I have in the past. I don't really do it nowadays

Every year the wife and I head to Dallas and TPF. It's something that we look forward to all year long. We catch up with our Texas pinball friends and drink some beer. It used to be easier (and cheaper) when we lived in Houston but it's worth the extra effort and expense to fly down from Seattle as the show gets bigger and better every year.

I travel a lot for work doing trade shows and what not.
I use the pin map on a regular basis to find places to play.
Doesn’t matter if it’s a bar, barcade, bowling alley etc.
Hell I even picked a place to do my laundry once in Germany because they had two pins at the laundromat.

I do travel to Pinball shows for fun if that counts as a vacation.

I don’t plan a trip solely on pinball, but I ALWAYS look the pinball in every city I visit.

I did a road trip to Florida in the early 90s and passed thru Disneyworld on my way to Key West and stayed at the onsite campground. I never went in any of the parks though but found a couple pinball machines and played them to pass the time.

They were a couple of new releases, Addams Family and Twilight Zone. I liked the new direction pinball was going in, but hoped they would come out with better games, which after I got home, I found out they did. But I'm not driving 3000 miles just to play pinball.

Head to rec bar in Louisville. Like going to a show. Horrible food though

I've made a couple of trips to Las Vegas to go to the Pinball Hall of fame.
I go to Arcade expo and Pinball madness in Banning.
in 2016 I made a trip to the Bay area to go to the Pacific Pinball Museum, Free Gold watch and California Extreme.

Road trip "vacation", no - I think that would be fun though, if the rest of your party is into it -

I go to Expo/Chicago every year, and Milwaukee/Midwest Gaming Classic, up to 4 other local MI and OH shows depending on my mood, but those arent really extended stays, just "the show and go".