Explore the Best of Oahu: A 5-Day Island Itinerary

Day 1: Historical Exploration

Honolulu, Hawaii

8:00AM

Breakfast at Leonard's Bakery

Start your day with a famous malasada from Leonard's, a beloved local bakery.
Take the bus or drive 15 minutes to Pearl Harbor.
USD10, 1 hour

9:30AM

Visit Pearl Harbor National Memorial

Explore the historic site where the attack on Pearl Harbor took place, including a tour of the USS Arizona Memorial.
On foot within the Pearl Harbor site.
USD0, 3 hours

1:00PM

Lunch at Nico's Pier 38

Enjoy fresh seafood overlooking the harbor, known for its poke and fish tacos.
Drive 15 minutes back to the restaurant.
USD25, 1 hour

2:30PM

Explore Iolani Palace

Take a guided tour of the only royal palace in the United States, rich in Hawaiian history.
Drive 10 minutes to the palace.
USD30, 1.5 hours

5:00PM

Stroll through the Honolulu Museum of Art

Enjoy diverse artworks from Hawaii and around the world.
Drive 10 minutes to the museum.
USD20, 2 hours

7:00PM

Dinner at The Pig and The Lady

Savor Vietnamese-inspired dishes in a trendy setting, popular for its pho and sandwiches.
A 10-minute drive from the museum.
USD30, 1.5 hours
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Day 2: Surf and Sun

North Shore, Hawaii

8:00AM

Breakfast at Haleiwa Beach House

Enjoy a hearty breakfast with a beautiful view of the ocean.
Drive 1 hour from Honolulu.
USD20, 1 hour

9:30AM

Surfing at Waimea Bay

Try your hand at surfing or just relax and watch the surfers ride the famous waves.
Drive 15 minutes to the bay.
USD0, 2 hours

12:00PM

Lunch at Giovanni's Shrimp Truck

Stop for shrimp scampi at this iconic food truck famous for its garlic shrimp.
Drive 10 minutes to the food truck.
USD15, 1 hour

1:30PM

Visit Turtle Beach

Look for green sea turtles basking on the shore at this beautiful beach.
Drive 10 minutes from lunch.
USD0, 1.5 hours

3:00PM

Explore the Dole Plantation

Discover the popular tourist spot with pineapple-themed attractions and a train ride.
Drive 30 minutes from Turtle Beach.
USD15, 2 hours

6:00PM

Dinner at Haleiwa Joe's

Enjoy a nice meal with stunning views in this welcoming restaurant.
Drive 20 minutes back to Haleiwa.
USD35, 1.5 hours
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Day 3: Nature and Relaxation

Kailua and Lanikai, Hawaii

7:30AM

Breakfast at Cinnamon's Restaurant

Indulge in the famous guava pancakes before your day of adventure.
Drive 30 minutes from North Shore.
USD20, 1.5 hours

9:00AM

Hike to Lanikai Pillbox

Enjoy breathtaking views of the ocean from the historic military pillboxes.
Drive 10 minutes to the trailhead.
USD0, 2 hours

11:30AM

Relax at Lanikai Beach

Spend time soaking up the sun on this stunning beach known for its turquoise waters.
Walk from the pillboxes to the beach.
USD0, 2 hours

1:30PM

Lunch at Kalapawai Market

Enjoy a delicious sandwich or poke bowl from this local favorite.
Drive 5 minutes from Lanikai Beach.
USD15, 1 hour

3:00PM

Kayaking to the Mokes

Rent a kayak and paddle over to the Mokulua Islands, exploring the serene natural beauty.
Kayak rental available at the beach.
USD60, 3 hours

7:00PM

Dinner at Buzz's Lanikai

Enjoy classic Hawaiian cuisine and local drinks in a beachy atmosphere.
Drive 10 minutes from Kailua.
USD30, 1.5 hours
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Day 4: Culture and Scenic Views

Pearl Harbor and Waianae, Hawaii

8:00AM

Breakfast at Kamehameha Bakery

Savor the famous haupia pie and enjoy local Hawaiian delicacies to start the day.
Drive back to Honolulu (30 minutes).
USD10, 1 hour

9:30AM

Visit the USS Missouri

Explore the battleship that witnessed the end of World War II at Pearl Harbor.
Drive 15 minutes to Pearl Harbor.
USD25, 1.5 hours

12:00PM

Lunch at Aloha Grill

Enjoy a simple lunch with fresh local ingredients, known for its plate lunches.
Drive 10 minutes from Pearl Harbor.
USD15, 1 hour

1:30PM

Attend a cultural exhibition at Waianae

Experience traditional Hawaiian culture through dance and music at this stunning coastal town.
Drive 30 minutes from lunch.
USD0, 2 hours

4:00PM

Relax at Makaha Beach

Unwind at one of Oahu's less crowded beaches and enjoy the picturesque views.
Drive 15 minutes from Waianae.
USD0, 1.5 hours

6:30PM

Dinner at Monkeypod Kitchen

Enjoy farm-to-table food with a focus on local ingredients, plus try their famous pies.
Drive 20 minutes from Makaha.
USD40, 2 hours
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Day 5: Resort Relaxation

Ko Olina, Hawaii

9:00AM

Breakfast at The Olelo Room

Enjoy a laid-back breakfast with an ocean view in this resort area.
Drive 30 minutes from Waianae.
USD20, 1 hour

10:30AM

Snorkeling at Ko Olina Lagoons

Spend your morning snorkeling in the calm, clear waters of Ko Olina Lagoons.
Walk to the lagoons.
USD0, 2 hours

1:00PM

Lunch at Roy's Ko Olina

Indulge in a delicious meal at this renowned restaurant for its fresh seafood and Hawaiian fusion cuisine.
Drive 5 minutes from the lagoons.
USD40, 1.5 hours

2:30PM

Relax by the beach

Spend the afternoon unwinding on the beach, soaking up the sun and enjoying the beautiful ocean.
Walk back to the lagoons.
USD0, 2.5 hours

5:00PM

Sunset at Paradise Cove

Watch the stunning sunset as you prepare for your farewell dinner with incredible views.
Drive 10 minutes from the beach.
USD0, 1 hour

6:30PM

Farewell Dinner at Paradise Cove Luau

Enjoy an authentic Hawaiian luau experience with traditional food and entertainment.
On foot within Paradise Cove.
USD130, 3 hours
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