Another fun thing I like to do is take the trolley to the end of the line and then ride back.
This is good if you are not into an all day sufferfest (not that there is anything wrong with that).
You get to see the soft underbelly of San Diego that a lot of natives haven't even seen.
To further enrich your experience take a map with you to orient yourself as you travel through the San Diego region. The place is sprawling.
ps I've been riding that hill up from Old Town to Mission Hills for 50 years. It never gets easier. Nowadays I usually have to walk it.