Hi,
I will assume you're talking about low-season travel? I like to book the first night or 2 and then just wing it. In SE Asia there are literally thousands of small guesthouses and hotels. Actually, in many places the hotels will find you - I've had them come out on the street soliciting me for a room in several places in Vietnam. The only trouble you'd have is at a holiday/fair/sports event when the whole town is booked - very rare. Hostel sites only list a small number of places - some places even rent out rooms in their homes (not always legal). You will have no problems finding a bed. Beware of taxi drivers suggesting a hotel - they're being paid to do so, and always inspect the room before you agree to it (cheaper rooms often have no window).
It depends where exactly you're going but in general I'd say in most places you can just turn up.
A couple of exceptions are Koh Phi Phi where The Rock backpackers hostel is generally booked up every day, but they don't take internet bookings anyway. And also the hostels in Koh Pha Ngan are usually booked out over Full Moon.
I usually book my first couple of night's accomodation for when I first start my trip, and then just turn up at places after that. But even if I don't book I still use hostelworld and hostelbookers to get an idea of which hostels are popular.
Another tip is to enter tomorrow's date for a hostel on hostelworld or hostelbookers and see if it comes up with vacancies or full. If every hostel in a certain location has vacancies then as a general rule you should be okay to turn up at any time and find somewhere (except maybe when there's festivals or sporting events happening).
Most of the time we don't book in advance. We just make a list of preferred hostels/hotels and their addresses and prices in our next destination, then take a walk around when we arrive - we take turns one of us stays with the bags while the other one goes and looks to find a place. The exception to this is if we are visiting a place during a public holiday then we definitely book in advance.
Maybe you should start by booking in advance at the beginning of your trip (before you reach each new place) and then see how comfortable you are with winging it? The thing we don't like about booking in advance is that you don't really know what you are getting and the rooms could be awful...much prefer turning up and inspecting the rooms properly!
Here's a little tip that is actually still somewhat undercover (we only just launched this properly last week, but haven't actually announced it ). Travellerspoint now includes all the hostels from both hostelworld and hostelbookers in our . All bookings are stored here on TP for you too, making managing existing bookings pretty convenient!
If I were you, I would book hostel in advance, and then I contact with hotel or hostel I book to ask further information such as taxi from airport or another travel plan, I think that all hotel can help you with this.
And maybe you can book 1 or 2 nights first, and then if you are interested in this place, you can stay longer.
Besides hostelworld, hostelbooker, we have travllerspoint, agoda,expedia.... to book room or even flight.
We rarely booked in advance during our 3 months in Asia. As loubylou says, it's nice to see the room beforehand so we would normally head to a certain area with a few establishments in mind and see what they were like when we got there.
but in another case, hotel is full already, how will you do at that time?
I don't always think it is necessary to book ahead except for events, festivals, national holidays...I often try and time my trips so that I can catch a film or music festival abroad.
So, if I were you, I would try and work out what celebrations are going on where then make sure you book these places in advance in case they fill up.
For example, book a hotel/hostel in areas around the full moon party or where you would like to be to celebrate the Songkran festival...
Also if you know where you are flying to, for instance, Bangkok, you should book ahead and spend a few days this exploring the city.
You can always access the internet and book the places in between whilst on route.
Enjoy!
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