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Flying with Air France and Alitalia

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Hi there,

In March I'm flying from Toronto to Milan, with a 1.5 hour layover in Paris. It's Alitalia, operated by Air France. On the back a week later, I'm flying nonstop from Rome to Toronto with Alitalia.

1)on the way there, is a 1.5 hour layover enough time, assuming my initial flight is not delayed? I've never dealt with a layover before and I'm travelling alone, so I'm starting to get really nervous about this.
2)I'm paranoid to check my baggage in case it doesn't make the layover. I'll have gifts in the bag which I don't want to get lost or delayed. They are bamboo embroidery hoops - I can't find any evidence anywhere of those not being allowed?
3)I have a small rolling carry-on suitcase (I believe the external dimensions are 22.5" high x 15 inches" x 10"). This seems to be above Air France and Alitalia's dimension limits? I was able to bring it onbaord a flight to Edinburgh two years ago. I'm guessing I should look for something a bit smaller?
-if I find a spinner suitcase the is within their dimensions and weight, can I also bring on board either a Fjallraven backpack (the regular kind the hipsters wear) or a Herschel Little Americana backpack? Or do they want you to bring a small purse as your addition carry-on and nothing bigger?
-last question - Air France's weight limit is 12kg for both bags. Fine. Alitalia's website says 5kg - surely that must be for both bags combined??

I'm a total spazz.

-lastly - any suggestions of things I must see or do in Milan and Rome? I am NOT well travelled, clearly.

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