-old private castle and taste exceptional wines and olive oil, all in a beautiful Tuscan setting. The small-group format, knowledgeable guides, and authentic tasting make it a memorable experience that’s worth the price.
It’s especially well-suited for travelers looking for a meaningful escape from busy city tours — those who want to see a piece of medieval Italy, learn about traditional food and drink, and enjoy some fantastic views along the way. Whether celebrating a special occasion or simply craving a genuine taste of Tuscany, this tour delivers on all fronts.
