Driving into Rome...that does not sounds like my idea of fun.
I concluded years ago, that having a fixed itinerary with reservations for accommodations that I could depend on actually provided me with more freedom than just "winging it." It may sound counter-intuitive, but...I'm at home now. I have fast, reliable internet, big-screen/multi-screen desktop computers, a hundred websites bookmarked, a stack of travel guide books at hand, and most importantly, all the time I need to research, find, shop around for, and then decide on where to stay and book that room. All I have to do is show up at my reserved room at check-in time, wave some ID and maybe a credit card, and I'm done. I can then go enjoy a heaping plate of pasta and a glass of wine, take a stroll for some gelato and go people-watching after dark - or do whatever the heck I want. That's freedom.
If I am "winging it" I have to try to do all that (well, most of that) at the end of a long day of sightseeing, driving, and dealing with foreign things, on a small screen, with possibly sketchy internet, and do it all long, long after all the best places have been taken, picking over the leftover rooms that others passed over...as the sun goes down and my remaining options dwindle with each passing minute. Been there, done that, often ending up in places that were funky, expensive, badly located, or some combination. After spending way too much and getting way too little on such places, I got over my perceived worry about being "locked in" to a fixed itinerary. No more winging it for me, I'm happier knowing that once I'm Over There, I'll make the best use of my limited time (see pasta, wine and gelato, above).
The way I look at it, the single most-limited commodity we all have is usable time at our destination. I would rather take care of the mundane tasks of shopping for a place to stay, in advance, in the comfort of my home, while I have plenty of time and other resources at hand, to research and decide long in advance, not when I/we are tired, getting cranky, and want to enjoy being in Europe. But that's me, YMMV.