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The biggest problem with planning long trips is getting so stuck on a schedule that you don't have enough time to spend getting to experience and savour the places you are traveling through.
For example, I could spend a whole season just exploring the nooks and crannies of Chesapeake Bay. The same holds true for Long Island Sound, the Hudson River, Narraganset Bay, Block Island, etc. A season-long exploration of Cape Cod, Boston, Rockport, etc. would also be a blast. Done properly, Maine and New Hampshire require a season of exploration, not just a couple weeks.
The point I'm trying to make is to take your time and plan your trip in segments that allow you enough time to "smell the roses". Trying to do everything in one trip will only cause you to miss many of the things that convinced you to make the trip in the first place.
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