To get to Windward O`ahu from Honolulu, continue past Waikiki and Diamond Head and head to Kalaniana`ole Highway (Highway 72) for a scenic trek that takes you out of busy Honolulu and into a natural paradise. Along the way, you'll pass one world-class resort, several natural attractions and several smaller and charming towns surrounded by some of the world's favorite beaches.
You can also get to Windward O`ahu by following Kalakaua Avenue out of Waikiki, heading toward Diamond Head. The road changes into Diamond Head Road and, instead of heading up to the peak, keep going right on Kahala Avenue. You'll pass gorgeous Kahala Beach and Wai`alae Beach Park before the road ends at The Kahala Hotel & Resort.
If you want to check out the glorious Kahala Hotel & Resort, take a break. If not, head back up Kealaolu Avenue and get onto Kalaniana`ole Highway (Highway 72) headed east. You'll follow along the south shore of the island, passing many beach parks (which I will detail below), passing through Hawaii Kai (this is where one Costco is located) and toward the Koko Head area. This drive is where you'll be happy you rented that convertible! Next up is Hanauma Bay State Park and the Halona Blow Hole.
Gossip Alert: Next to the Halona Blow Hole is Halona Cove where the steamy beach scene between Deborah Kerr and Burt Lancaster reportedly took place in From Here to Eternity. Keep in mind that I've heard of three beaches throughout the islands that claim to be the beach in the movie!
As you head up the west side of the island, you'll see Makapu`u Head (home to the Makapu`u Lighthouse) and then past Sea Life Park. Next up is Waimanalo Bay, home to O`ahu's longest sandy beach, and then the busy town of Kailua, which has shopping, great dining and lots of water activities. If you bypass Kailua, make sure you get onto Highway 83 headed north, which will keep you going up the Windward Coast. To get to Kailua, turn onto Kailua Road and head toward the ocean. To get back, follow the signs to Highway 83 and get on the northbound lanes.
Next up is Kane`ohe Bay, where, on the western end of the bay, you'll see famous and hard-to-miss Mokoli`i Island, better known as "Chinaman's Hat." This is also where you'll find 4,000-acre Kualoa Ranch, which offers many outdoor adventures. Highway 83 then continues up the coast, passing beach after beach, until you get to the town of La`ie, which is where the North Shore (another chapter!) begins.
Chinaman's Hat
Day Trip
If you only have one day to check out the windward side of O`ahu, there is a 35-mile loop that will present you with fabulous views, breathtaking cliffs and seascapes and honest, down-to-earth communities. Head east on Kalaniana`ole Highway (Highway 72) to get out of town and then return along the Pali Highway (Highway 62) on your way back. If you take this route in the opposite direction, you'll miss all the fantastic views!
First, you pass Hawaii Kai and the Koko Marina Center on your left. Keep driving until you see the sign for "Hanauma Bay" and, after that, you're officially out of the city. You'll then pass 642-foot-high Koko Head that is then dwarfed by 1,208-foot Koko Crater.
Kailua Beach and famous Lanikai beach are the next stops on your tour (don't forget the sunscreen!) and then its time to head back to Honolulu along the Pali Highway. Your last hurrah will be the Nu`uanu Pali Lookout on the right-hand side right after the two Pali tunnels. Make sure to signal when you turn or you may get "stink-eye" from other drivers. You can view the entire windward coast from the vista point. Hopefully, you'll be able to head back into Honolulu at sunset and get a view of the skyline during that magic time. If you're headed to Waikiki, take H-1 east once you get into town and follow the signs to Waikiki.
Now that you know your way around Windward O`ahu, I'll give you more details about the fantastic towns and quirky sites that make up this side of the island.
