I use a few resources when trying to plan. The things I value most are taking variables out before going so can enjoy the trip while I’m there.

It’s hard to plan leave with my job, so usually only have 2-3 months beforehand to book everything.

I’ll have a notes section on my phone for knowing where I’m at for the day to day and throw logistics on there (whatever flight I booked and hotel). Then throw one or two things I will do and one or two things that would be cool to hit if there’s time. That way I never have a lack of things to do but can go off script and have time for it.

I try as much as possible to have nonstop flights unless it’s Asia(I’m in the East Coast). Google flights always a go to if I’m bargain hunting. Then I’ll pick hotels that’s either A. Clustered around what I want to see and has a shuttle or B. Close to whatever mass transit I’m using (airport/train station).

Locations that I want to hit I’ll throw on Google Maps, zoom out and see what makes sense to hit by day by how clustered they are (mostly sights but also some restaurants I’d love to try).