I cannot say enough good things about trail riding with Maui Mountain Activities. The trail bosses were kind and knowledgeable, the horses were very good and well cared for, the tack was nice (not something you see everywhere,) and the scenery - well, what can I say, we rode through paradise!
Maui Mountain Adventures asks guest to self-identify their level of riding expertise: Beginner, Intermediate, or Advanced. Everyone rides together, but they ask so that they can put you on the horse appropriate for you. This is because, unlike on other trail rides, they let the horses RUN! TWICE! And by run, I mean full-on gallop. Not a nice little canter. For anyone who wants to run, you can run. If you don't want to, you don't have to, but these horses know what they are doing and you won't fall, even if you're a beginner.
I'm an experienced rider and I didn't feel like I was on the typical nose-to-tail trail ride. The whole experience was glorious. The bosses stop the ride twice for pictures, which they take for you using your camera/phone.
Oh - and they offer helmets if you want one (must sign waiver if you don't), saddlebags and water and snacks for the two-hour trip.