The 7 Most Picturesque Small Towns In Hawaii

While the world is not short of places whose appeal and charm would make anyone gasp in complete disbelief, only a handful of these places can hold a candle to Paradise of the Pacific, as Hawaii is known. Home to the largest dormant volcano in the world, Hawaii also boasts a stunning array of sandy beaches that will leave any visitor completely blown away. Hence, it is no surprise that Mark Twain called it "The loveliest fleet of islands that lies anchored in any ocean." And dotting these spectacular islands are a number of quaint, charming towns offering visitors a home away from home in a paradise. Here are some of Hawaii's most beautiful towns to visit on your next holiday to this wonderland.

Hana

Hana is isolated. Some call it "The Edge of the World." Of course, such a name conjures up images of a place that is wild, vast, and lonely. And to an extent, that is just how Hana is. Located in Maui County, Hana boasts a population of only 1,613. By all accounts, Hana is a small town. Secluded, yes, but beautiful and quaint. Yet Hana is not nearly as famous as the road that leads to it. The road to Hana cuts through one of the most breathtaking landscapes in the world. Mile after mile of hairpin turns and heart-sinking twists define what many consider the highlight of a trip to Hana. Expectedly, this road is among the country's most scenic roads.

Kalaupapa

Words will fail to give a true picture of one of the most enchanting gems in Hawaii; a secluded secret that is only accessible by boat, plane, or mule trail. Actually, Kalaupapa (meaning "flat leaf"), located on the fifth largest island in Hawaii, might very well be the most isolated town in the state. A breathtaking peninsula that juts out about two miles into the sea, Kalaupapa's rocky coastline and rough waters are always a ravishing sight. And in the town's backdrop, visitors will marvel at the cloud-cutting cliffs that are some of the tallest on the planet and which enclose the plain with exciting gloom and grandeur And then the lush greenery, a greenery that can calm any temper, perhaps even transform character.

Paia

Bohemian. That is the one word that does justice to this quaint little town on Maui's north shore. Boasting a population of only 2,410 as of 2023, Paia is surrounded by several windsurfing spots, many of which are known across the globe. Because of the impressive number of windsurfing spots, Paia is often called the "World's Windsurfing Capital." The town may not have a very dramatic landscape, but it is still super cool and laidback, while the beaches are all near and impressive — and are hands-down one of the town's major draws. Hookipa Beach is particularly a must-see, especially if someone wants a front-row seat to some of the world's largest waves.

Haleiwa

A town that was once named the best small town in Hawaii by Hawaii Magazine may have just earned its place for that achievement alone. While Haleiwa is principally a beach town, complete with world-famous surfing options, it also boasts other alluring attractions. These include an impressive offering of shopping and dining options that will satisfy every imaginable taste and fancy. Aside from its restaurants, Haleiwa is famous for its food trucks, where one can grab some delicious crispy tacos while strolling through the laid-back downtown. And for art lovers, the town has a decent number of eclectic art galleries and souvenir stores where one can get an item as a keepsake.

Hanalei

Those who've watched The Descendants, the American comedy-drama that was nominated for an impressive five Oscars at the 2012 Academy Awards—will find a compelling reason to visit Hanalei. Translated "lei valley" in reference to the frequent rainbows that tint the valley and encircle the town like a wreath, Hanalei is famous as the setting for some of the scenes of The Descendants. Of course, any location picked as a setting for an award-winning movie will be anything but boring. And Hanalei, with its pristine scenery, dreamy beaches, and historic pier, effortlessly meets expectations. No wonder Hawaii Magazine picked it as among the most beautiful small town in Hawaii for 2022. And for art lovers, Hanalei is still a perfect choice.

Lanai City

Lanai City is located on the island of Lanai, the smallest of all the inhabited islands in Hawaii. Known as "The Pineapple Island" because it's home to a farm that once produced 75% of all the pineapples in the world, the island that lends its name to this city is largely uninhabited and will be the perfect getaway for someone craving privacy, serenity, or both. Lanai City is a pretty small haven with a laid-back ambiance, yet not without the basic conveniences that should form part of a vacation trip. It has a few shops and several art galleries and is close to "the Garden of the Gods," a surreal, rocky landscape that may make one imagine she's walking on Mars or just somewhere out of this world.

Kailua-Kona

Nestled on the western side of Hawaiʻi Island is a little town that is one of the most beautiful in the fiftieth state. While it may not be the cheapest small town, Kailua-Kona is a dream town that is so relaxed and sleepy as to be immediately addictive. Shops are hardly open after 9:00 PM — and as a downside— it is not where one will want to go for a vibrant nightlife. However, for someone who enjoys the outdoors, as well as excellent access to beaches, Kailua-Kona is the next thing to perfect. Ali Drive, the town's main street that runs along the ocean, is particularly a must-do. It is not only one of the most scenic roads in the state — but is also lined with an impressive number of shopping and dining options, making exploring it a real adventure.

The Takeaway

Hawaii may have its downsides. It may not be as cheap as, say, Mexico. However, there's one thing none can take away from the fiftieth state: its breathtaking beauty. Consisting of eight main islands and more, Hawaii is where nature assembled some of the most breathtaking mountains on the globe, some of the most stunning beaches, and some of the highest waterfalls in the world — all in one place. Yet the many small towns that dot one of the most surreal landscapes on the planet are a fitting epilogue to any story about Hawaii.