There are a couple of ways to do it. I love mine and can't live without it now.
The first way I do it is to look at the maps on GC.com and find the ones I want to do and load those into the handheld and this way I know what one comes next after the one I have just done. You'll find out that the Nuvi search by spelling is kind of fussy. You'll want to have a good record of the name of the cache.
You can us GSAK and load just the ones you want to do that day and and pick them off one by one.
Another way I like to go is when you start it up and push the Custom POI's just leave that screen on and the closest cache names will be displayed and change as you travel along. It will also tell you how far you are away from them and what direction they are in.
I was going to go to the event in NH tomorrow, well technically today, but no one wants to go with me so if you want a Nuvi, GSAK, handheld 101 I could meet you and we could go out. I have not done hardly any down that way.
OK I know that's more than a couple.
I have no enemies, but I'm intensely disliked by my friends.