If you really like detailed descriptions, this is for you!
This was such an enjoyable and affordable way to truly experience the entire island. For about $150 a day including the required commercial insurance, you really can't beat the price compared to a traditional hotel/rental car combo. I had five days with Van-essa. I really can't say enough good things. The bed was really comfortable and there are a lot of thoughtful details. Communication, check in/out was a breeze and I was annoying and asked quite a lot of questions lol. I took advantage of the airport drop off option which was really easy and gives you a little more time to enjoy the island before leaving. Baldwin Beach Park is only about 15 minutes from the airport and that's where I hung out as long as possible before heading out. $45 is totally a fair price for drop off as an Uber trip from the airport to the vans location will cost nearly the same. * I had no problems with arriving about 2 hrs before the flight, parking, and getting to TSA check about 1 hour 45 minutes before boarding. I also never check bags. But heads up, I heard lots of stories about missed flights and needing to arrive three hours ahead of time.
If you're hesitant because of the vans size, I didn't really have any experience driving anything this big. As long as you're a pretty confident driver, I think you'll be okay. I became quite comfortable with it quickly. I never had any issues backing it in or parallel parking. Getting to destinations before 9 am helps with this. Or if you want to go to Makena Beach Wednesday morning, get there later in the evening Tuesday night and overnight. You'll find plenty of parking after 7/8 pm when most people have returned home or to hotels. Coming from the Portland, OR area I was worried the parking situation would be similar to that and more of a challenge. But the only area similar to that was Lahaina and Paia. There are public parking lots available as well as street parking in both cities. Free in Paia, the one I found in Lahaina was a paid lot.
I was able to do the Road to Hana in the van and felt pretty good about the whole thing. I went as far as allowed. It was totally worth it to hike the Pipiwai Trail at the end. In my opinion, the only true hairpin turn is the very first one. This was the only scary point for me on the drive and I thought about turning around. I'm so glad I didn't because the rest of it was completely manageable. That first turn you will see a sign that says "be prepared to stop" and I believe it's the only sign that says that along the whole stretch. It was scary because the turn is very sharp, you have to really slow down, but also as you make the turn the road becomes incredibly steep here. When I did it, this area was also a little slick. Due to all these factors (the tight turn, steepness, slickness, loss of momentum) the van actually got stuck in the middle of this curve, wheels spinning, unable to get up this hill, other cars behind me. Fortunately, there is a little turn out right there, but it is on the other side of the road. I had to use this to pull over, re-adjust the angle of approach and she then tackled it no problem. If you can make sure nobody is coming before making the turn, and take that turn a little wider, it would probably be way better. Otherwise, the rest of the road, just take your time and follow the yield signs and its no problem. My advice is to start the trip early, skip all the destinations along the way and reach your furthest desired point first! Then you can make all your little pit stops on the way back out. When I passed twin falls in the morning, the very small lot was packed because it's one of the first stops. With this approach, there's less pressure of traffic behind you while driving down, there was ample parking at the Pipiwai Trail when I arrived early, and on the way back I had twin falls all to myself and they were no longer charging parking at that point in the day! * So many things are advertised as pit stops along this route. However, just want to note that Kaihalulu Beach was gated off. It seems like a lot of people park and walk down but there are signs asking not to do that. I did not go down to the beach out of respect, and there's plenty of other things to see. I was surprised to find that Waiʻānapanapa State Park apparently requires a reservation just to park and see the beach as a pit stop! For sure, camping here requires reservations well ahead of time. * * There are many fruit stands and little businesses along the way. Hana Farms Roadside Stand had amazing banana bread, mango tea, farm fresh fruit, and handmade souvenirs from local artists. The pizza looked amazing but the restaurant was closed when I stopped. *** You really need to start early just to have time to do everything as the drive alone there and back takes several hours.
Not knowing exactly when and where I was going to be places, I was hesitant to book campgrounds ahead of time. I still had a good time and figured it out. That being said, the West side of Maui seems friendlier to this approach as there are numerous places to just pull off the road and overnight right along the beach for free near Olowalu Beach. If you want this experience to be a little less stressful, trying to figure out where to pee, shower, and park every