Should you or should you not book your accommodations in advance? This is a question I get asked a lot, and it's a tricky one to answer because it depends on a lot of different factors: Where are you going? When are you going? What kind of traveler are you? What kind of place are you looking for? Are there any special festivals happening while you’re in town? So many questions, but you need to consider all of them.

When I first started traveling, I used to pre-book all of my accommodations well in advance. I was still quite inexperienced and I wanted to have the reassurance that I had a place to sleep every night.
However, during my most recent travels (particularly backpacking in Southeast Asia) I found that I could often get better deals if I showed up at a guesthouse and asked to see a room rather than making reservations in advance. This generally involved doing a bit more legwork (ie. visiting 3 or 4 guesthouses until we found a decent one with availability and fair prices), but it paid off in the end.
That being said, there were also times when I just clicked 'book it now' because I didn't want to deal with the hassle of finding a place after having spent a full day in transit.

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