My wife and I took a mini-retirement trial run two years ago. She had just left a toxic job and then two weeks later my team was cut in a reorganization. My severance was generous because I'd been with the company for so long, so we decided to hit the road and see the sights before we panicked about work again. (Spoiler Alert: My company hired me back a few months after we returned, and my coworkers were all steamed at me for basically getting a paid sabbatical and going exploring while they had to deal with the reorg consequences.)
We only had three firm boundaries/destinations to plan around: We had to meet relatives in New Mexico on a certain date, we had to be in Sandusky, Ohio on a weekend because Cedar Point closed midweek after Labor Day and the record setting coasters were a big destination for us, and we had to be in Paso Robles, CA by a certain date because we had tickets to see Peter Frampton's farewell tour and our buddies would have been crushed if we cancelled.
Besides those three firm stakes in the ground, the trip was freeform. We only had one other soft rule: No backtracking.
We never had any reservations (pre-pandemic by about six months), so we were free to go wherever we felt like going. If we found someplace we liked, we'd stay there a few extra days.
The night before we'd hit the road again, I would tell my wife to pick one of the three available compass points (no backtracking on the 4th compass direction) and then I'd start looking at the map.
On the road the next day I would do the mental math and pick a rough destination and give my wife a 100 mile range within which she needed to pick us someplace to stay.
Every night was more or less a winner and we never regretted having no plans. Sometimes we were pleasantly surprised and sometimes we were moderately unimpressed but not disappointed. I think North Dakota surprised us in that there were so few places along I94 to camp, and the place we ended up felt like the RVers equivalent of The Shining (couldn't wait to get out of there the next morning).
We saw 19 U.S. states plus a lot of Ontario, Canada that way. The trip was just short of 11,000 miles.
We answered the questions for ourselves about our future retirement, compatibility after 31 years of marriage at the time, and whether our dogs were up to the adventure or not. By the end of the trip, the two of us were closer than ever and the dogs proved themselves to be perfect travelers and even more deeply bonded with us.
So my advise is to start out in a time of year when the country is emptier (spring or fall, or even winter if you can go further south) and just wing it for a while until you find your pace, style, and routines. Otherwise your trip will feel like a job if you have to make it to a bunch of committed reservations.
