Off Italy's Beaten Track: Tuscany and Umbria by Car

Florence is a tourist magnet for good reason, but to truly experience life like a local, we’ve secured you a private tour of Oltrarno. Situated on the south side of the Arno River, this trendy neighbourhood is filled with historical sites, artisanal boutiques and trendy eateries and offers some of the best views of Florence. Your local guide will take you around the best sites: Piazzale Michelangelo, a viewpoint that offers enviable vistas; Palazzo Pitti, a 15th-century palace that’s now home to a museum complex; and Forte Belvedere, where you can check out some of the city’s best contemporary art exhibitions.

Spend your second day in Florence in its magnificent centre, soaking up all the food, wine and attractions you can get your hands on. From Renaissance pieces at the Uffizi to Michelangelo's marble at the Accademia, there’s plenty to entertain art lovers. A visit to the Cathedral of Santa Maria del Fiore (also known as the Duomo) is a must too. With its location in Florence’s heart, it’s almost impossible to miss. When it’s time to do what the Italians do best – eat – ask your local Concierge to book you into one of the city’s best restaurants. Think traditional dishes like bistecca alla Fiorentina (Florentine beef steak) and coccoli prosciutto e stracchino (fried bread with prosciutto and soft cheese).

Wave goodbye to Florence, as today you’re off to the little village of Vagliagli. Today also marks the start of your road trip, so pick up your car in Florence and begin the drive through Tuscany’s tranquil countryside. You’ll arrive at your hotel after around an hour – nestled among vineyards and olive groves and housed in an 18th-century mansion, your three nights here will be a true Tuscan experience.

During the next two days, you’ll get to experience a private visit to Castello d’Albola, an estate in the mountainous Chianti Classico wine region. Perched atop the hills of Radda, near Siena, it boasts one of the highest vineyards in Tuscany, situated around 1,300ft above sea level. Your itinerary includes tours of the historic cellars, and – on one of the days – a delightful lunch which includes a tasting of four wines, each one carefully paired with dishes showcasing Tuscan culinary traditions.

Jump back in your car and continue south for today’s drive, around one and a half hours to Castiglione d’Orcia. Hidden away from the usual Tuscan stops, this commune is nestled in the countryside of Val d’Orcia and is known for its romantic rolling hills. Check into your hotel and admire the sweeping panoramic vistas before exploring the hiking trails and nearby towns.

Feast on a traditional Italian breakfast of espressos and pastries, the perfect fuel for today’s activity – a private tour around Pienza. Perched upon a hilltop, this small town is a UNESCO World Heritage site and offers captivating views across Val d’Ocrcia. Your local guide will take you to hotspots like the Palazzo Piccolomini (a Renaissance palace) and the scenic Brunello and Montepulciano wine fields, sharing stories that bring Pienza's history and culture to life along the way. Pienza is also home to pecorino, a creamy sheep’s cheese with historic origins, which you’ll get to taste alongside wine.

For your second day in Castiglione d’Orcia, you can continue exploring – with insider tips from our local Concierge – or, if you’re after some R&R, spend some time enjoying the facilities at your hotel. Dive into the outdoor pool for a refreshing swim before spreading out on the sunbeds to admire the views over Val d’Orcia. When you’re feeling peckish, head to the hotel’s restaurant which serves traditional Tuscan dishes paired with wine from down the road.

Leave Tuscany behind as you set off this morning for Chioano, a little village in Todi, Umbria. Your home for the next three nights is a tranquil hotel hideaway surrounded by the verdant Todi countryside and equipped with a dreamy spa. After your two-hour journey, settle in and while away the afternoon with sun, wine and spa treatments.

Tighten your helmets and lace up your trainers, because today you’re off on a bike tour around Lake Piediluco and the Marmore waterfalls. Pedal along the lake’s bank and admire the oak trees and colourful houses that make up the quaint fishing villages. With a guide leading the way, you only have to worry about mastering the art of photo snapping while bike riding.

Spend your next day appreciating the beautiful buildings and authentic food in Todi’s towns. Enjoy some people-watching at the Piazza del Popolo or indulge in a tipple or two in one of the many region’s wineries.