If most people were asked to name various cities throughout Hawaii, they would most likely give the same answer: Honolulu, Kailua-Kona, Lahaina, Lihue, or for anyone who is less familiar with the islands, Waikiki. While these cities are great, the Hawaiian Islands are home to some fantastic cities and towns that are off the beaten path, and often overlooked for their more popular neighbors. From inland cities to rural communities on the coast, these fourteen cities, while quite different from one another, are all underrated, and ultimately all deserve a second look.
- Kapa’a, Kauai
John Verive/Flickr With a population of just more than 10,000, Kapaa is a charming small town located on Kauai’s eastern shore. The town is home to great golfing, shopping and hiking as well as restaurants that will make your mouth water, picturesque beaches, and killer resorts. For some reason, this area is often overlooked by tourists and I can’t really figure out a good explanation as to why. In fact, Kapa’a was named as one of the most underrated cities in the United States by the Huffington Post in 2014.
- Wahiawa, Oahu
Surfing The Nations/Flickr Home to more than 16,000 residents, Wahiawa is located between the island’s two volcanic mountain ranges on Route 99, the road most commonly taken by those traveling to the North Shore from Honolulu. But if you were to stop in town and take a look around, you would see that there is more than meets the eye in this small inland city. We suggest stopping by the Wahiawa Botanical Garden, Surfers Coffee Bar, and Sunnyside.
- Honoka’a, Hawaii Island
Anna Lee/Flickr 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!
- Wailuku, Maui
Florent Lamoureux/Flickr While Wailuku is to popular local shops, restaurants and bakeries that have been around for generations, the town also features emerging boutiques and laid-back cafes and coffee shops. Conveniently located just 10 minutes from Kahului, Wailuku also serves as the gateway to the lush Iao Valley.
- Lanai City, Lanai
solpodude/Flickr 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.
- Hanapepe, Kauai
Alexander Rabb/Flickr 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 – 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.
- Kapolei, Oahu
Travis.Thurston/Wikipedia Unless they are staying at Ko Olina’s J.W. Marriot Ihilani Resort and Spa or Disney’s Aulani, many visitors don’t make it to this side of the island. And that’s what makes Kapolei such a great place to live – the city is growing exponentially, and homebuyers can expect to see a serious return on investment in this budding community.
- Hawi, Hawaii Island
Ewen Roberts/Flickr 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.
- Makawao, Maui
Frank Hamm/Flickr Located in upcountry Maui on the rural northwest slopes of Mount Haleakala is a charming little town worthy of a visit – and a little recognition. With a population of approximately 7,100, Makawao is one of Hawaii’s biggest little towns and is a haven for artists of all kinds. The town is famous for its Hawaiian cowboy, or paniolo, history; horseback-riding paniolo have wrangled cattle in the wide open fields of Maui’s upland since the 19th century.
- Old Koloa Town
Kanaka Rastamon/Flickr Home to Hawaii’s first ever commercially successful sugarcane plantation, Koloa is a relic of days gone by. Home to less than 2,200 residents and shops that now occupy the plantation-style buildings, Koloa is located along Kauai’s southern shores.
- Kaunakakai, Molokai
John Hyun/Flickr 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.
- Laie, Oahu
Daniel Ramirez/Flickr Most people who visit Hawaii find themselves in Laie for one of three reasons: they are taking in a luau at the Polynesian Cultural Center, they are visiting Brigham Young University’s Hawaii campus, or they are driving through on their way around the island. But Laie is also home to an incredible lookout point of the windward coast, as well as some phenomenal beaches and a laid-back, country vibe.
- Na’alehu, Hawaii Island
Jimmy Emerson, DVM/Flickr 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.
- Hana, Maui
Ron Jones/Flickr 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.
Love checking out Hawaii’s small towns? Why not visit these 10 peaceful towns where the tourists won’t find you or these 11 charming waterfront towns?
John Verive/Flickr
With a population of just more than 10,000, Kapaa is a charming small town located on Kauai’s eastern shore. The town is home to great golfing, shopping and hiking as well as restaurants that will make your mouth water, picturesque beaches, and killer resorts. For some reason, this area is often overlooked by tourists and I can’t really figure out a good explanation as to why. In fact, Kapa’a was named as one of the most underrated cities in the United States by the Huffington Post in 2014.
Surfing The Nations/Flickr
Home to more than 16,000 residents, Wahiawa is located between the island’s two volcanic mountain ranges on Route 99, the road most commonly taken by those traveling to the North Shore from Honolulu. But if you were to stop in town and take a look around, you would see that there is more than meets the eye in this small inland city. We suggest stopping by the Wahiawa Botanical Garden, Surfers Coffee Bar, and Sunnyside.
Anna Lee/Flickr
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!
Florent Lamoureux/Flickr
While Wailuku is to popular local shops, restaurants and bakeries that have been around for generations, the town also features emerging boutiques and laid-back cafes and coffee shops. Conveniently located just 10 minutes from Kahului, Wailuku also serves as the gateway to the lush Iao Valley.
solpodude/Flickr
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.
Alexander Rabb/Flickr
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 – 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.
Travis.Thurston/Wikipedia
Unless they are staying at Ko Olina’s J.W. Marriot Ihilani Resort and Spa or Disney’s Aulani, many visitors don’t make it to this side of the island. And that’s what makes Kapolei such a great place to live – the city is growing exponentially, and homebuyers can expect to see a serious return on investment in this budding community.
Ewen Roberts/Flickr
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.
Frank Hamm/Flickr
Located in upcountry Maui on the rural northwest slopes of Mount Haleakala is a charming little town worthy of a visit – and a little recognition. With a population of approximately 7,100, Makawao is one of Hawaii’s biggest little towns and is a haven for artists of all kinds. The town is famous for its Hawaiian cowboy, or paniolo, history; horseback-riding paniolo have wrangled cattle in the wide open fields of Maui’s upland since the 19th century.
Kanaka Rastamon/Flickr
Home to Hawaii’s first ever commercially successful sugarcane plantation, Koloa is a relic of days gone by. Home to less than 2,200 residents and shops that now occupy the plantation-style buildings, Koloa is located along Kauai’s southern shores.
John Hyun/Flickr
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.
Daniel Ramirez/Flickr
Most people who visit Hawaii find themselves in Laie for one of three reasons: they are taking in a luau at the Polynesian Cultural Center, they are visiting Brigham Young University’s Hawaii campus, or they are driving through on their way around the island. But Laie is also home to an incredible lookout point of the windward coast, as well as some phenomenal beaches and a laid-back, country vibe.
Jimmy Emerson, DVM/Flickr
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.
Ron Jones/Flickr
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.
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