The 6 Tiniest Towns in Hawaii Worth Visiting

Oahu | © Casey Horner / Unsplash
Marjorie Perlas

Contributing Writer

With a plethora of resorts and retreats to choose from, Hawaii is a haven for those who want to hide away and laze about in the sun. Although these resorts are all-inclusive—offering almost everything you could dream of—there is so much character and history waiting to be discovered in the smaller towns on these gorgeous islands.


Stepping into Makawao is like stepping into a time machine. This upcountry town of Maui was once the center of society for the island’s plantation population and paniolo, or Hawaiian cowboys. The town has a bit of that Wild West feel combined with the Asian influences you see all over Hawaii.

Fourth of July weekend is quite a sight to see in this charming town, as they host a rodeo and paniolo parade. If you happen to be there any other time of the year, don’t worry—there’s still plenty to do. This artistic area is known for their painting, sculpting, and glass blowing. Make sure to spend some time meandering through town and discovering different shops that feature local artisans. You may find something unique to take home.

Crossroads at Makawao Town


Once a town center for the sugarcane plantation society of Maui, Paia has held on to its character and charm. With colorful storefronts and some of the friendliest people you’ll ever meet, this town is a fantastic place to spend the day.

Just like Maui’s other small towns, Paia is an artistic community as well, with galleries proudly featuring local artists. Spend the day cruising around the boutiques and enjoy a quiet meal at one of the local restaurants. When you’re done, head down to Hookipa beach before sunset. Though not as much of a secret as it used to be, sea turtles have been known to take a breather on the beach around this time. Make sure not to touch them and just let them do their thing. However, we wouldn’t dare deny you the wonderful photo opportunity.

Storefronts on Main Street in Paia, Maui


These small Hawaiian towns have creatively positioned themselves as hubs for artists, and Hawi is no exception. Boasting organic food markets and particular artisanal products, such as handcrafted jewelry, the town of Hawi is still alive and well.

Located on the northern point of the island of Hawaii, Hawi is absolutely worth the trip for the hipster types that enjoy eclectic shops inside of ironic storefronts. We should probably also mention that there’s a candy and ice cream shop that moonlights as a kava bar in the evenings. If the relaxing tea isn’t your thing, be sure to stop by the Kohala Coffee Mill, which serves up 100% of that delectable Kona coffee.

Tropical Dreams & Kava Kafe, Akoni Pule Hwy, Hawi


Koloa’s history is a proud one, as it was the location of Hawaii’s very first successful sugar mill. After a day of experiencing the Koloa Heritage Trail, the old town center is a perfect place to relax and enjoy your surroundings.

Nestled in southern Kauai, the old plantation buildings have changed and are now home to many restaurants and shopping sites. However, the history of these buildings are not easily forgotten, as signs with photos are posted outside to describe and shine some light on their original purpose.

The Old Koloa Sugar Mill in Koloa, Kauai


The town of Hanalei is dotted with lovely art galleries and family-owned boutiques, offering a comforting small town vibe to those wanting to get away from the resort areas. The shoreline surrounding this town isn’t one to be missed either. The famous Irons brothers would surf here, giving you a good idea of how gnarly these waves can be. For the less adventurous, SUP and kayak shops can be found in town as well.

This tiny town not only attracts surfers and shoppers, but foodies too. People from all around have been known to visit Hanalei merely for its food truck scene. It’s really that good. From classic Hawaiian poke to some addictive fried katsu, the food is always fresh. Kauai has been promoting its sustainable food scene for a while, putting strong value on locally sourced ingredients.

Hanalei Town, Kauai


Perhaps Kauai’s most famous small town, Hanapepe’s exterior hasn’t changed much since its plantation days. Its historic wooden buildings have, like many other small towns in Hawaii, been repurposed for today’s consumer.

The largest collection of art galleries on Kauai can be found here and Fridays are a late night for the sleepy town. Local artists and galleries open their doors to the public, inviting visitors and locals to socialize among local snacks and lively music.

Historic pool hall building in Hanapepe

Culture Trips launched in 2011 with a simple yet passionate mission: to inspire people to go beyond their boundaries and experience what makes a place, its people and its culture special and meaningful. We are proud that, for more than a decade, millions like you have trusted our award-winning recommendations by people who deeply understand what makes places and communities so special.

Our immersive trips, led by Local Insiders, are once-in-a-lifetime experiences and an invitation to travel the world with like-minded explorers. Our Travel Experts are on hand to help you make perfect memories. All our Trips are suitable for both solo travelers, couples and friends who want to explore the world together.

All our travel guides are curated by the Culture Trip team working in tandem with local experts. From unique experiences to essential tips on how to make the most of your future travels, we’ve got you covered.

Edit article