12 Lazy Day Towns In Hawaii That Are Perfect For Your Next Outing
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Megan Shute
Author
Life is certainly a little slower across the Hawaiian Islands than it is on the mainland, and we absolutely love lazy days spent at the beach. Sometimes, though, you want to mix it up a little and spend your day exploring a new town: trying new restaurants, shopping, enjoying the scenery, and yes, checking out the local beaches. If you want to get away from it all for a day trip you won’t soon forget, head to one of these 12 towns. Trust us, there’s no better way to spend a lazy afternoon.
Located in upcountry Maui on the rural northwest slopes of Mount Haleakala is a charming little town worthy of a visit — and a little recognition. With a population of approximately 7,100, Makawao is one of Hawaii’s biggest little towns and is a haven for artists of all kinds. The town is famous for its Hawaiian cowboy, or paniolo, history; horseback-riding paniolo have wrangled cattle in the wide open fields of Maui’s upland since the 19th century.
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. It’s one of my personal favorite lazy Saturday destinations, and you’re sure to fall in love, too.
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With the greatest concentration of artists on the island, Hanapepe is known as "Kauai’s Biggest Little Town." Once one of Kauai’s largest communities, you may find that not much has changed over the last century in Hanapepe. Its historic, plantation style buildings, however, are now home to charming shops, eateries and a surprising amount of art galleries. Every Friday night from 5 – 9 p.m., local art studios keep their doors open late for Friday Art Night. Some artists sit on the sidewalk to paint or display their recent work while local performers play Hawaiian music.
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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. It doesn’t get much better than this.
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 incredible skydiving, ziplining, 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.
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. Rent a bicycle and explore in the morning, and then head to the beach in the afternoon.
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Though Hanalei is located just north of the Princeville resort area, it feels like worlds away from the Hawaiian tourism scene. 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 and natural beauty. Photographers will love spending a lazy day snapping photos of everything that makes this town beautiful.
This idyllic Hawaiian Island is often overlooked in favor of the larger, more populated islands, but Lanai, and its main city, are often touted as being the most authentically Hawaiian. The town was founded amidst the island’s booming pineapple industry and is now home to unique shopping, inexpensive dining, and two hotels. There's little better place to relax than this.
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While Wailuku is home to popular local shops, restaurants, and bakeries that have been around for generations, the town also features emerging boutiques and laid-back cafes and coffee shops. Conveniently located just 10 minutes from Kahului, Wailuku also serves as the gateway to the lush Iao Valley and is the perfect place to spend a leisurely day.
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. This lively seaside town full of boutiques, art galleries, souvenir shops, and magnificent restaurants with plenty of outdoor seating.
Most people who visit Hawaii find themselves in Laie for one of three reasons: they are taking in a luau at the Polynesian Cultural Center, they are visiting Brigham Young University’s Hawaii campus, or they are driving through on their way around the island. But Laie is also home to an incredible lookout point of the windward coast, as well as some phenomenal beaches and a laid-back, country vibe.
This historic Maui town is full of incredible shops and restaurants, a generous heap of local surf culture, and some killer Bohemian vibes. As the main hub of Maui’s north shore, Paia has undoubtedly experienced waves of change in the last several decades, but it still is overflowing with the energy of its plantation past. Hang out on the beach, at a local restaurant, or exploring the town’s many unique galleries and shopping destinations.
How many of these towns have you visited? Which is your favorite place to spend a lazy weekend day?
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