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Italy honeymoon Itinierary help!

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Hi everyone. I posted a couple months ago about Italy and a few other places and now we have decided that we want to stay completely within Italy and Sicily for 4 weeks. We want to see Sicily, Lecce (puglia), Rome, Tuscany and maybe Venice. We can go for 4 weeks anytime from June thru Aug 1, however July would be best because we the lease on our apartment goes through June, which means we will be paying rent through the entire month of June. Is July really that much more crowded and hot than June?

Folks in my previous post suggested to start in the south (sicily) and work our way north because it's hot down there earlier. We are using airline miles so we are pretty limited on our options and it seems easier to get a flight into Rome, rather than Sicily. We can definitely fly out of Milan, so that is not an issue. So my question is, would it be ok to fly from the states into Rome and then somehow have to get to Sicily to "start" our trip...then work our way by train up to the north? Or should we try to find a way to fly into Sicily (there are routes from the US on american, but using miles we would have like 4 stops to get to sicily and it would take forever!)

Another option is to use miles to fly into a hub like Paris or London and then try to find a cheap flight to sicily.

Any suggestions on how to make it work?

Thanks a million!