Driving down from Kahului you could be forgiven for expecting the usual resort strip with manicured verges and gatehouses, like somewhere you’d stay but never really visit. Wailea is all of that, on the face of it, with six big hotels along a mile and a half of coast, a golf course either side, and a shopping centre selling things nobody needs. The grass is cut so short it looks laid rather than grown, which is pretty, but feels unnatural.
The giveaway is the traffic at half seven in the morning, with people heading to work rather than to breakfast. Around 6,700 people live in Wailea and the figure climbs every year. It’s up nearly 8% since the 2020 census. Meanwhile, Maui County over the same stretch has been losing residents, down about 1% in the last twelve months.
So the island is shrinking yet this corner of it is filling up. You notice the knock-on effects everywhere, from the traffic on Piilani Highway to the number of local firms advertising Hawaii moving and storage on the noticeboards, and people are arriving here with everything they own.
Nobody can fence you off the sand, and the state is specific about it
This is the thing to understand before you go, because it changes how the whole coast works. Every beach in Hawaii is public up to the high water line. Not most beaches, all of them. The shoreline and what the law calls the beach transit corridor are public property under state statute, and that applies just as much in front of a Four Seasons as it does anywhere else.
The enforcement detail can feel amusing as landowners are required to keep their planting trimmed back so it doesn’t block the corridor, and the state names the culprits directly, such as Naupaka, Beach morning glory, and Beach heliotrope. There is a government office whose job includes making sure a resort hedge hasn’t quietly annexed a footpath.
So the beaches that look sealed off are not sealed off and every one of them has a public car park, a blue access sign and an outdoor shower. You can walk in past a hotel that charges four figures a night, put your towel down, and stay all day.
Start at Polo and walk north
This stretch is about a mile and a half long, and it’s flat and paved end to end. Wheelchairs and pushchairs are fine on all of it, which you can’t say for much else on this coast. Walk it north from Polo and you’ll hit Wailea, Ulua and Mokapu in that order. Keawakapu is just beyond the northern end if you want to keep going. In between the sand gives out and the ground turns to black lava, with the path climbing over Wailea Point on the way, which is the spot you want at sunset. There are old stone hale remains up there with a plaque explaining them, and almost nobody stops to read it.
You’ll pass the Four Seasons, which people recognise before they can place why. It’s where they filmed the first series of The White Lotus.
Here comes the practical bit. The lots fill early, from around nine in the morning between December and April. Polo Beach at the southern end is reliably the quietest and Wailea Beach in the middle is reliably the worst. Park at Polo, walk north, come back when you’ve had enough.
Whales are in the channel from about November to May which you can see from the shore, with no boat required.
Five minutes north and you’re somewhere else entirely
Drive up South Kihei Road and the change is almost comic. Kihei is strip malls, surf shops, fish tacos out of a window, condos from the seventies with the paint going. Cheaper, louder, considerably more fun on a Friday. The beaches at Kamaole are just as good as the ones in Wailea and the parking is easier.
This is the contrast the title is really about. Two places sharing a coastline and about four miles of road, and they don’t feel like the same island. Wailea is peaceful in a curated way, while Kihei has a more authentic feel since it’s all about everyday life.
Many visitors like to stay in Wailea and eat out in Kihei most nights, a combination that works well and costs less than doing either one properly.
Keep going south and the tidiness runs out
If you carry on after Polo Beach you’ll continue towards Makena where things start looking less over-polished and pristine. Big Beach in Makena State Park is a long stretch of gold sand with no hotels behind it, just kiawe scrub and a car park.
The shorebreak there is genuinely dangerous and people get hurt on it every year, so it’s one to look at rather than muck about in unless you know what you’re doing. Beyond that the tarmac gives way to old lava flows and the coast turns properly wild.
The part that you can’t not think about
You can’t visit Maui these days without hearing about Lahaina. The fires on 8 August 2023 killed 102 people and destroyed close to 4,000 buildings, most of them homes, on the other side of the island. Nearly three years on, rebuilding is still ongoing and a lot of families are still in interim housing. Rents across Maui went up afterwards and have not come back down. That is the pressure sitting underneath the population figures at the top of this article. Some of the people moving into South Maui chose it, while others had the choice made for them.
That’s not to say that visitors should keep away, indeed, quite the opposite is true. But it’s worth knowing what the island has been through, spending your money in local places rather than only inside the resort, and not treating any of it as just scenery.
The that people keep coming back to
Wailea works because of a law rather than a marketing decision. The resorts built here would happily have a private beach if the statute allowed it. It doesn’t, so a stretch of coast that could have been walled off is instead a public footpath with car parks on it, used by people who live in Kihei and people paying two grand a night, in roughly equal numbers.
That’s a better arrangement than most coastlines manage, and certainly not what many visitors expect when they see the first roundabout.
