Island fever is real, and despite living in a tropical island paradise, sometimes we need to get away for a while. Unfortunately, when you live in the world’s most isolated population center, vacations are tricky to plan – and don’t seem worth it when you only have a long weekend. Unless, that is, you hop on an hour long flight to explore one of the other incredible Hawaiian Islands. From sleepy surfing towns to cities bursting at the seams with history, here are 12 of the greatest Hawaiian cities for an idyllic weekend getaway.
This little surf town is not only the epicenter of Maui’s north shore surf spots, and the gateway to the Road to Hana, but a hip place to explore – 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.
2. Lanai City
The island’s only town sits at 1,645 feet above sea level, boasting a population of just 3,200. The historic plantation village was built in 1924, and not much has changed since then, preserving the town’s original charm. Take a step back in time to experience true Hawaii, and get away from it all on this tiny island.
Voted as the state’s favorite small town by Hawaii Magazine, Haleiwa seems like a world away from bustling Waikiki. This quintessential Hawaiian town was established in 1898, and boasts streets full of retailers, shave ice stands, restaurants, and surf shops. The town also serves as the gateway to infamous North Shore beaches and big waves during winter surf season.
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 of the greatest ziplining, skydiving, 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.
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. With fresh air, beautiful beaches, local history, and breathtaking views of ancient taro fields and the island’s valleys, Hanalei is the place to go to truly relax. Fun fact: from 1817 to 1853, three Russian forts near Hanalei were part of the tsarist Russian America.
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. Perfect for those who want to be on the water as much as possible, Lahaina Harbor is home to a variety of fishing charters, whale watch tour boats, snorkel tours, and sunset cruise options.
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.
Located on Hawaii Island’s eastern coast is Hilo, a town of 40,000 with so much to offer as a getaway. For one, the quaint city is full of Victorian-style houses overlooking a half-moon bay. And another perk (if you’re like me, that is) – it is actually the rainiest city in the United States, and is a welcome retreat from the constant sunshine of paradise.
The largest town on the island has a population of approximately 3,400 residents, and was once the location for King Kamehameha V's royal summer residence. The port town was bustling back in the days of pineapple and sugar exports, but has since calmed down, and is the perfect weekend escape from your busy life.
They say that it’s not the destination, but the journey that it takes to get there, and nowhere is this more true than Hana. The infamous Road to Hana is full of twists, turns, several one-lane bridges, waterfalls, and incredible vistas - and as one of the most isolated communities in the state, Hana will certainly appeal to anyone who truly wants to get away from it all.
With the greatest concentration of artists on the island, Hanapepe is known as "Kauai’s Biggest Little Town." Its historic, plantation-style buildings are now home to charming shops, eateries and a surprising amount of art galleries - and it’s a beautiful place for a weekend retreat.
Established by King Kamehameha I to be the seat of his government when he was he 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. Until the late 1900s, Kailua-Kona was a small fishing village, but the community witnessed a real estate and construction boom fueled by tourism, and is now a wildly popular vacation destination.
Where will your next weekend getaway take you? For more information on planning the ultimate getaway, check out these
15 luxury resorts, or these 10 amazing cabins across the Hawaiian Islands.
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