I probably have a mental list of places I'd like to visit. I also have a set of weeks I'm willing and able to take off. Then it's a combination of flights.goog

I probably have a mental list of places I'd like to visit. I also have a set of weeks I'm willing and able to take off. Then it's a combination of flights.google.com to check for less expensive travel fare for those destinations in those weeks, followed by also googling for nicer hotels in those areas. Depending on the trip, I might consider airbnb, like if it's a skiing trip or just some little beach town destination, but it doesn't apply to all destinations. Then once I've landed on 2-3 ideas, I also check if I can get those flights for miles rather than dollars. There's some correlation between "cheaper fares" and "lower miles" but I can't use google.flights.com to search directly with miles, so I use fares as a proxy. If no good deals on miles, then I just pay with hard earned dollars... It's an involved process, so I will spend some time on it, advance a little, discuss with my wife, sleep on it, come back to it later... it might take me up to a week to hammer out the best candidates, sometimes longer.