My family has been vacationing here since I was about 9 years old.  My first memory of Grand Cayman was being on a business trip with my parents and finding other kids to play with, we spent the week throwing water and ice on each other constantly.  Then one of the last nights my parents were walking back from a business dinner to find their 9 year old balancing  on the top of the pool bar trying to break in.  Not to drink, but to get some cups for water fights of course!   I had my balance perfectly, at least until my mother screamed at me to be careful.  

I have lots of memories here, many of which doing stuff I should not have been doing, like breaking and entering, clubbing under age, and hitch hiking.  Needless to say it is one of our favorite family spots because it is safe, even when your kids are not.

Things to do:  Stingray city, turtle farm, scuba diving, snorkeling, swimming on 7-mile beach

Favorite restaurants: Pappagallo (lobster, pasta, and deserts), Calypso Grill, Sunshine Grill (fish tacos), and Luca.

This town has a special place in my heart since it is where I was married.   Aside from my bias, it also has great shopping, eating, and views.  

I recommend this town as a day trip.  But if you do stay over  I stayed at Villa Fiorentino.  This Villa a beautiful family owned villa with a pool.  The views were amazing, the rooms were decent sized, and the family feel is something you couldn't put a price on.  Additionally, the hike from town up to the villa is rigorous enough that you can eat whatever you want when you are there (which was perfect for my big day on a pasta diet)!

Shopping - there is a great shoe store that has loafers every color you could imagine, as well as several ceramic shops and other local artwork. 

Eating - several options here but I will list a few at different price points.  
1. Max's - stuffed calamari is amazing! As well as any pasta or dessert.
2. Buca di Bacco - great wild boar and panna cotta, sit on the patio and enjoy the views
3. Next2 - I haven't been here but heard good things, I want to try it next time I visit.

Others - beach is typical euro pebble but decent sized.