We start seriously discussing vacation about 2 or 3 months before we think we want to go. We leave this Friday, so we started in February.

We start with the hotel - as Las Vegas can vary greatly day to day based on what conferences are happening / DJs playing, holidays occurring - we pick 2 or 3 hotels we want to possibly stay at and I start building an excel sheet of which consecutive 6-7 days is the cheapest and where. Once that's decided, book the hotel and flight. Our flight to LV is always via SouthWest. Anywhere else, just choose which airline is the cheapest for the time we want to leave and return. Same for the car rental - once we know which days we're going, choose the cheapest not shady looking rental company that has the car we want.

After that, it's just a matter of brain storming what we want to do when we get there and start buying tickets or booking reservations once it gets a bit closer. This year, we've booked shows or night clubs for almost every day of the trip already. Had to get an itinerary app so can remember when and where, lol...

Otherwise, we've only ever been to all inclusive resorts in the Caribbean and those are pretty much just decide when, book and go. We just do the package deals; flight, hotel and transportation to the resort.

I did it in reverse. I used points for my flights and hotels and booked those first. I had a rough itinerary planned. Going to Tokyo -> Osaka -> Hakone -> Tokyo. Once I booked all the rooms first, then I planned activities. Hakone was the hardest to book since it was a hot springs hotel and I got lucky with an opening.

I figured out what I wanted to do and then matched that up with the days. I ended up removing stuff since jet lag and delays can always ruin the best plans. My days are more guidelines now. I know if I want to go do something, I can and have a list of things, but if I don't feel well or just feel like exploring, I can do that too.

Edit: I made a google doc, then turned it into a spreadsheet. I also have a TripIT account and used that for any travel notifications. I also added all the locations to google maps and plan to download them in case of bad cell service. I also looked into Maps.me.

have you done that trip yet? if not i envy you. make sure to head to the outskirts of tokyo and check out kamakura and the awesome kawasaki warehouse before you leave

places i usually already have in mind, i usually get my flights on skyscanner but after that things get complicated, im known as the organised one of the group so i usually set everything out.

i start off researching the city as fully as i can, check out all the usual places like trip advisor but often hitting up the reddit for whichever city you are visiting can offer some really interesting possibilities, its also great for finding out about music events that may otherwise be hard to find out about.

after that i split the trip up, i never stay at a single hotel the whole trip, ill pick a few in different areas of the city where there are different things to do, it makes you explore the city a bit more. i dont do airbnb or hostels but im not above guest houses or low end hotels.

i dont stop there though, once hotels are booked ill still keep checking hotel sites at least a few times a week to see if any deals for better places come up, if they do i cancel the old and rebook. it pays not to have too rigid a schedule though as things dont always go quite as you plan them to

i dont write any of this down though, i generally just memorise it all (ive usually spent so long researching it that its burned into my brain!) as long as i have google maps for navigation im set (i never travel without a data connection these days)

of course this method only really works if youre visiting big cities, and if im honest its a while since ive done any that werent in japan (but if youve been there you probably understand why that is, and if you havent then its time to start planning a trip!) next month it all begins again for me as ill be booking my flights to head back to the land of the rising sun in november