I am (hopefully) going to Hawaii next year (planning on going in May). I am going to stay there for 4 weeks and I would like to travel to all the islands (or most of them).

The problem is that I don't know if I should book the hotels in advance, which would mean I have to stick to a schedule, or just book them when I get there. Personally I prefer to book them when I get there since I do not know how much time I need/want to spend on each island, however, I am afraid if i walk up to a hotel and ask for a room for x days (with an option to stay longer) they might charge me more then if I booked the rooms in advance.

So what should I do?

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    Of course it can vary, but in general, you'll get cheaper hotels on line (at least in cities where virtually all hotels are available online). Likely more importantly, you'll actually get a room by booking in advance. – Flimzy Oct 4 '15 at 18:17

Hotels usually have a full legally regulated rate (the one posted on the inside of the door inside the room), a walk in rate (what they charge if you just show up) and an advance booking rate.

The full rate that is posted is usually equal to the walk in rate during peak season and, with the exception of a holiday surcharge (NYE, Xmas, etc), is the highest amount they can legally charge for that room.

The walk in rate varies depending on the season, during shoulder season in Hawai'i it could be quite a bit lower than during peak summer season. While this rate is usually a set amount, most front desks have some leeway to discount that rate if the hotel has low occupancy.

The discounted rates offered by the hotel for advance bookings through its own website vs the rates offered through OTAs, like Agoda or Expedia, etc are becoming more equal as time goes by. The primary advantage of OTAs is being able to look at multiple options on one page AND since OTAs have blocks of rooms they committed to, they will offer the same discounted rate right up to check in day.

Hawai'i is busy but not totally sold out, with the exception of the peak seasons, you can find rooms available in most areas upon arrival. And even during peak summer and the new year period, there will be some room to be had somewhere.

Personally I would book my first stay before leaving for the islands, just for the ease of arriving and relaxing instead of hunting down rooms. Then as you piece together your next location, get online with the OTAs booking.com, hotels.com, agoda.com etc and see what they have available. If rooms are available you can book them right up until you arrive at the hotel. You can also use the price the OTAs quote as bargaining material if you want to walk in and book direct with the hotel.

And if you spot a really cool hotel while wandering around but the front desk tells you they have no rooms, check with the OTAs as they may have space in their blocks still, which the front desk can't access to sell direct.

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Typically online is cheaper (but not always). Hotels will try to maximize revenue. Advanced bookings makes planning a lot easier so some are willing to give a you better rate. Some hotels these day will charge you more for a "refundable" booking, i.e. the room is $150/night if you commit to it but $180/night if you want penalty free cancellation until the day before arrival.

So if you walk up and they are mostly empty, they will probably give you a good rate to fill the room. If it's busy and they know that other area hotels are fully booked they will charge you an arm and a leg for it.

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