I am just in the planning stages now, so I am very open to ideas and suggestions.
I would like to tow the boat to a fairly northern launch ramp (I live north of the area), and then spend a week cruising from one transient slip to another without going more than 120 miles per day and end up back at the original launch ramp. Another idea is to do a one-way trip where we launch in one place and arrange to have our truck and trailer transported to a distant launch ramp where we'll meet it at the end of our cruise.
I'd like to stop in interesting ports for meals and sight-seeing (they can also be overnight stops). I'm thinking Baltimore's inner harbor and Washington DC are a given. I'd also like to stop in smaller city ports (places like Newport, RI, Alexandria Bay, NY, and Portsmouth, NH for reference), and smaller port towns too (like Kingston NY, Wickford, RI, Perkins Cove, ME, and Wolfeboro, NH for reference). I am more interested in seeing museums and historic sites than shopping. My wife shares the same interests.
It would be just my wife and I and we'd like to do it in the Spring before the hot and humid weather hits since I don't have AC on my boat. We'd like to avoid rough water, but we understand it's not always possible and our boat is pretty heavy and has a 24 degree V-hull,so it's not a big deal if we encounter rough water. We also have a full cockpit enclosure, so rain is not an issue either.