I am looking for advice on planning a multi month US road trip that will take me from New England to the Pacific Northwest and back. However, there are places I need to be for specific dates, but other than that I'm free to travel as I see fit. I plan on being in many places for at least a few days if not longer and will be staying with friends along the way. This is where the planning issue I'm having is coming in. I'm trying to plan my trip to take into account my friends schedules as well.

I've checked out a few online planning tools, but can't seem to find one that makes it easy to play with dates and that will sync up the calendar view of my trip with a map.

Any advice on going about planning this? I'm currently trying to cobble together a Google Maps solution, but may just code something custom for my needs around Google Maps.