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A Guide to Living on Oahu’s Windward Side

Posted by admin on September 6, 2022

If you’re not familiar with the term, you’re probably asking yourself — what does windward mean? Windward means “upwind,” or the direction from which the wind is blowing. This side of the island sees a bit more rainfall than other parts of Oahu, making it very green and lush. Don’t be alarmed though, there are still plenty of sunny beach days coming your way if you choose to live on Oahu’s windward coast. Here’s our guide to this unique corner of paradise.


Overlooking Kaneohe and Kailua / Photo by: Zoar Morales

If you’re PCSing to Hawaii and are unsure where to live, there are two main residential neighborhoods on Oahu’s windward coast to consider: Kailua and Kaneohe. These towns are particularly attractive to military families because of their great schools, proximity to the beach, and strong sense of community. They are also conveniently located, making it easy to get to all the major bases on the island.

Kailua is the main shopping and dining district on the windward side, however, it is still very much residential. It strikes that perfect combination of things to do and suburban living. It is home to a mix of mom-and-pop shops and major retailers like Target and Whole Foods.

Kaneohe, on the other hand, is about 15 minutes from Kailua, but is even more residential. You’ll most likely drive into Kailua for grocery shopping and errands. On the bright side, you have easy access to the highway which means you can be in Honolulu in less than 30 minutes, the North Shore in 45, and the airport in just about 20.


Kailua Beach with MCBH in the distance / Photo by: Josh Glauser - Unsplash

The windward coast is home to some of the most esteemed beaches on the island. But don’t just take our word for it — Kailua Beach was named the best beach in America in 2019. It is a picture-perfect spot with white sand and turquoise waters. The beach park has parking, restrooms, picnic tables, and miles of shoreline. The waves are calm and clear, making it perfect for stand up paddleboarding and kayaking.

perfect for stand up paddleboarding and kayaking.

Xeo at Lanikai Beach / Photo by: Zoar Morales

Just down the road on the same stretch of sand is Lanikai Beach. This beach is more remote due to the lack of parking. If you want to visit you’ll have to arrive early and hope that street parking is still available. If it is, you’re in luck! Once your feet touch the sand you’ll see two small islets in the distance — these are known as the Mokulua Islands or “the Mokes.” The larger island on the left is known as Moku Nui and the smaller island to the right with just one hump is Moku Iki. The islands are bird sanctuaries and you can kayak out to explore Moku Nui — just respect the animals that call these islands home.

Waimanalo Bay / Photo by: Channey Tang-Ho

Another gem of the windward side is Waimanalo Beach. This beach shares a shoreline with Kailua and Lanikai so it has the same soft sand and blue waters, but it’s surrounded by a mountain range and lush greenery, giving it a unique feel.

No matter which beach you choose, you won’t be disappointed!


Lanikai Pillbox Hike / Photo by: Cosmin Surban - Unsplash

The east side of Oahu is home to hikes for adventurers of every skill level. Two of the most popular are the Lanikai Pillbox Hike and Makapu’u Point Lighthouse Trail. The former is considered moderate, with some steep and narrow portions, but when you reach the summit you’ll have an aerial view of the town’s famous and jaw-dropping beach.

Next up is Makapu’u Point Lighthouse Trail, this hike is rated easy and is a family-friendly option that the kiddos will love. It’s completely paved and when you get to the top you’ll see an early 20th-century lighthouse. During the winter (November – April) the trail is a great place for whale watching and on a clear day, you might even see Molokai in the distance. Oh, and Pro Tip — because these hikes sit on the east coast, they’re perfect spots to watch the sunrise.


Açai bowl / Photo by: Colin Meg - Unsplash

If you’re looking to dine out, the most options will be in Kailua. You’ll find loads of local restaurants serving up every cuisine from Mexican to Moroccan, Italian to Indian. Of course, there are some great Hawaiian options too! If you’re looking for fresh poke, check out Tamura’s or Foodland (we know, these are grocery stores but just trust us). If you want to try some kalua pork, there’s Kono’s in the center of town. And for some shave ice, pay a visit to Island Snow. We recommend natural flavors, double scoop of macadamia nut ice cream, and mochi.

This area is particularly popular for breakfast and lunch spots. Some good ones to try are Over Easy, Moke’s Bed and Breakfast, Boots and Kimo’s, and Egghead Cafe. For dinner check out Buzz’s, a local joint right across from the beach; Lanikai Brewing Company, which serves up local beer; and Kalapawai Cafe and Deli, a spot with an extensive wine list.

We didn’t even mention all the cute coffee shops, farmers’ markets and breweries; there are too many great places to count!

In Conclusion…

Mokulua Islands at sunrise / Photo by: Zoar Morales

We know we’ve said a lot, but we’re proud to call this region of Oahu home. If you’re looking for a spot with a laid-back, beachy feel that’s close to the ocean with a strong sense of community, you’ll be sure to find it on the windward side.

Do you want to adventure with us? We love taking clients out on pontoon boats, hiking, and sight seeing!

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