I know this question is probably too general but not sure where to start. This summer (August) the family vacation with just be myself and my almost 14 year old son. We have 10 days - two weeks depending on cost of the trip. Two years ago with the expertise and help from the CR forum, he and I had a great time is Costa Rica but it did get lonely at times with just the two of us. It just didn't work out to connect with other families at the various accommodations or tours we went on except one night time jungle tour - with a toddler and her father! We are not all inclusive resort travelers or family-theme vacationers. We like nature, beach and local culture. But are there organizations or places that specialize in getting families together or booked in the same locations?
As a larger family we have traveled to various parts of Mexico - which we love. Central and South America are of interest. We have not really traveled to much of the U.S. at all. The West Coast is of interest. And of course August weather takes some places out of the running.