Your 14 and 16 year-olds are past the splash-pad phase, which eliminates a lot of generic family resorts. These picks skew toward genuine experiences—whether that's riding horses all week, sailing on a pristine lake, or staying at properties where teens actually have things to do beyond supervised activities. The Cloister at Sea Island and Averill's Flathead Lake Lodge stand out because they're built for this exact age range: old enough to want real adventure (horseback riding, water sports, actual skill-building) but young enough to still want to be together as a family. Both are all-in commitments, not grab-bags of add-ons.