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iPhone and iPad - to bring or not to bring...

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So I am having an internal conflict about bringing my iPad and or iPhone. I am going with my boyfriend who also has an iPhone (3Gs) and I have a 4G, and we are tring to find out if there is a way to hack it so we can use it Europe without paying crazy fees (from canadian carrier). We think it would be useful to have the data capabilities on the iphone (such as maps) while moving around from place to place... the only thing is we are going to London, Paris, Italy, Greece, Istanbul, Germany, possibly Vienna and Prague, and Amsterdam (the countries I mentioned we are in multiple cities). Is there a data plan with a carrier we can get that is Europe wide for data? We are spending the most time in italy, so if not, atleast one for italy would be good...

Next. I want to bring my ipad because I want to have all of our bookings/itineraries and everything stored on it so I can just reference it whenever I want. I can go on the internet via Wifi (are there lots of places with wifi in the places I am going?) and find hostels/hotels etc. I am a planning freak and I feel I need to have access to all my planning and information at all times. My boyfriend things bringing the ipad is a bad idea because it will get stolen (allegedly) and we have to carry it (come on its so small).

We are doing train transportation, 2 night trains, and some flights in Europe, if that makes any difference with stealing potential. We will be staying in hostels mostly and hotels only if theyre cheap. I plan to carry a day bag around everywhere so I could always bring it with me then...
what does anyone think?

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