top of page

Windward Coast: A Travel Guide to Oahu, Hawaii - Part II

Updated: Dec 27, 2021

Hawaii Postcard

The beauty of Oahu's Windward Coast (east side) is not to be missed. It is just a short drive from Waikiki and I must say, it's the most stunning drive in the island. There are several places to stop and take in the views of the turquoise shimmering ocean, and you will want to stop at them all.

Every time I would think about Hawaii, I would imagine paradise, natural raw beauty. And that's what you'll find here.

What to See and Do

Lookout Points

Here are the main lookout points on the southeastern side with small parking available. Make sure to have your camera ready, on a clear day you can spot the islands of Lanai, Molokai and even Maui from here.

1- Lanai Lookout

2- Halona Blowhole Lookout (big waves send geysers as high as 30ft through the blowhole!)

3- Makapuu Lookout

Hike: Makapuu Lighthouse Trail

I absolutely loved this hike. It is much less crowded than Diamond Head and offers some of the most beautiful views of Oahu's coastline. In fact, if you have to choose between hiking Diamond Head and Makapuu, definitely go with Makapuu!

The trail is paved all the way up, and even though there's not a lot of shade, it's great for families with strollers. There are several viewpoints to stop and refresh on your way up. And once you get to the top, you'll want to stay for a while.

There's another trail about 3/4 up that takes to the tide pools, but we did not go there this time due to high surf. Make sure to check ocean conditions and tide report before you go.

Hike: Lanikai Pillbox

My favorite hike ever. The most beautiful place I've ever seen. No kidding guys, this is like, beyond breathtaking (see it for yourself). The trail is not the easiest but it is quite fast (about 30 minutes to get to the top), just under 2 miles total.

Trailhead signs are near the Mid Pacific Country Club. Parking is very scarce so be careful not to park in a tow away area.

Lanikai Beach / Kailua State Beach

After you've conquered the Lanikai Pillbox, rush to the beach to swim in the heavenly waters you were watching from up above. This is known as one of the most beautiful beaches in all of the Hawaiian islands as its name literally translates to "heavenly sea", and trust me on this one, the white sand and turquoise water will definitely take your breath away.

I've read in many blogs that Lanikai is a little overrated and that neighboring Kailua is just as gorgeous, without the crowd. Not sure if we got lucky but the day we visited Lanikai it was not that crowded, and even though Kailua is indeed beautiful and offers parking and more structure, there's something special about Lanikai that I just can't put down to words.

Chinaman's Hat - Scenic Viewpoint

As you make your way north on Kamehameha Hwy, stop by Kualoa Rock Beach to get closer to Chinaman's Hat (or Mokoliʻi Island). The islet is only 500 yards away from the coast so it is possible to kayak or paddle board over there, but seriously take in consideration the tides and surf conditions as they can change abruptly in Hawaii. You don't want to turn the trip of a lifetime into a tragedy. Respect the ocean and your limits.

The following are attractions on the east side that I didn't get to visit but are on my list for next time:

Hoomaluhia Botanical Garden

Byodo-In Temple

Kualoa Ranch

Nuuanu Pali State Lookout

Where to Eat / Drink

Crepes No Ka Oi

Island Brew Coffeehouse

Makai Bowls

Island Snow Shave Ice

This article is part of a 3 blog series (South Shore - Windward Coast - North Shore)

Find out more about where to stay, how to get around the island and all about Waikiki and Honolulu here.

Everything you need to know about the North Shore of Oahu is here.


bottom of page