We booked in advance with Portland Discovery Tours, Land & Sea. Part one was a trolley tour of the city and Portland Headlight. Part two was an hour, maybe 90 minute, long cruise visiting some of the other lighthouses.
Overall it was a bit too much for us. The trolley tour was nice because it was warm and I loved to hear about the history of Portland and I appreciated the opportunity to see the beautiful homes. We lucked out and got the back section of the trolley with panoramic windows and a bench. This worked nicely for my son. The cruise I could have done without. It was too long for us. This also happened to be the coldest day of the trip. Low 40s for most of the morning. The sun didn't show up until later in the afternoon.
I'm going to post a large group of photos from the trolley tour and harbor cruise. There are photos of the inside of the boat we were on, some of the lighthouses, forts, and beautiful homes!