I would put some effort into reducing your gear weight along with thinking about gearing as both are important when climbing hills.
I agree and if I was going alone weight wouldn't be an issue since I'm quick to walk but this ride is being planned and conducted buy a pretty fast 160 pound academic roadie. I've been in or worked for the U.S. Army since I've graduated from college so I understand that I want to =/= a plan and I like plans, so I'll compensate for any perceived lack of planning since .gov taught me and pays me to operationalize ideas.
This ride could easily be a credit card tour but the "man card" seems to be on the line for some reason so we'll camp and ride heavy bikes.
No matter how this plays out Lake Garda in August is great and bike rides are great so I'll "let it go" and prepare for the unexpected