I encouraged my sons to go on road trips, but put my foot down on one point; they needed to daven with minyan every day (over shabbos was not an issue, so we did not discuss guidlines for that)
I needed to be realistic. By the time a bocher is 20+, he needs to be getting some wings.
And yes, I think a bocher that learns hard and puts in the hours 10-11 months a year, is entitled to “chill” every now and then. I do, and so should he.