14-Day Hawaii Adventure Itinerary

Day 1: Arrival in Oahu

Honolulu, Hawaii

10:00AM

Check in to Hotel

Arrive at Honolulu International Airport and check in to your hotel in the Waikiki area.
Take a taxi or shuttle from the airport to your hotel.
USD200, 1 hour

12:00PM

Lunch at Duke's Waikiki

Enjoy a delicious beachfront lunch at Duke's, renowned for its Hawaiian-inspired dishes.
Walk approximately 10 minutes along the beach from your hotel.
USD25, 1 hour

1:30PM

Waikiki Beach Relaxation

Unwind on the famous Waikiki Beach, soaking in the sun and the ocean waves.
Use your hotel beach access or rent a beach chair.
USD10, 2 hours

4:00PM

Diamond Head Hike

Hike up to Diamond Head for stunning panoramic views of Honolulu and the Pacific Ocean.
Drive 15 minutes from Waikiki to the Diamond Head State Monument.
USD5, 2.5 hours

7:00PM

Dinner at House Without a Key

Enjoy dinner with live Hawaiian music and hula at this elegant venue.
Return to your hotel area, it’s only 10 minutes drive.
USD45, 2 hours
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Day 2: Exploring Oahu

Oahu, Hawaii

8:00AM

Breakfast at Liliha Bakery

Savor a traditional Hawaiian breakfast at Liliha Bakery, famous for its cocoa puffs.
Drive 15 minutes from Waikiki.
USD15, 1 hour

9:30AM

Snorkeling at Hanauma Bay

Spend the morning snorkeling in the crystal-clear waters of Hanauma Bay.
Drive approximately 30 minutes from Liliha Bakery.
USD25, 3 hours

1:00PM

Lunch at Rainbow Drive-In

Enjoy local comfort food with a plate lunch at Rainbow Drive-In.
Drive 25 minutes from Hanauma Bay.
USD12, 1 hour

2:30PM

Visit Pearl Harbor

Explore the history at Pearl Harbor and the USS Arizona Memorial.
A 20-minute drive from the drive-in.
USD1, 3 hours

6:00PM

Dinner at The Pig & The Lady

Dine at this upscale Vietnamese restaurant known for its delicious fusion dishes.
Drive about 30 minutes back towards Honolulu.
USD35, 2 hours
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Day 3: Cultural Experience

Oahu, Hawaii

8:00AM

Breakfast at Bogart's Cafe

Morning coffee and Hawaiian-style breakfast at Bogart's Cafe in Kailua.
Drive about 30 minutes from Waikiki.
USD12, 1 hour

9:30AM

Explore the Byodo-In Temple

Visit the serene Byodo-In Temple located in the Valley of the Temples.
A 10-minute drive from the cafe.
USD5, 1.5 hours

12:00PM

Lunch at Pearl City Convenience Market

Grab a quick lunch featuring local poke bowls.
Drive 30 minutes back toward Pearl City.
USD10, 1 hour

1:30PM

Hike the Manoa Falls Trail

A lush 1.6-mile round trip hike leads you to the picturesque Manoa Falls.
Head 20 minutes from lunch spot.
Free, 2 hours

4:00PM

Visit the Bishop Museum

Discover Hawaiian history and culture at one of the largest museums in Hawaii.
Drive 15 minutes from Manoa Falls.
USD22, 2 hours

7:00PM

Dinner at Aloha Kitchen

Taste traditional Hawaiian dishes at Aloha Kitchen, a local favorite.
About 20 minutes from the museum.
USD30, 1.5 hours
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Day 4: Travel to Kauai

Kauai, Hawaii

8:00AM

Breakfast at Hotel

Enjoy a quick breakfast at your hotel before departing for Kauai.
Hotel dining.
USD15, 1 hour

9:30AM

Flight to Kauai

Catch your scheduled flight from Honolulu to Kauai.
Take a short 30-minute flight with Hawaiian Airlines.
USD80, 3 hours including boarding

1:00PM

Check into Hotel in Kauai

Settle in your hotel and get ready for the afternoon.
Take a taxi from Lihue Airport to your hotel.
USD25, 1 hour

2:30PM

Lunch at Duke's Kauai

Have a scenic luncheon at Duke's Kauai overlooking the beautiful ocean view.
Located within the hotel vicinity.
USD30, 1 hour

4:00PM

Waimea Canyon Drive

Enjoy a drive through Waimea Canyon, known as the 'Grand Canyon of the Pacific'.
Approx. 1.5 hours drive from hotel enjoying various lookout stops.
Free, 2 hours

7:00PM

Dinner at The Beach House

Dine on delicious seafood while taking in a breathtaking sunset view.
Located in Poipu, 30 minutes from Waimea Canyon.
USD50, 2 hours
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Day 5: Exploring Kauai

Kauai, Hawaii

8:00AM

Breakfast at Kalaheo Café

Start your day with fresh local coffee and breakfast at the café.
A 20-minute drive from your hotel.
USD15, 1 hour

9:30AM

Kayak the Na Pali Coast

Experience the stunning Na Pali Coast by kayak, with breathtaking views of the cliffs.
Drive to the kayak rental location, approximately 1 hour.
USD120, 4 hours

2:00PM

Lunch at Taro Ko Farm

Enjoy farm-to-table dining featuring fresh produce from the garden.
About 15 minutes’ drive from kayaking spot.
USD30, 1.5 hours

4:00PM

Explore Hanalei Bay

Relax at the beautiful sandy beach of Hanalei Bay, ideal for swimming and sunbathing.
Short 30-minute drive from lunch.
Free, 2 hours

7:00PM

Dinner at Bar Acuda

Savor locally sourced dishes at this upscale farm-to-table restaurant.
Spend a 20 minute driving from Hanalei Bay.
USD45, 2 hours
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Day 6: Travel to Maui

Maui, Hawaii

8:00AM

Breakfast at Hotel

Have a hearty breakfast at your hotel before your flight to Maui.
Hotel dining.
USD20, 1 hour

9:30AM

Flight to Maui

Take your scheduled flight to Maui, relishing the view from the air.
30-minute flight.
USD80, 3 hours including boarding

1:00PM

Check into Hotel in Maui

Relax and settle into your hotel located in Lahaina.
Transfer from Kahului Airport to hotel, around 35 minutes.
USD25, 1 hour

2:30PM

Lunch at Leilani’s on the Beach

Enjoy beachside dining featuring fresh fish and poke bowls.
Located in Lahaina, close to the hotel.
USD30, 1 hour

4:00PM

Relax at Kaanapali Beach

Spend the afternoon relaxing at the famous Kaanapali Beach.
A short 10-minute drive from the restaurant.
Free, 3 hours

7:30PM

Dinner at Fleetwood's on Front St.

Enjoy gourmet dining with ocean views and live music at this iconic establishment.
Head back to Lahaina, it’s just about 15 minutes.
USD50, 2 hours
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Day 7: Exploring Maui

Maui, Hawaii

7:00AM

Breakfast at Paia Bay Coffee

Start the day with coffee and breakfast sandwiches at this local favorite.
Drive approximately 40 minutes to Paia.
USD15, 1 hour

8:30AM

Road to Hana Adventure

Embark on the iconic Road to Hana, enjoying the waterfalls and scenic views.
Follow the Hana Highway, stopping along the way.
Free to drive, but stops may cost., 8 hours

4:30PM

Lunch at Hana Fresh

Enjoy delicious local tacos and fresh fruits as you reach Hana.
Part of the Hana route.
USD25, 1 hour

6:00PM

Visit Wainapanapa State Park

Catch the sights of black sand beaches and sea caves at this state park.
Close to Hana, about 10-minute drive.
USD5, 2 hours

8:30PM

Dinner at Mama's Fish House

Conclude your adventurous day with an unforgettable dining experience on the beach.
Drive back to Paia, about 40 minutes.
USD70, 2 hours
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Day 8: Travel to Big Island

Big Island, Hawaii

7:30AM

Breakfast at Hotel

Savor breakfast at your hotel before heading to the airport.
Hotel dining.
USD20, 1 hour

9:00AM

Flight to Big Island

Catch your flight to the Big Island to continue your adventure.
About a 40-minute flight.
USD90, 2.5 hours including boarding

12:30PM

LUNCH at Kona Brewing Co.

Grab a bite at this popular brewery offering pizzas and local beers.
Located across from Kailua-Kona Airport.
USD30, 1.5 hours

2:00PM

Check into Hotel

Settle into your hotel in Kailua-Kona and refresh.
A brief taxi ride from the brewery.
USD25, 1 hour

3:30PM

Visit Pu'uhonua o Honaunau National Historical Park

Explore this ancient Hawaiian place of refuge and its beautiful coastline.
Drive approximately 30 minutes from the hotel.
USD10, 2 hours

6:00PM

Dinner at Da Poke Shack

Treat yourself to fresh poke bowls at this famous local eatery.
Drive back toward Kailua-Kona, only 25 minutes.
USD20, 1.5 hours
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Day 9: Exploring Big Island

Big Island, Hawaii

7:30AM

Breakfast at Hotel

Enjoy breakfast at your hotel to fuel up for another exciting day.
Hotel dining.
USD20, 1 hour

9:00AM

Visit Volcanoes National Park

Explore the unique landscapes of Volcanoes National Park and see active volcanoes.
Drive to the park, approximately 2 hours from Kailua-Kona.
USD30, 5 hours

2:30PM

Lunch at Volcano House Restaurant

Dine overlooking Kilauea Caldera. Enjoy local cuisine at this scenic spot.
Located within the national park.
USD40, 1 hour

4:00PM

Explore lava tubes

Wander through the fascinating lava tubes at the park.
Inside Volcanoes National Park.
Free, 1.5 hours

6:00PM

Dinner at The Fish Hopper

Enjoy fresh seafood dinner while overlooking the ocean.
Drive back to Kailua-Kona, about 2 hours.
USD50, 2 hours
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Day 10: Travel to Molokai

Molokai, Hawaii

8:00AM

Breakfast at Hotel

Fuel up with breakfast before departing to Molokai.
Hotel dining.
USD20, 1 hour

9:30AM

Flight to Molokai

Take your short flight to Molokai that will refresh your spirit.
About a 30-minute flight.
USD80, 2 hours

12:00PM

Check into Hotel in Molokai

Arrive and get settled at your quaint hotel.
Transfer from the airport, wish to rent a car.
USD25, 1 hour

1:00PM

Lunch at Kanemitsu Bakery

Try the famous hot bread and local sweet treats at this iconic bakery.
About 15 minutes from your hotel.
USD15, 1 hour

2:30PM

Explore Kalaupapa National Historical Park

Discover the history and beauty of Kalaupapa, a unique national park.
Drive to the park, approx. 15 minutes.
Free, 2 hours

5:00PM

Dinner at Molokai Pizza Café

Dine on gourmet pizzas while enjoying the local atmosphere.
Drive for about 15 minutes back to town.
USD25, 1.5 hours
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Day 11: Cultural Immersion in Molokai

Molokai, Hawaii

8:00AM

Breakfast at Hotel

Start your day with breakfast at the hotel before heading out.
Hotel dining.
USD20, 1 hour

9:30AM

Molokai Museum and Cultural Center

Gain insight into the unique culture and history of Molokai.
Only a short drive across town.
USD10, 1.5 hours

11:00AM

Visit a Local Farm

Take a tour of a local farm to learn about sustainable farming practices.
Drive to a nearby organic farm, approximately 20 minutes.
USD5, 2 hours

1:00PM

Lunch at Paddlers Restaurant & Bar

Enjoy local food and comfort fare with a view of the beach.
Drive on coastal roads for about 30 minutes.
USD25, 1.5 hours

3:00PM

Explore Papohaku Beach

Spend the rest of the afternoon relaxing at Molokai's largest beach.
Drive for about 45 minutes to the west side.
Free, 3 hours

6:30PM

Dinner at The Green House

Wrap up the day with a delightful meal at this local hotspot.
Return to town which is about 45 minutes.
USD30, 2 hours
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Day 12: Travel to Lanai

Lanai, Hawaii

8:00AM

Breakfast at Hotel

Have one last breakfast in Molokai before heading to Lanai.
Hotel dining.
USD20, 1 hour

9:30AM

Ferry to Lanai

Take the ferry from Molokai to Lanai for a scenic crossing.
Ferry terminal, about 15-minute drive from hotel.
USD50, 1.5 hours including boarding

11:00AM

Check into Hotel in Lanai

Arrive at Lanai and check in to your luxurious resort.
Short transfer from the ferry terminal.
USD25, 1 hour

12:30PM

Lunch at Lanai City Grill

Indulge in contemporary cuisine and local beer at this beloved grill.
Located in Lanai City, a short drive from the hotel.
USD30, 1 hour

2:00PM

Explore the Garden of the Gods

Marvel at dramatic landscapes of the mysterious Garden of the Gods.
Drive approximately 30 minutes from the restaurant.
Free, 2 hours

5:00PM

Dinner at Nobu Lanai

Experience exquisite dining with stunning ocean views at Nobu.
Return to the resort for dining.
USD80, 2 hours
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Day 13: Leisure Day in Lanai

Lanai, Hawaii

8:00AM

Breakfast at Hotel

Enjoy a leisurely breakfast at your resort's dining service.
Hotel dining.
USD25, 1 hour

9:30AM

Relax at Hulopoe Beach

Spend the morning sunbathing and swimming at Hulopoe Beach.
Just a short walk from your hotel.
Free, 3 hours

12:30PM

Lunch at The Four Seasons

Savor a lunch at the luxury resort featuring seasonal options.
At the Four Seasons Hotel near the beach.
USD70, 1.5 hours

2:00PM

Explore Shipwreck Beach

Take a short hike to Shipwreck Beach and explore the shore.
20-minute drive from Hulopoe Beach.
Free, 2 hours

4:30PM

Dinner at Lanai City Bar & Grill

Wrap up with local Hawaiian cuisine in a cozy atmosphere.
Drive back to Lanai City, about 30 minutes.
USD30, 2 hours

7:30PM

Evening Stroll

Enjoy a peaceful evening stroll along the beach under the stars.
Walk from your hotel area.
Free, 1 hour
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Day 14: Return to Oahu

Oahu, Hawaii

8:00AM

Breakfast at Hotel

Enjoy a final breakfast at your resort before your departure.
Hotel dining.
USD25, 1 hour

9:30AM

Ferry back to Maui

Take the ferry back to Maui to catch your flight back to Oahu.
Ferry terminal about 15 minutes from hotel.
USD50, 1.5 hours including boarding

11:00AM

Flight back to Oahu

Catch your scheduled flight back to Oahu to conclude your adventure.
About a 30-minute flight.
USD80, 2 hours including boarding

1:30PM

Lunch at Helena’s Hawaiian Food

Experience authentic Hawaiian home-cooked meals before your flight home.
Located near the airport, about 20 minutes drive.
USD20, 1.5 hours

3:00PM

Souvenir Shopping

Spend the rest of the afternoon shopping for souvenirs in Waikiki.
Head to various shops in Waikiki.
Free, 2 hours

5:00PM

Departure from Honolulu

Head to the airport for your flight back home, filled with unforgettable memories.
Drive to Honolulu International Airport.
USD20, 1 hour
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