Windward (East), Oahu
Tropical breezes blow, warm and balmy, and magnificent beaches beckon, while the majestic Koolau Mountains offer a backdrop of gorgeous green! Windward Oahu is 30 miles of scenic coastline, picturesque bays, beach communities, and powdery, white sand beaches! This is where Oahu’s windsurfers and kiteboarders flock to, adding a colorful flair to the ocean scene. Another point of interest on the windward side is the offshore islands, many of which are bird sanctuaries, and the numerous fishponds, a relic of old Hawaii and the days of royalty. With plenty of shopping, great places to dine, and no shortage of beautiful beaches and fun activities to keep you busy, this side of the island has a little of everything!
Windward Oahu Area Guide: Major Cities
This small rural town has a largely Hawaiian population and many continue the traditional ties to the land that are a part of their ancestry, producing much of the organic greens you find in Oahu markets, as well as bananas, papyas, and other fruits and vegetables. You will see fresh fruit stands, flower stands, and some great little shell shops too. With the verdant Ko`olau Range rising behind it, Waimanalo also has the longest continuous stretch of white sand beach on Oahu, about 5 miles, with a coral reef about a mile off shore that breaks up the big waves, making it excellent for swimming!
Known as the “biggest little beach town” in Hawaii, Kailua is situated right at the foot of the Ko`olau Mts and is a windsurfing mecca! With the trades blowing here on a regular basis, and the postcard pretty beaches like Lanikai, beachgoers abound, both visitor and local alike. There is more than one way to get here, but the Pali Highway takes you up and over the Ko`olau Mountains and in the process rewards you with a breath-taking view of Kailua town! Even though it is Windward Oahu’s largest town, you won’t find any of the high rises of Honolulu here, just a beautiful beach community.
One of the most scenic bays is found here, but the town itself is just a regular community made up largely of military personnel since this is where the Kane`ohe Marine Corps Base is located. In fact, many may not know it, but this was the first place on Oahu to be attacked by war planes on December 7, 1941, when Pearl Harbor was bombed! The looming Ko`olau Mts, the inviting bay with its offshore islands, and lush tropical botanical gardens all contribute to the beautiful appeal of Kane`ohe.
Situated at the northern end of Kane`ohe Bay, Kahalu`u is the first of a number of peaceful little towns in this scenic, rural drive from Windward Oahu to the North Shore. You may feel that certain spots around here look somehow familiar, and you would be right because this area has been used for scenes in many movies such as Karate Kid II, Parent Trap, and Jake and the Fat Man. The island in Kane`ohe Bay, called Coconut Island, was used in the opening scene of the famous TV show, Gilligan’s Island. Obviously, there is much beauty here to be enjoyed!
Waiahole and Waikane
Largely agricultural, these sleepy, Hawaiian grassroots communities raise traditional island fruits such as banana, coconut, papaya, and taro (used in making poi). You will see taro patches in many backyard gardens and this is a good spot to try some of the best, freshest poi on the island. Although they can’t be visited, the sheer cliffs of the Ko`olaus, which rise behind these towns, contain sacred places and ancient burial sites dating back to the days of Hawaiian royalty, and among the beaches you will find fishponds which were created by and for the royalty also!
Once sugar cane plantation land, it is now largely ranch land. The name Kualoa means “long ancestral background” and this land was originally the favorite place of the high chiefs of Oahu and a sacred area. Many royal children were raised and educated here. Another of the royal fishponds, Moli`i Fishpond, is on the southwestern end of Kualoa Regional Park, and the park itself is listed in the National Register of Historic Places.
Here is where the road literally hugs the coastline and the Pali (cliffs) come down so close that they barely leave room for homes, but tiny Ka`a`awa manages to squeeze itself in here. It’s a lush area and the greens and blues are so soothing as you drive through. Just past the town is a popular stone formation called Crouching Lion, and the peaceful Kahana Bay.