Sur la route, lors de votre voyage en Italien en Fiat 500 avec Planet Ride et Roberta

On the Mille Miglia in a convertible

Italy - 8 days trip with car - starting at € 885
7-day road trip in Fiat 500 Convertible through the routes of the legendary Mille Miglia race
Beauty, charm and variety of Italian landscapes
Extraordinarily rich culture and excellent gastronomy of the region
Guide speaks : French, English,
8 day trip
Driving 7 day
3h per day
without guide
800km in total
From February to November
Available Vehicle Option:
Vehicle Included
Available Travel Option:
Create a group - Choose your dates
Roberta - Italy - car


Spécialiste car


After having lived in Africa for a few years, I returned to Italy in 2002 and rediscovered my motherland through new eyes. My husband and I, therefore, decided to organise…

Located in Cérisoles

This road trip to Italy takes you on the roads of the legendary Mille Miglia race in a Fiat 500 Convertible

A great pretext to experience the timeless beauty and picture-perfect charms of Italy! Drive through the fabulous landscapes of Tuscany, Emilia Romagna, Le Marche and Umbria. From the Apennine Mountains to the Adriatic Coast, get lost in the beauty of Italian landscapes and drive through spectacular valleys and plains dotted with small villages and olive groves. Experience the rich culture heritage of Italy on this trip that takes you to ancient Etruscan remains and architectural gems of the Italian Renaissance. Taste the exceptional wines, local regional specialities, olive oils of rare finesse and other gastronomical delights on this special road trip to Italy in Fiat 500.

À Florence, lors de votre voyage en Italien en Fiat 500 avec Planet Ride et Roberta
Day 1


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.

Sur la route, lors de votre voyage en Italien en Fiat 500 avec Planet Ride et Roberta
Day 2

Florence - Bologna

119 km of roads – 3h of driving

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.

Dans un village, lors de votre voyage en Italien en Fiat 500 avec Planet Ride et Roberta
Day 3

Bologna – San Marino

144 km of roads  – 3h of driving

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.

Dans un village, lors de votre voyage en Italien en Fiat 500 avec Planet Ride et Roberta
Day 4

San Marino – Serra de’ Conti

112 km of roads – 3h of driving

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.

Sur la route, lors de votre voyage en Italien en Fiat 500 avec Planet Ride et Roberta
Day 5

Serra’ de Conti – Città della Pieve

144 km of roads – 3h of driving

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.

À Sienne, lors de votre voyage en Italien en Fiat 500 avec Planet Ride et Roberta
Day 6

Città della Pieve – Siena

122 km of road – 2h30 of driving

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.

À Montecarotto, lors de votre voyage en Italie en Vespa avec Roberta et Planet Ride
Day 7

Siena – San Casciano in Val di Pesa

123 km of road – 3h of driving

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.

Chateau ducal d'Urbino, lors de votre voyage en Italien en Fiat 500 avec Planet Ride et Roberta
Day 8

San Casciano in Val di Pesa – Florence

Return Flight

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.

For this trip, your vehicle is: a Fiat 500 convertible, recent model.

To drive this vehicle you need : permis moto inf. 125cc.

Dans un village, lors de votre voyage en Italien en Fiat 500 avec Planet Ride et Roberta Sur la route, lors de votre voyage en Italien en Fiat 500 avec Planet Ride et Roberta

Price for this road trip starts at 885€ for each rider .

This price corresponds to one person, with a Fiat 500 for 2 people.

  • The price includes:
  • 7-day rental of Fiat 500 convertible for 2 people
  • Unlimited mileage
  • Delivery of Fiat 500 upon your arrival at the train station or the airport in Florence
  • 7 nights stay in a double room (on twin sharing basis) in a hotel – a wide choice of hotels is available
  • Third-party insurance for Fiat 500
  • Fire and theft insurance for Fiat 500, with a deductible of € 350 in case of theft
  • GPS, detailed itinerary, trip notes in English and a list of recommended restaurants for each day
  • Transfer from San Casciano in Val di Pesa to the train station or airport in Florence
  • Technical assistance
  • Breakfast from days 2 to 8

The price does not include:

  • Internal and international flights
  • Personal insurance against repatriation and medical expenses
  • Fuel
  • Lunch, dinner, beverages
  • Parking fee
  • Various tours and activities mentioned in the road-trip schedule or guide
  • Insurance against cancellation of €20 per person
  • Optional ‘Limited Loss Damage Waiver’: By purchasing this option, you will not be liable for damage to the Fiat up to a maximum amount of €1,000. In the case of damage above €1,000 damage, you will be liable to pay the difference between the damage amount and 1,000 €.
  • Expenses of personal nature
  • Any services not mentioned in “The price includes” section


In the case of an accident, third-party insurance provides cover of up to €6,000,000 per accident.

In the case of theft, a deductible of €350 will be payable.

An imprint of your credit card will be taken as security.


Optional: “Limited Loss Damage Waiver”: In this case no security deposit will be required.

  • 1 to 2 days: €45
  • After 2nd day: €15 per Fiat per day of driving

The “Limited Loss Damage Waiver” provides coverage against damage of up to €1,000:

  • For damage of up to €1,000, you will not be liable to pay
  • For damage greater than € 1,000, you will be liable to pay the difference between the amount of damage and €1,000


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