School in Summer?

It's difficult to decide if we should take an entire summer off school or not. I'd prefer not but of course that's not D's preference! He'll at least have two to three weeks totally off but two to three months? Especially since I'll be working and we can't take off for long at a time. I'm fairly certain he'll homeschool next year as well so the breaks can be spread out differently. It's completely adjustable. His friend is in public school so we'll make time for them to get together more often and do some fun things.
The babies come over every weekend so that leaves us with no real time off to relax. I'm thinking that I'll start for next year having him do 4 days a week so he can have a day off in the middle of the week. That may require longer days those 4 days or I could have him do a half-day on the weekend - the schools here have half-days Wednesday or Friday depending on the district. I certainly don't recall that from my school days! Though I admit, my junior high only ran from 7am-12 noon or from 12 noon to 5pm. I was one of the lucky ones, I went from noon to 5pm, what a wonderful schedule that was! Sleeping in and still free time after dinner, aahhh, that was so nice.
The only thing I really need to consider is that when not on a school schedule, he's so very creative! I don't know why I'm so afraid to "unschool" him, it certainly worked well for his first three school-age years. But now we're not traveling the US with the ability to stop or go whenever and wherever we want anymore. Unschooling is perfect when the parent can provide plenty of opportunities. I'm afraid I don't have that option at this time. Too bad.