Yesterday, I advocated for waiting until after you arrive in a city to find a hotel. It’s something that has made my trips more spontaneous and rewarding, and I think everyone ought to at least give it a try.
But it’s important to remember that traveling, especially spontaneously, is a skill. And like any skill — playing the violin, say, or pitching baseballs — it requires both practice and trial and error. Here are a few tips for making that process go as smoothly as possible:
Focus your search.
Roving around looking for hotels takes time, so try to focus your search in a specific centrally located area. This works well in compact European cites where you take public transit into town, but I’ve also done it via car (Michigan, Oberamergau, etc.).
You will have hits and misses.
Not every place I’ve stayed has been amazing. But whereas booking a bad place in advance is just a bummer, ending up in a disappointing hotel that you found last minute tends to be a learning experience that makes you a better traveler. And in any case you’re choosing the least of all evils when you’re evaluating all available options in person.
Ask to see the rooms.
Most hotels let prospective guests check out rooms before making a decision. This gives you a chance to see how clean things are, what kind of bed you’ll be sleeping on, etc. It also gives the hotelier an incentive to offer you a good room; when I was looking for a place in Istanbul, we got the absolute best room in our hotel for a fraction of the listed price because we showed up last minute and asked to see the room. It was amazing.
If you’re traveling in a group, split up.
When Laura and I travel together, we typically split up to inquire at a few hotels that are right next to each other. (Note: this usually works when we’re on foot in walkable city centers, not when we’re in a car.) This lets us cover more ground quickly, and it gives us an excuse not to give into pressure to book immediately; after getting the rundown, we can always say we need to confer with our travel companion before making a decision.
Be aware of how busy a destination is likely to be.
If you’re visiting a busy place during a busy time of year — say, Paris, in the summer — you’re options will be limited. In my experience you’ll still be able to find a place, but all of the coolest and cheapest rooms will be gone. The best solution is to either visit during the off season or to choose more off-the-beaten-path sites. (Say, Chartes instead of Paris.) But if you must go to the busiest place at the busiest time, just be prepared to pay a little more and look a little longer.
Relatedly, be aware of special events going on at your destination.
A city might typically have plenty of extra rooms, but could fill completely up during a convention or festival. I once spent hours looking for a room in Amsterdam because I didn’t pay attention to how busy the city would be that weekend. It was a terrible experience — but one I have never repeated.
— Jim Dalrymple II