When we decided to drive the Road to Hana during our recent trip to Maui, I decided we would make a big loop of the southeastern area of the island, traveling the Road to Hana, staying in Hana, and then driving the Pi’ilani Highway back to upcountry Maui.

I read quite a bit in advance about making the loop because so many people carried on about the abysmal road conditions – in fact, many people wrote that driving the road would even negate your rental car agreement!

Spoiler alert: our rental car company didn’t say or have in writing anything about it, and while a small section of the road is graded with hairpin curves, zero visibility, and a sometimes troubling lack of guardrails around cliffside drop-offs, once we were through that section, the road was beautifully paved for the vast majority of our drive.

If any of that sounds worrisome to you, don’t take this route – there is a lot of local traffic and it didn’t appear they had a lot of patience for the tourists white-knuckling it around curves they can probably drive with their eyes closed. But if you’re up for a little adventure and have driven on backcountry roads before, you’re going to be fine and wondering what all of the hullabaloo was about.

Planning Your Drive: Top Places to Stop on the Pi’ilani Highway

Assuming you decide to continue on past Hana, there’s lots to see and do. Here are a few of our favorite spots outside Hana and on the Pi’ilani Highway.

Kaihalulu Beach (Red Sand Beach)

We got an early start on our drive from Hana to Kihei via Pi’ilani Highway after beginning our morning watching the sunrise by Hana’s red sand beach. Brian looked up where we needed to park and walk down to a coastal trail taking us around to the beach, and during our walk the sun rose over the ocean, setting everything ablaze.

It was a beautiful area to watch the sunrise, and although the trail was a little sketchy in places, we were able to make it down to the beach for some stunning photos. Sure enough, the sand is very red!

Wailua Falls

One of our first stops was at Wailua Falls – an 80-foot waterfall that is considered one of the most photographed in Hawaii.

This isn’t surprising to me because while it’s a beautiful waterfall, it’s exceedingly accessible with legit parking across the street and a bridge that allows you to look across a lush valley to the falls. If you want a quick waterfall photo opportunity, this is one of your best bets.

Haleakalā National Park

Our longest stop along this route was to hike in the national park. We parked at Kīpahulu Visitor Center, used their wonderful facilities, hiked to Waimoku Falls (which I wrote about separately) and then continued on our way.

Charles Lindbergh’s Grave

Most of what I know about Charles Lindbergh – including that he lived and was buried on Maui – I learned while reading The Aviator’s Wife several years ago. It did not paint a very flattering picture of this much revered pioneer of flight (Note: It did shed light on how many of his accomplishments were in partnership with his wife, Anne, who was often overlooked despite being the first licensed female glider pilot in the United States).

Nevertheless, their tragic story has captured the hearts and minds of so many people, including me, and I enjoyed a brief and solemn visit to his grave, which is in a modest and lovely church graveyard along the coast.

Kaupo General Store

When we were planning our trip, my mom sent me a few pictures from their honeymoon and asked if I could see whether the Kaupo General Store from their photo was still standing.

Turns out it is – and is still operational! – but it was closed on Sunday, which was the day we were passing by. It was still fun to stop and stand approximately where my mom and dad were standing 40+ years ago!

Driving the Coast

While in fact the opposite of a ‘stop’ along this route, I wanted to note that simply driving through this area of Maui was a wonderful experience in it’s own right.

There were very few cars or people and loads of places we could slow down or pull to the side of the road to admire the beautiful scenery, including Kaupo Gap, Nu’u Bay, and the Manawainui Valley, and glimpses toward the summit of Haleakalā volcano.

A favorite moment was spotting several goats heading into a low-hanging cloud! We also saw several people on horseback heading for the coast from Triple L Ranch, which had to be quite the experience.

Upcountry Maui

The highway ends in upcountry Maui, and we celebrated with a late lunch of Kalbi ribs with chili miso and teriyaki sauce at Ulupalakua Ranch Store before walking across the street to do a wine tasting at Maui Wine.

Both locations have awesome views so I’d recommend grabbing some refreshments, finding a spot outdoors, and revisiting all of your favorite spots from your day driving Pi’ilani Highway!