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Help Choosing a bag?

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I will be in Italy for 5 months staying in one spot, and then travelling around Europe for 1-2 months afterwards. I will be there for Winter and Summer

I need help choosing the right size bag? I am thinking 40-60 L

The bag I am looking at so far is the OSPREY Womens Waypoint 65

I am 18 yrs old travelling solo and about 5'7 54 kg. What bag do you recommend, and what can you fit in that bag?

I am thinking of taking
Laptop 2kg ( Do you reckon I should buy an Ipad or Chromebook instead ? )
Sony Nex 5 Camera
Toiletries (I hardly ever wear make up, so won't be to much)
Light weight Nike Free 5 Sneakers
Jandals
Ipod
Silk Sleep Sack
1 pair of Togs
4 x t-shirts
1 x thermal long sleeve top
1 x thermal bottoms
1 x puffer jacket
1 x rain jacket
1 x shirt
1 x skirt
1 x dress
5 x socks
5 x underwear
2 x bras
universal adapter
1 x scarf
1 x beanie
1 x shorts
1 x leggings
1 x pants
1 x travel towel

Anything I should leave or bring?

I'll be wearing black hi top chucks, jeans, anorak on plane

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