I'm sorry, but 20 miles on a Bianchi Milano just does not seem fun. Nor does that long of a ride on an mtb (the longest I did on an mtb in one day was 36 and that's when I started shopping for a road bike).

I'm not saying he needs to go out and get a Disco Trek. But a bike like the Bianchi Volpe or Surly Crosscheck would be fast, rugged, and comfortable.