Haleiwa, Oahu
Oahu is the most populated of the Hawaiian islands, with the state capital of Honolulu attracting millions of visitors each year. But just thirty miles north of the city, the famous but crowded, Waikiki Beach, lies Haleiwa: a city that exists almost exactly as it did decades ago. The town was developed amid several large sugar plantations, which defined Haleiwa’s commercial and production industry. Now, the town is better known as the surfing capital of the world. Experienced and professional surfers go to Haleiwa for world-class waves, but there is fun to be had for travelers of all age and experience in the pristine water and locally-owned shops of this small town.
Naalehu, Hawaii
Naalehu is a vibrant, small town that proudly claims to be the southernmost spot in the USA. With fewer than 1,000 residents, it’s a destination for visitors looking to get away from some of the large and more commercial cities in Hawaii. Naalehu sits on the edge of the Kau forest reserve, with the powerful Mauna Loa volcano just beyond that. Just nine miles north of Naalehu along the coastline, lies Punaluu: a famous black-sand beach. Naalehu is a sleepy town, where visitors can visit a few local restaurants, bars, and bakeries, and take in the natural beauty of the island.
Hawi, Hawaii
Perched on the northernmost tip of Hawaii’s Big Island, Hawi is the perfect town to while the time away in. The small central business district features a delightfully walkable stretch of art galleries, restaurants, and boutique shops. Hawi has a rich history of sugar production, with brightly-colored plantations offering tours and a glimpse into the area’s history. Each fall, the otherwise quiet town is abuzz of excitement, as athletes in the world-famous Ironman Triathlon turn around in the city during the biking portion of the race. For more adventurous spirits, travelers can tour the nearby Kohala fruit farm or ride the Kohala zip lines.
Honokaa, Hawaii
Like many other towns on the island of Hawaii, Honokaa grew out of a prolific and profitable sugar growing industry. Ever since the largest sugar company near Honokaa closed in 1994, the town has quieted down significantly. Now, it has a charming historic downtown area with a beloved community theater, restaurants, and shops. Beyond the well-known sugar, coffee, and pineapple crops, ranching is also a strong industry on the island. Every May, Honokaa hosts Western Week, a lively celebration of the town’s history of ranching, with live music, a festival, and rodeo events. For guests wanting to get in on the rodeo adventure, a handful of touring companies offer tours via horseback of the nearby Waipio Valley.
Kaunakakai, Molokai
Kaunakakai is a peaceful town on the lesser-known island of Molokai. The town boasts a history of fishing, ranching and farming, and is considered by locals to be a paniolo, or Hawaiian cowboy, destination. Just 12 miles north of Kaunakakai is Kalaupapa, a town that served as a colony for exiled lepers for nearly a century. The isolation law that banned people affected with leprosy was lifted in 1969, and the town returned to its previous state as a quiet fishing village. Today, the Kiowea Beach Park on the west end of town is a lovely place to see Kapuaiwa, an ancient royal coconut grove.
Lanai City, Lanai
The island of Lanai was once home to a Mormon colony. But in 1922, a company that would later be called known as Dole began growing pineapples. For seventy years, Lanai was the world’s largest producer of pineapples, growing 75% of the world’s supply. As a result, the small island appropriately gained the nickname, The Pineapple Island. Lanai City is geographically located near the center of the island, and is set at nearly 1,700 feet above sea level. The charming small town has several restaurants offering traditional Hawaiian cuisine, art galleries, jewelry shops, and coffee houses. Visitors can take biking tours of the town and nearby views of the coastline. Other outdoor activities, such as horseback riding, golf, and clay shooting are available in Lanai City.
Hana, Maui
The city of Hana is secluded and somewhat difficult to get to, which adds to the magic of this remote village. Hana is 52 miles from Maui’s largest city, Kahului, and is connected by a winding and precipitous highway. The Road to Hana has become famous for its stunning views, narrow passes, and hairpin turns. Once arriving in Hana, the experience is unlike any other. The town is pristine and austere, seemingly stuck in an era long-gone. Popular attractions and activities include snorkeling, hiking, a tropical botanical garden, and a black sand beach. Hana is also home to Pi’ilanihale Heiau, a basalt temple dating back to the fourteenth century.
Lahaina, Maui
Lahaina is one of the larger cities on our list, but this historic town is not to be missed. The city was once the capital of the entire Hawaiian Kingdom, and its port was extremely busy during the nineteenth century as hub for whaling. Herman Melville, the author of the literary classic Moby Dick, even passed through, taking a leave in Lahaina during his years at sea. A large section of the city is designated as a historic district, and has been preserved for locals and visitors as a delightful homage to the past. Lahaina’s Front Street is home to dozens of shops, art galleries, restaurants, and an upbeat nightlife. A number of theaters also offer world-class shows and performances, theatrically highlighting and sharing local dances, dress, and customs.
Koloa, Kauai
The first Europeans in Hawaii landed on Kauai in Waimea, just 16 miles from Koloa. The town is tiny: covering just over one square mile. Koloa was one of the first places in Hawaii to open a sugar mill, which dominated industry in the islands during the nineteenth century. Sugar production brought an influx of immigrants to Koloa, contributing to a colorful and diverse population today. Retail business now inhabit former plantation buildings in the quaint Old Town Koloa. A hiking and biking route, called the Koloa Heritage trail, is a ten mile stretch popular for hiking and biking, that passes by parks, churches, historic sights, and beautiful beaches.
Hanalei, Kauai
Across the island from Koloa, lies the North-shore city of Hanalei. The town has a unique history, with a Russian imperial presence that occupied to forts in nearby Princeville. Today, Hanalei is known for stunning beaches, and a plethora of opportunity for outdoor adventure. Windsurfing, ziplining, hiking, river-rafting, and snorkeling are all available activities in Hanalei. The town hosts regular ukulele concerts and music festivals that are enjoyed by both locals and visitors. Hanalei’s Waioli Mission House and Church is was established by early Christian missionaries, and stands today national historic landmark, and would be a perfect place to spend an afternoon.