The drive from Hana to the entrance is probably 45 min and I wouldn’t really want to do that drive in the dark. You have to pay and go through the gate to access the trail. Just plan to be there right at 9.

If I am understanding you correctly, you want to get to the Pipiwai Trailhead driving ENE along the southern side of Maui. Assuming you will be renting a car, be sure to check the agency's policies for driving on this road. My understanding is that this road is very rough and driving on it would void the insurance offered by most car rental companies.

We did not encounter any mosquitoes personally but they do exist on Maui, especially on the Hana side. They tend to be more active in the early morning and early evening.

I drove the Road to Hana from Lahaina and eventually ended up at the Pipwai Trail. The drive is long, and the road has a lot of curves and one lane bridges, but I did not think it was scary at all.

Definitely not a same day type trip.. Road to Hana will take one full day..with minimal stops before hiking the Pipiwai trail. IF I were to do this again I would drive straight to the trail do the the hike then make the sightseeing stops on the way back.. they crowds would have thinned out by then and you wont be driving that road in the dark like we did :)

We actually did this same day. We found 3 trails in the park - 1 small and 2 very long trails. Shifting sands starts near the same parking lot as the sunrise service but I was too cold to start a hike there - they aren’t kidding about the temperature difference. And my husband did not want to do the longer trail. We googled how to get to the other side of the park and made the mistake (although I got some of my best pictures on this side) of taking the reverse road to Hana. I would not suggest doing this without a higher clearance car since many of the sections of road are barely paved. It took us about 3 hours to get there since we stopped often for pictures but it’s only a few hours hike round trip. We were back to our condo by 4. It was well worth it for me.

The trailhead for both the Pipiwai Trail and Ohe'o Gulch (Seven Sacred Pools) is at the north end of the parking lot at the Kipahulu Visitor Center south of Hana. The address for the Seven Sacred Pools on TripAdvisor is very, very wrong; I've tried multiple times to get it corrected but haven't been successful yet.

The Pipiwai Trail is just 10 miles past Hana on same road. The road to this trail does not look any different before or after Hana. You are allowed to take your rental car to this Trail (and the National Park that it sits in). The Parking lot is about 30 feet from the road and if that one is full you have to park in the overflow lot a block away. At some point the road turns to dirt and many rental cars are not allowed on it (I have never driven that far past Hana but know someone who has). Also, the road to Hana leads to Hana. Bring motion sickness pills as it is easy to get car sick if you are not in the driver seat (lots of curves on this road).

If the weather is good (not pouring rain) it is not that hard of a hike. Wear good shoes as it is a bit rocky and there are some tree roots to look out for.