Downtown Paia, Hawaii. Image credit EQRoy via Shutterstock

8 Of The Most Captivating Small Towns In Hawaii

Ask anyone for their dream destination and vacation spot, and many of them might likely choose Hawaii — for a number of good reasons. Besides the soothing tropical climate, the dynamic jungle and mountain landscapes, the beaches, and historic sites, such as Pearl Harbor, visitors will likely also be mesmerized by the most captivating small towns in Hawaii. So whichever small town you visit in the islands of Hawaiʻi, Maui, Kahoʻolawe, Lānaʻi, Molokaʻi, Oʻahu, Kauaʻi, and Niʻihau, you will undoubtedly be captivated by the historical, natural, and cultural charms of Hawaii’s small towns. Find out for yourself why Hawaii is one of the most talked-about destinations in all of the US.

Hale’iwa, Oahu

Waimea Bay near Haleiwa, Oahu, Hawaii.
Waimea Bay near Haleiwa, Oahu, Hawaii.

About an hour away from the city of Waikiki on Oahu, the beloved small town of Hale’iwa is a perfect nesting ground for tourists and frigatebirds alike. Indeed, Hale’iwa combines the words Hale meaning “house” and iwa meaning “frigatebird” due to the abundance of the species on Oahu’s North Shore. But aside from the avian activity, Hale’iwa is renowned for its beautiful beachside amenities as best seen in the ‘Ehukai Beach Park (aka the Banzai Pipeline), Sunset Beach, and Waimea Bay.

If you are an animal enthusiast, then you will definitely fall in love with the many species of female turtles that deposit thousands of their eggs into Laniakea Beach’s sand. One can also admire the sugarcane plantations of the Waialua Sugar Mill or cross the historic Rainbow Bridge spanning the Anahulu River. Most of all, you can admire the remains of a former landing field airport from World War II at the Pua'ena Point. Hale’iwa may be a home for frigatebirds, but for you it can be a beautiful destination spot in your memorable vacation throughout Hawaii’s captivating small towns.

Holualoa, Hawaii Island

Holualoa, Hawaii: A photo of the entrance at the Hula Daddy coffee plantation shop.
Holualoa, Hawaii: A photo of the entrance at the Hula Daddy coffee plantation shop. Editorial Credit: Chris Allan via Shutterstock.

On the Big Island of Hawaii lies the resplendent town of Holualoa, where people used to sled down steep mountain slopes with only wooden sleds. Holualoa encourages and energizes people on new adventures. Speaking of energizing, Holualoa is, much like its neighbors Keauhou and Kailua Village (Kailua-Kona), a renowned producer of the state-famous Kona coffee, whose beans can be found all over the volcanic mountainsides of Hualalai volcano, one of the five volcanos that made Hawaii. Among these coffee orchards and farms that you can explore is Mauka Meadows, one of dozens of coffee farms along the Kona Coffee Belt. Once you are sufficiently awake for exploration, you might want to traipse through the bewildering terrains of the Honuaʻula Forest Reserve and the Pu'u Wa'awa'a Forest Reserve, or you can always wait for November to attend the town’s annual celebration: the Holualoa Village Coffee & Art Stroll.

Makawao, Maui

Paniolo statue.

Paniolo statue. Editorial credit: Sandra Foyt / Shutterstock.com

Makawao has endured as the cultural and historic epicenter of Upcountry Maui on the island named after the mythic hero Maui. Where Hawaiian cowboys known locally as paniolo continue to roam since the 19th century and where artisans’ workshops like the Hui No’eau Visual Arts Center and Hot Island Glass provide insightful teachings on techniques like glassblowing, you will be mesmerized by Makawao’s stunning simplicities and beautiful landscapes. One can admire the aforementioned paniolo wrangling long-horned bulls and Maui alpacas across the Haleakalā volcano, and even attend the largest paniolo competition known as the Makawao Rodeo around the Fourth of July holiday. And if you are a lover of the outdoors, you will certainly be enamored by the Kula Botanical Garden, the thick jungles of Ko'olau Forest Reserve, the Twin Falls Maui Waterfall, and an exhilarating trip through the air at the Jungle Zipline Maui-HI.

Lanai City, Lanai

Garden of the Gods on Lanai.
Garden of the Gods on Lanai.

As the primary community the island of Lanai, Lanai City encapsulates the diverse wonders and surprises on an island named in part from the Hawaiian phrase for “day of the conquest.” Whether you are learning all about the extinct volcano Lānaʻihale, which created the island, or what once was the largest pineapple plantation in the US, Lanai City, leaves visitors feeling rejuvenated and relaxed after a delightful vacation in this amazing small town on its cute little island.

In the far past, the island of Lanai was once a royal retreat for King Kamehameha the First. Much of his vacation estates, such as the 15th-century Hawaiian village at Kaunolu and a ceremonial and religious structure called a heiau, continue to fascinate tourists and locals alike. More remnants of the past can be seen in the 18th-century Luahiwa petroglyphs at the Palawai Basin. Among the more modern allures you can cherish are the Lanai Bamboo Garden Retreat, the rescued cats at the Lanai Cat Sanctuary, and Keahiakawelo, the rock-strewn Garden of the Gods.

Honokaʻa, Hawaii Island

View of the Waipio Valley near Honoka'a.
View of the Waipio Valley near Honoka'a.

If the main reasons one travels to Hawaii are for surfing and for beaches, then visitors should definitely seek out the magnificent small town of Honokaʻa. Only an hour away from Holualoa, Honokaʻa’s Hamakua Coast has seen thousands of surfers and beachgoers lounging about beneath the sun. The Honokaʻa People’s Theatre entertains newcomers with all sorts of films, classes, concerts, and educational events. The lush biomes and habitats surrounding Honoka’a, especially Waipi'o Valley, the Kohala Forest Reserve, and the Pu'u O Umi Natural Area Reserve, shelter some of the most enduring animal species on the Big Island. More bounties of nature can be enjoyed at either the Hilo Forest Reserve, the Kalōpā State Recreation Area, or the Hāmākua Forest Reserve.

Paia, Hawaii

Baldwin Beach Park near Paia.
Baldwin Beach Park near Paia.

Paia, the windsurfing capital of the world, will have you soaring and bobbing over the rhythmic tides splashing on Ho’okipa Beach. One can either become a windsurfer and a professional kite surfer or simply be dazzled by their display of mastery over the waves and winds from the Pacific Ocean. Other beaches aside from Ho’okipa Beach include Kaulahao Beach — which connects to the waters of Mantokuji Bay and Ku’au Bay — Baldwin Beach Park, and Paia Secret Beach (clothing optional). There is also the Great Paia Lha Bab Peace Stupa at the Maui Dharma Center, which the late Venerable Lama Tenzin, the center's first full-time resident spiritual director, once supervised. More spiritual relaxation can be gained at the village of Haiku, where Jimi Hendrix and Janis Joplin reportedly stayed during the production of "Rainbow Bridge," and the nearby Sacred Garden of Maliko.

Hana, Maui

The winding Road to Hana on Maui.
The winding Road to Hana on Maui.

Many people proclaim that the town of Hana on Maui is the “Real Hawaii” because of its isolation from outside influences. In order to reach this remote town deep in Maui’s untamed wildlands, one will have to take the Road to Hana which goes through 52 miles of Maui’s rural landscapes starting from the community of Kahului. Once you do reach Hana, you will definitely be amazed by the unique rock formations at Koki Beach that were supposedly created by the conflicts between the fire and volcano goddess Pele and the ocean goddess Namakaokaha'i. The hills of Ka'uiki Head, likewise, are a place of mythic importance.

Speaking of spirits and Hawaiian myths, one might be interested in the largest Hawaiian temple, a heiau, known as Pi'ilanihale. Travelers might also enjoy seeing the Kahanu Garden, one of five National Tropical Botanical Gardens in Hawaii, as well as scenic tours through Sunbathe at Waiʻānapanapa State Park, the Hana Lava Tube, Hāna Bay Beach Park or Hamoa Beach, the Hana Forest Reserve, and Waioka Pond (sometimes called the Venus Pool). And if you are curious to know more about Hana’s true history and cultural attitudes, you can always see the exhibits at the Hana Cultural Center and Museum.

Waimea, Hawaii Island

Cattle grazing in the Waimea countryside.

Cattle grazing in the Waimea countryside.

Waimea, meaning “reddish water” due to the red clay soil in the region, is the cultural nexus of the Big Island’s paniolo culture. With a deep history of ranching at the Parker Ranch which has been around since the year 1847, Waimea has protected one of the largest Hereford cattle ranches in the US. For centuries, Waimea practiced King Kamehameha the First’s kapu or royal taboo on the killing of the cattle by first protecting them from outside harm. For fun and games, one can go skiing down Mauna Kea, watching the stars from the Mauna Kea Observatories, wading about at the Hapuna Beach State Recreation Area, or the black sand beaches at the Waipiʻo and Pololu valleys. There are also opportunities for you to ride an ATV or a horse as you proceed in your leisurely journey through Waimea.

According to some of the myths of Polynesian culture, either the great hero Maui pulled the Pacific islands like Hawaii from the ocean’s depths or Hawaii was formed between volcanic battles between the god-sisters Pele and Nāmaka. Even though, in truth, Hawaii was formed by natural volcanic processes, you will nonetheless be dazzled by each of these eight most captivating small towns In Hawaii. From the non-Wild West cowboys of Hawaii and delicious Kona coffee to the enticing surf and natrual wonders, visitors continue to create lasting memories in the beautiful island state of Hawaii.

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