Discover the Best Weekend Getaways From Kailua, Hawaii

Kailua is perfectly positioned on the windward side of Oahu, offering easy access to several enjoyable weekend destinations. If you're looking for new experiences beyond Kailua's charming neighborhoods and stunning beaches, these quick trips around the island and nearby areas provide relaxation, adventure, and scenic beauty. Here are some of the best weekend trips from Kailua HI to consider for your next getaway.

Just north of Kailua, Laie is home to the Polynesian Cultural Center. This attraction allows visitors to experience authentic Polynesian culture through interactive villages, cultural performances, and delicious traditional meals. You can spend an entire day learning about the rich traditions of Pacific island nations.

Nearby beaches like Hukilau Beach provide a peaceful spot for relaxation and swimming. A quick drive to Laie Point offers dramatic ocean views and photo opportunities. This weekend excursion blends cultural education and natural beauty, making it memorable for visitors and residents alike.

Haleiwa, the main town on the North Shore, offers an easygoing atmosphere with local charm. Spend your weekend exploring boutiques and art galleries filled with unique creations. Afterward, lunch at one of the town's casual eateries, many of which serve freshly caught seafood.

Surfers and beachgoers will appreciate the North Shore’s famous surf spots like Waimea Bay and Sunset Beach. While winter brings giant waves suitable for watching professional surfers, summer conditions are calmer and ideal for swimming or snorkeling. Haleiwa town also features tasty shaved ice, local boutiques, and art galleries worth exploring.

A short inter-island flight brings you to Maui’s charming historic town of Lahaina. Lahaina’s streets are lined with galleries, unique shops, and popular restaurants. You can spend the weekend exploring this picturesque town and trying fresh island cuisine.

Nearby Ka'anapali Beach offers pristine sands, luxury resorts, and beachfront dining. Take advantage of snorkeling excursions to Black Rock or swim in Maui’s clear ocean waters. Ending your day with a sunset cruise completes a perfect weekend getaway from Kailua HI.

For an adventurous weekend, consider visiting Hawaii Volcanoes National Park on Hawaii Island (Big Island). Walk along trails through lava fields and observe active volcanic activity at Kilauea Crater. The park’s visitor center provides information about the area’s volcanic history.

Stay overnight in the nearby town of Volcano, where cozy inns and local dining await. Experiencing the awe-inspiring power of volcanic landscapes makes this weekend trip unforgettable. This unique destination offers a fascinating contrast to Kailua’s coastal environment.

Kauai’s north shore is a quick flight from O'ahu and worth exploring. Hanalei Bay is renowned for its stunning scenery, lush surroundings, and friendly small-town atmosphere. As a visitor, you can get beach access and go swimming or paddleboarding.

Princeville, adjacent to Hanalei, offers luxury accommodations, golf courses, and cliffside views of the Pacific Ocean. You can dine at excellent restaurants or explore local boutiques and markets. This combination of beach relaxation and upscale comfort makes Hanalei an ideal weekend retreat.

A short inter-island flight brings you to Maui’s charming historic town of Lahaina. Lahaina’s streets are lined with galleries, unique shops, and popular restaurants. You can easily spend a weekend exploring this picturesque town, especially its great local restaurants.

Nearby Ka'anapali Beach offers pristine sands, luxury resorts, and beachfront dining. You can also take advantage of snorkeling excursions to Black Rock. Ending your day with a sunset cruise completes a perfect weekend getaway from Kailua HI.

For an adventurous weekend, consider visiting Hawaii Volcanoes National Park on Hawaii Island (Big Island). Walk along trails through lava fields and observe active volcanic activity at Kilauea Crater. The park’s visitor center provides information about the area’s volcanic history.

Stay overnight in the nearby town of Volcano, where cozy inns and local dining await. Experiencing the awe-inspiring power of volcanic landscapes makes this weekend trip unforgettable. This unique destination offers a fascinating contrast to Kailua’s coastal environment.

Molokai offers a quieter, authentic Hawaiian experience. Spend your weekend exploring remote beaches, hiking trails, and the dramatic sea cliffs of Kalaupapa Peninsula. The town of Kaunakakai has friendly local restaurants serving delicious, home-cooked meals.

Molokai preserves much of Hawaii's traditional charm and unspoiled landscapes. The peaceful setting encourages relaxation, reflection, and appreciation for nature. Visiting Molokai allows you to recharge and experience Hawaii’s rich cultural heritage.

Lanai is a unique weekend destination combining luxury resorts with rugged beauty. The Four Seasons resorts offer world-class amenities, including golf, spa treatments, and fine dining. Relaxing in this exclusive setting is ideal for those seeking comfort and indulgence.

Lanai also offers adventure opportunities, such as off-road excursions, hiking trails, and snorkeling at Hulopoe Bay. Explore the historic town of Lanai City, where boutiques, cafes, and galleries provide local charm. This luxurious and adventurous weekend contrasts nicely with Kailua’s laid-back lifestyle.

Kailua, Hawaii, is a paradise for those seeking adventure, relaxation, and cultural experiences. Whether you're exploring the pristine beaches, savoring local culinary delights, or immersing yourself in the vibrant community, there's always something new to discover. If you're considering making Kailua your home, local real estate expert Alesia Barnes can guide you through the process with ease. Contact Alesia Barnes today to start your journey to living in this beautiful part of Oahu.