You’ve done Florence. The Duomo, the Uffizi, the sunset scrum at Piazzale Michelangelo. It’s genuinely spectacular, but if you never leave the city you miss out on a ton that the region has to offer.

So go out there. On a Vespa.

Riding through Chianti was one of the best days I’ve spent in Italy. Cypress-lined roads, vineyards in every direction, tiny hilltop towns, and the more specific joy of leaning into a hairpin turn with nothing around except wide, expansive views.

This is the full one-day plan: where to rent the Vespa, the route through Greve, Panzano, Radda and Castellina, and why I’d strongly suggest not racing back to Florence the same night.

Let’s ride.

At a Glance

Route: Florence → Greve in Chianti → Panzano → Radda in Chianti → Castellina in Chianti (+ aimless exploring)
The road: Almost all on the SR222, aka the Chiantigiana – one of Italy’s great driving roads
Time needed: A full day. Riding and taking in the scenery, plus taking time to explore Chianti’s many towns
Vespa rental: ~€55/day as of 2026, ~€90 for overnight rental
Licence: Driver’s license and (technically) an international permit for the Vespa, though rental companies don’t really check. Details below.
Best time: Spring and fall are ideal – but if you’re in Florence at all, it’s worth doing. Even in peak summer heat, you’re far better off on a Vespa in the hills than melting in the city.
My verdict: Stay a night in Chianti so you can ride around peacefully at sunset and early morning.

Note: If you don’t know how to ride a scooter, don’t learn on main roads in Italy. Take a look at some tour options below or skip down to this section of the post!

Can You Legally Ride? (License + IDP)

You can legally ride up to a 125cc motorbike with a valid driver’s license and IDP (International Driving Permit).

As the standard Vespa engine is 125cc, there’s no need for a motorcycle license – although if you have one, you can try and find something a bit faster.

Now, if you don’t have an IDP, you’re still most likely going to be able to rent the bike – they never even asked me for mine. Just be aware that if you get pulled over by the dreaded carabinieri, they will most definitely be asking you for yours. And if you fail to produce one, a hefty fine will be in order.

Where to Rent a Vespa in Florence

There are several good spots to rent a Vespa in Florence, but the one I would recommend is Florence Station Rental.

They have good prices, and a great rating on Google. The guy who works there is very friendly and helpful.

I was able to find a Product Red Vespa, which I happen to have the same model of at home in New York. It was very surprising and fun to find one there, because it’s a pretty rare model. It’s the same as a normal red Vespa, except the seat and wheels are red instead of black.

I would recommend booking your scooter on their website in advance, as they tend to go pretty quickly (especially in summer). You have to pay online for the reservation to be made. If you don’t want to do that, just try and show up right when they open (9:30 AM).

Note: There are plenty of other rental shops around Florence – I picked this one both because of its ratings/prices, and because it was in a convenient location for me. Do a Google Maps search for ‘scooter rental florence’ to look for other options (but choose one with good ratings!)

The Route

Greve in Chianti

Around 50 minutes from Florence, you’ll arrive in Greve in Chianti.

Greve is a pretty little town with a unique triangular main square, filled with little restaurants and shops. Walk around for a little, and grab a snack from the bakery – their grape tart is fantastic.

Montefioralle

While Greve is nice, the real star of the show is the small mountaintop town of Montefioralle just up the road.

Montefioralle is super small, and you can walk it in just a few minutes. But what it lacks in size it makes up for in charming cobbled streets and beautiful views.

Panzano

Less than 15 minutes down the SR222 from Greve will bring you to Panzano.

Ride up into the old town at the top of the hill, where there’s a church and a stunning viewpoint that I couldn’t quite capture in the photo below – just take my word for it.

On the way out of Panzano, stop at Antica Macelleria Cecchini, the butcher shop run by Dario Cecchini, an eighth-generation butcher who is widely acknowledged to be the most famous butcher in the world.

Castellina in Chianti

Hop back on your Vespa and ride another 20 minutes to Castellina.

This section of the ride is one of my favorites, with great windy roads and beautiful views.

When you get to Castellina, park close to the entrance to the old town. Then spend a little while walking around, making sure to head up to the castle and down to the covered passageway.

Radda in Chianti

Just Ride: Getting Lost in the Hills at Golden Hour

This is the best part of the day, in my opinion. And you can only do it if you stay in Chianti overnight.

After dropping off my stuff and taking a quick shower at the place I booked, I got back on the Vespa and just explored with no destination in mind.

I ventured off the SR222 and stumbled upon some amazing spots, a few of which hadn’t popped up in research and were still probably my favorite spots of the day.

If you want to follow my route, I basically drove back up to Montefioralle but kept on going past it. Eventually, you crest this hill where you get beautiful views of rolling vineyards, before heading down to a small town called Badia a Passignano.

I also found this incredible road leading to a guesthouse that resembles that photo of Tuscany everyone always sees, with the winding road surrounded by cypress trees. Not the exact postcard shot but pretty damn close!

Same Day or Stay Overnight? (Stay Over)

Answer is simple. Stay overnight.

Unless you’re really crunched for time and only have one night in Florence or something, spend a night in a town in Chianti.

It’s not so important where exactly you stay – but by being in the region and not having to rush back to Florence to return the Vespa, you can take your time enjoying sunset and the early morning hours.

I personally stayed at the Bella Vista Hotel in Impruneta, and it was a great spot. Nice and quiet, and you get much more bang for your buck compared to a place in Florence.

I paid $50 USD for a very solid private bedroom and bathroom, a price you can only find hostels for in Florence in peak season. Book the Bella Vista here.

If you want to see some other options, search for places to stay in the region on Booking.com!

Note: Use my links to book! It adds no extra cost for you and I get a small commission to spend on something stupid, most likely.

Can’t Ride? Take a Tour

While I highly recommend having prior motorbike experience for renting a Vespa in Florence and Tuscany, tours are always an option if you don’t.

There are plenty of tour options, and they definitely have their bonuses. For one, you can indulge in as much Chianti wine as you like.

I’ve posted links to a few of the better tour options below – considering the rental cost, the overall price you pay isn’t that much higher. It more so depends on whether you prefer to explore places independently or with a guide.