Ask HN: You're planning a vacation to somewhere, what's your process?

I'm planning a trip in November. I'm curious if anyone has some novel way to find interesting places and places at their trip's destination. I personally am the type of planner that plans a few major things and leaves room for what my friends and I call "side quests". We're never too formal which sometimes bites us in the butt but overall gives us a lot of flexibility.

I'm wondering if there might be some tool or framework others use to plan trips.

Putting artificial constraints on part of your trip (say, travel only by canal boat and on foot in NW Europe) can work quite well.

But it depends greatly on your destination. Finding cool stuff in Denali Nat'l Park (Alaskan wilderness) is rather different from NYC, which is rather different from P’yŏngyang, which is...

Whether, whether, whether.

You cannot predict it this far out but you can have an idea looking at the closest NOAA/WMO station hisorical data.

Whether what? Whether the weather will be good?

To OP: Last time I went on holiday I winged it and only went to 1 interesting thing which would have been much better booking in advance. I suggest discovering now what you might want to do. Landmarks, events, other cities.

Step 1 - Look at my savings account

Step 2 - Put it off until next year

Repeat indefinitely.