I have flown while on vacation a number of times. Usually, it's just a local flight with an instructor because, for flight when I take the airplane, it means a checkout flight before I take it myself. As much as I love flying, I really do choose vacation spots for other reasons. And there can be other bars to rental, especially in other countries.
So my Hawaii flight was an afternoon with my wife and a CFI. Our flight from England to France was with another pilot. turns around a point, the "point" being Mt Hood, was an afternoon break from a conference with an instructor. Same for a trip to Catalina.
OTOT, my first flight around Florida to visit friends and family in three places, while on vacation in Orlando, was after a checkout. Worth it since we had been to Disney many times before. I continued that tradition when my inlaws moved to Florida and took advantage of Christmas weeks with them to fly to visit other family. Northern California and KISP to Block Island are other examples.
BTW, some of the stories of these flights are collected on my website in the "Taking Wing" pages.