Oahu’s windward side is breathtaking. Once you see it in person, you won’t be able to forget it. Although Waikiki and the North Shore of Oahu get the lion’s share of attention, the humble windward side is where the magic happens. Here you’ll find towering mountains meeting the sea, and bobbing boats on silvery water in a quiet harbor. Sunny beaches named the best of the best, year after year. Dense rainforests so fertile…even the air smells green. Winding roads offering treasures around every corner. This is Oahu’s windward side, and we can’t wait to share it with you!

Where is Oahu’s Windward Side?

All of the Hawaiian Islands have a windward and leeward side. Typically, the windward side is on the eastern or northeastern side. For the sake of this article, we’re going to focus mainly on the eastern side of the island. It is the rainier, and therefore lusher, side. Windward sides also enjoy the cooling effects of the trade winds. For comparison, the leeward side is hotter and drier.

If you’re driving from Oahu’s South Shore, such as Waikiki, head east by northeast. You’ll travel around Diamond Head and through Kahala and Hawaii Kai. Continue on past Hanauma Bay, Sandy Beach and Makapu’u.

Once you reach the town of Waimanalo, you’re considered on the windward side. This lasts until roughly Hauula. Although Kahuku and Laie are technically on the eastern side of the island, we consider them to be part of Oahu’s North Shore.

From the North Shore, travel southeast on Kamehameha Highway, and from the west – hop on the H3 Freeway near Aiea. You can also access the windward side from downtown Honolulu via the Pali or Likelike Highways. If you take the Pali Highway, be sure to stop at Pali Lookout for incredible views of windward Oahu.

Towns on Oahu’s Windward Side

Kaneohe

The largest town on Oahu’s east side, Kaneohe is equal parts bustling and sleepy. Come here for glimpses of an Oahu of a bygone era. In addition to Windward Mall, the largest shopping mall on this side, mom and pop shops and restaurants are still in abundance. Kaneohe is also home to Marine Corps Base Hawaii.

Kailua

If Kaneohe offers whispers of “old Hawaii”, Kailua is its polar opposite. This sun-drenched uberpopular town is an outlier on the windward side, not only for its dry and sunny climate, but also for its trendy restaurants and retail chains. Kailua is also home to stunning Kailua Beach and Lanikai Beach.

Waimanalo

Waimanalo Town is down-home local. Although Waimanalo is a sleepy, mostly residential area, this town has delicious plate lunches joints and a strip mall featuring a few shops and Dave’s Hawaiian Ice Cream.

Kaaawa & Hauula

You’ll pass through both of these “blink and you might miss them towns” as you head to the North Shore from Honolulu. The surrounding scenery is breathtaking, and definitely worth the trip.

Best Beaches on Oahu’s Windward Side

Waimanalo Beach

Popular beach ringed by ironwood trees. Powdery white sand and lime-green water make for a dreamy setting.

Lanikai

Consistently rated one of the most beautiful beaches in the world. White sand, aquamarine water and the Mokulele Islands off the shore will knock your socks off. Only street parking available, so get there early. You can rent kayaks and head out to the Moks for an added adventure.

Kailua Beach Park

Although Lanikai wins the awards, Kailua Beach Park may be an even better option. Located only minutes from Lanikai, this beach offers an equally pretty setting with additional perks such as a parking lot, shaded grassy areas and public restrooms.

Kahana Bay

Tucked away deep on Oahu’s windward side is Kahana Bay. Just down the road from Kaaawa, this is one of the most stunning areas on the island. With the Koolaus towering behind it, it’s not the best beach for sunbathing, but it is idyllic for strolling, camping, kayaking and daydreaming. The Beach Swing is also nearby.

Kualoa Regional Park

Picturesque beach park popular for bbq’s, bird-watching, camping and kayaking. Perfect view of the small islet of  Mokoli’i, also known as Chinaman’s Hat.

Highlights of Oahu’s Windward Side

Windward Snorkel & Sandbar Sail

One of the best things you can do on the east side, this activity is offered in our Waikiki Oahu All-Inclusive Vacation Package. Departing from tranquil He’eia Small Boat Harbor, you’ll sail on a catamaran to one of the world’s largest sandbars. Spend the day snorkeling, swimming and playing water volleyball as you soak in the beauty around you.

Kualoa Ranch

Kualoa Ranch has served as a filming location for many popular productions such as Jurassic Park, 50 First Dates and Lost. Activities include movie set tours, horseback riding, UTV rides & more. Also home to Secret Beach, where you can snorkel, sail, kayak or relax in a hammock – beachside. Available as an option for all of our All-Inclusive Waikiki Oahu Vacations.

Byodo-In Temple

Hidden away at the foot of the emerald Ko’olau Mountains is Byodo-In Temple. Serenity abounds here, it’s as if you’ve stepped into another world. As a non-practicing Buddhist temple, people of all faiths are welcome here. Aside from the temple, the lush gardens and ponds teeming with koi and black swans will also enchant you.

Tropical Farms of Hawaii

Dubbed “The Little Country Store On Your Way To The North Shore“, this is a must-stop. Their wide selection of macadamia nut flavors, coffees, local foods and gifts make perfect souvenirs. You can also take a stroll through their lovely gardens.

Ultimately, Oahu’s windward side is absolutely worth your time, and we hope you will visit this mesmerizing side of the island. Even if you only see it from your rental car, you will still fall in love. We would be honored to assist you in planning your vacation to Oahu, windward side and all. Contact us today to start making your dream a reality!