8 Coolest Small Towns in Hawaii for a Summer Vacation
Hawaii is the cool Aloha State from every side you look, with some of the nation's best variety of natural sights and wonders. Immerse yourself in local culture at one of these charming towns and explore the beaches and outwards into the verdant forests and countryside. The 50th state, with some of the world's most beautiful beaches, is a dream escape for anyone, particularly surfers, sailors, and other water sport fans.
Enjoy kaleidoscopic colors all throughout as you sunbathe on some alien sands or watch the otherworldly spectacle at the Volcanic National Park. Visit in any season to bask in all the sun-kissed glory and have an unforgettable, nostalgia-inducing experience that you will cherish forever.
Haleiwa, Oahu
Haleiwa is a special little town that makes it on nearly every list mentioning Hawaii as the globe-renowned cool-dude surfing destination along Oahu's legendary North Shore, near some of the greatest waves in the world for fans and surf competitions. Visit Haleiwa for any other purpose than pursuit, just 30 miles from the bustling capital of Honolulu, and you will not be disappointed by the real detached vibe amid some of the state's best natural scenery. Appreciate the beachy feels as you absorb the culture by eating and shopping your way through town on a sunny morning stroll.
Spend the day shopping for souvenirs and strolling between art galleries, with a stop at shaved ice stands for a treat to cool off. Gorge on freshly fried fish tacos at Surf & Salsa and head to the beach for the spectacular North Shore sunset. You can even try mastering surfing in Haleiwa, which will help you handle your first wave of many to become a pro. Sign up with the expert instructors from North Shore Surf Girls, or if you are still hesitant, bask along the pristine sands at one of the nearby beaches and watch the locals shred waves like they were born on a board.
Hana, Maui
Feel the cool vibes as early as the drive into Hana, a cute town near waterfalls and verdant forests, and the historic St. Sophia’s Church greeting you at the entrance. Hana is a real dream for history buffs and curious sightseers to discover Hawaii’s unique cultural heritage, like at the Hana Cultural Center and Museum with its one-of-a-kind artifacts. The town is equally marvelous for those wishing to dive even deeper into the ocean's blue, where snorkeling beneath the surf in Hana Bay is like no other.
Hana lets you explore the taste of unspoiled Hawaiian culture through natural beauty and charming history along Maui’s rugged eastern coastline. The gorgeous small town is "real Hawaii" to its bones, where you can escape on an exciting adventure or relax on the beach at the mercy of the dramatic seascape doing all of the work while you sip on a chilled cocktail.
Hanalei, Kauai
This part of the North Shore of Kauai, just minutes north of Princeville resort areas, feels like a world of its own making. Hanalei is a real dreamscape, with Kauai beach and a tropically-infused center that exudes luxury like no other place around. Head to the shore of Hanalei Bay, backdropped by marvellous green mountains, where you can sprawl out on the marvelous soft sands or join others in handling those ideal waves rolling in.
Take the small, one-lane bridge into town, which houses an unusual mix of shopping and dining options amid only 0.8 square miles full of old-world charm. Explore the perimeter on foot, where the friendly locals will gladly share their proud heritage through traditional art and freshly prepared cuisine. You are right to recognize this town as the star of the set, featured in the 1958 musical classic South Pacific, among other films.
Hilo, Big Island
The town along its own "unofficial Hilo side" of the Big Island is a vacation destination unmarred by tourism cuteness. Its beach, one of the whole country's most gorgeous, will captivate you for days, but there's so much to see and do around there that it would be sinful not to. Venture into the magnificent Waikuku State Park, check out the boiling pots, and set up a picnic at the site of the spectacular Rainbow Falls. Hilo is also your gateway to exploring the overwhelmingly spectacular Hawaii Volcanoes National Park.
Stroll through the historic downtown Hilo area for the "Old Hawaii" experience and to discover more about the Big Island amid plantation-style architecture and old storefronts safekeeping various treasures. You have to see to believe the local preservation efforts for the old-school charms and locally owned businesses that will open your eyes and mind to the mysteries of Hawaii’s culture and heritage. This enticing little town is one of the few left to really appreciate Hawaii as it once was.
Kailua-Kona, Big Island
You're not wrong to associate this town with the coffee capital of Kona, Hawaii. Set in between the towns of Holualoa and Kalaoa, in the heart of Kona coffee country, the town is not as touristy as you expect to appreciate your morning Java and every coffee break til sunset in scenic serenity. The upcountry small town amid some 600 coffee farms is your gateway into historic Hualalai, with just a few farming families, an old theater, and art galleries along the narrow country street.
One of Hawaii’s best little towns, sometimes called just "Kona", bursts with authentic Hawaiian culture, history, and sights. Celebrate the artistic beauty of Kona and cherish what their giving home continues to stand for over a fragrant cup of Joe. Venture seaside on the Kona coast to the Kailua-Kona waterfront, which you can explore through a myriad of activities in between all the time spent in the ocean.
Kapa'a, Kauai
From party animals to luxury seekers and those looking for some peaceful shopping on a stroll through the sights, Kapa'a is one cute town with something for everyone. Explore the area for local flora at Smith’s Tropical Paradise and enjoy island-style dining at Hukilau Lanai Restaurant. Check out the atmospheric Coconut Marketplace for local finds and unique souvenirs from the stunning Kauai island.
Nestled north of Wailua, the paradise for shopaholics at destinations like the Kinipopo Shopping Village and Wailua Shopping Plaza, which offer local dining, is not without water either. Get inspired for your next wet adventure right at the Village's water sports shop, with rentable equipment to ride the waves at the nearby beach. Check into the Aston Aloha Beach Hotel, where Hawaiian-style rooms and traditional service will make you feel the true spirit of local hospitality.
Kaunakakai, Molokai
The cool town of Kaunakakai is so chill that you get a real taste of Hawaii’s simplistic lifestyle, just like locals do. Nestled on Molokai’s south shore, the tranquil small town of Kaunakakai will transport you right back into the 1900s with an old-timey vibe and sights along the streets, void of traffic lights and big chain stores. Molokai's shopping hub is full of culture you can absorb on a stroll amid small shops and boutiques, including Friendly Market, Imamura’s Store, and Outpost Natural Foods.
Check out some beautiful 19th-century churches along "Church Row," like its seven missionary-style small churches. Head harborside, where local fisherman have long found their niche along the scenic Kaunakakai Harbor, and grab a snack from Kanemitsu’s Bakery of their famous onion-and-cheese bread, along with other delicious eateries like the Molokai Pizza Café.
Pa’ia, Maui
The historic town of Paia, once a booming plantation town along Maui’s north coast, is colorful and vibrant today, with scenic vestiges from the past. Stroll amid old-west-style buildings with appealing restaurants, art galleries, and eclectic shopping boutiques. The town's Hookipa Beach is a wintering destination for pro windsurfers and kite surfers that you can watch along with the big waves rolling in as you relax under warm sunrays while it snows back home.
The hot summers call for a cooling dip headfirst into the more calm waters and sprawling out on a golden sandy beach in its sun-kissed glory. Enjoy easy access into town, just 8 miles east of the Kahului Airport, the main hub of Maui’s North Shore, which makes it a popular place among historians, business travelers, and for conferences. The lively town's center is full of shopping and dining experiences to really immerse yourself in local culture, along with historic buildings and a variety of locally owned businesses.
The Takeaway
Hawaii will blow you away with its specter of islands, each different from the last, and small towns will be even more varied in their characters. These towns are all gems that you could choose with your eyes closed to get to know personally and not go wrong when it comes to beaches, scenery, and local culture. Visit the coffee capital of Kona or the surfing scene of Haleiwa, all oozing with authenticity and fitting the whole essence of Hawaii into one small place.
