We love the trolley. We take the trolley every few months regardless if we have visitors or if. It is just one of those things that we feel like we should be taking advantage of. I've talked to so many locals that haven't rode the trolley in years. That's quite sad in my book. It's just so fun.
The trolley is expensive at $5 each way, however, it's a little bit a vacation in our own city and it makes us smile. We have figured out that if you walk up the hill at Union Square to the next stop up from the 1st one, you will never have to wait in the horrendous lines at the start. All you have to do is have $5 cash in hand and jump on. The trolley conductor typically keeps some open seats or standing room (my preference...especially when I have the Rice-a-Roni song in my head) so you can just jump on and away you go. The pictures above are from when my parents were visiting and we jumped on at Union Square. Mike got the best standing spot in the house - at the front of the trolley so he took pictures the entire way to the wharf. These pictures are in no particular order. I could have figured it out, however I didn't think you would mind.