Weigh the enjoyment and the costs.... to the trailering....depending upon the depth of yer wallet....and time available to devote to the trip (either method)...then make your decision.
Life without a bit of adventure is boring....but we have to be realistic about it.
After all....it is not like this is a Lindbergh/Bleriot trip all rolled up in one! Tap the knowledge of those that have done similar trips in Italy and France...and draw upon their experience.
Post the photos when you get done!