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How do your kids do when you do keep them up later for a special occasion? Do they sleep in at all the next day? That may give you a little clue as to how well they will adapt to a later bedtime/wake time.

DD has a late bedtime and sleeps in pretty late, too. We may have to start her in school in the fall, and the earlier bedtime is the part I am dreading most!

I also agree that you just won't know what will happen till you try.
My 3yo for a long time had 7/7:30 bedtime, 7am wake up and 1-3/3:30 nap. He just started needing his nap to be pushed back to 1:30/2 which means bedtime is now more like 8pm. He still doesn't sleep past 7 and has actually even been waking a little earlier. 6am some mornings. I know that SOMEDAY he will sleep in and I'll have to drag his butt out of bed

As for how to attempt it, I would see if you can manipulate nap to be a little later to try and get a slightly later bedtime and maybe you'll then be lucky to get a later wake up in the morning. I would do it 15 mins every couple of days and keep adjusting. See how it goes and if it's working, decide how late you want to go.

When we've changed bed time it's been by half an hour and we always just go to the new bedtime.

i wouldn't expect sleep in results the first night but after s few days I would.

Do you have any summer vacation plans? The one thing that has shifted my kids bedtimes later was being completely out of the normal routine, and it took a few days...but both a Disney trip last fall and a beach trip this summer have pushed bedtimes later, and a few days into it wake up times were later as well. We tried to keep to the later schedule once we got home, and we're now somewhat later than we used to be..

Pretend it's a time change. Shift everything - wakeup, naps, meal times, bedtime by 15 min a day until you get the right time. And if they wake early, treat it as a MOTN wakeup.

Or bedtime naturally got a little later in the summer, I would try spending time outside when it's still light and moving everything in the evening a bit later.

Or whole routine has shifted 45 minutes to an hour later.

That being said, sometimes the baby passes out early. Depends on his naps.