Hello Sophie..great name BTW my granddaughter is called Sophie
I can only offer help regardingTuscany I went on this tour a few years ago, have a look in the review section if you type in Highlights of Tuscany I am sure you will find many reviews from people, this is a very popular tour, it's not to hectic, I am not sure what the weather would be like in September I went spring time and it was HOT!, there's a nice village near by, and the trips out are worth doing I did not do the boat trip as I am not a lover of water. Hotel right by the beach. I am not sure what your idea of fun activities are? Most evening were spent hotel based there is a nice veranda to have one or two or more drinks sitting watching the world go by, when you have an idea of which date your going for ask Julia on the editors board if she can give you some information IE age range tour group size, male / female ratio that might help you make your mind up..
As for doing one tour after another I think you would need to speak to the Girls/Boys in the office who are very helpful I am sure they can point you in the right direction with that question.
I hope someone can give you information regarding Sorrento, Good Luck
Cindy