How I plan or don't plan depends on the night.
For example Monday night I got up from watching TV, done for the evening.
Did my usual look outside to see how the sky looked. It was clear and beautiful.
I said to my wife, I am going outside for a while and headed out the door.
I grabbed one of my 3 scopes, all of which live in an unheated garage so they are always ready to go.
I pulled out the 8" Dob, which is on a cart. Put my observing chair on the cart.
I grabbed my bucket of accessorizes and rolled along the driveway and sidewalk
to my observing spot and spent 45 minutes on Jupiter.
Sometimes I pull out a Planisphere or a star chart, "Turn Left at Orion, or an app
on the phone with no pre planning. These are usually short sessions of 30 minutes to an hour.
Other times my sessions are planned.
I might sit with Stellarium and see what is in my prime viewing area and work out the star hops
on the screen.
Other nights I start with a target list using "Tonight's Sky", a free web site that will
allow me to run a report of what is in the sky tonight. It will let me select the difficulty of
the targets and will provide a printed, PDF or HTML report that I can use
when you are at your telescope.
Since all of my scopes are computer assisted I can just align them and work off the list.
Sometimes I will use a chart to star hop. Depends on my mood.
The default sort is by difficulty, from brightest to dimmest. That is
great but you could end up all over the sky trying to work the list. I
normally sort it by constellation. Then I can mark the constellations that
are in my best part of the sky and focus on them. You could spend an
entire evening working on small part of the sky finding all sorts of cool
stuff.
Aside from making it easier to observe, I can get to know a specific region of
the sky. I can focus on Orion, for example. See all that is in Orion
up to the capability of the telescope. Then move on to Taurus or
Cassiopeia or whatever constellations are in the best area.
Not sure which constellations are in your best viewing area? I use
Stellarium to help me see which constellations are in my best viewing area.
For me that is NE to SE and directly overhead.
Here is how you do it.
Tonight's Sky Web site
http://www.tonightssky.com/MainPage.php
Put in your location and time settings and click the box to remember them
Select the difficulty level - If you are using binoculars then select that.
If you are in a highly light polluted area work naked eye and binoculars
first, maybe small telescope. If you can find all of those then on the next
report raise the difficulty level.
Select what types of targets you want to see - Planets, clusters, whatever
you want.
Run the report - standard sort that will be displayed is by increasing
magnitude number, that is to say brightest to dimmest
Choose which ones you want in the printed report, or select all.
Select Print or right click and select print. If you want a PDF select
"save as"
I change default print out sort to "by constellation"
Run the report and it will be sorted by constellation. This is how I
normally sort it.
You can print it or save it as a PDF or a web page. If you save it as a web
page there are live links to resources for each item.
That's how I do it.