Feasible Lakes and Alps trip ?

[Bluedot]

It's always been a dream of mine to do the Italian lakes and Swiss Alps in a 2 seater with the sun shining. However I'm not getting any younger and decided that the Cayman probably won't be coming any time soon (unless Spud sorts out some winnign numbers on the lottery thread) so have dumbed it down a bit and am looking to fly into Milan then hire a car for 8 or so days.
This is my first pass at an itinerary and am looking for feedback as to whether it's feasible or to much or to take longer etc., any ideas welcomed. It is very much a work in progress, the idea is that we can take our time most days and then have time where we're staying to have a mooch about as well. Maybe have a rest day in the middle somewhere ?

Day	Start	End	Feature	Rough Time
Day One	Milan Airport	Como
Day Two	Como	Colico	(Lake Como)	2 hours
Day Three	Colico	Gomagoi	(Stelvio Pass)	4 hours
Day Four	Gomagoi	Pontresina	via Livigno pass	3 hours
Day Five	Pontresina	Rheinwald		2 hours
Day Six	Rheinwald	Handegg	(Furka Pass)	4 hours
Day Seven	Handegg	Arona	(Lake Maggiore)	3 hours
Day Eight	Arona	Milan Airport

I've added an image for context but have added in stops that aren't actually stops, just waypoints (any suggestions for a decent route planner welcomed).
We did the NC500 a few years back, this is on a different scale though.