Cycling in Tuscany - renting and routes


My husband and I are planning a self-guided tour in Tuscany by bike in order to combine sport, discovery of the region at our own rythme and visits at the end of september.

1. Rent : We want to rent bikes in Firenze (we land there and we plan to spend two days there before the bike "expedition").
Moreover we also need to rent a sort of "trailer" for our small lugages.
So do you know where we can rent good bikes and a trailer in Firenze ?
Which kind of bike do we need to rent ?

2. Route : I would also take the opportunity to detail the route we plan and have your comments in return :
day 1 : Firenze to Greve or Castellina (if it's not to long)
day 2 : Greve/Castellina to Abbey di Monte Olivetto
day 3 : Monte olivetto to Montepulciano
day 4 : off
day 4 : Sienna to San Gimignano
day 5 : San Gimignano to Firenze
Does this route seems to be doable ? (we like cycling - even if we have very little opportunity to do long outings during the year - but we are very sporty)
Does it leaves time to enjoy landscaps and visits of the villages along the route ?

3. Eroica : I read on the forum a message in which the "Eroica" route is mentionned. Which kind of road/path does it follow ? Does it be well marked ? Which kind of bike do we need if we take it ? Is it possible with the trailer (luggages) ?

Thanks in advance,


The Tuscan Expert ;-)
Staff member
Ciao Mathilde and welcome to the forum!

You have a great tour planned, you can definitely do it on your own. It is a great way to see the region and combine it with your own rhythm. The two things that come to mind as soon as I read your plans are these:

1. LUGGAGE and HILLS - You don't even want to consider a trailer to carry luggage, major no-no. You will want saddle bags and need to fit everything into them, with any additional stuff tied to the top of the back rack. Tuscany is made of HILLS, lots of them. Let's say Chianti and the Val d'Orcia are not bad in terms of the hills, they are "soft" but if you're going up 200 meters and then losing them again after the next hill... well, it is a workout!!

My husband is a big cyclist and he says Florence - Greve - Castellina is about 3 hours, with no luggage at all. So it is definitely doable in one day... but he definitely recommends NO trailer, he's never ever seen anyone with one, only with saddle bags.

2. REST - I just calculated distances using Google maps:
Florence - Castellina: 42km
Castellina - Asciano : 56km
Asciano - Montepulciano: 33km
Montepulciano - Siena: 60km
Siena - San Gimignano: 35km
San Gimignano - Florence: 47km

I think even if you are in wonderful shape, you will want to take some time off the bike and give them rest. You can do that by taking the train with your bikes for certain parts of the route: regional trains often have a wagon at the end that allows for bikes as well, so you could theoretically cut back on the time on the bike by taking the train from Montepulciano to Siena, for example and from Siena to Poggibonsi and then bike only from Poggibonsi to San Gimignano.

If you look at train timetables on, you'll see by clicking on "i" symbol for the train whether they allow bikes on that particular one. Do take note, as not all of the trains always have that wagon and will not let you get on with your bikes if they don't.

Take these considerations to adapt your itinerary..... keep in mind what roads you'll follow. Most people here follow the same roads cars travel on, many can be quite narrow and definitely no place for a trailer.

As far as the Eroica goes, it is an bike racing event in the fall but the route has been marked permanently so you can definitely also follow it! It however doesn't fall along the route you have planned up to now. It is around Gaiole in Chianti, it is mostly all on "white" roads which are the unpaved roads that go off the main road to the wine estates and houses in the countryside. It is a great way to see the area. But it doesn't cover any of the route you were planning so if you want to do this, it would mean major changes in your plan. Check out site for the Eroica to see the route here:

Finally, as far as bike rentals in Florence - road racing bikes are out with saddle bags, so you'll want a hybrid or mountain bike. The biggest rental in Florence is but you can also find other places such as in the same area offering bike rentals, too.

HAHA, I just saw the first site has proposed itineraries from 2 to 5 days for self-tours with train travel back to Florence included... so it reinforces what I was telling you above about getting some rest. See the routes here. If you look at the first route of the 3 days section, it is the same one you have planned all the way down to Montepulciano ;-), then you can follow the part of the next route from Siena to San Gimignano and Certaldo and from there even take the train back into Florence.

Once you have the days set, you need to check out to book accommodation for each night. You don't want to arrive into the small towns and discover that the few hotels in town are all booked (many are outside of the towns, too). None have "vacancy" signs so it will be hard to see who has a room, and end of September is still pretty popular, so you'll want to have the place to stay planned out and not have to worry about that at all - just concentrate on the ride and seeing beautiful Tuscany!!

Feel free to post any other questions - and also know we'd love to hear how the whole trip turns out!!! :)


New member
Similar plans

Wow- thanks for all the great ideas/suggestions.

I will be doing a very similar trip in the first week of October. @ Mathilde, I am not sure if your dates are exact but perhaps there is a luggage service we could use and have them take luggage for 4 people to cut costs? Does anyone know of luggage couriers?

Are there any places out there that provide maps alone and no other services?

There are a lot of tour operators but they all seem pretty pricey. We are avid cyclists and my bf is a bike mechanic so we arent sure we need the support. Least lets hope not :)

Please let me know what else you have found out. Thanks for the post!

Caio, Layla


The Tuscan Expert ;-)
Staff member
Ciao Lander,

I think many of those tour companies might be willing to offer just part of the services that you need since many of them are willing to customize their tours - this one for example -
offers customized tours on what you want to do. It just makes me think that they'll likely be willing to offer baggage service as well as maps to help you do the itinerary you want with just the right amount of support you need, particularl if you're avid cyclists and your BF is actually a bike mechanic!
So you might want to contact those tour operators you found (I'd particularly look at local ones specialized in that service) and ask - shouldn't hurt, right? ;-)