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help planning trip Italy to Spain

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Hello, I would love any advice and help for a trip to Italy and Spain.

We have about 8-10 days.

Italy--Rome, Florence, Venice **Milan if possible.

Spain--Barcelona, Madrid, and a beach or Spanish Islands (The Canary Islands is the best one??)

We are happy to back-pack, hostel stay, or do airBnB, etc.

Advice on:
1- which city to start and end in
2-best places to look for transportation within the two cities
3-MUST SEE AND DO at any or all of the cities.
4-anything else you feel I should know.

THANK YOU!!! All you experts. I am sooo appreciative for any ones time with comments and suggestions.

I have backpacked Greece and Thailand...it is time for Italy and Spain!

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