Plan it for the new moon
The moon decides what you see, not the stars. A new moon gives you the most sky; a full one gives you enough light to walk back by.
From people who go out and look, comparing what actually spoiled a night and what did not — and with their own corrections to each other respected, including a date somebody had wrong by twenty years, which is therefore not printed here.
The stars do not vary. They are where they always are, in the same numbers, on every night of the year. What varies is how much other light is in the sky between you and them — and almost all of that is one object, on a schedule you can look up.
Plan it for the new moon, when there is no moonlight competing — and plan a walk for the full one, when there is enough light to see the ground.
The same fact, useful twice. A full moon is a floodlight; it washes out everything faint and it is also the reason you can cross open country at night without a torch. Two different good nights, for two different things.
There is a better version of that, from somebody who clearly does this often: you do not have to wait for a new moon. The moon sets. If it is up at midnight, it may well be down by four, and four in the morning is the same dark sky the new moon would have given you. Look up when it rises and sets rather than only what phase it is in, and most months have a window in them somewhere.
Where, which matters more than when
Light pollution is the other half and it is the half people underestimate. A city puts enough into the sky to matter from twenty-odd miles away on a clear night, so driving twenty minutes out of town is usually not far enough.
The way to solve this properly is a dark-sky map — they exist, they are free, and they show you where the nearest genuinely dark ground is, which is very often not where you would have guessed. There are also formally designated dark-sky places, which have been protected for exactly this and are worth the drive once.
And if none of that is available to you: it still works badly, which is better than not at all. Going outside for twenty or thirty minutes after sunset gets you the last colour in the sky and the first planets, both of which are entirely visible from a town and both of which get missed because people look up once on the way to the car.
What will actually ruin it
Cloud. Not moonlight, not light pollution — cloud, which people consistently fail to plan for because it cannot be planned for. Forecasts more than a couple of days out are unreliable for this, so the practical approach is to hold the date loosely and be willing to go on short notice.
For one-off events — a total eclipse, particularly — the pattern people described is to book accommodation months ahead because it does sell out, and to make sure it is refundable, because you may drive a very long way to stand under a cloud. Both halves of that, not just the first.
A note for whoever is nervous about the dark
Somebody raised this and it is worth taking seriously rather than laughing at. Genuine darkness — the kind you need for this — is unsettling if you have not been in it. No ambient glow, no shapes, and sounds you cannot place. People who camp regularly forget how strange that is the first time.
If that is you, the answer is not to toughen up. Go somewhere with other people in it, or go on a night with some moon, or start from a car park you can walk back to in three minutes. And it is worth knowing that in a genuinely dark place you can see the Milky Way even with the moon up — so the frightening version is not the only version that works.
The last thing, and the reason people keep going back rather than ticking it off: what you are actually doing out there is standing still in the dark for an hour looking at something enormous and very old, which turns out to be good for a particular kind of week. No one ever needed a technique for that part.
Full tip: https://findangel.org/tips/plan-it-for-the-new-moon · FindAngel.org — free, always.