I guess we approach this differently on Guenevere than most of the posters.
We normally cruise full time, or for months at a time so we are not in a hurry to get something into our plotter.
What we do is have a final destination in mind. Knowing that it might change along the way.
I then plot the route with many way points to our first destination. This is normally a days sail away in closed in water, or for open water overnight trips. Then, once at anchor we rest and I then plot the next days trip the evening before we depart. It's a relaxing exercise for me
and the next trip is fresh in this old mind.
I do LOVE OpenCPN and keep it handy on a new tablet handy below. I am also excited about the Active Captain and especially the Interactive Cruising Guidebook feature!!! I am using it now to do some rough planning for our next cruise.