We did the Galaxy Canada/New England cruise out of Baltimore last May and enjoyed it very much. As far as ports go, Quebec City is the most interesting port you'll visit. As mentioned in previous posts, it's a great city to visit on foot. The ship docks just below the old walled city which is very picturesque and reminiscent of France. In fact, you may have to pinch yourself a few times to remind yourself that you're not in Europe! You can spend the entire day just roaming through the city, without ever venturing beyond the wall into the newer, more modern part of Quebec City. There are some great restaurants for lunch and lots of nice shops. There's also an outdoor "gallery" where local artists sell their works. Some of it is very touristy, but some of it is quite good.
Portland, Maine is ok - nothing special to write home about, but the gentrified area near the pier has some nice restaurants and shops. A walk through these streets is pleasant. Beyond that the city is somewhat depressed.
Halifax, Nova Scotia was a pleasant surprise. It's small and walkable. The citadel is interesting and there's a beautiful park near the univeristy. The walk along the waterfront is very nice, and the old brewery has some nice shops in which to browse. The downtown is a bustling business center.
We, and most people on our cruise, could have done without Sydney. Unless there's been a major overhaul of the city during the last twelve months (and most likely there has not been), it will still be blighted when you get there. The main drag was perhaps four blocks long and was filled with empty stores. It sort of looks like everyone left town. We're still not sure why it is a port of call, but I seem to remember there being a shore excursion that goes beyond the city, which some people said was interesting. Should we ever visit Sydney again on a cruise, we won't bother getting off the ship.
Bar Harbor was very "Maine" and charming. It's nice to just meander through the streets. We were there just prior to the "season" and you'll probably be there just after the "season," but we enjoyed visiting. There's an old drug store on the main street, complete with working soda fountain. Pop in and have a nostalgic look.
Re the weather - pack some warm clothes. We cruised late May/early June and it was still cold. Layering is a good idea, since you can cover up/uncover as the weather dictates throughout the day.
Hope this helps a bit. Enjoy your cruise!