While we love Hawaii’s capital city of Honolulu, as well as the various cities and resort towns that populate the islands’ shores, we are slightly obsessed with the charming small towns that can be found across the islands — from Kauai’s western shores to the southern tip of Hawaii Island. These 16 tiny Hawaiian towns are all home to less than 3,500 residents and plenty of charm. They also have one more thing in common: they are always worth a visit.
1. Captain Cook
Located just 12 miles south of the famous Kailua-Kona is a lovely Hawaiian town that is unfortunately all too often overlooked for more resort-saturated spots along Hawaii Island’s Kona Coast. Captain Cook, a small town with a population of just 3,400 individuals, is full of Hawaiian history, and plenty of charm.
Though Hanalei is located just north of the Princeville resort area, it feels like worlds away from the Hawaiian tourism scene. With a small one-lane bridge leading into town, and an unusual mix of shopping and dining options, the very small town — approximately 0.8 square miles — is full of old world charm.
The largest town on the island of Molokai has a population of approximately 3,400 residents. When pineapple and sugar exports were huge in Hawaii, Kaunakakai was a bustling port town. King Kamehameha V’s royal summer residence was once in this ancient canoe landing, and now the Old Western-style storefronts paint the picture of a town stuck in time.
Approximately 2,700 people call the sleepy surfside town of Paia home. With a variety of stellar restaurants, charming galleries, adorable boutiques, and the best windsurfing spot in Hawaii, it’s no wonder why many Maui residents travel to Paia for a weekend getaway.
Home to Hawaii’s first ever commercially successful sugarcane plantation, Koloa is a relic of days gone by with charming shops now occupying the plantation-style buildings. Less than 2,200 residents live in this town nestled along Kauai’s southern shores.
Located on the Hamakua Coast of Hawaii Island at nearly 1,000 feet above sea level, Honoka'a was once the third largest town in Hawaii, but is no home to less than 2,300 residents. Don't forget to visit Tex Drive-In while you're in town!
7. Lanai City
This idyllic Hawaiian Island is often overlooked in favor of the larger, more populated islands, but Lanai, and its main city, are often touted as being the most authentically Hawaiian. The town was founded amidst the island’s booming pineapple industry, and is now home to unique shopping, inexpensive dining and two hotels.
Nestled near the West Maui Mountains, this quiet plantation town was once home to the Waikapu Sugar Mill, opened in the 1830s by a New York transplant and his brother-in-law. But before sugar took over the Hawaiian Islands, this area was home to pineapple production, and one of the first coffee plantations in Hawaii.
Home to less than 1,000 residents, Na'alehu is the southernmost town in the United States (with a post office, that is). Highlights include visits to the Punalu'u Bake Shop and Hana Hou restaurant — and of course a lazy morning spent at the nearby Punalu'u Black Sand Beach.
With the greatest concentration of artists on the island, Hanapepe is known as "Kauai’s Biggest Little Town." Once one of Kauai’s largest communities, you may find that not much has changed over the last century in Hanapepe. Its historic, plantation style buildings, however, are now home to charming shops, eateries and a surprising amount of art galleries. Every Friday night from 5 to 9 p.m., local art studios keep their doors open late for Friday Art Night. Some artists sit on the sidewalk to paint or display their recent work while local performers play Hawaiian music.
Tucked into Hawaii Island's Puna district near Hawaii Volcanoes National Park, Volcano Village is home to 2,500 residents, and little else. This artistic little community is home to countless galleries and is the perfect place for a creative retreat.
They say that it’s not the destination, but the journey that it takes to get there, and nowhere is this more true than Hana. The infamous Road to Hana is full of twists, turns, several one-lane bridges, waterfalls, and incredible vistas — and as one of the most isolated communities in the state, Hana will certainly appeal to anyone who truly wants to experience small town life.
Often described as one of Hawaii Island’s best-kept secrets, Hawi is perched along the northern coastline of the Kohala coast, and is home to some incredible skydiving, ziplining, farm tours, and a pretty charming vibe. Two decades ago, a new generation of entrepreneurs and artists flocked to the former plantation village and, with the help of longtime residents, moved bookstores, galleries, boutiques and restaurants into the town’s decaying storefronts.
Did you notice something missing from this list? Well, there is: Oahu’s many charming small towns, which you can visit on
this road trip.