If heaven exists, it might just be Greve in Chianti and the sun-drenched Tuscan hills that surround it. Every curve of the road brought us deeper into postcard-worthy scenery – rolling vineyards, silvery olive groves, and cypress trees lining golden hills. Our first stop was the impossibly charming village of Montefioralle, where we stepped back in time for a cozy cellar tour and wine tasting that felt like a secret shared by locals. After a pizza lunch in the village, we made our way to Castellinuzza B&B, a 19th-century villa perched on a hill, where we were greeted with sweeping vineyard views, 22 cuddly cats, and owners so warm they welcomed us with a free, generous tasting in their stone cellar. (Spoiler: it instantly became my favorite place I’ve ever stayed.) We continued on to the storybook estate of Villa di Vignamaggio – rumored to be the birthplace of Mona Lisa – for a tasting surrounded by historic elegance and vineyard views. Then came the grand finale: Castello di Verrazzano, where we wandered through Renaissance gardens, hillside cellars carved into the rock, and sipped wine, olive oil, and balsamic drizzled over pecorino while gazing out at Tuscan castles. Chianti didn’t just steal our hearts – it poured us into a dream we never wanted to wake up from. 🍷✨

Itinerary

This itinerary is based on our visit to the Greve in Chianti region during our 2016 Italy trip (September 2).

• 🚗 8:00 AM: Pick up rental car (Hertz – Firenze)
• 🚗 8:30 AM: Drive (50-min) via SR222 to Montefioralle
• 🍷 10:00 AM – 11:30 AM: Montefioralle wine tasting (🎟️ Reservation recommended, €15)
  • Includes the visit of the cellar and the tasting of 6-7 wines with light appetizers.
  • Duration: 1.5 hrs
• 🍕 Lunch in Montefioralle
• 🏨 Check-in to Castellinuzza B&B
  • Stunning views of the Chianti countryside on a private winery🍷 set in a 19th-century villa with 22 cat companions 🐈.
  • Owners provided free, generous wine tasting in their cellar. They spoke no English and we spoke very little Italian, which made the experience all the more memorable!
  • This is my favorite place I’ve ever stayed!
• 🍷 Villa di Vignamaggio wine tasting (alleged birthplace of Mona Lisa)
  • Walk-in tastings from 10 AM – 6 PM.
• 🍷 3:00 PM – 4:30 PM: Castello di Verrazzano classic wine tour (🎟️ Reservation recommended)
  • Stunning views of Tuscan castles
  • Tour of the Renaissance gardens
  • Visit historic aging cellars, built into the hillside beneath the castle
  • Taste 3 Italian wines
  • Taste extra virgin olive oil and balsamic vinegar served over pecorino cheese
• 🍝 Dinner in Greve in Chianti

Greve in Chianti

Montefioralle

A tiny medieval village just outside Greve in Chianti, Montefioralle is one of the most beautiful and peaceful hill towns in Tuscany. With its cobbled streets, stone houses, and panoramic vineyard views, it offers an intimate wine tasting experience in a setting that feels untouched by time. Montefioralle Winery is a small, family-run estate nestled just outside the village walls, offering intimate tastings and cellar tours that showcase their passion for traditional Chianti winemaking in a truly picturesque setting.

Castellinuzza B&B

Nestled in the Chianti hills, Castellinuzza B&B is a charming 19th-century villa surrounded by vineyards and home to 22 friendly cats. The family-run agriturismo offers stunning views, warm hospitality, and a generous wine tasting experience in its cozy cellar – easily our most memorable stay in Tuscany.

Castello di Verrazzano

Perched on a hilltop with sweeping views of the Tuscan countryside, Castello di Verrazzano offers a classic wine experience rooted in history. The tour includes Renaissance gardens, hillside cellars carved into the rock, and tastings of wine, olive oil, and balsamic vinegar over pecorino – perfectly blending Tuscan tradition with timeless flavor.

Villa di Vignamaggio

Steeped in history and rumored to be the birthplace of Mona Lisa, Villa di Vignamaggio is a picturesque wine estate that combines Renaissance elegance with rustic Tuscan charm. Even during a private event, we were able to enjoy a walk-in tasting of their exceptional wines in a beautiful, relaxed setting.