For many years, I've usually planned one long cross country per month and do shorter trips or training in between. From Dallas to Wisconsin to see family, Dad was in San Diego until he passed a few years ago, Daughter and family in Virginia, now South Carolina. Mom in Orlando and I attend SIMCOM there for recurrent training.
My big one this year is Dallas to Madison, WI to pick up family, to Charlotte area, to Nassau and back this August. Last year, I did the same trip but to Kiawah Island, SC instead of the Bahamas.
Best,
Dave