If you are looking to climb the infamous Stairway to Heaven (aka Haiku Stairs) in Oahu, there are plenty of ways to do it without getting a $1000 citation.
There is a security guard at the base of the stairs, poised and ready to call the cops. He generally does not call law enforcement, or will cancel a call if hikers decend a different path that leads through the drainage ditch and out of the area. It is harder to catch trespassers this way, and Hawaii doesn’t have the manpower (or the care) to find trespassers if you exit the Haiku Stairs away from the trespassing signs.
On the other side, there is a completely legal way to get to the top of the Stairway to Heaven: The Moanalua Valley Trail . It´s actually a much nicer hike because walking up 4000 steps is not really a “hike”….
It´s a pretty long trail ( I would recommend you to download the app AllTrails to find the start) and the sun can be really strong, so make sure you start quite early in the morning. After you arrived at the top you can hike back the same way (completely legal) or go down the stairs (watch the guard). You can probably ask some guys on the top if there is a guard on that day and if he does care or not.
Bring plenty of water as well and get some nuts/chocolate for more power ( Trail Mix from Walmart is highly recommended). Have fun!