From Florence to Rome with stop in Pienza e Montepulciano

Known as the “Ideal City,” Pienza was transformed from the humble village of Corsignano into a masterpiece of urban planning by Pope Pius II. It represents the first application of humanist concepts to a town center, creating a model for all European urban design that followed.

• Piazza Pio II: The heart of the city is a trapezoidal square defined by four architectural gems designed by Bernardo Rossellino.
• Palazzo Piccolomini: The Pope’s principal residence features a stunning internal court and a hanging “Italian Garden” with spectacular views over the Val d’Orcia.
• The Duomo: The Cathedral’s facade is one of the earliest Renaissance designs, while its “hall church” interior reflects the light-filled Germanic style admired by the Pope during his travels.
• Pecorino di Pienza: No visit is complete without tasting the town’s world-famous sheep’s milk cheese, aged to perfection and available in the charming artisanal boutiques lining the streets.

A short, scenic drive brings us to Montepulciano, a medieval and Renaissance hilltop town perched on a high limestone ridge. Renowned for its walkable, car-free streets, it offers a blend of architectural elegance and world-class gastronomy.

• Piazza Grande: The monumental center of the town, featuring the Palazzo Comunale (designed by Michelozzo) and the imposing Duomo, which houses Taddeo di Bartolo’s 1401 masterpiece, the Assumption of the Virgin.
• Vino Nobile di Montepulciano: Connoisseurs consider this one of Italy’s best red wines. (Note: Not to be confused with the Montepulciano d’Abruzzo grape). We can arrange a stop at an ancient underground cellar for a tasting of this “Noble” wine.
• San Biagio Sanctuary: On the road outside the city walls, we will admire this 16th-century Greek-cross temple, built in white travertine and considered a masterpiece of the high Renaissance.

After a day spent between “Ideal Cities” and historic vineyards, your driver will take you through the changing landscapes of Southern Tuscany and Lazio, arriving directly at your hotel or apartment in Rome. You will arrive refreshed, having turned a 3-hour transfer into a 10-hour deep dive into the heart of Italian beauty.

• Optimize Your Schedule: Turn a travel day into a full day of sightseeing in the Val d’Orcia.
• Luggage Security: Your belongings remain safely in the vehicle while you visit palaces, churches, and shops.
• Door-to-Door Convenience: Private pickup in Florence and drop-off in Rome (or vice versa).
• Expert Chauffeur: Travel in style with a driver who knows the history, the best photo spots, and the finest local trattorias.