Hello all and thank you in advance.
Hubby and I going to Tuscany for the first time June 8th. Reading and reading and reading we came up with an itinerary/route for the days we are going to be driving in the area and wanted to see if the experts had any thoughts on the routes to follow... looked at previous posts and ViaMichelin to pick the scenic roads. Wondering if anybody has alternative suggestions or any input.

Not sure what the best format is for this question so I'm listing the road names I saw in the maps...apologize if the post is too long. As usual, thank you so very much!

Leaving Florence follow SR222, then SP2bis to Radda in Chianti.
Jump on SR429, then SP1 to San Gimignano.
Jump on SP1, SP69, SP62, SP4 then SP15 to Volterra.
Follow SR68 and then Raccordo Autostradale Firenze - Siena to Monteriggioni
and then follow SR2, SP51and then SR222 to Siena
https://tinyurl.com/y95mwfu6

From Siena SR2, Strada Provinciale del Brunello and then SP14 to Montalcino.
Leave Montalcino via SP14, SR2, SP137 and SP146 to Pienza and then follow SP146 to Montepulciano.
https://tinyurl.com/yc9n7vv6

FInally Montepulciano to Orvieto via SP146, SP40, SP53, Strada Provinciale della Valle del Rigo, SP321, SP82, SP50, SP49, SP48, and SP44.
https://tinyurl.com/y8yfepny

I am laying out this as a general route to follow on the days we have, always keeping in mind that we might not get to see it all because of the number of days we have in the area. I have an Airbnb reservation in Florence already, but I was actually thinking about taking a chance and finding accommodation as we go during this road trip... I usually leave home with everything booked because my budget is always very restricted. That was another question I had, do you think finding small, cheap accommodation as we go each day would be too hard/become too expensive in June? (I am finding places around $50 USD right now) We are both carrying just a 40L backpack and we really don't mind changing places to stay as we go when on road trips.

Thank you very much!

Sandra






Thank you very much. Always appreciate all the help.

It's hard to make specific comments without knowing where you'd be stopping for the nights, and for that matter knowing how many days/nights you have. FWIW, I don't like a string of single nights and prefer a hub-and-spoke strategy for sightseeing. I like to keep the destinations within about an hour of the hub and visit only one or two towns on any given day.

You have prioritized using secondary roads, which is my preference, but my Siena to Montepulciano route would include stopping at Abbazia di Monte Oliveto Maggiore which I find more interesting than Sant'Antimo, but you have to time your visit carefully as the monastery closes for a few hours in the middle of the day. It's an especially enjoyable place to go on a hot day because of its forest setting.

https://www.discovertuscany.com/what...-maggiore.html

June accom; I do this sort of thing all the time in June when I cycle through Italy. My advice would be

1) don't use this technique on Friday or Saturday nights
2) do use something like booking.com to review possibilities at breakfast for the coming night, I would tend to book them at that time when you have the day's plan in mind
3) Tuscany has far fewer "rooms to let" signs in windows than it used to
4) AirBnB hosts are not always organised to leap to be ready to serve new customers if they only get the booking that morning (they often have day jobs) so if using that service book at least the afternoon before to have time to respond and so everyone is happy campers.

On Jean's advice, Monte Oliveto Maggiore was one of Christendom's most famous sites in the middleages and the position especially on a hot June day was well selected. The Monks lease out the gate house as a restaurant which is expensive, however on the road up from the valley bottom are two good restaurants with rooms one of which was very good to us when we turned up un-announced.