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Ultimate 31-Day Hawaiian Islands Adventure

Ultimate 31-Day Hawaiian Islands Adventure Itinerary

Last updated: 2024 Jun 14

Iconic Waikiki and Snorkeling Delights

Morning
Start your Hawaiian adventure with a hearty breakfast at Back Alley Cafe, known for its local flavors. Afterward, embark on the Waikiki Trolley to get an overview of the area and hop off at the famous Waikiki Beach for a morning stroll.
Afternoon
For lunch, head to Trees Bar & Grill for a casual dining experience. Spend your afternoon snorkeling at the vibrant Oahu Turtle Canyon and then enjoy a relaxing Glass Bottom Boat Tour along Oahu's South Shore to witness the underwater world without getting wet.
Evening
Dine at ARISU Bar & Grill for a fusion of Hawaiian and international cuisine. Cap off the evening with a Waikiki Sunset Catamaran Sail and Swim, sipping on tropical drinks as you watch the sun dip below the horizon.
Bedtime
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Waikiki Trolley

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Waikiki Trolley

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Oahu Turtle Canyon Snorkeling Boat Tour

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Honolulu Glass Bottom Boat Tour along Oahu's South Shore

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Oahu Waikiki Sunset Catamaran Sail and Swim

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Historic Remembrance and Luau Experience

Morning
Begin with a visit to the solemn Pearl Harbor and USS Arizona Memorial, where you'll pay respects to the fallen and learn about the events of December 7, 1941. Have a light lunch at the memorial's cafe.
Afternoon
Immerse yourself in Hawaiian culture with the Oahu Ka Moana Luau Dinner and Show at Aloha Tower. Enjoy traditional dances, music, and a feast of local delicacies. After the luau, take a stroll around the Aloha Tower Marketplace to enjoy the harbor views.
Evening
For a more laid-back evening, head to the ROW Kaka'ako for a dinner with a view. The restaurant offers a wide selection of dishes and a vibrant atmosphere. Afterward, take a leisurely walk around the Kaka'ako neighborhood, known for its street art and trendy shops.
Bedtime
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Oahu Pearl Harbor, Arizona Memorial & Honolulu City Tour

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Oahu Ka Moana Luau Dinner and Show at Aloha Tower

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Oahu Ka Moana Luau Dinner and Show at Aloha Tower

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Aerial Thrills and Culinary Delights

Morning
Enjoy breakfast at Tipsy Pig 2 Bar & Grill, a local favorite. Today's adventure takes you high above the islands on the Oahu Helicopter Tour with Doors On or Off. Take in breathtaking views of the coastline, lush valleys, and iconic landmarks.
Afternoon
After the exhilarating flight, land and have lunch at Merriman's Honolulu, known for its farm-to-table concept. Spend the rest of the afternoon at the Oahu Grand Circle Island Tour, exploring the diverse landscapes and hidden gems of the island.
Evening
Dine at 8 Fat Fat 8 Bar & Grille, where you can indulge in Asian fusion cuisine. If you're up for some entertainment, visit Waikiki Beach for the Waikiki Trolley Hop-on Hop-off All-Line Pass, which will take you to various evening hotspots and attractions.
Bedtime
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From Honolulu Oahu Helicopter Tour with Doors On or Off

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Oahu Oahu Ultimate Grand Circle Island Tour

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Oahu Waikiki Trolley Hop-on Hop-off All-Line Pass

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Oahu Waikiki Trolley Hop-on Hop-off All-Line Pass

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Underwater Wonders and Evening Entertainment

Morning
Start your day with breakfast at Azure, a restaurant known for its ocean-inspired dishes. Then, head out for a morning of adventure with the Waikiki Submarine Tour, where you'll explore the vibrant marine life and underwater landscapes of Oahu.
Afternoon
After resurfacing, enjoy a leisurely lunch at Rock Bottom Sports Bar & Grill, a casual spot with a wide menu. Spend your afternoon at the Waikiki Beach, taking in the sun, sand, and surf. You can also use your Waikiki Trolley Hop-on Hop-off All-Line Pass to explore nearby attractions.
Evening
For dinner, experience the rooftop ambiance and cuisine at Rooftop Restaurant and Bar. Afterward, if you're in the mood for some gaming and entertainment, visit Dave & Buster's Honolulu for a fun-filled evening.
Bedtime
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Oahu Waikiki Submarine Tour

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Oahu Waikiki Trolley Hop-on Hop-off All-Line Pass

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Oahu Waikiki Trolley Hop-on Hop-off All-Line Pass

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Oahu Pearl Harbor, USS Arizona, and City Highlights Tour

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Waterfalls, Hikes, and Evening Breezes

Morning
Have a filling breakfast at King Restaurant & Bar to prepare for a morning of adventure. Take the Manoa Falls Waterfall Hike with Lunch and Transfers and immerse yourself in the lush rainforest, culminating in the majestic Manoa Falls.
Afternoon
After the hike, enjoy a well-deserved lunch at the falls. Then, spend a relaxing afternoon at Waikiki Beach, lounging on the sand or taking a dip in the ocean. Use your Waikiki Trolley Hop-on Hop-off All-Line Pass to explore other parts of the city if you wish.
Evening
Dine at Mai Tai's, a restaurant that captures the essence of Hawaiian cuisine and cocktails. As the evening sets in, take the Oahu Waikiki BYOB Sunset Cruise for a memorable experience on the waters, bringing your favorite drinks to enjoy the sunset.
Bedtime
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Oahu Hike to the Manoa Falls Waterfall with Lunch

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Oahu Waikiki Trolley Hop-on Hop-off All-Line Pass

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Oahu Waikiki Trolley Hop-on Hop-off All-Line Pass

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Oahu Waikiki BYOB Sunset Cruise

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Island History and Evening Delights

Morning
Start with breakfast at Y's Sports Bar & Grill, a local spot with a diverse menu. Then, embark on the Oahu Pearl Harbor, Arizona Memorial & Honolulu City Tour, where you'll gain insights into the island's history and visit the iconic USS Arizona Memorial.
Afternoon
After the tour, have lunch at Off The Wall Craft Beer & Wine, a place known for its laid-back atmosphere and great drinks. Spend your afternoon at the Waikiki Beach, enjoying the sun and the waves, or explore the nearby shops and attractions.
Evening
For dinner, head to Highway Inn Kaka'ako, a restaurant that specializes in traditional Hawaiian dishes. Afterward, take a walk along the Waikiki Beach and enjoy the evening entertainment and vibrant nightlife of the area.
Bedtime
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Oahu Pearl Harbor, Arizona Memorial & Honolulu City Tour

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Oahu Waikiki Trolley Hop-on Hop-off All-Line Pass

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Oahu Waikiki Trolley Hop-on Hop-off All-Line Pass

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Dolphin Encounters and Evening Entertainment

Morning
Enjoy breakfast at The Manifest, a cafe with a relaxed vibe. Then, kick off your day with the Monk Seal Bay Dolphin and Turtle Jet Snorkel Tour, where you'll have the chance to swim with dolphins and observe turtles in their natural habitat.
Afternoon
After the tour, have lunch at Mahina & Sun's, a restaurant with a focus on local, seasonal ingredients. Spend your afternoon at the Waikiki Beach, soaking up the sun and the lively atmosphere. You can also use your Waikiki Trolley Hop-on Hop-off All-Line Pass to explore other parts of the city.
Evening
Dine at 100 Sails Restaurant & Bar, which offers a modern take on traditional Hawaiian cuisine. Cap off the evening with a visit to Y's Sports Bar & Grill for some drinks and live music, or choose to unwind with a walk along the beach.
Bedtime
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Waikiki Monk Seal Bay Dolphin and Turtle Jet Snorkel Tour

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Oahu Waikiki Trolley Hop-on Hop-off All-Line Pass

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Oahu Waikiki Trolley Hop-on Hop-off All-Line Pass

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Oahu Pearl Harbor, USS Arizona, and City Highlights Tour

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City Sights and Evening Elegance

Morning
Start your day with breakfast at Back Alley Cafe, a local favorite. Then, take the Oahu Pearl Harbor, USS Arizona, and City Highlights Tour, which provides a comprehensive look at the island's history and key landmarks.
Afternoon
After the tour, have lunch at Trees Bar & Grill, known for its casual atmosphere and diverse menu. Spend your afternoon at the Waikiki Beach, where you can relax on the sand, take a swim, or engage in water sports. Use your Waikiki Trolley Hop-on Hop-off All-Line Pass to explore other parts of the city if you wish.
Evening
For a sophisticated dinner, head to Azure, a restaurant with a focus on seafood and ocean views. Afterward, enjoy a performance at the Hawaii Opera Theatre or take a moonlit stroll along the beach.
Bedtime
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Oahu Pearl Harbor, USS Arizona, and City Highlights Tour

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Oahu Waikiki Trolley Hop-on Hop-off All-Line Pass

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Oahu Waikiki Trolley Hop-on Hop-off All-Line Pass

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Oahu Pearl Harbor, USS Arizona, and City Highlights Tour

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Island Exploration and Evening Entertainment

Morning
Have breakfast at Rock Bottom Sports Bar & Grill, a casual spot with a wide menu. Then, set out for the Oahu Ultimate Grand Circle Island Tour, which will take you to some of the most scenic and iconic spots on the island.
Afternoon
Enjoy a picnic lunch at one of the tour stops, or visit a local market to pick up some fresh produce. After the tour, spend a relaxing afternoon at Waikiki Beach, or use your Waikiki Trolley Hop-on Hop-off All-Line Pass to explore other parts of the city.
Evening
Dine at Rooftop Restaurant and Bar, where you can enjoy a meal with a view. After dinner, take a Waikiki BYOB Sunset Cruise for a memorable evening on the water, bringing your favorite drinks to enjoy as you watch the sunset.
Bedtime
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Oahu Oahu Ultimate Grand Circle Island Tour

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Oahu Waikiki Trolley Hop-on Hop-off All-Line Pass

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Oahu Waikiki Trolley Hop-on Hop-off All-Line Pass

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Oahu Waikiki BYOB Sunset Cruise

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Island Hopping and Evening Relaxation

Morning
Start with breakfast at King Restaurant & Bar, a spot known for its local flavors. Then, catch a morning flight to the neighboring island of Maui. Upon arrival, settle in and spend the morning exploring the area around your accommodation.
Afternoon
For lunch, try a local favorite like Mai Tai's, which offers a taste of Hawaiian cuisine. Afterward, take a leisurely drive along the Road to Hana, stopping at waterfalls, viewpoints, and other points of interest.
Evening
Return to your accommodation for a relaxing evening. Order in from a nearby restaurant or enjoy a quiet dinner at the hotel. If you're up for some entertainment, check out any live music or cultural performances happening in the area.
Bedtime
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Oahu Pearl Harbor, USS Arizona, and City Highlights Tour

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Maui's Natural Wonders

Morning
Enjoy breakfast at Merriman's Honolulu, then set out to explore the natural beauty of Maui. Start with a visit to the otherworldly Haleakalā National Park, where you can witness the sunrise from the summit or take a hike through the unique landscape.
Afternoon
After the park, have lunch at 8 Fat Fat 8 Bar & Grille, a spot with a diverse menu. Spend your afternoon at the Iao Valley State Park, where you can take a short walk to the iconic Iao Needle and learn about the valley's history and significance.
Evening
Dine at 100 Sails Restaurant & Bar, which offers a modern take on traditional Hawaiian cuisine. After dinner, take a stroll along the beach or relax with a drink at your accommodation.
Bedtime
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Oahu Pearl Harbor, USS Arizona, and City Highlights Tour

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Oahu Pearl Harbor, USS Arizona, and City Highlights Tour

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Maui's Coastal Charms

Morning
Start your day with breakfast at The Manifest, a cafe with a relaxed vibe. Then, spend the morning exploring the stunning Road to Hana, with its lush rainforests, cascading waterfalls, and panoramic ocean views. Take your time to stop at various points of interest along the way.
Afternoon
Pack a picnic lunch from a local market or stop at a roadside stand for some fresh fruits and snacks. After reaching Hana, continue on to the Ohe'o Gulch (Seven Sacred Pools) in the Haleakalā National Park for a refreshing swim in the natural pools.
Evening
Head back to your accommodation for a relaxing evening. If you're in the mood for a special dinner, consider Azure, which offers a sophisticated oceanfront dining experience.
Bedtime
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Oahu Pearl Harbor, USS Arizona, and City Highlights Tour

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Oahu Pearl Harbor, USS Arizona, and City Highlights Tour

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Oahu Pearl Harbor, USS Arizona, and City Highlights Tour

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Maui's Upcountry and Sunset Views

Morning
Enjoy breakfast at Tipsy Pig 2 Bar & Grill, a local favorite. Then, spend the morning exploring Maui's upcountry. Visit the Ali'i Kula Lavender Farm and the MauiWine for a taste of the local produce and wines.
Afternoon
Have lunch at Rock Bottom Sports Bar & Grill, a casual spot with a wide menu. Afterward, take a scenic drive to the Haleakalā National Park and explore the park's unique landscapes. If you're up for it, consider a guided Haleakalā Downhill Bike Ride for an exhilarating experience.
Evening
Dine at Rooftop Restaurant and Bar, where you can enjoy a meal with a view. After dinner, take a Waikiki BYOB Sunset Cruise for a memorable evening on the water, bringing your favorite drinks to enjoy as you watch the sunset.
Bedtime
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Oahu Pearl Harbor, USS Arizona, and City Highlights Tour

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Oahu Pearl Harbor, USS Arizona, and City Highlights Tour

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Oahu Pearl Harbor, USS Arizona, and City Highlights Tour

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Oahu Pearl Harbor, USS Arizona, and City Highlights Tour

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Oahu Waikiki BYOB Sunset Cruise

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Maui's Underwater World

Morning
Start with breakfast at King Restaurant & Bar, a spot known for its local flavors. Then, head out for a morning of snorkeling at Molokini Crater, one of the best spots for underwater exploration in Maui.
Afternoon
After the snorkeling adventure, have lunch at Mai Tai's, which offers a taste of Hawaiian cuisine. Spend your afternoon at the Makena Beach State Park, where you can relax on the pristine sands and take in the beautiful surroundings.
Evening
Dine at 100 Sails Restaurant & Bar, which offers a modern take on traditional Hawaiian cuisine. After dinner, take a stroll along the beach or relax with a drink at your accommodation.
Bedtime
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Oahu Pearl Harbor, USS Arizona, and City Highlights Tour

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Oahu Pearl Harbor, USS Arizona, and City Highlights Tour

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Maui's Cultural and Culinary Delights

Morning
Enjoy breakfast at Merriman's Honolulu, then set out to explore the Lahaina Historic District. Visit the historic sites, art galleries, and shops, and learn about the rich history of this former whaling village.
Afternoon
For lunch, try a local favorite like 8 Fat Fat 8 Bar & Grille, a spot with a diverse menu. Afterward, take a Self-Guided Maui Tour and explore the island at your own pace, visiting the places that interest you the most.
Evening
Dine at 100 Sails Restaurant & Bar, which offers a modern take on traditional Hawaiian cuisine. After dinner, take a stroll along the beach or relax with a drink at your accommodation.
Bedtime
Find amazing hotels in Maui, Hawaii.
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Oahu Pearl Harbor, USS Arizona, and City Highlights Tour

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Oahu Pearl Harbor, USS Arizona, and City Highlights Tour

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Maui's Upcountry and Sunset Views

Morning
Enjoy breakfast at Tipsy Pig 2 Bar & Grill, a local favorite. Then, spend the morning exploring Maui's upcountry. Visit the Ali'i Kula Lavender Farm and the MauiWine for a taste of the local produce and wines.
Afternoon
Have lunch at Rock Bottom Sports Bar & Grill, a casual spot with a wide menu. Afterward, take a scenic drive to the Haleakalā National Park and explore the park's unique landscapes. If you're up for it, consider a guided Haleakalā Downhill Bike Ride for an exhilarating experience.
Evening
Dine at Rooftop Restaurant and Bar, where you can enjoy a meal with a view. After dinner, take a Waikiki BYOB Sunset Cruise for a memorable evening on the water, bringing your favorite drinks to enjoy as you watch the sunset.
Bedtime
Find amazing hotels in Maui, Hawaii.
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Oahu Pearl Harbor, USS Arizona, and City Highlights Tour

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Oahu Pearl Harbor, USS Arizona, and City Highlights Tour

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Oahu Pearl Harbor, USS Arizona, and City Highlights Tour

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Oahu Pearl Harbor, USS Arizona, and City Highlights Tour

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Oahu Waikiki BYOB Sunset Cruise

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Maui's Underwater World

Morning
Start with breakfast at King Restaurant & Bar, a spot known for its local flavors. Then, head out for a morning of snorkeling at Molokini Crater, one of the best spots for underwater exploration in Maui.
Afternoon
After the snorkeling adventure, have lunch at Mai Tai's, which offers a taste of Hawaiian cuisine. Spend your afternoon at the Makena Beach State Park, where you can relax on the pristine sands and take in the beautiful surroundings.
Evening
Dine at 100 Sails Restaurant & Bar, which offers a modern take on traditional Hawaiian cuisine. After dinner, take a stroll along the beach or relax with a drink at your accommodation.
Bedtime
Find amazing hotels in Maui, Hawaii.
Popular
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Oahu Pearl Harbor, USS Arizona, and City Highlights Tour

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Oahu Pearl Harbor, USS Arizona, and City Highlights Tour

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Maui's Cultural and Culinary Delights

Morning
Enjoy breakfast at Merriman's Honolulu, then set out to explore the Lahaina Historic District. Visit the historic sites, art galleries, and shops, and learn about the rich history of this former whaling village.
Afternoon
For lunch, try a local favorite like 8 Fat Fat 8 Bar & Grille, a spot with a diverse menu. Afterward, take a Self-Guided Maui Tour and explore the island at your own pace, visiting the places that interest you the most.
Evening
Dine at 100 Sails Restaurant & Bar, which offers a modern take on traditional Hawaiian cuisine. After dinner, take a stroll along the beach or relax with a drink at your accommodation.
Bedtime
Find amazing hotels in Maui, Hawaii.
Popular
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Oahu Pearl Harbor, USS Arizona, and City Highlights Tour

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Oahu Pearl Harbor, USS Arizona, and City Highlights Tour

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Maui's Upcountry and Sunset Views

Morning
Enjoy breakfast at Tipsy Pig 2 Bar & Grill, a local favorite. Then, spend the morning exploring Maui's upcountry. Visit the Ali'i Kula Lavender Farm and the MauiWine for a taste of the local produce and wines.
Afternoon
Have lunch at Rock Bottom Sports Bar & Grill, a casual spot with a wide menu. Afterward, take a scenic drive to the Haleakalā National Park and explore the park's unique landscapes. If you're up for it, consider
Evening
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Oahu Pearl Harbor, USS Arizona, and City Highlights Tour

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Oahu Pearl Harbor, USS Arizona, and City Highlights Tour

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Oahu Pearl Harbor, USS Arizona, and City Highlights Tour

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