That really depends on the type of traveler you are and what kind of accommodations you are looking for. Before we moved here, we made many trips without booking any hotels ahead of time. We were staying in mostly budget places and were able to find something just by strolling through town usually. Mid-range and high-end options tend to be pre-booked more often though. If you are flexible and don’t mind spending some time looking for places you should be fine. Also, just as a tip, we like to use booking.com nowadays for last minute trips. They often have good deals at the last minute, most of the CR hotels are on there, and they only show you what’s available for the nights you are looking at. Hope this helps!