Carefree Hawaiian Island Hopping

Whether it’s a 3-day getaway or a week-long retreat, island hopping is a thrilling way to explore the diversity and beauty of the Hawaiian archipelago. Interisland travel is a great way to experience all that Hawaii has to offer, and with flight times between 20-50 minutes, island day trips can be a breeze. For a perfect home base, you can find resorts on four of the biggest islands — The Big Island, Maui, Oahu, and Kauai. 

Each island showcases a different style of paradise, so you really can’t go wrong. To help you spend less time planning and more time soaking up paradise, here are a few highlights of each, so you can choose the best home base for your island-hopping adventure. 

For health mandates, be sure to check the state’s travel requirements for each island prior to planning your vacation.

1. Kailua-Kona, Big Island: A Paradise For Sightseeing

Booking your stay in Kailua-Kona puts you on the west coast of the Hawai’i, also called the “Big Island,” the largest island in the Hawaiian archipelago. Famous for its variety of climate zones, the island of Hawai’i offers a diversity of natural landscapes. Visit rare green and black sand beaches, encounter two of the world’s most active volcanoes at Hawaii Volcanoes National Park, stargaze atop Mauna Kea, the world’s largest sea mountain, and swim with manta rays in dazzling jade waters. Tour one of Kona’s picturesque coffee fields and sample famous Kona coffee straight from the source. Stroll through the seaside town of Historic Kailua Village for local cuisine, artisan souvenirs, and historical landmarks, like the Hulihee Palace. Follow a paved footpath through the lush rainforest of 'Akaka Falls State Park for a stunning view of 442-foot ‘Akaka Falls. 

Stay Here: Club Wyndham Kona Hawaiian Resort, Club Wyndham Mauna Loa Village, Club Wyndham Royal Sea Cliff

2. Kihei, Maui: A Paradise For Fun In The Sun

With 6 miles of golden beaches, sun-kissed Kihei is a haven for oceanfront activities, from surfing and kayaking to sunbathing and snorkeling. Head to Kalama Park for an action-packed day of beachside sports with 36-acres of athletic fields and recreation areas. Spot humpbacks on a whale watching excursion in Maalaea Bay or a state-of-the-art 3-D sphere experience at the impressive Maui Ocean Center, home to the largest tropical reef aquarium in the Western Hemisphere. Take a scenic drive up the coast to the historic town of Lahaina. Once a major whaling port, Lahaina is now a lively cultural hub with dozens of art galleries, fine dining, and shopping. Trace the town’s past on a self-guided tour of the Lahaina Historic Trail. Stroll the pubs, eateries, shops, and galleries of Front Street. 

Stay Here With Wyndham Club Pass: WorldMark Kihei

3. Honolulu, Oahu: A Paradise For Leisure

Nicknamed the “Gathering Place,” Oahu embraces a fusion of ancient and modern cultures. The island itself is as diverse as its population and you’ll find the perfect blend of big city energy and tropical island vibes. Oahu is also home to Hawaii’s capital and largest city, Honolulu. Whether you’re in the mood for shopping, sunbathing, or sightseeing, Honolulu offers a vibrant hub of luxurious amenities and historical attractions surrounded by pristine beaches and striking mountain ranges. For soft sand and calm, clear water, visit Ala Moana Beach Park, a local favorite. Enjoy over 350 shopping and dining options at Ala Moana Center, the world’s largest open-air shopping center. Watch the sunset in Waikiki and explore Waikiki Beach Walk, an oasis of high-end shops, specialty boutiques, and award-winning restaurants in a two-level open-air mall. 

Stay Here: Club Wyndham at Waikiki Beach Walk, Club Wyndham Royal Garden at Waikiki

4. Princeville, Kauai: A Paradise For Outdoor Thrills

Crowned Hawaii’s “Garden Island,” Kauai is a treasure trove of natural splendor and thrilling outdoor adventures. The oldest in the island chain, Kauai is home to some of Hawaii’s most unique and iconic natural wonders. From dramatic cliffs and emerald valleys to luxuriant rainforests and thundering waterfalls, Kauai’s epic landscape has been featured in movies and television since the 1930s. Hike the majestic Waimea Canyon, the “Grand Canyon of the Pacific.” Explore enchanting sea caves on the breathtaking Napali Coast, where the water glows blue. Kayak the Wailua, Hawaii’s largest navigable river, retracing an ancient path. Soar over emerald valleys and mountain sides on a backcountry zip line tour. Embark on an off-roading expedition through tropical jungle and historic landscapes, including famous movie locations like Jurassic Park and Raiders of the Lost Ark. 

Stay Here: Club Wyndham Bali Hai Villas, Club Wyndham Ka Eo Kai, Club Wyndham Shearwater