We did, 10 years ago. The kids missing elementary or middle school days wasn't a big deal, like, at all. Once the kids started hitting high school, though, our vacations became more strategic. It would be long weekends so any of them in high school would only miss a day or two. Of course, they all have iPads so distance learning is far more feasible over the past 8-9 years than it was prior to that.
The first years that I went to WDW starting in 1983 all of Vermont had a mid-winter break which ran from the last week in February through the first Tuesday in March. Why so long? If you lived in Vermont in February you wouldn't ask.
Anyway the first Tuesday in March was Town Meeting Day. The town meeting was held in the school gym so they started back up the day after. Of course the dates changed but it was always consisting of Two Weekend, 7 weekdays. At any rate it was the tail end of February through the first Tuesday of March. The eleven days gave us time to drive to Orlando, go to all the parks (mostly MK and Epcot and a short time with DHS). One or two extra days to go elsewhere and then drive home in time for school on Wednesday. Sounds a little confusing, but it really wasn't and worked out great for our yearly Florida trip.
All of the public schools had the same schedules so one of the games we had with the kids was counting cars with Vermont License Plates. It wasn't hard because we always used a horn signal and wave as they passed us or we passed them on I-95. It was common to meet neighbors that we didn't even know were going there at the same time. I guess that is where my early fun memories formed and carried through for many years.
Might be clearer with the calendar below... That first year we left on the 19th and arrived in the morning of the 21st checked into our hotel and the next two days were in MK and briefly in Epcot. Epcot was only about three months old and to us it was just unorganized madhouse so we left and went to Kennedy Space Center. That left us to decide to leave on the 25th and head up Rte. 27, I think it was, to visit Silver Springs and off to Walterboro, SC. Then the next morning we headed to Washington arriving late afternoon. The following day we went on a guided tour of DC and left there for someplace in Jersey on the 28th we arrive back home gave ourselves a full day to get out of our magic cloud on Tuesday and life began again on the 2nd of March. I can only speak for myself but that adventure, the first big one since we got married and had children, has cemented solidly in some file in my brain. It's possible that a couple of details have escaped but most of it is intact. The following years the dates changed, but the same schedule was continued.
Sorry, I didn't mean to bore anyone with details of 42 years ago. Some will think that we spent more time on the road than necessary, but it was our first trip and I had no idea how long it would take, so I planned for three days each way. I'm not exaggerating but I feel that was the best family vacation we ever took. We tried year after year to duplicate it and even though they were great, they never seemed to measure up to that first road trip and, of course, WDW! I'll end the travelog now.