Island hopping in Hawaii: Your itinerary for adventure, culture and relaxation

Your island-hopping adventure begins on Oahu, home to iconic Waikiki Beach and a rich blend of history and modernity.

• Surf’s up in Waikiki: Dive into the quintessential Hawaiian experience with a surfing lesson from Faith Surf School. Located right in front of the OUTRIGGER Waikiki Beach Resort, you’ll be riding waves in the shadow of Diamond Head.
• 'Auana by Cirque du Soleil: Be mesmerized by Cirque du Soleil’s first residency show in Hawaii at the OUTRIGGER Waikiki Beachcomber Hotel. This dazzling performance combines breathtaking acrobatics, music and storytelling, bringing an extra touch of wonder to your Waikiki evenings.
• Culinary showmanship at Tanaka of Tokyo: Head to the OUTRIGGER Waikīkī Paradise Hotel for an unforgettable teppanyaki experience at Tanaka of Tokyo, where expert chefs turn cooking into a captivating art form.
• Evenings at Kani Ka Pila Grille: As the sun dips below the horizon, head to the OUTRIGGER Reef Waikiki Beach Resort for cocktails and nightly live music at Kani Ka Pila Grille, famously known as the Home of Hawaiian Music.
• Sunday serenade with Henry Kapono: End your Oahu stay with legendary vibes at Duke’s Waikiki. Every Sunday from 4 to 6 pm, Henry Kapono graces the stage, blending soulful melodies with beachfront views.
• Visit historic Pearl Harbor: Step back in time at Pearl Harbor, where you can explore the USS Arizona Memorial and learn about Hawaii’s pivotal role in World War II. A deeply moving experience, it’s a must-visit to connect with history.

Next, take a short flight to Maui, where natural beauty and cultural richness reign supreme.

• Cultural immersion at OUTRIGGER Kāʻanapali Beach Resort: Join daily Hawaiian cultural activities to connect with Maui’s traditions and stories. From lei-making to ukulele lessons, it’s a hands-on way to embrace aloha spirit.
• Explore world-famous Kāʻanapali Beach: Voted the best beach in the world, Kāʻanapali Beach offers golden sands and crystal-clear waters perfect for a variety of ocean activities or lounging on the warm sand.
• Sunset serenades at Maui Brewing Co.: As the day winds down, enjoy live music oceanside at Maui Brewing Co., located at the OUTRIGGER Kāʻanapali Beach Resort. With a cold brew in hand and the sunset painting the sky, it’s pure island bliss.
• Take a Helicopter Tour: Marvel at Maui’s nickname, "The Valley Isle," from above. A helicopter ride gives you unparalleled views of lush valleys, towering waterfalls and the dramatic coastline, offering a perspective like no other.

Hawaii Island, affectionately known as the Big Island, offers thrilling adventures and deep cultural connections.

• Swim with manta rays: Embark on a magical night snorkel in Keauhou Bay, where you’ll glide alongside graceful manta rays in their natural habitat.
• Feast and Fire Luau: Mondays and Thursdays from 5 to 8 pm, experience the best luau on the island at OUTRIGGER Kona Resort & Spa. This unforgettable evening of food, dance and storytelling celebrates Hawaii’s rich heritage.
• Cultural walking tour: Stroll the historic grounds of King Kamehameha III at the OUTRIGGER Kona Resort & Spa. This tour brings the island’s history to life with tales of royalty and resilience.
• Hawaii Volcanoes National Park: Witness the awe-inspiring power of nature with a visit to Hawaiʻi Volcanoes National Park. Explore lava fields, craters and active volcanic vents while learning about the island’s fiery origins.

Finish your Hawaiian adventure on Kauai, where lush landscapes and serene vibes await.

• Happy hour at OUTRIGGER Kauaʻi Beach Resort & Spa: Savor the best happy hour on the island and then cap your evening off with live music and refreshing drinks, the perfect way to unwind after exploring.
• Pamper yourself at Hawaiian Rainforest Spa: Treat your mind, body and soul at the Hawaiian Rainforest Spa, conveniently located at OUTRIGGER Kauaʻi Beach Resort & Spa.
• Explore Waimea Canyon and Na Pali Coast: Take a day trip to Waimea Canyon, often called the Grand Canyon of the Pacific. Then cap off your adventure with a dinner cruise along the dramatic cliffs of the Na Pali Coast, where the sunset views will leave you breathless.
• Kayak and hike to Secret Falls: Paddle through serene waterways and hike to Secret Falls, a breathtaking waterfall hidden within Kauai’s lush greenery. This adventure is a must for nature lovers.

From the history of Pearl Harbor to the fiery landscapes of Hawaiʻi Volcanoes National Park, each Hawaiian island offers unforgettable moments that bring the spirit of aloha to life. Let OUTRIGGER Resorts & Hotels be your gateway to paradise, ensuring comfort, connection and unforgettable memories at every stop.

For the ultimate convenience, book your activities at OutriggerActivities.com. Whether you're surfing Waikiki’s waves, exploring Maui’s valleys by helicopter or kayaking to Secret Falls in Kauai, OUTRIGGER Activities & Experiences makes planning your dream Hawaiian adventure effortless.