The windward side of O‘ahu, the eastern shore of the island, spans the entire length of the Ko‘olau Mountain Range. It’s known for its ample rainfall, the lush and dramatic corduroy cliffs of the Ko‘olaus, and the chance to pull off the winding Kamehameha Highway right to the water’s edge. Windward towns, save for Kailua and Kane‘ohe, are primarily residential and historically rooted in agriculture and aquaculture: kalo lo‘i, banana plantations, papaya, and fishponds. A drive up the windward coast is a trip back in time, with weathered wooden fruit stands offering family farm goods. It’s a leisurely drive that should be enjoyed at every turn in the road.

A woman rests on a park bench in the sand at Kailua beach.

Stunning Kailua Beach on Oahu. Photo © Eddy Galeotti/123rf.

A drive up the windward coast is a trip back in time, with weathered wooden fruit stands offering family farm goods.Kailua and Kane‘ohe have developed into major population centers and desirable destinations, each with its own draw. Kailua is full of hip shops, restaurants, and some of the best fine, white sand beaches on O‘ahu. It’s also known for kitesurfing and kayaking, with several islets just offshore. Kane‘ohe town definitely caters to locals with its dining and shopping services, but there are more than enough reasons for a visit with the Ho‘omaluhia Botanical Garden and the famous Kane‘ohe Bay Sandbar, perfect for a half-day kayaking adventure.

The southeast corner of O‘ahu is one of the drier locales of the island. Makapu‘u and Sandy Beach are O‘ahu’s premier bodysurfing beaches, and Makapu‘u offers a short hike to its lighthouse and prime whale-watching opportunities during the humpback whales’ annual stay in the Hawaiian Islands from November to March. Constantly battered by wind and chop, the coastline is dramatic; the island seems to fall into the ocean here. Koko Crater is home to a dryland botanical garden with a plumeria grove. Across the highway is Hanauma Bay marine preserve and Koko Head, which gives way to Maunalua Bay, known for its ample water sports activities, from surf and stand-up paddle lessons to Jet Ski rentals and wakeboarding.

Map of Southeast O‘ahu, Hawaii

Southeast O‘ahu

Excerpted from the First Edition of Moon Hawaiian Islands.