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The 10 Most Charming Towns in Hawaii

by Paul Joseph  |  Published February 8, 2017

A TravelMag survey of travel experts has revealed the ten most charming towns in Hawaii, where stunning natural beauty and a thriving local culture combine to create a truly idyllic destination, utterly different to any other US state.

Lahaina Town

Lahaina Town illuminated by street lamps at dusk (Photo: Chuck via Flickr)

We invited 50 travel writers, photographers and selected professionals to name the towns in Hawaii that they consider the most appealing. Those surveyed were asked to pick their three favourites, in no particular order, and we then took these results to compile the Top 10.

So what do we know about the so-called “Aloha State”? An isolated volcanic archipelago in the Central Pacific, Hawaii’s islands are renowned for their rugged landscapes of cliffs, waterfalls, tropical foliage and beaches with gold, red, black and even green sands.

Whichever part of Hawaii you visit, you’re guaranteed to find miles of sun, sand, nightlife, pretty colonial architecture, historical monuments and culture, with many local trades and industries still thriving here, such as breweries, art galleries and crafts stores. Of course, helping Hawaii prosper are the large numbers of visitors who descend here each year, from other parts of America and far beyond too.

And so without further ado, here, in alphabetical order, you will find what many consider Hawaii’s most charming towns.

Haleiwa

Initial impressions of Haleiwa are of a relaxed, laid back surf town, but dig a little deeper and you soon find its multi-layered appeal. The town is in fact a hub of creative energy and endeavour, with a large number of art galleries dotted throughout its pretty streets, each offering the chance for visitors to pick up some authentic locally produced art for your home. Also to be found here are distinctive plantation-era buildings that hark back to the town’s past, while casual, understated restaurants serve local dishes using original recipes steeped in Hawaii’s culinary folklore.

Haleiwa

A sign welcoming people to Haleiwa (Frank Duck via Flickr)

Hanalei

Sensational views every which way you turn are among the first things to greet visitors to this picture-perfect town, which is cradled by the verdant north shore mountains on one side and the golden sand beaches and crystal clear waters of Hanalei Bay on the other. The town’s idyllic ocean setting makes it a popular spot with watersports fans, while those who venture inland to the town centre find plenty to enjoy too, including historic buildings, art galleries, boutiques, surf and bikini shops and a multitude of restaurants from the casual to the high-end.

Hanalei

A striking looking church in Hanelei (seanmugs via Flickr)

Hawi

Once the epicentre of the region’s now defunct sugar industry, the historical town of Hawi rests gently in the green northern tip of Hawaii. It is home to a delightful smattering of art galleries, boutiques and restaurants set amid colourful plantation buildings, lending the town a bustling and friendly ambience. Whether it’s handmade jewellery, crafts, homemade fudge or 100% Kina coffee, you’re sure to depart with a souvenir or two. As an extra fun fact, Hawi also plays host to the bicycle turnaround of the annual Ironman World Championship.

Hawi

The downtown district of Hawi (J. Stephen conn via Flickr)

Hilo

Lush, green vegetation characterises the town of Hilo more than anything else, owed in part to the fact that it welcomes more rain than any other city in the US. But don’t fret, there are plenty of sun-kissed days to enjoy here too, which may well explain why it made it into our top ten. A University town, it is also brimming with youthful energy, while a weekend farmers’ market adds plenty of character and charm.

Hilo

A peaceful waterside view in Hilo (Curtis and Juanita via Flickr)

Kailua-Kona

The bustling centre of Hawaii’s so-called “Kona Side”, this town is home to a number of historical sites, entertainment venues and shopping opportunities. Dry and sunny, its pristine white sand beaches are perennially busy with sunbathers, snorkelers and swimmers, who help to create a buzzing but relaxed atmosphere. Indeed, snorkeling at sunrise is one of the most popular activities here – we suspect that those who voted for Kailua-Kona to make our top ten will have enjoyed such an opportunity.

Kailua-Kona

A church spire peeks out above the trees in Kailua-Kona (Alastair Battson via Flickr)

Kapaa

Hawaiian mementos, fine artwork, antiques, jewellery and craft items – if you’re keen to pick up gifts and souvenirs during your visit to Hawaii, there’s nowhere better than the fabulous town of Kapaa. It is also a popular spot with watersports enthusiasts, with a store selling a huge variety of aquatic-related garb, gadgets and gizmos. You can even arrange water skiing or kayak rental here. Add to the mix several well regarded restaurants and an atmospheric market, then kapaa’s position in our top en begins to make plenty of sense.

Kapaa

The Coconut Cup Juice Bar in Kapaa (Braveheart via Flickr)

Lahaina

Once the capital of the Hawaiian Kingdom, this historic old town is an intriguing place to explore. It is dotted with interesting landmarks that speak to the town’s past as a whaling village, while there’s also numerous art galleries and unique stores selling unusual wares. The town’s sunny climate and oceanfront setting offers the ideal backdrop for a range of outdoor activities including cycling and surfing, while the winter months present the chance to enjoy a whale watching tour.

Lahaina

A street in the historic whaling village of Lahaina (Jasperdo via Flickr)

Lanai City

Positioned in Hawaii’s highlands, Lanai City is an ideal destination for those who prefer a cooler climate. It is also a great place for finding locally-made gifts and souvenirs including authentic Hawaiian jewellery, art and clothing, while Dole Park is often described as the town’s heartbeat, a scenic meeting place for all ages who come to picnic or simply chat. There are also two exceptional hotels here, one owned by the renowned Four Seasons international hotel group and another a country inn boasting charming plantation-styled décor.

Lanai City

A sign welcomes visitors to Lanai City’s Commercial Square (prettyhip via Flickr)

Na’alehu

Pretty monkeypod trees flanking quaint old plantation homes is just one of the pleasing scenes that greets you in Na’alehu. Situated near South Point in Hawaii’s Ka’u District, the town is charm personified and, aside from once a year when it hosts a popular Rodeo festival, it generally oozes calm and tranquillity. It is also blessed with natural beauty, thanks to its lush vegetation, green valleys and picturesque hills that surround the town, while nearby black sand beaches attract visitors all year round.

A view of the historic Naalehu Theater (gre99qd via Flickr)

Paia

Nestled on the northern coast of the island of Maui, Paia is one of the best towns in Hawaii to visit. Perhaps its defining characteristic is the passion for surfing shared by virtually everyone who lives here – and indeed those who come to visit too, many of whom quickly find themselves immersed in what is more a way of life than just a hobby. Paia is also a fabulous place to pick up souvenirs, with a wide selection of quirky boutiques and gift shops to be found here, all adding to the town’s unique charm.

Paia

A woman cycling on the pavement in downtown Paia (Damir Alljagic via Flickr)

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