Hi Marty,
For my trips to Rome, I reserve the airfare far in advance (because of the excellent prices from BA when they run their RT flash deals - very inexpensive.) I also reserve my hotel in Rome - stayed there last year and the year before - it's like I never left :)
I will reserve again this year.
I am a planner, but, I am also a free spirit. A nice balance, and it works for me.
Some of my best memories are those that were happenstance - first trip getting a bit lost and discovering little out of the way places (off the beaten path) and having conversations that turned into friendships and recently experiencing Rome through my friends.
One thing I will always cherish - in 12/2017, coming out of the Pantheon and setting up were professional street musicians. It was close to lunch time, so the crowd of travelers and business people were increasing. I found a seat on the wall adjacent to the Pantheon.
Each guy had a different instrument. When they started to play and sing, it was mesmerizing. The lead singer (who also played keyboard) has an unusual, beautiful, melodic voice. That particular day, they played haunting and soulful tunes. I lost track of time and stayed to listen for almost two hours. (I caught them at Piazza Navona one night and also at Camp de' Fiori.) Sometimes, they play tunes from the Eagles, Pink Floyd, Stones and some other rock 'n roll & George Michael. Nice memories. (I pull up skylinewebcams of Italy and catch them at night. It brings me "right back.")
For this trip in 12/2018, I revisited friends I made the year before. Most of my evenings (and a couple of days) changed - for the better! I made some loose itineraries leaving open a change of mind or whatever.
One day, on my walk to the Trevi, I came upon a "marching band" with its members dressed as Santa, blaring their horns with jazzy renditions of Christmas songs. It was a lot of fun and had many people dancing and smiling - getting into the Christmas Spirit!
I visited Saint Peter's a couple of days at different times. Seeing the day change into dusk while at the Piazza was beautiful. It was magical lit up. Hearing the church bells was both chilling and relaxing. Looking up and staring at the huge tree and pondering last year's interesting "sand art" Nativity was really something.
I went to see my friend to congratulate him on the opening of his new store near St. Peter's. He opened in the Spring, and it's different than his other store (which is a bit closer to the Vatican.) He has additional plans for this store to be completed by this year's end.
An example, I wanted to attend a mini concert at St. Paul's Church - the trio performed only certain dates. Tickets could be bought the day of the evening performance. I thought, "if I go, I go." It would have been nice, but, I really had great times with friends. I also did not make advanced reservations for any sites though - saw a lot of them on my first trip.
And, at a restaurant I frequented, I was treated like a friend of the family with a little extra attention. I had a lot of fun with them as well as talking to some regulars and "strangers."
I favor Rome because of its big city stance; tons to do or not do. You can "get lost but not be lost." Rome is a walking museum -wander into any neighborhood, down any street, or turn any corner and see something of interest or meet someone special...
Orvieto is sweet and quaint with a home-town feel. You can spend a couple of days there and maybe not see it all. I hope to explore this special, medieval city in depth.
But, for now, Rome has me hooked.
Whatever you decide or wherever you choose to go, have fun and "go with it." The adventure awaits...