Italy & Switzerland in 10 days. Rome to Zurich in August

I’m taking my son & a friend to Italy & Switzerland for 10 days in August. I’m the trip planner. Looking for honest feedback on our itinerary. Flying to Rome and depart from Zurich. He wants to see as much as he can in between, but I don’t want it to be too stressful. I know this is ambitious & we are energetic. Also looking for input on if we should get/which rail passes or rent a car at any point? We are not married to these ideas, but here’s our rough draft & maybe you can help us fill in the blanks since it’s a busy time to travel. Should we just stop by Milan on our way or base there and take day trips? Should we try to fit in the Glacier express or Bernina express route? Lmk what you think of what we have so far. TIA!

*Rome- 2 nights
*Cinque Terre- 1 night
*Portofino- 1 night
*Milan/Lake Como/Lugano- 2 nights
*Where in the Alps? Express?- 1 night
*Interlaken/Grindewald- 1 night
*Zurich- 1 night