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Italy for 17 days- 1st night in verona or straight to Venice?

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My dear friend and I will be traveling to Italy in about 10 days and staying for 17...I have been 3 times and to Europe a dozen. This is his first time abroad.

His only request was that we "wander" and not have a hard plan. If we like some place we stop and stay if we feel we want to keep going to the next town we do.
I feel comfortable with the plan. Our only set in stone items are:
1) We fly into Milan and out of Rome
2) I have rented a car from the Milan airport to be returned in Rome 3 days before we fly out. And then a scooter rental for the days in Rome
3) Tickets 2 days before we leave for the Scavi tour of St Peters.
4) Hotel room for Rome.

Otherwise...we wander.

Now...to my dilemma:
We land at 9am in Milan. While yes we could stop and see Milan, I have decided not to (the duomo museum is currently closed and I wasn't able to get tix that day to the Last Supper) So we will be heading towards Venice where I would like to spend 2 days (ish) before heading south...
I am a traveling machine...I have no problem hopping off an international flight, scooping up a rental in a foreign land, and driving for 3 hours then plopping myself into one of the most intense visual experiences of any city on the planet...
BUT I'm concerned it might be too much for the first timer. I have thought it over so much as to lose perspective so I turn to you all for help!
On the up side, 3 hours is not a big deal...even with some relaxing stops we could be there by late afternoon. Then check into our pre-booked hotel (the one I will get as soon as I decide) and wander the amazing streets of venice for the evening before crashing early, get a good nights sleep and waking already at our destination.
On the down side, he could be so overwhelmed by the jet lag, driving a rental in europe, all the new sites and such that he just gets off on the wrong foot at the very beginning of his 1st european adventure!

So that is the question: Stop somewhere in the middle like Verona and spend the afternoon napping or wandering...or head for the beauty of Venice.
Advice??

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