We wanted to take a sailboat or schooner cruise in the Portland harbor. Maine Sailing Adventures is located right next to the Portland Schooner Company so we checked out both companies. PSC was $5 cheaper and allowed for the carry-on of drinks and food, but they did not have sunset cruise availability. We opted for the MSA option of a sunset cruise because they did have availability and also had an on-ship bar so we did not have to worry about carrying anything with us as we toured the city.
The cruise itself was relaxing and enjoyable. The sailboat makes its way around the Portland harbor area. It was not particulary adventurous, and we didn't see any marine mammals. However, it does provide views of three old war forts, Bug lighthouse, Spring Point lighthouse, and a distant view of the Portland Head Light. You also cruise near Peaks Island.
The return of the sailboat provided amazing sunset views of Portland. The crew was helpful in answering questions when asked, but an overall tour explanation was not provided unless asked. This probably helped contribute to the calm appreciation of the area and sail atmosphere, but if it something you are looking for in a sailboat cruise, be prepared to ask the questions you want answered as they will not be provided by the crew without the questioning.
Overall, it was a nice experience that was incredibly relaxing and provided beautiful harbor views.