Chianti
Timeless style meets Tuscan vines: the iconic Fiat 500
A contemporary icon built for city life. Compact, efficient, and packed with smart technology, the modern Fiat 500 blends unmistakable Italian style with everyday practicality. Easy to park, fun to drive, and designed to stand out, it’s urban freedom, redefined.
The original city legend. Small, simple, and full of character, the vintage Fiat 500 delivered freedom to a generation. With its charming curves and classic details, it’s not just a car, it’s a piece of Italian history on four wheels.
Your starting point is ideally located just outside of the small town of Impruneta. From here you have the possibility to follow three different itineraries, which will take you to discover the Chianti and Florence region from every angle.
The order of the routes is flexible. Each day you head out to explore your own (with your digital roadbook & GPS)! So let’s go!
Nestled in the serene countryside of Impruneta, just moments from Florence, Villa Cesi Resort & Spa offers an elegant retreat defined by refined comfort and understated luxury. Guests can unwind in beautifully appointed rooms, relax by the inviting pool, and indulge in a sumptuous breakfast each morning.
Perfectly positioned, the resort provides effortless access to the renowned Chianti wine region and the timeless cultural treasures of Florence.
In the nearby village, sophisticated bars and authentic restaurants set the scene for enchanting summer evenings under the Tuscan sky.
The price starts from €610 per person* and includes:
The fuel (around €50 – €60 for the whole week), excursions, your lunch and dinner are not included.
*This price is calculated on two people per car.
In order to drive our Fiat 500 in Chianti, you must have a driving license (B) and be 19+.
You have a European driving license? That’s perfect! Your license isn’t for Europe? Then you’ll need to apply for an international driving license.
The designed routes are uploaded on a GPS, or you can navigate with our app. With this GPS (+ €30) you’ll come by the most beautiful roads and arrive at the most stunning stops
Every morning, you can enjoy an included breakfast. For lunch or dinner, we always recommend some of our favorite restaurants. In Impruneta, the home base for your Cinquecento Trip, you will find many cozy restaurants and nice bars.
Your Fiat 500 automatically includes insurance for damage to third parties. For coverage of damage to your own car, you can choose between two options. You may opt for the damage waiver at €109 per Fiat 500, which brings your liability to €0 and requires no deposit. If you prefer not to take the waiver, a €600 deposit will be required, for which you are fully liable in the event of damage.
About a month before departure, you’ll receive an email where you can select the option that suits you best.
CANCELLATION INSURANCE
This insurance gives you the opportunity to book without worries. You’ll be able to cancel your trip to Chianti until the day of departure and receive a full refund, provided that you can show a valid reason for doing so. You can read the conditions here.
TRAVEL INSURANCE
This travel insurance provides assistance in the event of an accident. Make sure you never travel uninsured! Residents of Europe can arrange a travel insurance through us when booking.
Want to find out more about this trip? Take a look at the answers to our most frequently asked questions.
The best way to travel to Italy for your Tuscany trip is to fly to the airport of Florence (FLR). The Cinquecento Trip does not offer flights, so you have to book these yourself. Should you have any doubts, feel free to email us, and we will help you!
If you come by car, you can easily park it for free in the spacious parking in front of the hotel. The address of the hotel is Via delle Terre Bianche, 1, 50023 Impruneta
From the airport you can take an metro (T2) to Florence trainstation. From there you can take a bus (36 or 36B) to Impruneta. It takes around 1,5h to get from Florence to the hotel.
On the first and last day of your Cinquecento Trip, you can book a shuttle for €40 p.p. (per ride) that will bring you directly from the airport to hotel Villa Cesi Hotel & Spa, and from the hotel back to the airport.
Please note! You can only book this shuttle on the first day and the last day of your Trip. You can find the complete time schedule here.
The shuttle can wait at the airport for up to 30 minutes. As flight delays are unfortunately beyond our control, we’re not able to offer a refund in case the shuttle is missed.
From Florence airport to the hotel is about an half an hour by taxi (25km). If you book a taxi in advance, you will pay around €130 – €160. If you don’t book a taxi and take one at the airport, you will easily pay a bit more.
Experience Italy in timeless style. Choose your ideal travel period below and secure your Fiat 500 journey.
It’s completely up to you to decide how you travel. As you drive your Fiat 500, you can stop wherever you want, guided by our personalized roadbook, which brings you towards the most beautiful spots.
From the moment you subscribe to the moment you get back home from an unforgettable Fiat 500 experience, you’ll be in touch with the same people.
The Cinquecento Trip is organized by the team that organizes The Vespa Trip successfully since 2015. Throughout the years, the team has developed strong ties with trusted Italian partners in Tuscany.
This unique way of travelling also means your time ‘on the road’ is actually an amazing part of the experience. Thanks to your Fiat 500, you’ll enjoy the combination of comfort and freedom.