6 Best Hawaii Towns For A Weekend Trip

Hawaii, an island state in the Pacific Ocean southwest of the contiguous United States, is a dream destination for tourists. The state spans over 100 islands with all sorts of natural scenery, including active volcanoes, oceanside beaches, and verdant forests. Hawaii’s small towns offer a unique insight into the state’s charm with a mix of local views and culture. From the white sandy beaches of Kailua to whale-watching tours in Lahania, each town has something special to discover. Booking a weekend trip to these destinations is a great way to spend your holiday amidst Mother Nature’s allure.

Kailua

Spend a weekend along white-sand beaches and pristine waters in the town of Kailua. Located on the Island of O’ahu, this bustling town of 40,000 invites visitors with natural experiences. Most head straight to Lanikai Beach of Kailua Beach Park, both family-friendly destinations with views rarely seen elsewhere. Those looking for a more involving experience can head out on one of many kayaking trips that showcase Kailua Bay. Kailua Beach Adventures is a great option, with multi-hour trips averaging around $100. Back on land, the Lanikai Pillbox Trail is a challenging hike showcasing historic pillboxes and panoramic viewpoints.

With so much to see, Kailua is one of Hawaii’s most popular tourist destinations, and the amenities follow suit. The local farmers market takes place on Sundays in the downtown area, and visitors can peruse through dozens of local vendors who sell exotic and organic items. For something a bit stronger, the Lanikai Brewing Company sells delicious craft beer with a homely vibe. As the sun sets, Papaya Paradise Bed & Breakfast is an ideal place to call it a night.

Lahaina

Once a whaling town where whalers came to restock their provisions, Lahania is a lovely town holding strong to its roots. A weekend here must start with whales, specifically with one of the many nearby whale-watching tours. Hawaii Ocean Rafting offers a highly rated Eye-Level Eco-Raft Tour crossing humpback whale territory for two hours. On the more luxurious end, Sea Maui has a Whale Watching Cruise with an open bar and spacious seating, so you can relax and wait for these majestic mammals.

If you’re not one to head out on the water, plenty of places inland make Lahania perfect for a weekend. For example, Ka’anapali Beach and Napili Beach are touted as some of Hawaii’s best beaches, boasting clear waters and opportunities for snorkeling, swimming, and paddleboarding. Instead of whales, these beaches are often home to sea turtles, so you won’t miss out on all the marine life. Further in town, Whalers Village beckons with lively businesses, whether you are looking for a meal at Joey’s Kitchen or swimwear at Maui Waterwear. Next door, The Whaler Resort and Outrigger Ka’anapali Beach Resort offer quality rooms and amenities for a night’s stay.

Waimea

Unlike Lahania’s whaling past, Waimea was once a hub of pasture lands and horseback riding. Those interested in this side of town adore the 1847 Parker Ranch, one of the oldest of its kind in the United States. The ranch is spread over 130,000 acres and allows people to take self-guided tours of the grazing lands, heritage center, two historic homes, and racetrack. On the flip side, Waialea Beach and Spencer Beach Park are more of the typical Hawaii attractions with palm trees, a calm coastline, and abundant picnic tables.

Along with the outdoors, Waimea also hides an artistic side, palpable in its galleries and theaters. Art enthusiasts can opt for Isaacs Art Center, a museum and gallery lined with intricate paintings and rustic furniture. Meanwhile, concert fans opt for Kahilu Theatre instead, a 490-seat venue hosting stage productions, youth programs, and more. Many quaint inns and rooms are spread across the town, such as Belle Vue Waimea and Kamuela Inn, which offer reasonable pricing and comfortable stays.

Hilo

Hilo is one of Hawaii’s larger settlements, home to a community of 44,000 people. Even with so many people, the town has a tight-knit vibe, palpable through plenty of events and cultural hotspots. The Merrie Monarch Festival on Easter Sunday is a prime example, bringing the locals together with a week of hula competitions, performances, and food. This contest is considered one of the best in the world, with international performers showcasing their skills. The town is also home to the ‘Imiloa Astronomy Center, which boasts a 120-sea planetarium with one of the world’s only 3D shows, making it an ideal destination for the family to learn about space. Afterward, a simple stroll through town is full of vibrance, from the town’s historic wooden storefronts to the friendly farmers market each week.

While the culture may be the prime attraction, no trip to Hawaii is complete without some natural fun. Hilo is no exception, and landmarks like the Akaka Falls State Park and Coconut Island make it a hotspot. The latter is a small island off the coast with verdant greenery, sandy beaches, and great waters for swimming. Some believe that swimming around the island thrice brings healing powers, so you can try it out for yourself. Meanwhile, Akaka Falls State Park is home to a 70-foot tall waterfall, perfect for some scenic photos of your weekend. Continue the outdoor vibe at night by camping in nearby areas such as Arnotts Lodge.

Kahului

Kahului is a wonderful destination to visit in Maui County, Hawaii. The town is an economic hub featuring the region’s airport, harbor, and shopping centers. The latter is a top draw, and downtown beckons with plenty of vibrant businesses. Visitors can grab a bite at Ono Tacos, drink some beer at the Ale House, or get a surfboard from Second Wind Sail Sirf & Kite. With a brand new surfboard, tackle Kanaha Beach Park, an ideal place to ride some waves and enjoy your food along the ocean’s waters. Visitors interested in a more relaxing way to witness nature should opt for the West Maui Circle Drive instead. This 60-mile route takes two hours to traverse, with plenty of open vistas and landmarks, such as Kahakuloa Bay. End the day back in town at Maui Seaside Hotel or Maui Beach Hotel for a view of the coast while you sleep.

Hawi

Whether you are looking for nature, history, or culture, Hawi is a town that has it all. A trip to this community starts even before you arrive, as one can take the Kohala Mountain Road from Waimea. The route boasts winding mountain roads where one can witness Kohala Mountain, the oldest of Hawaii’s volcanoes. Upon arriving in town, the farmer’s market is a hub of life, selling fresh fruits, crafts, and ingredients every Saturday. Nearby, cultural enthusiasts have a blast at sites like Tiffany’s Art Agency and the Bamboo Restaurant & Gallery. The latter is perfect for some spicy papaya salad, while the former showcases quality artwork from local artists.

In addition to its current charm, Hawi has a longstanding history with tons of interesting facts. The town is near the birthplace of King Kamehameha I, and one can learn more at the Kohala Historical Sites State Monument. Here, the Kamehameha Akahi ʻĀina Hānau marks the exact place of his birth in 1758. Surrounding the landmark, Moʻokini Heiau is a temple from the 1300s considered Hawaii’s most sacred historical site. A short drive from the site, Kohala Lodge is a vacation rental house that’ll meet all your accommodation requirements.

Hawaii’s small towns blend natural beauty, history, and culture, offering unforgettable getaways. Each town has a unique charm, from Kailua’s pristine beaches to whale-watching in Lahania and Waimea’s ranches. Hilo captivates with vibrant festivals and stunning waterfalls, while Kahului offers shopping, surfing, and scenic drives. Hawi combines rich history with artistic flair, creating a serene escape. Whether you seek adventure or relaxation, these towns showcase Hawaii’s allure, making them perfect destinations for an unforgettable island experience.