That's the short version. It isn't laziness and it isn't ambivalence. People who can't get a trip booked are usually people who are very good at getting other things done. The trip is the one thing on the list that nobody is waiting on.
What's actually happening
Planning a trip is not one decision. It's a few hundred, arranged so that most of them depend on the ones before.
Where. How long. Which season. Fly into which city. One base or three. Which neighbourhood. Which of the eleven places that all have good reviews and none of which you can tell apart. Whether the five-hour transfer on day six is a scenic drive or a mistake you'll regret at hour three.
Each one is small. Together they add up to something that needs a clear head and an open evening, and those two things rarely show up on the same night.
So you open the laptop at nine, look at four tabs, feel the shape of how long this will take, and close it. The trip doesn't get rejected. It gets postponed, which looks identical from the outside and feels completely different from the inside.
Why it gets worse the more the trip matters
A trip you don't care much about is easy to book. Pick a beach, choose a hotel with decent photos, done.
The one you've been thinking about for two years is harder, because now there's a version of it in your head that the real one has to live up to. Every choice carries the weight of possibly being the wrong one. That's a reasonable feeling. It's also why the good trip stays unbooked while the forgettable one gets booked in an afternoon.
The trip matters. Which is exactly why it keeps not getting booked.
What actually breaks the loop
One thing, reliably: having something concrete to react to.
Reacting is cheap. Generating is expensive. Handed a full itinerary, most people can tell you within ninety seconds what's right and what's wrong with it. Day four is too much. That town should be two nights, not one. The second hotel is the wrong idea entirely, and by the way, here's why.
That same person, handed a blank search bar, can sit there for a month.
This is why more options don't help. A shortlist of five trips isn't a relief, it's five times the work you already couldn't do, now with the added job of comparing them. What helps is one trip, built on purpose, that you can say yes to or push back on.
What to do about it this week
If you're planning it yourself, make the sequence smaller. Decide the kind of trip first. Then the country. Then how long. Then the shape of the route. Don't look at a single property until the first four are settled, because that's where the tabs come from.
Give yourself permission to decide badly on the small things. There is no wrong choice between two good hotels in the same town. The trip does not hinge on it.
And if the planning has been the obstacle for months, notice that it's unlikely to stop being the obstacle on its own. The thing standing between you and the trip isn't the flights. It's the planning, and the planning is a job.
Common questions
Is it normal to take months to book a trip?
Common, yes. Planning a multi-stop trip takes most people somewhere between ten and twenty hours of real work, spread across evenings that already have other things in them. The gap is usually the scheduling, not the wanting.
Would a travel advisor help with this specifically?
It depends what they do. A service that sends you options adds to the problem. A service that makes the decisions and hands you one complete plan removes it.
What if I don't know what I want yet?
That's the normal starting point, and it's a separate decision from the destination.
How to decide where to go when you have no idea