Tuscany Wine Trip 2019

A Journey Through Chianti, Montalcino & Montepulciano

In 2019, we returned to the enchanting winelands of Tuscany for our second unforgettable wine tour. Following the success of our 2017 journey, this updated program blended historic wineries, modern estates, medieval towns, and authentic Tuscan gastronomy. Over four days, we explored the iconic regions of Montalcino, Montepulciano, Siena, San Gimignano, Chianti Classico, and beyond—immersing ourselves in the traditions of Brunello, Vernaccia, and Super Tuscan wines.

Our journey began in the Montepulciano wine area, world-famous for Vino Nobile di Montepulciano. Our first stop was at Palazzo Vecchio Winery a remarkable estate dating back to the 1300s. Located on a Tuscan hilltop with a breathtaking 360-degree view of vineyards, Palazzo Vecchio embodies both tradition and beauty. Maria Luisa proved to be an amazing host. We then revisited Cantina Avignonesi , known for its strong commitment to biodynamic winemaking. Avignonesi continues to inspire with its dedication to sustainable practices.

From there, we drove to the medieval town of Montepulciano, strolling through its narrow cobblestone streets and piazzas. During lunch time, Christian welcomed us back to Enoteca La Dolce Vita, where we enjoyed a truly gastronomic wine and food pairing.

The day ended in Siena, where a gentle walk through the city center and gelato at Paleo gave us a sweet Tuscan night.

On our second day we began the morning with a guided walking tour of Siena led by Silvia, whose engaging storytelling brought the city’s medieval history alive.

In the afternoon, we visited San Gimignano, famed for its high stone towers and the crisp white Vernaccia di San Gimignano. After sightseeing, we returned to Siena for a traditional Tuscan dinner in one of its authentic trattorias and enotecas.

Day three was dedicated to exploring Chianti Classico, the heart of Tuscan winemaking.

Our first stop was at the Antinori nel Chianti Classico. This architectural masterpiece of modern winemaking combines innovation with sustainability. Built entirely underground and surrounded by vineyards, it is a landmark of wine tourism in Tuscany. Here, we enjoyed an exclusive masterclass tasting of Antinori’s flagship wines, guided by the estate’s oenologist—a sensory experience to remember.

After the tasting, we savored a legendary Tuscan lunch at Dario Cecchini’s butcher shop – Antica Macelleria Cecchini, in Panzano – where the robust flavors of grilled meats paired perfectly with Sangiovese and Super Tuscan wines.

We concluded the day with a premium masterclass tasting at the historic estate of Barone Ricasoli – Castello di Brolio. Dating back to the 11th century, Barone Ricasoli is one of the oldest wineries in Italy, offering wines that embody centuries of Tuscan tradition.

On our final day, we returned to the Montalcino region, south of Siena.

This organic winery of Col d’Orcia , located on the southwestern edge of Brunello di Montalcino territory, showcased how innovation and terroir can elevate wines that now rival the prestige of Chianti. Our last stop was at the historic estate of the Frescobaldi family Tenuta Castelgiocondo, whose winemaking heritage dates back to the 13th century. Having visited in 2017, we enhanced the experience this time with a premium experience. Our visit began with sparkling wine and local appetizers, followed by a gastronomic lunch paired with Castelgiocondo’s wines—all enjoyed beneath a line of iconic Tuscan cypress trees.

From Brunello di Montalcino to Chianti Classico and Vernaccia di San Gimignano, our 2019 Tuscany wine trip was a celebration of tradition, innovation, and hospitality. Between vineyard landscapes, medieval towns, and unforgettable culinary experiences, we once again discovered why Tuscany remains a dream destination for wine lovers and cultural travelers alike.