Tuscany without reservations?
 

We are flying into Milan, will rent a car and make our way towards Tuscany. At this point in our trip we would like to be spontaneous & are not sure yet where we want to stay - definitely somwhere in the countryside - villa or castle, etc. Since we are goin mid-June, for 5 days, do you think we will absolutely need reservations as it's high season? Or should we be OK just having a few places in mind & go from there? Has anyone done this in summer? Thanks!!

PS Also any suggestions on coastal cities in Tuscany - ex Livorno - any recs???

Do you mean next month??
I just returned from Italy, and the tourists are there already. I'd get resies if possible.
A town where we stayed and highly recommend is Santa Margherita Ligure. It's a charming little port town that doesn't seem to be overwhelmed with tourism. Lots of little shops, markets, restaurants, in a low key atmosphere and a beautiful setting.
We stayed at a little bed and breakfast called the Nuova Riviera, that was very charming, and a short few blocks walk to the little port area. Really lovely there. An easy day trip from there to Cinque Terre and to Portofino.

Maureen thanks for the tip. Yes, I do mean next month. We would really like to be spontaneous with the reservations, but do not want to get stuck.

Angela,

I would highly recommend reservations. The towns are small and so are the various forms of lodging. How much time are you willing to spend out of your 5 days going from town to town between various B&Bs, hotels, etc. to find a room? Could get very frustrating very quickly.