I am hoping my best ride will be the one I take at the end of this month. I am going to start in DC and ride/camp my way south. I'll be keeping coastal, though not right on the shore. Honestly, I want flat and no wind, and I am going for distance, though I know the scenery will be spectacular. My primary objective for this ride is distance, a personal best sort of thing. Unfortunately, my training hasn't been much beyond commuting to work, sitting behind a computer all day, then rushing home and making repairs/purchases or both, depending on the day. It's a three-week ride, so I am sure the ole legs will start to cooperate 'round day three. My route is taking me through Dismal Swamp and the tidewater regions of NC & SC.
I prefer solo rides versus riding with two or three other people. Perhaps that is because real life keeps my training erratic. I never really know how well prepared I'll be for the ride, and that makes it difficult to find the right riding partner.
Huge group rides are great in a different way. A friend does RAGBRAI each year, and it's a huge party.
Finally, the best rides aren't loops. Just ride till you're out of road, money, time, legs... and hop a train or plane home.