Wow. Cruising with a 2 year-old. I'm sure it's been done but I can tell it may be a real challenge. My wife and I sailed extensively in the Ches Bay with our kids, now 15 and 11, when they were infants and up. The two year old presents the challenge in that she is now mobile and cannot be strapped into a car seat, which I always had strapped right next to the helmsman seat. The two year-old will be naturally inquisitive and restless which can cause safety concerns when she explores the boat. She also will not be a strong enough swimmer to survive any type of overboard situation. My concern would be boredom. We tried to stick to the 4 to 5 hour rule when our kids were young in that we would only cruise 4 or 5 hours without getting to an achorage or marina and we made sure to find things to do ashore like marina pools, kids' musuems, ice cream shops, etc. that would make them "like" the cruising lifestyle not abhor it. Insuring that your kids "like" or take to sailing in the long run is the most important thing, in my opinion.
Not saying it can't be done, but I am saying it may be a challenge.