I've never used travellers checks ('did' South-America for 8 months last year by the way). Instead I left home with 2 cards (debit and credit) and a emergency line with my bank (the Netherlands) able to provide me with extra cash in case I run into trouble. The week before I left home I had both of my cards changed (new magnetic strip). Also I gave my parents full acces to my bank account, so that they could act on my behalf I would run into trouble.
Unfortunately I ran into a lot of trouble. About 4 months into my trip (inside Bolivia) my creditcard died. Well it didn't die. The magnetic strip just got damaged. So I called my bank and my parents. Great, they could send me a new card. Asked my hostel to see if they could send it there. They could. I was happy. In about a month a new card would be waiting for me and the bank had a number of secret codes and stuff to activate it, so I wouldnt have to worry about safety anytime soon.
A month waiting is long, but since I was already planning on staying in Bolivia for another month, living in a place where I wouldn't spend much it didn't seem bad at the time. Besides, what else could I have done? I needed that card to purchase things, and my debit card didn't work on most of the ATMs.
So I waited, and waited.. The card never came. Am not sure who do blame. Maybe it was my dodgy hostel (though they seemed reliable at the time, there were all kinds of strange things happening), the card got stuck in mail somewhere or there was something else wrong. Whatever it was.. I decided to continue traveling with just a debit card and my emergency line. 6 weeks later my debit card died. Called the bank again. 'We're very sorry for your inconvenience but your credit and debit card are linked. We have send you both cards by mail, and our policy is to cancel old cards 6 weeks after the new ones are send. We can send you new ones if you want but it'll take you another 6 weeks.'
That was pretty shitty and unexpected. So I called my emergency line (I was already traveling with some extra money, didn't feel comfortable with just one card). 'Can you send me some money please?' 'Sure, which country are you in right now?' 'Brasil' 'Oh let me see. Wait... Unfortunately our bank doesn't do business with Brasil. You'll have to go to another country to collect your money.'
It all turned out fine. I went to Paraguay, got some money. Luckily I only had 2 weeks left on my trip when my second card died, and I'd been traveling with enough money to be able to go to Brasil. Had my plane ticket home, and all I had to do was enjoy and guard my money carefully.
Met some other travelers who also ran into money issues. One of the guys I met there was actually traveling from bank to bank (he lost both of his cards but luckily his bank had offices all across south america. All he had to do was show his passport.). Of course, most travelers didn't have this kind of luck, and were traveling with others who could help them (I was all by myself for the most part).
Looking back on my trip there are many things I'd do differently. First of all: Getting at least 2 creditcards from different banks. Secondly: look up if my bank has offices in the countries where I'm traveling to (offices mean passport are sufficient, and passports can be given within a week by your ambassade. Getting cards send over is much more difficult) Third: See if banks offer an emergency line where they can send money within 24 hours (VISA apparently does). Fourth: Travel with a bit of emergency money at any time. Fifth: If you lose cards don't forget you can still purchase a lot of things with just the numbers (for instance: for making hostel reservations all you need are the codes. You never need to show anyone the actual card). Sixth: Look up whether traveller cheques are a good option and read other people's experiences. Seventh: Give someone you trust and who lives in your country of residence full acces to your bank account. It might sounds unneccesary but in case you do run into trouble, banks have additional means to help you.
Wow. This message turns out to be pretty long. Anyway I hope it is of some use.
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