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Annoying Practicalities
I have learned the HARD WAY that these things are very important, although they are easy to blow off:

1) Travel insurance!! Please please take some out because I never have and as a result had to spend lots of money, particularly in Australia where I needed to get 22 stitches and loads of pain meds.

2) Cover travel books with postcards or book covers so that people don't realize you're a tourist.  This used to be more applicable in the BRIGHT YELLOW Let's Go days, now the revamped ones are much less conspicuous.

It would be painfully obvious to any local of any country that I am a tourist.  I try to use the language and dress inconspicuously, but the minute I open my mouth, they'll know. And that's okay; to me, that sort of exchange part of what travel is all about.

3) Make a Xerox copy of your passport, driver's license and credit cards. Leave one copy at HOME, take the other copy with you and carry separately to the originals. I have been the victim of many thefts.  I never did the making-copies thing when younger, but I certainly do now.

4) Internet access is prevalent everywhere.  I keep a scan copy of my pass and important traveller's checks online.

If I happen to lose anything I can download it easy enough. I do the same with my own 'guidebooks'. I prepare info on places I want to visit, restaurants, etc. and print it when I'm in that area.

5) Try to reduce your guidebooks by gluing them in a little notepad,  Tgus dispenses with internet access and you can write things on it as you hear and read more. Small maps are great and timetables too. Servers can crash or go down and it kills the colourful guidebook 'rob me' advert

6) Everyday before I head out in a city, I pre-fold my maps so that the area I'm going to cover is readily accessible. That way, I don't have to fumble around on the street trying to figure out where I am; I'll have the general area ready to go.

7) Before hopping onto a public transportation, I study a map and jot down on a piece of paper any transfers or stops I need to know. Then it's easily accessible and I don't need to fumble with a map during the trip over there.

For example, if I wanted to go from the Young & Happy Hostel in the Latin Quarter to the Eiffel Tower, I'd write:

M5 (towards Villejuif) PLACE MONGE --> PLACE D'ITALIE
M6 (Charles de Gualle) PLACE D' ITALIE --> TOUR EIFFEL

The worst thing on a windy or crowded day is unfolding the wrong side to a cumbersome map. It's especially bad for females, because without a doubt, only the strangest men approach you with the "best" route they want you to follow.

8) We got a free cell phone to use on our trip for Germany, so we took it along in case of emergencies--never took it out of the case. I don't want to be in touch with anyone other than my travel companions when on vacation.

9) Bring a watch!  You like to think that you are this free spirit when travelling, but the 'annoying practicality' is that sometimes you need to know what time it is.

10) Avoiding Pickpockets

Many people like to wear either a money belt or an around-the-neck pouch. There are all kinds, but here is a link with an example:
money belts & pouches

I do like to keep my money for the day in my trouser pocket, to make it easier to get to. I have a couple of pairs of trousers and skirts that have little zippered pockets in them, so try to wear those while travelling. I've also got a couple of those little embroidered cloth coin purses, and I'll sometimes pin one to the waistband of my trousers or skirt if I'm planning to wear my shirt un-tucked, and keep my money for the day in that.