My family (DH, DMom and DDad) like to go for the fun desserts on vacation also...since we're four adults, we justify it by saying that we can have ice cream for dinner if we want!
Anyway, the ESPN Club on the Boardwalk has the "Superbowl Sundae"...it comes in a big bowl that looks like the Vince Lombardi trophy! I'm not sure how many scoops of ice cream there are, but it's large...with a two blondie brownies at the bottom and whipped cream, cherries, nuts on top.
There's also the, ugh, I'm blanking...the Earthquake (I think that's what it's called) at Ghirardelli's in DTD. That's our FAVORITE! You can pick the 8 scoops of ice cream that you want and all the toppings, candies, etc. Again, it's topped with whipped cream, cherries and nuts, standard.
A lot of people also talk about the Volcano at the Rainforest Cafe, but we've yet to try that one!!
sarah