Itinerary Highlights
    • See some of Florence’s most spectacular architecture in the Grand Duomo Museum
    • Drive through the verdant hills of the Tuscan countryside
    • Stay in historic villas between the vineyards
    • Take a private tour of the artistic town of Arezzo

Contact one of our specialists + 44 (0) 20 3958 6120

Whether its Florentine steaks cooked on hot coals or glasses of Chianti overlooking the vineyards, Italy knows a thing or two about living well. During this nine-day road trip in Tuscany and Umbria, you’ll experience the best of Italian style and sophistication as you marvel at magnificent architecture, tuck into regional cuisine and enjoy the breathtaking countryside. Your trip begins in Florence, on either side of the Arno’s tranquil waters. This city’s palaces, museums and fountains never fail to impress, nor do the cafés and restaurants found in shady piazzas. We’ll also get you tickets for the dazzling Grand Duomo Museum. Then you’ll drive into the rolling hills of the Tuscan countryside.
In San Casciano in Val di Pesa, you’ll have two days to spend sipping Chianti, wandering around Romanesque churches and visiting the studios of famous artists. Your next stop is Cortona, where you’ll stay in a beautiful villa amid the vineyards. While you’re here, we’ll arrange for you to take a private tour of nearby Arezzo, a quiet country town known for its food and frescoes. Finally, you’ll head to Perugia, Umbria, a charming university city full of Etruscan, Roman and Gothic architecture. With a splendid castle as your base, all that’s left to do is soak up your magnificent surroundings.


Everything is 100% tailored to you


Your nine-day trip to Italy begins with a two-hour flight to Florence. When you land, you’ll be privately transferred to your accommodation for the first two nights: a 15th-century house full of original beams and frescoes. Located in the heart of Florence, this property has you perfectly placed to enjoy everything this captivating city has to offer.



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.

DAYS 3 & 4


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.

DAYS 7 & 8


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.



It’s time to say arrivederci to Italy, so today you’ll drive to Rome airport where you’ll return your rental car before boarding your flight back to the UK.

A la carte


At the age of 26, the genius sculptor Michelangelo began his Florentine masterpiece: ‘David’. He went on to be involved in many of the city’s important artistic projects including the façade of the San Lorenzo church and the Medici Chapel. During this private tour of the Accademia Gallery, you’ll come face-to-face with some of his incredible pieces including ‘Prisoners’ (or ‘Slaves’) and ‘David’, his most famous work.


Clinging to three clay hillsides, the streets of this medieval city wind inside impressive walls before converging on the beating heart of the city: the Piazza del Campo. Every summer, this is the site of a horse race, the Palio di Siena, which sees competitors from the city’s 17 districts compete in a historic competition. During this private tour, you’ll go off the beaten track through Siena’s alleyways as you learn about daily life in this fascinating city.


In a remarkable location on a hill between the valleys of Chiana and Orcia, Montepulciano is a small Renaissance town with a Medieval soul. This is the undisputed capital of vino nobile, one of Tuscany’s most popular wines. During this private tour of the old town, you’ll see the Piazza Grande, the cathedral, the Palazzo Comunale, the Contucci and Nobili-Tarugi Palaces, and the San Biagio church. Afterwards, you’ll head to the wine cellars of Villa S.Anna for a tasting at this family-run business that’s overseen by the women of the household.


Listed as a UNESCO World Heritage Site, the small medieval town of Assisi was the birthplace of Saint Francis and is closely associated with the work of the Franciscan Order. During this private tour, you’ll learn more about the masterpieces it contains, and why it’s a benchmark for the artistic and architectural development of Italy and Europe.

A Rough Idea of Price

Dependent on season, accommodation and activities
The estimated cost for this trip starts from £1,720 to £2,605 per person. The final cost of the trip depends on the way we tailor it especially for you. The final cost varies according to several factors, which include the level of service, length of trip and advance booking time. The exact price will be provided on your personalised quote. The average starting price for this trip is £2,260 per person.
A few of the benefits of travelling with us
Get in touch
Our experts have the inside track on the destinations they sell and will tailor-make a holiday to your unique requirements.
Contact one of our Italy specialists