FL7 - Montepulciano, Montalcino & Pienza

Turn postcard views into reality! Spend a whole day discovering the stunning Tuscan countryside south of Siena, immersing yourself in picturesque landscapes and beautiful medieval villages. This private tour starts from your accommodation in Florence, making it easy and convenient.

Montalcino

After passing Siena, your journey continues through the breathtaking ‘Crete Senesi’ region, arriving at the famous wine town of Montalcino. Here, the scenery is mesmerizing—cypress trees, fields, and livestock create extraordinary combinations of green, grey, and brown landscapes.

Brunello Wine Montalcino is renowned for its Brunello wine, made from local Sangiovese grapes. Every aspect of this charming town revolves around wine production, as Brunello is one of the finest and most prestigious wines in the world! Visit the ‘Enoteca La Fortezza’ within Montalcino’s imposing fortress to explore a wide selection of local Brunello. Stroll through the picturesque village, admiring sights like Piazza del Popolo, Palazzo dei Priori, and the churches of Sant’Agostino and Sant’Egidio, along with the beautiful Cathedral.

Pienza

Next, stop in Pienza, a delightful Tuscan town recognized by UNESCO as a cultural and natural heritage site. Pienza’s history is closely tied to Pope Pio II, born here in 1405 as Enea Silvio Piccolomini. A great Humanist, he transformed his hometown from a small medieval hamlet into a Renaissance-style papal residence. Many of Pienza’s palaces date back to this transformative period.

Walk in the Street of Love! Climb to the top of Pienza's hilltop location for unforgettable views over the picturesque Val d’Orcia valley and surrounding countryside. The streets have charming names such as ‘Via dell’Amore’ (Street of Love) and ‘Via del Bacio’ (Street of Kiss).

Artisan Shops and Pecorino CheeseExplore the streets lined with small shops selling local crafts and specialties, including delicious ‘pecorino di Pienza’ cheese, with many shops offering samples to taste.

Montepulciano

The final stop of your Tuscan day is Montepulciano, situated in one of the most breathtaking areas of Tuscany. This intriguing wine town, built on volcanic rock, stands about 600 meters above sea level. Montepulciano is known for its impressive Renaissance architecture and particularly for its ‘Vino Nobile’ (Noble Wine), one of Italy’s most distinguished wines.The town features a steep incline, stretching between the gates of Porta al Prato and Piazza Grande, crisscrossed by narrow streets and alleys. Don’t miss sights such as the Cathedral, Palazzo Comunale, the Temple of Madonna of San Biagio, and the Church of Saint Augustine.

After a delightful day exploring the medieval treasures of Montalcino, Pienza, and Montepulciano, relax during your scenic drive back to your accommodation in Florence. This private tour offers a perfect way to experience the best of Tuscany—an ideal choice for those looking for tours from Florence. Please note that lunch and tastings are not included, and the order of visits may vary based on winery availability.