Things To Do in Kailua This Weekend

Kailua is a twenty-five minute drive from Honolulu and a completely different pace once you're over the Pali. The best things to do in Kailua happen before ten in the morning, when the water is glass and the parking still exists. Here's how to spend a weekend day out there without fighting the crowd for it.

The best things to do in Kailua start on the water#

The windward side is where Oʻahu gets flat, calm mornings and long stretches of sand you can actually walk. Almost everything below is within a few miles of the same intersection, so you can stack three of them into one day and still be home by afternoon.

Kailua Beach Park#

Wide sand, turquoise water, ironwood shade, and real bathrooms. It's the easiest beach day on this side of the island and the launching point for most of the paddling.

Kayak and stand-up paddleboard rentals operate in town, and the standard trip is out to the Mokulua islands — the two you've been staring at from shore. Only Moku Nui, the larger one, is open for landing, and there are rules about where you can go once you're there. Ask the rental shop for the current rules before you push off, and don't land on Moku Iki at all.

Go in the morning. Wind builds through the day and the paddle back gets a lot less fun after lunch.

Lanikai Beach#

A mile of pale sand with the Mokulua islands sitting right offshore. It's small, it's residential, and there is essentially no parking — the neighborhood streets have restrictions that tighten on weekends and get enforced.

Park near Kailua Beach Park and walk or bike the last stretch. It takes ten or fifteen minutes and saves you a ticket. There are no bathrooms or lifeguards at Lanikai, so handle that at Kailua Beach first.

Lanikai Pillbox hike at sunrise#

Short, steep, and one of the best payoffs per minute of effort on the island. You climb a ridge behind Lanikai and end up looking straight down at the beach and the Mokulua islands while the sun comes up behind them.

It's dirt, it's slick after rain, and the drop-offs are real — wear actual shoes and bring a headlamp if you're starting in the dark. Parking is the same problem as the beach, so arrive early and park legally down the hill.

More options in the best sunrise hikes on Oʻahu if you want to make a habit of it.

Kailua town#

Two blocks of cafes, surf shops, boutiques, and a shave ice line. It's a good rain plan and a good after-beach plan.

Get coffee, get malasadas, get shave ice in the afternoon when it's hot. The Kailua farmers market runs in town — days and hours have changed over the years, so check the current schedule before you build your morning around it.

Kawainui Marsh trail#

The flat, quiet option. A paved path runs along the levee on the edge of Kawainui Marsh, one of the largest wetlands in Hawaiʻi, with mountain views on one side and open water and reeds on the other.

Bring binoculars if you have them — the marsh is habitat for native waterbirds, including some you won't see anywhere else. There's no shade to speak of, so go early or late.

The drive to Waimānalo#

Head south out of Kailua and the road opens up along the coast. Waimānalo Beach is longer, emptier, and softer underfoot than anything in Kailua town, with the Koʻolau wall right behind you.

It's a good ending to the day: fewer people, easier parking, and the drive itself is one of the prettiest ten minutes on Oʻahu. Keep your valuables out of sight at every beach lot on this stretch.

A few tips#

• Weekends get crowded by 9am. Early is the whole strategy.
• Bring cash — small shops, food trucks, and market vendors don't all take cards.
• Wear reef-safe mineral sunscreen. Hawaiʻi bans the reef-harming kinds, and the reef is right under you.
• Respect residential streets in Lanikai. Don't block driveways, don't park on the grass, keep the noise down.
• No shade at most of these spots. Hat, water, rash guard.
• Check the wind before you paddle. Offshore days are not beginner days.
• Pack out everything, and give turtles plenty of room if one hauls out.

More Oʻahu guides#

If you're pricing out a weekend, free things to do on Oʻahu covers the rest of the island, and the Oʻahu farmers markets guide tells you which morning markets are worth the drive.

Make it a plan#

Kailua is better with somebody. A double kayak, a sunrise pillbox climb, coffee in town after — those are exactly the kind of plans people open a line for on YKnot. You already know when you're going and where you'll park. Open the spare seats and let a verified local nearby ask to come along.

See you on the windward side. 🌊