My wife and I will be taking the Hana Highway drive to at least Charles Lindbergh’s grave. We were also thinking about just keeping on going that way and take Highway 31 around the south south of Haleakala and the island and then Highway 37 and the Kula Highway. However, I remember reading in a few places that only 4 wheel drive vehicles should take that road and most car rental companies explicitly state that you cannot take their car on that road. But I’ve been talking to a few folks lately that have taken that road in the last few years and they said it was in just as good a shape as the Hana Highway and any car could make the trip. Do you know the exact status of Highway 31 and/or can a standard car make that trip?
If you take the road past Oheo Gulch (Seven Pools) and past Lindbergh’s grave and continue around the south side of Maui to go all the way around, you will have to drive on about 5 miles of unpaved dirt and gravel road. (This is NOT like the Hana Highway normal route around the north side, which is paved all the way.) It may be possible to drive on the dirt and gravel road in a normal car IF IT HAS NOT RAINED in the preceding couple days, and if there have not been any recent rock slides or washed out sections of the road. However, you never know whether those things have happened or not until you get to that part of the road, and then it is too late, so I do not recommend it. The car rental companies prohibit you from driving their cars on unpaved roads, and they will not come to tow you out or assist you if you get stuck on that unpaved road.
Even if you drive on the unpaved road, the road around the south side of Maui from Hana DOES NOT CONNECT to the roads in Wailea or Kihei. So if you drive all the way around the island from Hana, you will end up back in Kahului.