Discover three iconic gems of Tuscany on an exclusive tour through the breathtaking Val d’Orcia and Val di Chiana. In a small premium group and with an expert guide, experience the magnetic charm of Cortona, a hilltop town renowned for its ancient Etruscan roots and as the set of the beloved film Under the Tuscan Sun.

Visit Montepulciano, a Renaissance jewel famous for its Vino Nobile, and enjoy a tasting in a secret historic cellar. Be captivated by the rolling landscapes featured in The Gladiator as you make your way to Montalcino, the home of the prestigious Brunello wine, which you will taste at a renowned winery. This intimate and authentic experience offers a true taste of Tuscan culture and heritage, combining cinema setting, fine wines, and breathtaking UNESCO-listed scenery.

Description

Starting from Florence, the journey takes you to Cortona, one of the most ancient and charming villages in Tuscany. Perched on a hill in the Val di Chiana and made famous by the movie Under the Tuscan Sun, Cortona boasts Etruscan origins, evidenced by the imposing walls surrounding it, which date back to the 4th century BC. The village offers a perfect blend of medieval architecture, authentic atmospheres, and local culture, making it an unmissable destination for those seeking timeless beauty and authenticity.

The next stop is Montepulciano: in this captivating Renaissance town, you’ll have the opportunity to taste the prestigious Nobile di Montepulciano wine in a charming and historic underground cellar, learning the secrets of its production and having the chance to purchase bottles at attractive prices. After the included tasting, you’ll have free time for lunch at a typical trattoria and to explore the beauty of the historic center, famous as the set for films like Twilight: New Moon and the series Medici: Masters of Florence featuring Dustin Hoffman and Richard Madden.

As you continue toward the Val d’Orcia, you will enter the heart of one of Tuscany’s most scenic areas, where you can admire the iconic landscapes of rolling hills dotted with cypress trees, known worldwide for their ineffable beauty and recognized as a UNESCO heritage site. Along the way to Montalcino, you will spot the settings of famous films like The Gladiator—a perfect opportunity for taking iconic photos.

The final stop is Montalcino, home to Brunello, one of the world’s most renowned wines. Here, after exploring the quaint historic center, we’ll visit a renowned winery, where you’ll taste Brunello and Rosso di Montalcino wines, immersing yourself in the storytelling of the region’s rich winemaking traditions. Before returning, you’ll have the chance to purchase fine wines directly from the producer—an opportunity not to be missed.

The tour concludes with a return to Florence in the late afternoon, leaving you with unforgettable memories of breathtaking landscapes and a collection of authentic experiences in art, history, and wine that will carry the flavors and aromas of this unparalleled region with you.

Includes Licensed Tour Escort and wine tasting!

Available from May to October 2025

*Contact Us at 800-621-2259 or info@tourcrafters.com to book today!

*Package descriptions and pricing are subject to change without notice.