It depends on where I’m going, what I want to do, and the time of year.
If I want to stay in a particular property in an area that I know will be busy with other visitors, it makes sense to book ahead. In off season, or in areas less frequented by other travelers, I’ve never had a problem finding a place for a night or two—and sometimes for a longer period if I’ve hit on a winner!
More and more I find myself delighted when I opt to look just a bit further out than the full-on tourist haunts. Staying in quieter settings like a smaller, less well-known town/village/city can drastically cut the price and offer a much more interesting experience. The bigger, flashier “must see” places are usually easily reached by local transportation or hired cars. It’s the ease of meeting people, and the local advice, which makes me fall in love with off-the-beaten track—plus being offered a villa (huge terrace, swimming pool, gardens, and a gorgeous room) for a week at the same price as one-night stay in a tiny city hotel room (thanks to having coffee with a local who had a grandmother…very easy decision!)
The two times, though, when I ALWAYS book my room is my first and last night when I’m traveling overseas. I usually pick a really good hotel at, or near, the airport with 24-hour room service, and the option to extend my checkout time. The extra cost is worth its weight in gold since I don’t need to fret about delays, traffic jams, changed schedules—-or to arrive exhausted in a strange environment needing to find somewhere to sleep. A good bed, blackout curtains, 24-hour room service, and friendly concierge can turn things around pretty quickly.