The Hāna Highway is not the road to a place. It is the place. Highway 36 becomes Highway 360 a few miles past Pāʻia, and from there it runs roughly 64 miles out along the windward flank of Haleakalā to Hāna town, bending about 600 times and crossing 59 bridges on the way. Most of those bridges are one lane. Many were poured in the 1910s, when the route was cut by hand and by dynamite to reach a town that until then had no land connection to the rest of Maui. Average speed on the twisting section is somewhere near 20 miles an hour, and that is not a flaw in the road. It is the road.
First-timers usually get the framing backwards. They set Hāna as the target, drive hard to reach it, arrive to find a small quiet town with a bay, a general store and no attraction that repays three hours of hairpins, and drive back disappointed in the dark. Hāna is lovely and it is worth a night if you can get one. But the thing you came for happened between mile markers: the smell of guava and rotting fruit through an open window, a one-lane bridge with a waterfall falling directly into the streambed under it, the taro loʻi laid out on the black lava shelf at Keʻanae, the point near Honomanū Bay where the trees break and a thousand feet of green coastline appears at once.
Three things shape the day more than any list of stops. The first is water. This is the wettest quadrant of Maui, and the rain that makes it green also makes streams rise fast, closes waterfall pools without warning and turns red-dirt pullouts to grease. The second is who else is on the road. Several thousand people live in Keʻanae, Wailua, Nāhiku, Hāna and Kīpahulu, and the highway is their only way to a hospital, a job or a school run. A visitor stopped in a blind curve for a photograph is a real problem, not a minor discourtesy. The third is that the good things past Hāna are further than people budget for. ʻOheʻo Gulch and the Pipiwai Trail sit in the Kīpahulu district of Haleakalā National Park, about ten miles and thirty-five slow minutes beyond Hāna town, and reaching them turns a long day into a very long one.
Then there is the question this page exists to answer: drive or be driven. Doing it yourself is cheaper, you set your own stops, and you can leave at 6:45am when the road is nearly empty. Booking a small van means somebody else takes the curves while you look out of the window, the guide knows which pullouts are legal and which streams are running, and nobody in the car has to do six hours of steering wheel work on the way home. The honest answer depends on who is driving, whether anyone gets carsick, and how much the day is worth to you. Both are covered below, with prices.