5. Family / Kids
My prior trips have been all-adult trips. Any advice on:
a) family-friendly areas or family centric must-do activities?

We have been taking our now 10yo to the VIs ever since he was 4mo, a couple of times a year, land based.

I think the VIs are very family friendly with many things kids will love. In no particular order, my son enjoyed -

On STJ:
Al the north shore beaches, Maho especially for the turtles
Both ruins - Annenburg and Catherineburg
Any Friends of the National Park program
The ranger-led Reef Bay trail hike. Call ahead, reservations needed.
STJ carnival, used to have a good kids area

VG:
Dinner at coco maya
Anything at Leverick
Saba Rock happy hour tarpon and tank talk
Copper mine
Spring Bay - probably his favorite ever
Gumption's Necker Island tour. The lemers rocked his world.
Michael Beans and the Jumbie nights, don't know about the summer schedule for those.

Cooper Island

Walking the trail on Sandy Cay

I am sure I am forgetting something.

b) suggestions on where my kids might meet other cruising kids? or we might meet other cruising families w/ kids?

There is a great blog I read written by a live abroad family who are currently in STT. She writes extensively about activities with kids. When I get to work, I will post the link.

Sounds like a dream trip! What a perfect age to take the kids.