FYI in my opinion there are only a few travel sites.

sure theres plenty of hotel or airfare or rental or 'town of xyz events calendar' sites but no one solving the entire problem.

I've yet to find an end to end trip planning site, especially one that is family oriented.

Exactly. Places like TripAdvisor simply isn't going to cut it. I have a friend who tried to tackle the problem a couple of times but still haven't succeeded.

My guess is that the solution is something simple, something that isn't algorithmic but rather a platform for travel agents who can listen to and understand the individual needs.

Why are smaller boutiques family friendlier? I assumed the big all-inclusive resorts were more family friendly because you can just let the kids roam around in a contained environment.

LOL. I just paid for an all inclusive which came out to be an additional $25/day/person over the hotel room rate. The food was shit but the drinks were okay and unlimlite. And thus we found out that all-inclusive can mean different things.

I would say the Atlantis, Bahamas resort does a good all-inclusive. It has activities for kids and adults. The resort I stayed in Malta was clearly for young adults. The kid and I were practically chased out the pool once the sun set.

They aren't normally thats the point :)

We are looking for those that are but without the tediousness of the all inclusive crowd.

I like these sorts of ideas because they come down to trust. One thought I had was to begin curating lists of the best airbnb/homeaway listings to help people find places to stay if they are overwhelmed by the sheer number of available listings.

Any suggestions on family friendly places you've found?

What you are looking for is simply called very expensive hotels :)

Hehe if it only was that simple. :)

I have stayed on many expensive hotels but that is not what we are looking for. We are looking for hotels that are family friendly so other families go there but without it being a family hotel.

We will pay whatever it cost but it's not so easy to find that the balance.

This is on the high end, but have you checked out the relatively new "destination clubs" like Inspirato or Exclusive Resorts? Family-friendly and extremely vetted, to the point of having on-site personnel in most locations. We're a member of Inspirato, and it's been great. Private residences and hotels.

Would you mind posting more information about your experience? I'm interested.

High end is fine. I will have a look thanks.