How much planning is really needed?

Basically, I plan on taking a pre uni gap year next year/end of this year. I want to venture over to thailand, and basically do all the countries there and around that have things to see, exciting and new experiences, people to meet and not really a neccessity but somewhere to have a nice relaxing drink. Also i want to check out New Zealand!

My current dialemma is that i dont know how much to plan it all! I like the idea of just booking my flight out there and just seeing where I end up, by any means sort of thing, wether it be trains, busses, tuk tuks or sailing! and when i run out of money getting the first possible plane home, or even a bit of bar work to keep the party going!

But is this realistic, for example will i be limited because of the visas I will be able to get on the road? and obvisously some visas are only a few weeks long, but can you extend them? Will i be able to get travel to all manor of places without planning? And one of my main queries is that will i be able to travel around and find something to do and somewhere to go without reading up on it first? 

Thanks everyone who replies to this, i need some travel wisdom! 

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