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9 Days of Adventure in Oahu and Maui

9 Days of Adventure in Oahu and Maui Itinerary

Last updated: 2024 Jun 14

Exploring Oahu's Natural Wonders

Morning
Start your day with a visit to the iconic Diamond Head State Monument. This volcanic tuff cone offers a moderately challenging hike with rewarding panoramic views of Waikiki and the Pacific Ocean. It's a perfect introduction to Oahu's natural beauty and hiking opportunities. After your hike, enjoy a refreshing breakfast at Koko Head Cafe, known for its inventive island-style brunch dishes.
Afternoon
In the afternoon, head to Hanauma Bay Nature Preserve for some world-class snorkeling. This marine embayment formed within a tuff ring is renowned for its vibrant coral reefs and diverse marine life. Spend your time exploring the underwater world or relaxing on the beach. For lunch, visit Teddy's Bigger Burgers nearby for some delicious burgers and shakes.
Evening
As evening approaches, take part in Fort Myers Guided Sunset Kayaking Tour through Pelican Bay. While this activity is typically associated with Fort Myers, you can find similar sunset kayaking tours in Oahu that offer serene paddling experiences along the coastlines while enjoying breathtaking sunset views. Conclude your day with dinner at Duke's Waikiki, where you can savor Hawaiian cuisine while listening to live music.
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Cultural Immersion in Oahu

Morning
Begin your second day with a visit to Pearl Harbor National Memorial. This historic site offers a deep dive into World War II history and includes attractions like the USS Arizona Memorial and Battleship Missouri Memorial. It's an educational experience that provides insight into significant events that shaped modern history. Enjoy breakfast at Morning Glass Coffee + Cafe before heading out.
Afternoon
In the afternoon, explore the Polynesian Cultural Center located on Oahu's North Shore. This living museum showcases traditional Polynesian culture through interactive exhibits, performances, and activities. It's an excellent way to immerse yourself in local traditions and customs. For lunch, try Seven Brothers known for their tasty burgers and island-inspired dishes.
Evening
Wrap up your day by participating in Fort Myers Beach Tiki Pub Sunset Cruise with BYOB. Similar tiki pub cruises are available in Oahu where you can enjoy drinks on board while cruising along the coastline during sunset hours. End your evening with dinner at Haleiwa Joe's, offering fresh seafood dishes with stunning ocean views.
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Fort Myers Beach Tiki Pub Sunset Cruise with BYOB

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Adventures on Land and Sea

Morning
Kick off your third day by visiting Lanikai Beach, one of Oahu's most picturesque beaches known for its soft white sand and clear turquoise waters. It's an ideal spot for swimming or simply soaking up the sun amidst beautiful surroundings. Have breakfast at Cinnamon's Restaurant which is famous for its delicious pancakes.
Afternoon
After spending time at Lanikai Beach, head over to Kualoa Ranch for an exciting afternoon filled with adventure activities such as ATV tours or zip-lining through lush landscapes featured in numerous movies like Jurassic Park. Enjoy lunch at Auntie Pasto’s located nearby before embarking on these thrilling experiences.
Evening
End your day by engaging in Fort Myers Guided Standup Paddleboarding or Kayaking Tour. Although originally from Fort Myers area activities like standup paddleboarding are also popular around Kailua Bay offering serene paddling experiences amidst scenic coastal views as dusk falls over Hawaii’s horizon line . Conclude this adventurous day dining at Buzz’s Original Steak House, known for its hearty meals.
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Scenic Drives and Beach Relaxation

Morning
Start your Maui adventure with a scenic drive along the famous Road to Hana (Hana Highway). This winding road offers breathtaking views of lush rainforests, cascading waterfalls, and dramatic coastal cliffs. Make sure to stop at various lookout points and small towns along the way to fully appreciate the natural beauty of Maui. For breakfast, grab a bite at Aunty Sandy's Banana Bread, known for its delicious homemade banana bread.
Afternoon
After your drive, head to Wailea Beach for a relaxing afternoon by the sea. This beautiful beach is perfect for swimming, sunbathing, and snorkeling. The calm waters and pristine sands make it an ideal spot to unwind after a morning of exploration. For lunch, visit Monkeypod Kitchen in Wailea for some fresh island cuisine.
Evening
In the evening, enjoy From Ma'alaea Maui Sunset Cruise with Drinks and Snacks. This sunset cruise offers stunning views of the coastline as you sail along the waters of Ma'alaea Bay. Enjoy drinks and snacks on board while watching the sun dip below the horizon. End your day with dinner at Mama's Fish House, renowned for its fresh seafood and romantic ambiance.
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Road to Hana (Hana Highway)

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Exploring Maui's Natural Wonders

Morning
Haleakala National Park is a must-visit destination in Maui. Start your day early with a sunrise visit to Haleakala Crater. The view from the summit is absolutely breathtaking as you watch the sun rise above the clouds. It's an unforgettable experience that showcases Maui's natural beauty at its finest. Afterward, have breakfast at Kula Lodge Restaurant, which offers stunning views and hearty meals.
Afternoon
Pipiwai Trail awaits you in the afternoon. This trail takes you through lush bamboo forests and past cascading waterfalls within Haleakala National Park. It's a moderately challenging hike that rewards you with spectacular scenery along the way. For lunch, pack a picnic or grab something from Braddah Hutts BBQ Grill before starting your hike.
Evening
Maui 2 Hour Sunset Sail with Open Bar and Appetizers provides another opportunity to enjoy Maui's beautiful coastline during sunset hours while sipping on drinks from an open bar accompanied by delicious appetizers served onboard . Conclude this adventurous day dining at Lahaina Grill, known for its gourmet dishes made using locally sourced ingredients.
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Pipiwai Trail

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Cultural Experiences and Marine Adventures

Morning
Maui Ocean Center is perfect place start off sixth day exploring underwater world without getting wet! This aquarium features exhibits showcasing diverse marine life found around Hawaiian Islands including sharks rays turtles more! Afterward enjoy breakfast nearby at Leoda’s Kitchen Pie Shop famous their savory sweet pies alike!
Afternoon
Head over next towards historic town Lahaina where can participate in unique activity likeLahaina Maui Ku'ia Estate Guided Cacao Farm Tour & Tasting[399423]. Learn about process behind making chocolate taste some finest products produced right there farm itself! For lunch try out popular spot calledCool Cat Cafe offering variety burgers shakes sure satisfy any craving might have!
Evening
Conclude sixth day embarking upon thrilling experience such asSouth Maui Premium Turtle Town Kayak Snorkel Tour[194552]. Paddle through crystal clear waters encounter friendly sea turtles up close personal snorkel amongst vibrant coral reefs teeming colorful fish other marine creatures too!. End night enjoying dinner exquisite restaurant calledMerriman’s Kapalua boasting stunning oceanfront views delectable farm-to-table cuisine sure leave lasting impression!
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Maui Ocean Center

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Lahaina Maui Ku'ia Estate Guided Cacao Farm Tour & Tasting[399423]

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Adventure and Relaxation in Maui

Morning
Start your day with a visit to ʻIao Valley State Monument. This lush, green valley is home to the iconic ʻIao Needle, a natural rock formation that rises 1,200 feet from the valley floor. The area is rich in history and offers several hiking trails that provide stunning views of the surrounding landscape. For breakfast, stop by The Mill House for a farm-to-table dining experience with picturesque views.
Afternoon
In the afternoon, head to Kaʻanapali Beach, one of Maui's most famous beaches. Spend your time swimming, snorkeling, or simply relaxing on the golden sands. The beach is also home to several beachfront resorts and restaurants. For lunch, visit Hula Grill Ka'anapali for some delicious island-inspired dishes.
Evening
Maui Private All-Inclusive Road to Hana Tour with Pickup offers an exclusive way to explore one of Maui's most scenic drives without worrying about navigation or planning stops along way! Enjoy personalized tour complete with knowledgeable guide who will take you hidden gems off beaten path ensuring unforgettable experience!. Conclude day dining atPacific'O Restaurant known its innovative cuisine breathtaking oceanfront setting.
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ʻIao Valley State Monument

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Kaʻanapali Beach

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Exploring Maui's Hidden Gems

Morning
Waihee Ridge Trail offers moderately challenging hike through lush forests up ridge providing panoramic views coastline below! Perfect way start off eighth day surrounded by nature’s beauty!. Afterward enjoy hearty breakfast nearbyTasty Crust Restaurant famous their pancakes other comfort food classics!
Afternoon
Maui Tropical Plantation provides unique opportunity learn about island’s agricultural heritage while exploring beautiful grounds filled tropical plants flowers more!. Take guided tram tour sample fresh produce grown right there plantation itself!. For lunch try out popular spot calledCafe O'Lei at The Mill House offering variety dishes made using locally sourced ingredients sure satisfy any craving might have!
Evening
South Maui Sunset Cruise with 4-Course Dinner and Drinks perfect way end eighth day sailing along coast enjoying stunning sunset views while indulging delicious multi-course meal accompanied by refreshing drinks served onboard!. Conclude night relaxing back at your accommodation reflecting upon amazing experiences had throughout day!
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Waihee Ridge Trail

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Maui Tropical Plantation

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Final Day of Fun and Farewell

Morning
Haleakala Crater must-see destination before leaving island! Early morning visit allows witness breathtaking sunrise above clouds from summit highest peak Maui truly unforgettable sight worth waking up early for!. Afterward enjoy breakfast nearbyKula Bistro known its hearty meals friendly atmosphere perfect place fuel up after exhilarating experience!
Afternoon
Molokini Snorkel & Slide 7AM - 12PM provides exciting adventure exploring underwater world around Molokini Crater renowned its crystal clear waters vibrant coral reefs teeming marine life including colorful fish sea turtles more!. For lunch visit popular spot calledDown the Hatch offering variety seafood dishes sure satisfy any craving might have!
Evening
Conclude final evening participating in unique activity likeRoyal Lahaina Luau (Myths of Maui Luau). Experience traditional Hawaiian luau complete with cultural performances music dance feast featuring local delicacies all set against backdrop stunning oceanfront location perfect way bid farewell beautiful island paradise enjoyed past nine days!. End night enjoying dinner exquisite restaurant calledStar Noodle boasting innovative Asian-inspired cuisine sure leave lasting impression!
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Haleakala Crater

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Molokini Snorkel & Slide 7AM - 12PM

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