Florence & Tuscany

Have you ever driven on the 'other side' of the road, as they do in Italy?
If not, would you feel comfortable doing so, with hard streets to negotiate and difficult parking ?
May is coming into peak season and anything decent will be impossible to secure without prior booking.
You can't really ask the Forum for accommodation advice, without specifying a budget (and as you're travelling in the next few weeks you should really indicate exact dates as well).

Thanks,
we are looking 2 or 3 stars
need recommendation about how many days Tuscany and Umbria by car, don't want to rush really like to Enjoy and relax.
will be a good idea to stay in two or three places and from there visit around, no idea where and how many days.
I don't have a problem driving from the other side

waiting for your advise
cheers

If you don't mind moving every few days then 3 locations works...
North - near Lucca (can visit Pisa from here too)
Central - near Siena (can visit San Gimignano from here)
South - near Montepulciano (can visit Pienza and Montalcino from here)

In Florence, this 3 star is well located, well priced, and well reviewed ...
http://www.hoteldeimacchiaioli.com/

We have done trips to Tuscany (outside of Florence) 3 times; twice for one week each and once most recently for 2 weeks. What we chose to do was rent a place for a week in or very near a hill town so we had the restaurants and such in the evenings and could drive to sites to visit during the day. We like the area south of Siena in the Val d'Orcia. Most apartments rent for a week sat to sat. If you want to move around I would not choose more than 2 locations; you need to arrange lodging before traveling. If you want shorter stays then hotels in the historic centers of smaller hill towns with parking would be IMHO the best choice.

Thanks. Now is time to have a car. I booked Florence 3 nights and from there We like to do Tuscany and Umbria
we have approximately 12/13 days.
One village I really like to see and enjoy is san giminiano.So I will need advise where to stay
some people say that Chiani is nice ( but from here which towns or city Can I visit?
Montepulciano which towns or city Can I visit?
and perhaps Cortona which towns or city Can I visit?
and to see Umbria what do you recommend to stay which city I should go,?
we think to drop off car in Sorrento.
from the way from umbria to south which place to stay and visit ?
Then Sorrento 5 nights without car and please can I have some advise places to visit. Positano is better than Sorrento or is
more expensive.
Need to book ferryes to positano in advance ? and capri. please let me know if 5 night is too long or will be better to stay 2 nights in positano.
we don't like to go for one hotel to the other perhaps Sorrento is goos to base, waiting for your advise.
Then soreento to naples ( how I get there??stay 2 nights and finish in Rome
thanks