Our highpointing trips became a family event each year. The trip through the South included Disney World and the other Orlando attractions. Our New England trip included Cooperstown and Sturbridge Yankee Village. The upper midwest included Mt. Rushmore and Chimney Rock (the year Nathan studied the Oregon Trail in school). AR/LA included a Christmas season visit to San Antonio and the Riverwalk for my wife.
Sell them to your wife as educational for the kids, plot loops that bags 3 to 7 highpoints and haul 'em all along!
For examples, check the "highpointing" section of my WWW site
Now, Denali may be a bit of a tough sell...