Alaska cruises go from May-September, depending on the ice build-up.
Any cruise line can be very accomodating for mobility issues; they all have rooms that are designed to be wheelchair accessible, and the public areas have lots of handholds and seating areas for resting. To get between floors, there are lots of elevators, so your parents wouldn’t have to climb the stairs.
From a quick look at tripcentral.ca, Princess, Norwegian and Royal Caribbean all have departures from San Francisco, but some end the cruise in Vancouver. The majority of these cruises seem to leave and return from Vancouver or Seattle. The Inside Passage is generally less expensive than the Alaska Glacier routes.
For less than a 1 week cruise, you’re looking at September and May, with Celebrity and Princess cruises respectively (there’s only one showing up for each month!). Your options go up significantly if you look at a 7 day cruise.
I’d recommend 7 days, simply because it tends to take most first-time cruisers 2 days or so to figure out how things work, and to start relaxing and enjoying the trip.
I can’t really comment on structure, since I’ve only cruised with Royal Caribbean. We happen to enjoy getting dressed up for dinner but spending the rest of the day doing what we want, and so loved RC for that! If we didn’t want the formality of the main dining room, there was always the buffets and the pizza/sandwich/cookie shop, or Johnny Rockets (on the larger ships… Voyager and Freedom class). The only real time constraints are those related to how early you’re allowed off the boat and how late you’re allowed to return at the various stops. We always felt that the service was of very high quality, the ship was always spotless, there was good crowd control, the staff were pleasant, and all-in-all, both our cruises were wonderful experiences. Which is why our family is going for another one this year!
As for planning, we tend to do the following:
Pick a time of year. If your parents are restricted to certain times (Xmas, Spring Break, school summers) due to their jobs, then where they can go will be decided by that as much as anything else.
Decide on a budget. This is the big thing, because you’ll start looking at prices, tell yourself “that’s not so bad” and then look for a flight… for Canadians, the flight to the cruise port is sometimes nearly as expensive as the cruise itself! Your budget might also decide from which port you can depart - you might not be able to afford to travel to San Francisco, but there’s a sale to Seattle and that puts everything into your budget.
Once you know what’s possible in terms of time and finances, just start looking at cruise websites. The individual cruise lines have good webpages, but I like looking at www.tripcentral.ca or http://www.cruiseshipcenters.com/ (well, .ca) to get a general idea of what the prices are throughout the year, and start whittling away at the possibilities. Both of these are going to be more expensive than buying from Royal Caribbean or other cruise lines directly, though, so it’s just a starting point. At this point, my parents and my husband and I are Royal Caribbean fans, so we might start looking there right away, since they really do have the best prices.
We also start checking the airlines on our own, to find out the “true” cost of the trip, and then perhaps deal with a travel agent friend of ours to see what package (with insurance and guarantees) she can give us, and go from there.
Have fun!