Vineyards, Food and Frescoes: Italian Road Trip in Tuscany and Umbria

Today we’ll organise queue-jumping tickets for the Grand Duomo Museum, the largest museum in Florence which grants you access to Brunelleschi's dome, the Cathedral, the Campanile, the Baptistery, the Crypt and the museum. Inside the museum, you’ll find original and reconstructed architecture and sculptures from some of Florence’s most iconic buildings, including the Florence Duomo, the Baptistery of Saint John and Giotto's Campanile. The grandeur of these historic buildings is clear to see, whether in Lorenzo Ghiberti’s Gates of Paradise – a gleaming set of doors created for the Baptistry – or the reconstructed façade of the Duomo itself, which contains 40 exact replicas of the sculptures on the original façade. You’ll also find a poignant, unfinished Michelangelo sculpture here, which he carved for his own tomb. If you’d like to see more of Michelangelo’s work, we can also arrange for you to take a private tour of The Accademia Gallery.

Today, you’ll pick up your rental car and drive to San Casciano, about 35 minutes south of Florence. You’ll stay here for two nights in a beautiful Renaissance villa amid the vineyards. Since you’re in the Chianti region, carve out some time to visit a vineyard and sample their creations ¬– you’ll have beautiful views across the rolling Tuscan hillsides up at the historic winery of Gabbiano castle. The remainder of your time here can be spent visiting the Romanesque churches and fortresses, or admiring the frescoes of Cosimo Gheri's studio. If you like, we can also arrange for you to take a private tour of nearby Siena.

Your next stop is Cortona, about an hour and a half away. Your home for the next two nights is a historic villa where the beautiful garden converges on fields of vines and tobacco. Sunny days can be spent cooling off in the swimming pool, and when you get peckish, tuck into inventive seasonal cuisine in the hotel restaurant.

Far from the hustle and bustle of Florence, Arezzo is a small country town that’s known for its artistic heritage and fabulous food. Specifically, this town owes its reputation as a city of art to Piero della Francesca and his frescoes in the Basílica de San Francisco. We’ll arrange for you to visit Arezzo with a private guide today, who will show you the town’s must-sees including the Basílica de San Francisco along with the church of Santa Maria della Pieve, the Piazza Grande, the Duomo and the Basilica of San Domenico. If you’d prefer to continue discovering Tuscany’s wine regions, we can arrange for you to visit the hilltop town of Montepulciano for a private wine tasting.

You’ll swap Tuscany for Umbria today, driving for just under an hour until you reach its capital, Perugia. Your accommodation for the next two nights will be a splendid castle just a stone’s throw from the historic centre, offering you beautiful views from the garden and terraces. In the evenings, enjoy some classic Umbrian cuisine in the hotel restaurant.

This beautiful city has a charming medieval centre full of cobbled alleyways and piazzas. Your final two days here are yours to spend as you please, whether that means shopping for traditional ceramics or sipping Aperol spritz with a view across the rooftops. If you like, we can also arrange for you to visit Assisi and the Basilica of San Francesco with a private guide.