Upon your arrival at the airport or railway station in Florence, you pick up your Fiat 500 convertible, equipped with GPS and the trip guidebook in English. Roberta’s team will brief you on the vehicle and the trip. You can then enjoy a leisurely day in Florence, where you will stay overnight in a hotel.

You leave Florence, Tuscany and its olive, pine and cypress trees and head towards the forested mountains of Tuscan-Emilian Apennines. You drive on the legendary La Futa Pass, one of the greatest driving roads of all times. This drive is sure to evoke the memories and thrills from the time of the legendary Mille Miglia race. There is no adrenaline rush quite like driving on the magnificent twists and turns of this road.

You then head towards Bologna, lovingly nicknamed “la dotta, la grassa, la rossa” (“the learned one, the fat one, the red one”) for its ancient university founded in 1088, its rich gastronomy and the ubiquitous red roofs. Beyond Bologna’s magnificent historic centre, the region is also the birthplace of some of the most famous automobile brands in the world. Do not hesitate to take some time out to visit one of the many automobile museums in the region – the Ducati Museum in Bologna, the Lamborghini Museum in Sant’Agata Bolognese or the Galleria Ferrari in Maranello. You stay overnight in Bologna.

You take Via Aemilia, the historic Roman road which passes through the fertile plains of the Po Valley, to drive towards the Adriatic coast. You cross Imola and the Autodromo Internazionale Enzo e Dino Ferrari, also known as the racing circuit of Imola. You then reach Faenza, birthplace of Faenza majolica pottery, where you can visit the International Museum of Ceramics. Your guide Roberta suggests that you stop at Cesenatico on the Adriatic coast and stroll along the canal harbour that was built according to the plans of Leonardo Da Vinci. Here you will also find the floating section of the Maritime Museum, which is home to a unique and charming collection of ancient boats with colourful sails that were traditionally used in the Adriatic Sea. From here you drive towards Rimini and then San Marino, where you stop for the night.

You leave San Marino and drive along the twisting and turning Apennine roads in your Fiat 500. Your first stop is in Urbino, a World Heritage Site and one of the important cultural capitals for the Italian Renaissance. You can visit the splendid Ducal Palace, before resuming your journey.

You then drive across lush green Cesano valley and then, the beautiful hills of Le Marche, known for Verdicchio, a fascinating white wine grape variety. Enjoy this exceptional regional wine with pleasant scents of apples and almonds. You drive towards Serra de’ Conti, where you stay overnight.

You drive across the Apennine mountains to arrive in the green and fertile region of Umbria. You stop in Gubbio, a pretty village perched on the steep slopes of Mount Ingino. Dominated by Gothic architecture, you visit the imposing Palazzo dei Consoli, which sits above a series of terraces corresponding to the palace’s lower floors.

You get back on the road and arrive in Perugia, known for its many Etruscan ruins. You then drive your Fiat 500 to Città della Pieve, your stop for the night.

You leave Città della Pieve in your Fiat 500 towards the beautiful landscapes of Val d’Orcia. Driving through cypress-lined roads and crisscrossing the rolling hills of the valley, you arrive in the small villages perched on hilltops. You discover the beautiful town of San Quiricio d’Orcia, the historic stop for the Mille Miglia race. The graffiti honouring the drivers are still visible on the ‘bridges of Mille Miglia’. You will also find a statue of Tazio Nuvolari, the Italian racing legend and winner of two Mille Miglias in 1930 and 1933 in his Alfa Romeo. You then drive to the lovely medieval city of Siena, known worldwide for Palio, one of the most famous horse races in the world. Il Campo, the sloping piazza where the Palio takes place, is worthy of a visit. You stay overnight in Siena.

Departure from Siena. Today, you drive towards Chianti, a region well-known for the production of some of the most famous Italian wines. Vineyards and olive groves provide a mesmerising backdrop to the soft geometric slopes of this hilly region. Nearby villages are dotted with numerous castles, towers and fortified monasteries, including some that were ruined during the conflict between Guelphs and Ghibellines in the Middle Ages. You then visit San Gimignano, known for its white wine, Vernaccia. The many towers of this walled town make it look like a medieval Manhattan. You then drive your Fiat 500 to San Casciano in Val di Pesa, your stop for the night, after passing through Certando. For dinner, your guide Roberta highly recommends that you try the Florentine steak at one of the fine restaurants of San Casciano in Val di Pesa.

End of your road trip to Italy in a Fiat 500.  Roberta’s team will pick up your vehicle, followed by transfer in a private vehicle to Florence for your return flight.