This is an awesome topic and it's really interesting to read through everyone's responses!
The last few years, I've been training offshore so planning extends more toward weather forecasting and more or less choosing a direction, heading off for a week or so, and then monitoring onboard to make sure we're back at the dock on schedule. We do some work on what harbors/marinas are around to duck into in the event of breakages or weather problems, but the waters are generally pretty familiar to us.
When I've gone on more of vacation cruises to more unknown areas, I definitely do a lot more planning...but I think it's more of a wanderlust than planning for an exact itinerary. I basically just sit down the my Navionics app and measure distances, check out harbors that look interesting, and see what routes I can come up with that are doable. I usually end up with a few potential itineraries and then the trip usually ends up being a mash-up of all of them!
The last few years, I've been training offshore so planning extends more toward weather forecasting and more or less choosing a direction, heading off for a week or so, and then monitoring onboard to make sure we're back at the dock on schedule. We do some work on what harbors/marinas are around to duck into in the event of breakages or weather problems, but the waters are generally pretty familiar to us.
When I've gone on more of vacation cruises to more unknown areas, I definitely do a lot more planning...but I think it's more of a wanderlust than planning for an exact itinerary. I basically just sit down the my Navionics app and measure distances, check out harbors that look interesting, and see what routes I can come up with that are doable. I usually end up with a few potential itineraries and then the trip usually ends up being a mash-up of all of them!