Hmm....not sure I'd take a stroller on that trial. I've done the trail many times, including this past November. The bamboo forest is very cool, but the mud, rocks, and width of the trail will be an issue. I've seen 2-3 year olds on the trail, but they've been in a hiking backpack that's made for kids to ride in. I have one made by Deuter for my daughter. There are some drop-offs, but like you said, if you respect the trail, which is well marked with some fences etc., you'll be fine.
But- you could walk down to the 7 Sacred Pools with a stroller, at least most of the way. That's a 10 minute walk that a lot of people do.
One thing to for sure do is continue driving past that area as opposed to turning around and going back through Hana. Very cool views that not a lot of people see. The road gets hairy for a few miles, but it's worth it. These pictures were taken back in this area. I like cool road pictures...

Cool, thanks for the input. Ya, I have a backpack for my littlest one. Reading a maui guide right now that also recommends going all the way around, so I will have to put the mini van to the test. LOL.


