Nestled on the windward side of O'ahu, Kailua is one of Hawai'i’s most scenic and historically rich towns. Known for its stunning beaches, laid-back atmosphere, and deep cultural roots, Kailua has evolved from an ancient Hawaiian settlement into one of the most desirable places to live and visit in the islands.
Early History and Cultural Significance
Kailua’s name means “two seas” or “two currents” in Hawaiian, likely referring to the two lagoons in the area or the ocean currents that meet along its shores. Long before Western contact, Kailua was a thriving center of Hawaiian civilization, favored by ali'i (Hawaiian royalty) for its fertile lands, plentiful fishing grounds, and stunning natural beauty.
The area was home to many heiau (Hawaiian temples), including Ulupo Heiau, a sacred site believed to have been built as early as the 12th century. Ulupo Heiau served as an important agricultural and religious center, where early Hawaiians cultivated taro and other crops in the lush landscape surrounding Kawainui Marsh.
During the rule of King Kamehameha I in the late 18th and early 19th centuries, Kailua played a role in his efforts to unite the Hawaiian Islands. He stationed some of his warriors in the area and used Kailua’s strategic position on the windward side of O'ahu to his advantage.
Kailua in the Modern Era
Through the 19th and early 20th centuries, Kailua remained a relatively quiet agricultural community, with sugarcane and cattle ranching shaping much of the local economy. It wasn’t until World War II that Kailua saw major development, as the U.S. military built roads and infrastructure, leading to increased settlement.
In the post-war years, Kailua grew into a vibrant residential town, attracting families and visitors seeking a quieter alternative to Honolulu. Today, it is known for its charming small-town feel, strong sense of community, and commitment to preserving its natural beauty.
What Makes Kailua Special?
1. World-Class Beaches
Kailua Beach and neighboring Lanikai Beach are frequently ranked among the most beautiful beaches in the world. Their powdery white sand, turquoise waters, and steady trade winds make them perfect for swimming, kayaking, stand-up paddleboarding, and windsurfing.
2. Outdoor Adventures
Beyond the beaches, Kailua offers incredible hiking opportunities, including the popular Lanikai Pillbox Hike (Ka'iwa Ridge Trail), which provides breathtaking panoramic views of the Mokulua Islands and the Pacific Ocean. For a more immersive natural experience, visitors can explore Kawainui Marsh, the largest wetlands in Hawai'i, home to native birds and plant species.
3. Unique Local Culture
Unlike the bustling tourism hub of Waikíkí, Kailua has maintained a more relaxed, residential atmosphere. The town is known for its boutique shops, farmers’ markets, and locally owned cafes. The community places a strong emphasis on sustainability and environmental conservation, with many residents advocating for responsible tourism.
4. Presidential Connections
Kailua has gained national recognition as a favorite vacation spot for former U.S. President Barack Obama, who spent many holidays with his family in a beachfront rental home near Kailua Beach.
Fun Facts About Kailua
• The Mokulua Islands (or “The Mokes”), located just offshore from Lanikai Beach, are a popular kayaking destination. While one of the islands is a bird sanctuary, the other (Moku Nui) allows visitors to land on its shores.
• The region’s trade winds keep Kailua cooler and more comfortable than many other parts of O'ahu.
• Kailua is home to one of the few Whole Foods locations in Hawai'i, reflecting the town’s demand for organic and locally sourced products.
• The name “Lanikai” means “heavenly sea,” though it is not a traditional Hawaiian name—it was coined by a developer in the early 20th century.
A Must-Visit Destination
Whether you’re a history enthusiast, nature lover, or simply someone seeking a peaceful Hawaiian getaway, Kailua offers something special. Its deep historical roots, stunning natural landscapes, and commitment to preserving its charm make it one of O'ahu’s most treasured communities.