The region around Siena is known for its sumptuous landscapes, filled with world-famous vineyards.


There's no better way to discover Chianti than on an authentic Italian Vespa. During your trip you'll cross vineyards, timeless villages like San Gimignano and Montepulciano and you'll be treated to endless amazing sights across the hills of Tuscany.

You'll stay in Siena, a medieval city where you can find numerous traces of the past. It's the perfect place to start your adventure on the roads of the Chianti region.


Picture of the Vespa Trip in Chianti
Picture of the Vespa Trip in Chianti
Picture of the Vespa Trip in Chianti
Picture of the Vespa Trip in Chianti



Starting from Siena, we have planned three beautiful day trips that will allow you to discover as much of the Tuscan backwoods as possible. You can take these trips on your own (with the help of GPS & our road book) or with the help of our local guide. In addition to these day trips, we also designed two shorter routes that you can explore on your arrival or departure day.


This first track (140 km) takes you via Greve & Radda in Chianti to the gates of Florence, the city of Michelangelo & Da Vinci


The second track (85 km) guides you to some gems of the region: San Gimignano, Volterra & Monteriggioni.


The third route brings you South of Siena where high quality wines are produced. Every village you'll drive past will ring a bell for the wine connaisseurs. Montepulciano and Montalcino became world famous.

Chianti map Chianti map Chianti map Chianti map
Chianti route Part #1 FLORENCE
Chianti route Part #2 SAN GIMIGNANO
Chianti route Part #3 MONTEPULCIANO



Hotel Garden**** is situated just 600m from the medieval town center of Siena. It has typical Italian rooms, a refreshing pool and a breathtaking view you can enjoy during a delicious breakfast.*

*For the period 27th - 31st May this is the Four Points by the Sheraton hotel.

Picture of a hotel during the Vespa Trip in Chianti
Picture of a hotel during the Vespa Trip in Chianti
Picture of a hotel during the Vespa Trip in Chianti





your own vespa

You get your own Vespa during the entire trip. You will receive it on the day of arrival at 5 p.m. and return it on the last day at 12 p.m. in the afternoon. If you want to receive the keys of the Vespa a little earlier or keep hold of it for a bit longer, you can choose the "Early pickup" and / or "Late drop-off" . For example, the Vespa is yours the first day from 12 p.m. and you can return it at 7 p.m. the last day.

Driver's licence

You will need a driver’s license for a normal car (B) or a motorcycle license (A). The license AM is not accepted. You need to be 18 to drive the Vespa's, but minors can always join as passengers. If you're a European citizen, your national license is sufficient, but if you're from outside the EU, you will need an international one.


Never driven a Vespa before? Not a problem! We offer the option to arrive early in the day (preferably before noon) and take a Start-to-Vespa course (+50€ per Vespa). Our guide will explain you the tips and tricks of driving a Vespa and make a calm test drive the day before the trip actually starts.


With the keys of your Vespa you'll also receive a GPS, mounted on your scooter, where you can see all the tracks of this trip. If you don't follow our guide, Mario, you can go on your own adventure without getting lost.


Daily breakfast is included. We recommend restaurants for lunch and dinner although the hotel also offers light lunch and amazing dinners. In our basecamp, Siena, you will find some of the best restaurants in the region and for after dinner entertainment you can visit various local pubs.


Every arrival and departure day you're invited to hop on our transfer bus to get to either Pisa or Florence airport or the hotel. The shuttle will go twice a day (before noon and in the later afternoon).


Yes, that's possible. However, there is a single driver supplement of €120 per person. If you sleep alone in the room, there's a supplement of €250.
Both are possible, so you decide! With our road book and GPS you should be able to drive the journey independently. However, you can also opt to follow our front Vespa driver, who knows the entire area like the back of his hand.
The best way to get to Siena is to fly to the International Airport of Pisa or Florence and take our shuttle service to the hotel. Another option is to take a taxi to the hotel (around €70). You can also drive here and park your car on the parking of the hotel.
Upon your arrival at the hotel you will arrange the administrative check-in. You can check in from 2 p.m. onwards. Then you'll receive the keys to your Vespa, your road book, the GPS and you can already go for a short first trip. The next three days, our guide will show you all around the hills of Tuscany or you can go and discover the area by yourself. On the 5th and final day, you can go for a last trip before you return the keys.


You are automatically insured for all damages to third parties. You will be asked to block an amount on your credit card to insure any damage to your own Vespa. You will be able to choose between different insurance policies after your registration.


We recommend that you take out a cancellation insurance, it doesn't cost much and it can potentially save you a lot of money.

If you can no longer participate, but you can find a replacement, you must send all the necessary information no later than 7 days before the departure date so that we can change the reservation free of charge.

If you take out a cancellation insurance and you apply to the conditions, you will be reimbursed for your trip (with the exception of the cancellation insurance costs).

If you have not taken out a cancellation insurance and you wish to cancel your trip, you will receive a maximum of 50% of the total amount in case you let us know more than 4 weeks before your departure date, 25% if you contact us 2-4 weeks before your departure and 0% if you let us know less than 2 weeks before the departure date.

Travel Insurance

We also offer travel insurance that helps you in the event of an accident on the spot.

If you have never driven a Vespa we strongly recommend you to book a 'Start-to-Vespa' course. The first day, your guide will give you a practical explanation and you will be able to make a test ride. This will cost an additional €50.
We recommend the best Italian restaurants in the evening. You can choose to opt in and have dinner with the other Vespa trippers or pick your own place to have dinner. It's completely up to you.
Five days and four nights at our four star hotel, breakfast, the rental of your amazing Vespa per 2, helmets and a lock, a GPS with the uploaded routes, a road book, the care of our Vespa Trip Guides and the experience of a lifetime. The fuel for your Vespa (around €20) is not included.

Other questions, check our FAQ!




Below you can find all available dates for The Vespa Trip Chianti. Click on your departure date to book your adventure.

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Any doubts? Check our other destinations: The Amalfi Coast or Sicily.

Rather travel around and stay in different hotels? Check out our Giro Classico in Tuscany here!