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Ultimate 10-Day Oahu and Maui Adventure Itinerary
Last updated: 2024 Jun 14Aloha, Honolulu!
Morning
Start your Hawaiian journey with a delicious breakfast at Musubi Cafe Iyasume, known for its authentic Japanese rice balls. Afterward, head to the iconic Diamond Head for a morning hike and panoramic views of Waikiki.
Afternoon
For lunch, savor the local flavors at Rainbow Drive-In, a beloved spot for plate lunches. In the afternoon, visit the Hanauma Bay for some of the best snorkeling on the island.
Evening
Enjoy a sunset dinner at Duke's Waikiki, a classic beachfront restaurant. Afterward, take a leisurely stroll along Waikiki Beach and soak in the vibrant nightlife.
Bedtime
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Diamond Head
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Hanauma Bay
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Waikiki Beach
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Pearl Harbor and City Sights
Morning
Begin your day with a somber yet important visit to the Pearl Harbor USS Arizona Memorial. Afterward, take a city tour that includes stops at the Iolani Palace and the King Kamehameha Statue.
Afternoon
For lunch, try the innovative Hawaiian cuisine at Merriman's Honolulu. In the afternoon, continue your historical journey with a visit to the Battleship Missouri Memorial.
Evening
Indulge in a fine dining experience at La Mer at Halekulani, known for its exquisite French cuisine and ocean views.
Bedtime
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USS Arizona Memorial
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Iolani Palace
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Battleship Missouri Memorial
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Nature and Culture
Morning
Enjoy a leisurely morning at the Byodo-In Temple on the lush Windward Coast. Afterward, take a scenic drive to the Nu'uanu Pali Lookout for breathtaking views of the Oahu's windward side.
Afternoon
Have a casual lunch at Nico's Pier 38, a local favorite for seafood. In the afternoon, immerse yourself in the Polynesian culture at the Polynesian Cultural Center.
Evening
For dinner, experience a traditional Hawaiian luau at Paradise Cove Luau, complete with hula dancing and a feast.
Bedtime
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Byodo-In Temple
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Nu'uanu Pali Lookout
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Polynesian Cultural Center
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North Shore Adventure
Morning
Wake up early and head to the famous North Shore. Stop at Dole Plantation on the way for some pineapple treats and a ride on the Pineapple Express Train.
Afternoon
For lunch, try the garlic shrimp from one of the food trucks in Kahuku. Afterward, visit the Banzai Pipeline and Sunset Beach.
Evening
Enjoy a casual dinner at Ted's Bakery, known for its pies. End the day with a sunset at Waimea Bay.
Bedtime
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Oahu North Shore
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Milan Segway Tour
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Banzai Pipeline
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Bioluminescent Bay (Mosquito Bay)
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Camelback Mountain Resort
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Maui Bliss
Morning
Catch a flight to Maui and start your day with a hearty breakfast at The Gazebo Restaurant in Napili. Then, embark on the famous Road to Hana drive, stopping at waterfalls, black sand beaches, and the Seven Sacred Pools.
Afternoon
Pack a picnic lunch from Tamura's Market in Hana and continue your journey. Visit the Wai'anapanapa State Park and enjoy the stunning views.
Evening
Check into your hotel in Kaanapali and have a relaxing dinner at Leilani's on the Beach, with your toes in the sand.
Bedtime
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Milan Wine Tasting Experience
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Field Museum
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Grant Park
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Upcountry Maui Delights
Morning
Start your day with a farm-to-table breakfast at O'o Farm in Kula. Then, explore the Ali'i Kula Lavender Farm and enjoy the panoramic views.
Afternoon
For lunch, visit Kula Bistro for a taste of local cuisine. Afterward, take a tour of the MauiWine vineyard and enjoy a wine tasting.
Evening
Head back to the coast for a sunset dinner at Mama's Fish House, known for its fresh seafood and romantic ambiance.
Bedtime
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360 Chicago Observation Deck (Formerly John Hancock Observatory)
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Haleakalā and Beach Relaxation
Morning
Wake up early to witness the sunrise at the summit of Haleakalā. Afterward, warm up with a hearty breakfast at Kula Lodge.
Afternoon
Spend the afternoon relaxing at Paia or Kihei beach. For lunch, grab some fish tacos from a local food truck.
Evening
Enjoy a laid-back dinner at Coconuts Fish Cafe and savor the flavors of the island.
Bedtime
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Adler Planetarium
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Ocean Adventures
Morning
Embark on a snorkeling excursion to Molokini Crater and Turtle Town. Enjoy the vibrant marine life and crystal-clear waters. Have a light breakfast on the boat.
Afternoon
For lunch, indulge in a seafood feast at Paia Fish Market. In the afternoon, try your hand at stand-up paddleboarding or kayaking.
Evening
Dine at Mala Ocean Tavern and watch the sunset over the ocean.
Bedtime
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Shedd Aquarium
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Lincoln Park & Zoo
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Road Trip to Upcountry
Morning
Take a scenic drive to Lahaina and explore the historic town. Stop for a quick breakfast at The Gazebo Restaurant.
Afternoon
Visit the Lahaina Jodo Mission and the Bailey House Museum. For lunch, try the famous banana bread from Auntie Sandy's.
Evening
Enjoy a sunset dinner cruise with Pacific Whale Foundation and savor a gourmet meal on the water.
Bedtime
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Millennium Park
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Museum of Science and Industry
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Navy Pier
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Farewell to Paradise
Morning
Spend your last morning in Maui relaxing at the beach or by the pool. Enjoy a leisurely brunch at Longhi's in Lahaina.
Afternoon
Take a surfing lesson or a whale watching cruise, depending on the season. For your final lunch, indulge in the fresh catch of the day at Fleetwood's on Front St..
Evening
Watch the sunset from Kaanapali Beach and have a memorable farewell dinner at Merriman's Kapalua.
Bedtime
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Skydeck Chicago at Willis Tower (Sears Tower)
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