Chianti Wine Tasting Day Trip - Our Experience

We just did a day trip to the Chianti wine region and it was one of the best days of our entire Italy trip. Here's everything you need to know.

The Route We Took:

Florence → Greve in Chianti → Castellina in Chianti → a small family winery near Radda → back to Florence. Total driving time was about 2.5 hours spread across the day, but we stopped constantly because the views were too beautiful to ignore.

The Wineries:

We visited three wineries, which felt like the right amount — enough variety without becoming a blur.

1. A large estate near Greve — Beautiful property, professional tour, good introduction to Chianti Classico. €15 per person for tour + 4-wine tasting with snacks.
2. A medium family vineyard near Castellina — This was our favorite. The owner himself walked us through the cellar and told stories about his grandfather planting the first vines. We bought 3 bottles. €20 for a private tasting with cheese and salami.
3. A small organic winery near Radda — Very casual, met the winemaker's dog, sat in a garden overlooking the valley. €12 per person, and we were the only visitors. Magical.

Practical Tips:

• Book tastings in advance — most wineries require reservations, even small ones
• Designate a driver or book a tour — the roads are narrow and winding, and Italian drink-driving laws are strict (0.05% limit)
• Bring cash — smaller wineries may not take cards
• Leave Florence by 9am — wineries usually do tastings 10am-12pm and 2-5pm
• Stop in Greve in Chianti for lunch — the central piazza has several excellent trattorias

The Chianti landscape in autumn is honestly one of the most beautiful things I've ever seen. Rolling hills, cypress trees, medieval villages perched on hilltops, vineyards turning gold. Bring a good camera.