Guess it depends on how adventurous you are feeling.
Whether you are up for getting yourself a gps map for Italy and driving around...
If you feel up to booking your own accommodations and having the freedom to roam.
Think my favourite part about traveling Europe (roadtrip) was stumbling across all the amazing things that each country has to offer that you wouldn't normally have the opportunity to see.
Driving in the dark on tiny winding roads until the headlights meet a set of eyes, we got to stop the car and jump out for a photo...when in the world will you ever find that you are staring at a Donkey in a fenced off area at the road side beside an abandoned swing set in the pyrenees mountains!
Or taking the wrong turn whilst searching for a bite to eat and stumbling upon a hippie-style art fest in the mountains complete with pool, Bbq, art, culture and oh so welcoming they were!
Pulling over to pick wild berries at the side of the road...
ohhh the memories...
Our youngest wasn't really bothered about any of it, but the oldest spent MONTHS researching, planning, saving for special things that she wanted and getting really excited about all the things that Europe had to offer. It was actually alot less hell than we had imagined it might have been with 3 weeks on the road, but we booked lovely holiday homes to stay in throughout and really dove in to the culture.
The smallest little things like buying long loaves of fresh bread and sausage gave the kids a reason to be excited...
We bought a portable dvd player for the ride that didn't get turned on once!
As for booking~we used Holiday Lettings
for all of our bookings and were extremely pleased.
I think that no matter what you choose you'll have a fab time.