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need to book hotels or can I make it up as I go along?

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for independent "wandering" through Laos, Nepal and ? from 11-10 through 11-23, can I book same day/2 or 3 day ahead good accomodations in Laos, Nepal and (fill in the blank based upon geography and time--maybe Thailand?--though I went to BKK, Chang Mai, Chang Rais and Chang Sen a few years ago)? I also need to arrive in Nepal on 11-23, and begin this journey on 11-10 in Vietiane. Ideas for where to go, how long to stay, and how to travel are greatly appreciated!

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