I’ve rated this third, as far as road trips go. Mainly because, if you decide to circle this entire side of Maui, it gets a very curvy and narrow toward the end (But, don't let that discourage you! I found it much improved last year). The road here hugs the edge of a cliff and it gets down to one lane for small stretches. So, if you encounter someone coming in the opposite direction, you may find yourself backing up to the nearest turn-out. However, there are some pretty sights while the road is still two lanes. You could turn around there and head back, like you will in Hana.
This is the route you’ll take to go to Lahaina, which is a must see, even if you decide not to do this entire drive. I’ll go more into depth on Lahaina later. Beyond there are the beaches and hotels of Ka’anapali. Kapalua is further north, and hosts a PGA tournament annually. You can even play this course, if you're interested. Other nice sights include,D.T Fleming Beach, Honolua Bay and Nakalele Blowhole. The Olivine Pools lay just beyond where the road turns into one lane. One of the best reasons to complete this drive, is because close to the end you'll see a little road side stand on the left. Curley Fruit Stand is located near mile marker 10. Here you will find the best banana bread on the planet. No kidding, it broke da mouf! (see, Hawaiian Language)However, you could decide to head toward Wailuku first, and get the tricky driving out of the way early (and get your banana bread early). Last year, we went the Wailuku way and found it very enjoyable. It was a good call to do most of the stops for hiking, gawking and rock climbing earlier in the day. That left a few hours in the afternoon to stop at Maui Brewing Co. for a beer, and walk around Lahaina for a bit.