I wish. Not something I'd usually do (hence the call for help) - its a gratis invite.

ride a vespa, smoke lots, shout "ciao bella" at pretty girls.

or if you want to wind them up, order a cappuccino after lunch

hang out in the town square of an evening.

That's about equidistant between rome and florence so I'd suggest them two if you are feeling active, or just guzzling pizza pasta and wine if not

Eat, drink, sleep, repeat.

Cortona, Montepulciano both nice, as are the obvious Siena, Orvieto and Assisi.

Stay away from Rome, Florence, Siena and Montepulciano.

For mid August, Tricky is probably right on Siena and Montepulciano

Had potentially the option of a couple of days in Pisa, but giving that a miss.

Anyone have a solid local knowledge of any classically Italian restaurants/cafes in the area? I'm thinking ivy on the (external..) walls, run by the same family since the 40s, couple of Italian convertibles parked outside etc, etc

Yes, in Italy they are just called "restaurants"

Pinkerton - ivy on walls etc La Falcionere outside Cortona. Most memorable meal pretty much ever there, outside on the terrace, overlooking the valley. Sublime food. But nb this was 15 yrs ago. Same family i believe however. Also, Trattoria del Pescatore on shores of Lake Trasimeno. V simple lunchtime place.  Effing unbelievable fish esp the soup thingy full of tiny clams in there just for flavour as well as varied fish, mr asked for a toothpick to get them out, i dont think diners usually bother!

i would love to return to either place.

* Il Falconiere, sorry

(when i went they had a stunningly beautiful boxer, a pup still, most massive balls i hav ever seen incl human!)

Thanks Minkie! For all descriptions... 

pinkerton, please report back, if you partake,