This Is The Friendliest Small Town in Hawaii
On the island of O’ahu in Hawaii, the friendliest small town in the state, Kailua, treats one and all with merriment and marvels worth seeing. Only about 12 miles northeast of Hawaii’s capital of Honolulu, Kailua has been a popular vacation destination for many people, from the Hawaiian aristocracy known as ali’i to American icons like Beyoncé, Jay-Z, Rihanna, Jessica Simpson, and President Barack Obama. Many know of Kailua because of the wave-kissed beaches, tropical atmospheres, and cultural amicabilities that Hawaii is renowned for. However, many will definitely stay for a long time in Kailua because it is the friendliest small town in Hawaii for a variety of reasons. With a population of over 40,500 people and popular sports, including stand-up paddleboarding, kayaking, and surfing, the friendly town of Kailua will treat you well and comfortably on your vacation this year.
Local Activities and Festivities
Kailua promotes a plethora of yearly events and festivities for visitors to experience. One of the most famous events is the Kailua Fall Festival, held in late September. During this event, the town’s Hahani Street comes alive with vendors, food, drinks, music, and lively entertainment. For those over 21, access wristbands and commemorative steins allow entry to participating bars, along with a party bus transporting guests between venues.
The Kailua Night Market, held on select Saturdays throughout the year, showcases local businesses, food trucks, live music, and artisan crafts. This vibrant market provides visitors with the perfect opportunity to explore local flavors, handmade goods, and live entertainment. Meanwhile, the Kailua Farmers’ Market is another regular event which takes place every Thursday evening at Kailua Town Center. It features fresh produce, prepared foods, and unique handcrafted items, perfect to support local businesses.
These are just some of the many events you can discover and partake in Kailua. However, for more daily and occasional activities, you can watch new or vintage movies at Kailua Cinemas or go strolling through Kailua District Park.
Natural Landmarks
Kailua Bay
Located on the windward side of Oʻahu, Kailua Bay is a breathtaking expanse of turquoise waters framed by golden sands and lush greenery. Known for its gentle trade winds, this bay is a prime spot for windsurfing and sailing. Its calm yet consistent waves also make it a fantastic destination for beginner surfers looking to practice in a serene environment. Kayakers frequently paddle out to the nearby Mokulua Islands, commonly referred to as "The Mokes," where Moku Nui provides excellent snorkeling and a nesting site for seabirds. For those who prefer to stay on land, a peaceful walk along Kailua Bay’s shoreline offers stunning panoramic views of the Pacific and a chance to spot the famous Hawaiian green sea turtles or honu as they bask in the sun.
Kailua Beaches
Beyond the scenic beauty of Kailua Bay, the town is home to several distinct beaches, each offering a different experience. Lanikai Beach, consistently ranked among the world’s most beautiful, is famous for its powdery white sand and calm, clear waters, making it ideal for swimming and paddleboarding. The backdrop of the iconic Mokulua Islands enhances its postcard-perfect charm. Meanwhile, Kailua Beach Park, just a short drive away, is more energetic, drawing windsurfers, kitesurfers, and boogie boarders to its lively shores. For a more laid-back vibe, Kalama Beach Park is a hidden gem where locals enjoy stand-up paddleboarding and leisurely picnics under the ironwood trees. Whether visitors seek thrilling water sports or quiet relaxation, Kailua’s beaches provide an unforgettable slice of Hawaiian paradise.
The Ko'olau Range
According to Hawaiian mythology, the mountains sheltering Kailua were formed when a giant transformed into stone. Although there is nothing mythological about the Ko'olau Range—since they, like the rest of Hawaii, were formed from volcanic eruptions long ago—this stretch of mountains has an air of magic and tranquility due to the serene waterfalls and streams trickling through Kailua. The Ko'olau Range is also characterized by serrated precipices known as the palis (“cliffs”) that rise abruptly on the range’s eastern side and reach varying heights (500 to 2,500 feet) from the sea. The Nu’uanu Pali is a historically relevant cliffside. King Kamehameha the First and his troops forced Oahu warriors up the valley and over the cliff to be killed on the jagged rocks below in 1795. The twin peaks of Konahuanui, the highest point of the Ko'olau Range at the head of the Nuuanu Valley, can be an arduous endpoint for many to reach. A much easier destination that is as equally rewarding to arrive at is the Waimānalo Forest Reserve, where the vast jungles of O’ahu remain eternal and energetic.
History and Culture
Kawainui Marsh and Maunawili Valley may be scenic tourist destinations now, but back then Hawaiian families from 1,500 years ago made these wetlands their home. The Kawainui Marsh, now a Ramsar Convention Site, was where early Hawaiian families fished regularly. The region houses many significant heiau, Hawaiian temples and places of worship.
By the time Captain James Cook arrived in Hawaii, Kailua prospered as the ancient capital for many Hawaiian kings. Among these regal rulers was King Kamehameha I, who conquered O’ahu in his quest to unite the Hawaiian Islands. Kaiwainui Marsh and Kailua, especially the freshwater fish ponds and saltwater ponds at Mokapu, were rewards for the warriors and chiefs who aided in his conquest. One of the ali’i encouraged the construction of the Ulupō Heiau, a Hawaiian place of worship besides the farmlands of Kailua, which you can visit anytime.
Around the period when America was roped into World War II after Pearl Harbor and when military barracks were built at the Lanikai Pillbox, a businessman named Harold Castle donated his holdings and lands like the Kaneohe Ranch in order to build churches, schools, hospitals, and other enterprises after the war. Because of his generous and friendly endeavor and the continuous work of the Harold K.L. Castle Foundation, Kailua is now the friendliest small town in Hawaii worth visiting in 2025.
A Friendly Trip To Hawaii
Kailua is undoubtedly the friendliest small town in Hawaii due to its tropical landscapes and its amicable and thriving communities and industries. Ever since the ancient royal families of Hawaii made Kailua their vacation retreat, Kailua continues to accommodate thousands of newcomers—famous and unknown—for the sun, and the fun one can attain from the beaches all the way up to the powerful mountains nestling the town. Many flock to this pristine and exquisite town because of the popular Hawaiian amenities like beaches and waves, but many will spend a long time in Kailua because of its friendly attitudes and heartwarming accommodations afforded to everyone.
