A Guide to Living on Oahu's Windward Side
Oahu’s windward side sits along the eastern coast of the island.
Nestled between Honolulu and Kahuku on the North Shore, The majestic Koolau Mountain Range provides the backdrop to this region that’s filled with award-winning beaches and vibrant communities.
(Ph: Honolulu Magazine)
If you’re not familiar with the term, you’re probably asking yourself -- what does windward mean? Windward is the direction that the wind is coming; oftentimes this side of the island sees a bit more rainfall than other parts of Oahu. Don’t be alarmed though, there are still plenty of 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.
Towns
Kalapawai Market in Kailua, image: Flickr / Hawaii Adventures
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 military families because of their great schools, proximity to the beach, and strong sense of community. They are also conveniently located to get to all the major bases on 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’s 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, but 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.
Beaches
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 -- a picture-perfect spot with white sand and turquoise waters -- was named the best beach in America in 2019. It has parking, restrooms, picnic tables, and miles of shoreline. The waves are calm and clear, making it perfect for stand up paddleboarding and kayaking.
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 islands in the distance -- these are known as the mokes. They’re bird sanctuaries and you can kayak out and explore -- just respect these animals that call these islands home.
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!
Hikes
Ph: Trip 101
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.
Restaurants
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 a Kono’s in the center of town. And for some shave ice, pay a visit to Island Snow.
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; Maui Brew Co, 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, wine bars and breweries; there are too many great places to count!
In Conclusion…
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.