I love all inclusive vacations! For the last years, we have done AI in the winter/spring, and WDW in September. The feel is very different, much more relaxing, and so "pampering". We don't have kids, so we never looked much at activities, since we are content with the beach, pool, drinks! However, the hotels we went to all had "kids club", where all the kids can hang out together with some sort of supervision and entertainment.
My first choice is Cuba, because of prices, stunning beaches, and good service. I know some people fear the food, but I must say I always ate well. Not magnificently, but simple and well. Lots of fresh veggies, fish of the day is always great, chicken often nice as well. Just don't expect the big steak/potato dinner, and all is well. Go for food that is somewhat cooked like the locals do, it will be tastier than most Americanized (and Canadianised??) imitations. I know those are the most popular options, one time we got in at buffet opening, and there was already empty serving dish. After wondering what could be so good as to go that fast, we spotted one lone onion ring in there!! No need to say we quickly moved on to the untouched smoked salmon plate...
This year, we are going to Jamaica, which is way more than our usual budget, at Couples Swept Away, an adult and king bed double occupancy rooms only. Suppose to be very romantic... The big reason for the splurge is: (shut...) we are eloping and getting married on the beach. It's a secret, so please don't tell anyone should you know me!
Next year, it will be back to Cuba, because there is no way I can afford this type of AI (or Beaches, Sandals, Breezes, ...) every year, unless it's our only vacation.