Depends on the purpose of the trip. If we don't have a purpose - just want to get out on the boat
and sail around a little, we look at the weather - north wind
, sail south. Since we are in the Chesapeake, we will look for a nice anchorage using Shellenberger's book
(Cruising the Chesapeake: A Gunkholer's Guide by William H. Shellenberger)
Or we will look for a marina that has a reasonable price
and amenities - a place within walking distance to eat or shop, and (or course) one that has a deep enough approach so we don't go aground and a slip that we can get into. (wide enough and hopefully with either a finger pier that is long enough or a face dock
so that I can get off without unusual gymnastics).
If we are going someplace specific - sailing south for the winter - I decide first if we are going outside or in the ICW
- we usually go outside from Charleston to Fernandina and we always go outside from Ft Pierce to Miami
because of the Julia Tuttle Bridge. If we are going to be in the ICW
I pick a place to stops that are about 35-40 miles apart, where there is a marina that meets the parameters above, and also if possible has free wi-fi.