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21 Days Exploring Hawaii's Islands Itinerary
Last updated: 2024 Jun 14Welcome to Oahu's Wonders
Morning
Start your day with a visit to the iconic Waikiki Beach. This world-famous beach is perfect for a morning swim or surf session. Stroll along the shoreline and enjoy the stunning views of Diamond Head.
Afternoon
Head over to Pearl Harbor to explore the historic USS Arizona Memorial. This solemn site offers a deep dive into World War II history and is a must-visit for history enthusiasts.
Evening
Dine at one of Oahu's top-rated restaurants, Duke's Waikiki, where you can enjoy delicious Hawaiian cuisine with a beautiful ocean view.
Bedtime
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Oahu’s Natural Beauty and Culture
Morning
Begin your day with a hike up Diamond Head Crater. The trail offers panoramic views of Honolulu and the Pacific Ocean, making it worth the effort.
Afternoon
Visit the Polynesian Cultural Center to immerse yourself in Hawaiian culture. Enjoy interactive exhibits, traditional performances, and learn about the islands' rich heritage.
Evening
Have dinner at Michel's at the Colony Surf, known for its elegant French cuisine and romantic beachfront setting.
Bedtime
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Oahu’s Adventure Day
Morning
Hanauma Bay Nature Preserve is ideal for snorkeling. The bay is home to vibrant coral reefs and diverse marine life, making it a must-visit for underwater enthusiasts.
Afternoon
Visit Nuuanu Pali Lookout for breathtaking views of Oahu's windward coast. The lookout offers panoramic vistas of lush valleys and towering cliffs.
Evening
Dine at Alan Wong's Honolulu, renowned for its innovative Hawaiian cuisine that blends local flavors with international influences.
Bedtime
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Oahu’s Cultural and Natural Highlights
Morning
Start your day with a visit to the Bishop Museum. This museum offers an in-depth look at Hawaiian history, culture, and natural science. It's a great way to understand the rich heritage of the islands.
Afternoon
Head to Ho'omaluhia Botanical Garden for a peaceful afternoon surrounded by lush greenery. The garden features a variety of tropical plants and serene walking paths.
Maui’s Coastal Adventures
Morning
Start your Maui adventure by visiting Kaʻanapali Beach. This beautiful beach is perfect for swimming, snorkeling, or simply relaxing on the golden sands.
Afternoon
Explore Lahaina, a historic town known for its charming streets, art galleries, and shops. Don't miss Banyan Tree Park, home to one of the largest banyan trees in the U.S.
Evening
Enjoy dinner at Mama's Fish House, renowned for its fresh seafood and stunning oceanfront location.
Bedtime
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4.86Kaʻanapali Beach
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4.86Kaʻanapali Beach
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4.80Lahaina
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4.80Lahaina
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Maui’s Scenic Trails and Local Flavors
Morning
Embark on a scenic drive along Road to Hana (Hana Highway). Stop at various waterfalls, beaches, and viewpoints along this picturesque route.
Afternoon
Visit Waiʻanapanapa State Park to see its famous black sand beach and coastal trails. It's an excellent spot for photography and nature walks.
Evening
Conclude your day with dinner at Lahaina Grill, offering an exquisite menu featuring local ingredients in an elegant setting.
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4.76Road to Hana (Hana Highway)
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4.76Road to Hana (Hana Highway)
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4.74Waiʻanapanapa State Park
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4.74Waiʻanapanapa State Park
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Maui’s Adventure Awaits
Morning
Start your day with an exhilarating zipline adventure at Maui Ka'anapali 8 Line Zipline Adventure. Soar above lush landscapes and enjoy breathtaking views of Maui's coastline.
Afternoon
Explore the charming town of Paia. Stroll through its eclectic shops, art galleries, and enjoy lunch at one of its cozy cafes.
Evening
Conclude your day with dinner at Fleetwood's on Front St., offering rooftop dining with stunning sunset views and live music.
Bedtime
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5.00Maui Ka'anapali 8 Line Zipline Adventure
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5.00Maui Ka'anapali 8 Line Zipline Adventure
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Maui’s Majestic Landscapes
Morning
Begin your day with a visit to Haleakala National Park. Watch the sunrise from the summit of Haleakala Crater, an unforgettable experience that offers breathtaking views.
Afternoon
Explore ʻIao Valley State Monument, known for its lush landscapes and historical significance. Take a leisurely hike through the valley and enjoy the natural beauty.
Evening
Enjoy dinner at Merriman's, offering farm-to-table dining with spectacular ocean views.
Bedtime
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4.57Haleakala National Park
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4.57Haleakala National Park
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4.33ʻIao Valley State Monument
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4.33ʻIao Valley State Monument
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Big Island’s Volcanic Wonders
Morning
Start your day with a visit to Hawaii Volcanoes National Park. Explore the Kilauea Visitor Center and take a short hike to see the active volcano and its lava flows.
Afternoon
Head to the Thurston Lava Tube, a fascinating underground tunnel formed by ancient lava flows. It's an easy walk and offers a unique perspective on volcanic activity.
Evening
Dine at Millstone Tea Room, known for its charming ambiance and delicious local cuisine.
Bedtime
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Big Island’s Natural Beauty
Morning
Begin your day with a visit to Akaka Falls State Park. Take the short trail to view the stunning 442-foot waterfall surrounded by lush rainforest.
Afternoon
Explore the Waipio Valley Lookout for breathtaking views of cliffs, waterfalls, and black sand beaches. If you're feeling adventurous, you can hike down into the valley.
Evening
Enjoy dinner at Piney River Barrel House, offering a variety of craft beers and hearty dishes.
Bedtime
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Big Island’s Coastal Charms
Morning
Hapuna Beach State Recreation Area is perfect for a morning swim or sunbathing session. This white sand beach is one of the largest on the Big Island and offers crystal-clear waters.
Afternoon
Pu'uhonua o Honaunau National Historical Park provides a glimpse into ancient Hawaiian culture. Explore the royal grounds, sacred temples, and learn about traditional Hawaiian life.
Evening
The Neighbors Place offers a delightful dining experience with a menu that features local ingredients and flavors.
Bedtime
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Big Island’s Unique Experiences
Morning
Start your day with a visit to Punalu'u Black Sand Beach. This unique beach is famous for its black sand and is often visited by sea turtles basking in the sun.
Afternoon
Explore Hawaii Tropical Botanical Garden, home to a diverse collection of tropical plants. The garden's scenic trails offer beautiful views of waterfalls, streams, and exotic flora.
Evening
Dine at Liberty Station, known for its creative menu featuring local ingredients and flavors.
Bedtime
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Kauai’s Coastal Treasures
Morning
Start your Kauai adventure with a visit to Na Pali Coast. Take a boat tour or helicopter ride to see the dramatic cliffs, lush valleys, and pristine beaches from above.
Afternoon
Head to Hanalei Bay for some beach time. This crescent-shaped bay is perfect for swimming, paddleboarding, or simply relaxing on the sandy shore.
Evening
Dine at Beach House Restaurant, offering spectacular sunset views and delicious Pacific Rim cuisine.
Bedtime
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4.79Na Pali Coast
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4.79Na Pali Coast
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4.74Hanalei Bay
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4.74Hanalei Bay
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Kauai’s Scenic Wonders
Morning
Visit Waimea Canyon, often referred to as the 'Grand Canyon of the Pacific.' Hike along its trails for panoramic views of deep red canyons and lush green valleys.
Afternoon
Explore Koke'e State Park, located just beyond Waimea Canyon. The park offers additional hiking trails with stunning vistas and opportunities for birdwatching.
Evening
Conclude your day with dinner at Merriman's Fish House, known for its farm-to-table approach and fresh seafood dishes.
Bedtime
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4.77Waimea Canyon
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4.77Waimea Canyon
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4.77Koke'e State Park
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4.77Koke'e State Park
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Kauai’s Botanical and Historical Delights
Morning
Begin your day with a visit to Limahuli Garden and Preserve. This beautiful botanical garden showcases native Hawaiian plants and offers stunning views of the surrounding mountains and ocean.
Afternoon
Head to Daniel K. Inouye Kilauea Point Lighthouse. This historic lighthouse is located on a dramatic cliffside and provides excellent opportunities for birdwatching and photography.
5.00Limahuli Garden and Preserve
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5.00Limahuli Garden and Preserve
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4.82Daniel K. Inouye Kilauea Point Lighthouse
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4.82Daniel K. Inouye Kilauea Point Lighthouse
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Kauai’s Adventure Day
Morning
Begin your day with an exciting zipline adventure at Koloa Zipline. Soar above Kauai's lush landscapes and enjoy breathtaking views from above.
Afternoon
Visit Allerton Garden, one of Kauai's premier botanical gardens. Explore its beautifully landscaped grounds filled with exotic plants and water features.
Evening
Conclude your day with dinner at Duke's Kauai, offering delicious Hawaiian cuisine in a relaxed beachfront setting.
Bedtime
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4.50Allerton Garden
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4.50Allerton Garden
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Exploring Lanai's Hidden Gems
Morning
Start your day with a visit to Lanai Island. Explore the island's beautiful beaches, such as Hulopoe Bay, known for its clear waters and excellent snorkeling opportunities.
Afternoon
Head to the Garden of the Gods, a unique rock garden with otherworldly landscapes. The red rock formations and panoramic views make it a great spot for photography.
Lanai Island
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Lanai Island
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Lanai’s Tranquil Escapes
Morning
Start your day with some relaxation at Manele Bay. The bay's clear waters are perfect for snorkeling or simply lounging on the beach.
Afternoon
Visit Keahiakawelo (Garden of the Gods) to explore its unique rock formations. The landscape here is otherworldly, offering great photo opportunities.
Molokai’s Cultural Heritage
Morning
Begin your day with a visit to Kalaupapa National Historical Park. Learn about the history of the leprosy settlement and take in the stunning coastal views.
Afternoon
Molokai Island offers an authentic Hawaiian experience. Visit local farms, such as Purdy's Natural Macadamia Nuts, to sample fresh produce and learn about traditional farming practices.
Evening
Southern Smoke BBQ & Brewhouse is perfect for dinner, offering delicious barbecue dishes and craft beers in a relaxed setting.
Bedtime
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4.81Molokai Island
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4.81Molokai Island
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Molokai’s Natural Wonders
Morning
Halawa Valley is ideal for an adventurous hike. The valley is rich in history, culture, and natural beauty, featuring waterfalls, lush vegetation, and ancient ruins.
Afternoon
Kalaupapa Peninsula offers breathtaking views of sea cliffs and historical significance. Take a guided tour to learn about the area's past as a leprosy settlement.
Evening
Rattler's Bar B Que serves up delicious barbecue dishes in a casual setting, perfect for unwinding after a day of exploration.
Bedtime
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Molokai’s Final Day of Serenity
Morning
Start your final day with a visit to Papohaku Beach, one of Hawaii's largest white sand beaches. Enjoy a peaceful morning walk along the shore or simply relax and take in the serene surroundings.
Afternoon
Head to Kaunakakai, Molokai's main town, to explore its charming shops and local markets. Don't miss the chance to visit the historic Molokai Fishponds, which offer a glimpse into ancient Hawaiian aquaculture practices.
Evening
Conclude your Hawaiian adventure with dinner at Egg Plantation, known for its hearty dishes and friendly atmosphere. Reflect on your incredible journey across Hawaii's islands as you enjoy your meal.
Bedtime
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