"Caminante, no hay camino, se hace camino al andar. "
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okay this is a candela question as i have a completely guaranteed non-tourist-look formula...it involves a lot of no's:
no shorts first of all (though jer and adrian insist on defying this first rule of spanish summer fashion..but then again they are they and not tourists at all.)
no tshirts advertising bob's truck shop or the u of m drama club or anything with an american flag...wait you're canadian, maple leaves are cool
socks with sandals....puhleeze don't do it
running shoes with dark socks...actually running shoes with any socks larger then those little ankley things
okay i'll stop being such a grouchy fashionista and give you some dos....
layers, light jacket, preferably black so you can wear it day or night (late may/early june is still psycho weather time here, one day sunny, the next chilly)
light crinkly free pants, again that can swing from tromping through the streets to sliding around on a dance floor or slipping into the opera if that is your thing
comfy shoes that don't look like what your standard walmart cashier might don for 10 hours of pricecutting cashiering
sunglasses, hats are nice but not baseball caps because even though they are starting to be seen around, they are still an a-one sign of a tourist.
on to pickpockets...yes madrid is plagued with them and the more touristy you look, the more likely you are to draw their attention...but really they go after anyone who looks like they are not paying attention....i caught one with his hand in my jacket on the metro the other day...my very fashionable gray trench worn with red heeled mary janes and fishnets, i mean i wasn't screaming tourist, i was however closing my eyes against the flourescent lights...silly girl!
be smart, take money out of machines that are preferably indoors and during the day. keep your wallet in your front pants pocket or somewhere like that. if you do the backpack thing, keep it zipped and pull it around front when manuevering crowds. if you look at a map, do so against a wall or something so you can't be bumped. in bars, rests, etc, keep your bag/backpack close by...i like to slip the strap through the chair leg if i am feeling uncomfortable.
bottomline, the pickpockets here are very wiley, but they like easy pickings, don't make it easy. know where your money is, your wallet, your credit cards, and keep them secure...and it is a good idea to have two wallets...one easily accesible with your spending cash and one with your passport, cards, etc. you can tuck the second one in your boot or down your pants or whatever.
oh, and don't assume the waiter/waitress of a bar is on your side, i was the victim of a purse snatching facilitated by the waitress. that said, most of the camereros are perfectly nice and respectable.
other than that, have fun! madrid is a great great great city full of life, wonder, art, culture, garlicky shrimp, yummy red wine, jamon jamon jamon, and basically anything at all you could want. cheers C
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