Voted as the state’s favorite small town by HAWAII Magazine, Haleiwa seems like a world away from bustling Waikiki. This sleepy surfer town on Oahu’s north shore has a laid-back vibe and charming aesthetic, but also luxuries like killer beaches, mouthwatering restaurants, art galleries galore, adorable shops, and stellar vacation rentals.
Located along Hawaii Island’s scenic Kona coast is Kailua-Kona, a historic seaside village full of natural beauty, royal history, and plenty of charm. Established by King Kamehameha I to be the seat of his government when he was the chief of Mona before he consolidated rule of the island chain. The historic town later became the capital of a newly unified kingdom, before it moved to Lahaina, and later, Honolulu.
Just four miles from Kahalui on Maui’s famous Road to Hana is Paia, a small beach town big on charm. The town is not only known for its epic surfing and windsurfing waves, but is the epicenter of Maui’s north shore, and is full of artsy, bohemian vibes. While the adorable seaside town is gaining traction with tourists, it is still often seen as merely a spot to refuel, grab some food, and head out on the Hana Highway.
With a population of little more than 470, Hanalei has got it all: a charming small town vibe, pristine white sand beaches, magnificent, lush surroundings, a plethora of shopping and restaurant options, as well as an impressive dedication to the spirit of Hawaii and cultural preservation.
While Kahului serves as Maui’s retail and business center, it is not devoid of all fun – the city is, in fact, home to countless beautiful beaches, museums, art galleries and eateries. Kahului is located nearby the lush and serene Iao Valley, and is home to Maui’s main airport. Spend a day exploring the area at the beginning or end of your Maui vacation – it will not disappoint!
With a population of approximately 43,200, Hilo is the state’s fourth largest city. Unlike many big Hawaiian cities, Hilo has never experienced huge tourist draws, which means it has stayed true to the state’s pre-World War II persona, and is full of plantation-style architecture and historic storefronts.
Located on Oahu’s windward shore is the breathtaking – and award-winning – Kailua Beach and historic Kailua Town. The beach is a haven for water sports enthusiasts, and an influx of residents and visitors alike have caused real estate prices to skyrocket. But there’s still a sort of charm in this bustling community – and the adjacent beach’s crystal turquoise waters and white sand.
Once the original seat of Hawaiian monarch and King Kamehameha the Great’s royal playground, this beachside oasis is full of history – and natural beauty. For a quintessential day in Lahaina, park on Front Street and explore the town’s surf shops, art galleries, fishing charters, and boat tours – and don’t forget to stay to watch a magical Hawaiian sunset.
The largest town on the small island of Molokai, Kaunakakai is full of history. 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.
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.
On Maui’s sunny southwest shore is Kihei, a beautiful little town home to six miles of magnificent beaches. Once a popular destination for vacationing Hawaiian royalty, Kihei is ideal for both lazy days on the beach and bustling nightlife – from karaoke bars and dance clubs to sports bars and restaurants.
Tell us, which one of these charming towns is your favorite? I’d have to say that I’m partial to hanging out in either Hilo or Haleiwa.