7-Day Off the Beaten Path Tuscany Vacation

Your flight will land at Florence Peretola International Airport, where your private transfer will meet you upon your arrival. You will arrive in Siena with time to settle into the comforts of your luxurious accommodation. The 12th-century tower of Torre del Mangia reaches nearly 289 feet tall and looms over the main square of Piazza del Campo. You can visit a traditional garden, where the residents tend to vegetables, goats, geese, and chickens. Here, the chefs create traditional local cuisine using only local and seasonal flavors, providing you with a fabulous introduction.

Your guide will meet you at your hotel in the morning and lead you into the heart of Tuscany for a discovery of the fascinating medieval towns outside of Florence, beginning with the city of Pistoia. The city sits at the base of the Apennines Mountains and reflects the best of Tuscany without the crowds. You will continue to the town of Montefioralle, which crowns a cresting hill that rises over the sun-drenched landscape of Tuscany. Fragrant olive groves and vineyards wash over the bordering slopes, and the village shimmers among the splendor of fig trees. After wandering cobbled lanes, you can enjoy the traditional flavors of a Chianti Classico.

You will continue your exploration of Tuscany in Murlo, which is a town that is known for olives and cattle. The foundations of the city date back to the 12th century and feature the remains of a dramatic castle wall. Once in Arezzo, you will find a charming Renaissance town that brims from the slanted design of Piazza Grande. South of Arezzo stretches the classical image of rolling hills, olive groves, and fields, which lead to Cortona. This city is known as the location for the book and film Under the Tuscan Sun.

In the morning, your guide will take you on the Strada del Vino e dell’Olio along the Tuscan coastline from Livorno to Piombino. The city of Livorno is a port town that has attracted traders from around the world for centuries. You will travel along the 93-miles of winding road known for the Etruscan settlements and beaches. Family-run wine bars fill the town, and each provides new insight into the local Super Tuscan wines.

In Pitigliano, you will discover a tremendous town that is perched on a rocky outcrop, towering over the lush landscape. The fort that crowns the town completes the picture of an impenetrable stronghold. The Jewish quarter dates back to the 16th century and often supports the town’s nickname Little Jerusalem. You will find the aromas of sfratto dei goym, which is a dessert of dough that is made with white wine. Your day will end in Sorano, which is a nearby town with views of the Lente River and the gorge.

You will travel by private transfer to Florence in the morning and enjoy the luxuries of your hotel. Instead of the familiar museums of the Uffizi and Galleria dell’Accademia, your guide will lead you on a tour of the city to hidden and treasured gems, beginning with the Church of San Lorenzo. Brunelleschi designed the church, and Michelangelo designed the chapel and lavish tombs. Here, you can find hidden drawings of Michelangelo, Jesus, and a possible reproduction of the Sistine Chapel.

In the morning, Florence returns to life. The aromas of roasted coffee beans and brioches will fill the cafes and neighborhood bars. Your private driver will be waiting to escort you to Florence Peretola Airport for your flight home.