It looks to me that your time is limited, so I would drive the fastest route, that is the motorway through Brescia, Verona and Trento. It is 4 hours driving without traffic - but in August there is much traffic in the section north of Verona. I would avoid driving north of Verona on August Saturdays and Sundays, as traffic may be so intense that often comes to standstills.
All other itineraries are more scenic but much slower. The Stelvio itinerary is superb but as the pass has 36 hairpin curves ascending and 48 descending, it is not for casual drivers.
As a long but easier alternative to Stelvio: Milano - Lecco - Chiavenna - St. Moritz - Zernez - Müstair - Merano - Bolzano. Very long (6 or 7 hours driving) but not as strenuous as Stelvio, crossing Switzerland and the Swiss National Park. If you are asked at the border, declare your itinerary and that you do not need the Swiss motorway sticker as you are not driving Swiss motorways.