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How and what to pack for 2 weeks in Spain in October?

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Hi everyone!
I will be going on my honeymoon to Spain for the last two weeks of October!
We will be flying to:

with at least 3-5 nights in Granada, Seville and Barcelona. We have a shorter stay in Malaga.

What size suitcase should we each (or together) bring to make for easy traveling? We will be taking the bus, train, and a flight within Spain.

What are the basics to ensure we are comfortable (we also like to dress fashionably :)
in sight-seeing, dining out, and of course hitting the nightlife? :)

Also- I'm concerned about the pick-pocketing and want to be smart. What kind of bag/purse should I bring? My fiance wants to bring a backpack- if he carried it in front of him would that be safe enough?

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