While most of the Hawaiian Islands could be considered picturesque, there are some places and towns that are a cut above the rest. Home to quaint main streets, charming storefronts, and panoramic views of the mountains and the Pacific Ocean, these ten Hawaiian towns look as though they could be featured on postcards.
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 beautiful town and neighboring Hanalei Bay have been featured in various films, including the 1958 musical classic, South Pacific.
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.
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.
Voted as the state’s favorite small town by Hawaii Magazine, Haleiwa seems like a world away from bustling Waikiki. This sleepy surfer town has a laid-back vibe and charming aesthetic, but also luxuries like killer beaches, great restaurants and adorable shops.
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.
The first European settlers to reach Hawaii landed in Waimea in 1778, and I’m sure they were absolutely blown away by the stunning coastline. The historic town is home to approximately 1,700 residents, and is full of charm.
A small Polynesian paradise, Kapa’a was recognized as one of America’s prettiest towns by Forbes. The small-town Hawaiian vibe with a ton of hotels and vacation rentals pairs perfectly with lovely little shops, and some ono grinds from one of the town’s amazing fish taco trucks.
8. Lanai City
Sitting at 1,600 feet above sea level, Lanai City is the island’s only town, with a population of just 3,200. The city is home to a tidy grid of pastel-colored, tin-roofed cottages that date to when the town was first settled in the 1920s.
Once a crazy whaling town and the original seat of Hawaiian royalty, Lahaina has since been tamed and is now full of restaurants, surf shops, boutiques, and galleries lining the city’s Front Street.
With the greatest concentration of artists on the island, Hanapepe is known as “Kauai’s Biggest Little Town.” Its historic, plantation-style buildings, however, are now home to charming shops, eateries and a surprising amount of art galleries.