On cruising the coast, the same coast, over and over and over....
We play leap frog, we hop, skip and jump. We don't try to get to every place of interest every time. Yes, we have some places we always want to go but others that going north we'll skip and pick up coming south. In fact, our trip north and our trip south will almost always have very different stops. As to high spots, it's the not so high in between on the next trip that may surprise you.
Now, one other thing in reading your last post. We never have spent 3 1/2 months on a boat. Two months is our record. We leave the boat, we come back to it, we pick different areas each time. That leaves us always ready to return, anxious to return. When we move on from each stop, there's always something else we would have liked to see there. That something else is why we enjoy returning to see it next time.
Just take the Chesapeake, I'm sure I could point out dozens of places you didn't get to within the area that are great stops. Even when we pass back through the Tidewater area we go to a different town each time. Perhaps Hampton Roads, or Va. Beach, or Norfolk. How long did you spend on the Potomac? Most who do the Chesapeake go right by. Yet, it's such a wonderful side trip. It got bad rap by the false story that George threw a rock across it. Well, it wasn't the Potomac as it's too wide.
We've been to the Bahamas 20 times or so since 2012. I figure we've explored less than 10% of the islands there, and the ones we've seen less than 50% of what we could have seen on them. That would say there are 400 trips before we run out of new things to see and since that would take us 60 years and by then I'll be over 100 years old and memory shot, it will all seem new again.
Variety is the spice of life although there is a charm in the familiar. We tend to mix them. Spend some time cruising familiar areas but then go see new. I mentioned Potomac. Well, how many here have cruised up the Delaware to Philadelphia? I'd guess a very small percentage. We haven't yet, but that's in plans sometime. Plus do different things even in the same places. For Chesapeake fans St. Michael's is a popular stop. How many have gone horseback riding there? Unique, different way to see it.
Ocean City MD is another example I'll toss out. We met a couple that had stopped there many times. They'd been to the boardwalk and to Northside Park, I believe. But never to the Life-Saving Station Museum. And never to Trimper's or Frontier Town or Jolly Roger or Ripley's or the Mirror Maze or any of the game and entertainment centers. Their comment was they were too old for that. My wife's comment back was "maybe that's why you are old." Even if you just observe, just watching kids play and all the fun there would be entertaining. Ocean City is a wonderful playground. Don't miss that part.
I lived the first 42 years of my life in NC. We've cruised through or past NC at least 6 times, maybe 8. There is so much I haven't seen yet. I went to the outer banks when perhaps I was 12. I haven't gone to Manteo yet by water. My wife has never been there. I saw the Lost Colony but I don't remember it or really remember the story very well.
Now, we prefer all these adventures by water, but back to the OP, there are similar adventures available by land. Life is an adventure. Doesn't all have to be expensive either. We love NYC (no booing please) and everyone talks about how expensive it is. However, Central Park, Washington Park...free. Amazing to me and free. Stay in NJ and go into the city for the day by train.
So the real challenge. Make a list of things you want to do, places you want to do, things you want to see. Not a bucket list but a fun list. Everyone should have lists such as those. We have cruising lists with far more on them than we can ever see. We've not yet been anywhere we don't want to go again. Make these lists and then select within your interests, your tolerances, your health, your affordability. It might be a retreat near home. Perhaps national parks. Perhaps places you've been through but never spent time.
There's far more to enjoy than any of us can in our lifetime. Each day is new. Walk to the park down the street and you'll see something today you've never seen before. Maybe the crazy silly little girl and her puppy. Maybe the ducks at the pond.
Perhaps the approach is instead of what one doesn't want to do starting a list of things you'd really like to do and would enjoy. Then decide how to start approaching it.