To this day our sons (now 40 and 45) say their favorite family vacation was our eleven-day junket in a rented Turbo Arrow in 1990. From Van Nuys we flew to Grants Pass OR to visit my side of the family; Portland OR to visit Mrs. P's relatives across the river in Vancouver WA (not knowing we would move there five years later); Glacier Park MT, Durango CO, and home via the Grand Canyon.
Fortunately the Arrow's hydraulic pump waited until the last leg to go out. Shortly after takeoff from our last fuel stop at Kingman AZ the gear plopped down, and we flew the rest of the way home with the gear down.
Other favorites:
-- Taking my 14-year-old grandson -- just the two of us -- to Rome and Munich in 2015.
-- 40th anniversary trip with Mrs. P in 2013 to my favorite Bavarian lakeside village, then train over the Alps to Venice, then five nights in Assisi (heavenly!), then Rome. Cheapest flight from Rome back home to Portland was via Dublin on Aer Lingus, so we extended the Dublin layover a couple of days for sightseeing.
-- Last year's pilgrimage to Melbourne, Australia, so Mrs. P could visit where her mother, a war bride, came from, and to meet several of her cousins.
-- Camping trips with friends in the Idaho backcountry in my Sport Cub.
-- My solo 9-day trip to Bavaria in 2014, which included a flight in an Antonov An-2.