Cape Ann Whale Watch in Gloucester, MA is a must do ! I was on the trip in late Oct and the whales were pretty active, much more so when we were heading back to the harbor. But still, active the whole time we were out there in the area of the whales. The best thing about the trip was the whales!
The boat had food, snacks, drinks, an indooor space on the boat with tables and bench seats, restrooms. Some people took their dogs an the boat and the dogs didnt seem to enjoy the trip. I wouldn't take my dog out there. You can take your own food and drink and might be a good idea if you don;t want to pay the prices on the boat. The boat wasn't crowded like the other one that came out. Cape Ann Whale watch was the first boat out there, which was great. The crew was informative about the area and the whales. Do take a camera, digital camera recommended. A light jacket is useful in late Oct when I went. The water was calm so the day was ideal for picture taking. The trip was approximately 3.5 hours long and around 25 miles from the harbor. Boston could be seen in the distance as we left the harbor.
I would highly recommend going with Cape Ann Whale Watch and will go again the next time I visit the Gloucester, MA area.