Lady walking on the beach
October 29, 2020
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Jana Free

Visit Oahu: A Complete 5-Day Itinerary for Oahu

Visiting Oahu? This Oahu Travel Guide article tells you how to plan a trip that will let you experience the best beaches, things to do, restaurants, attractions and activities on Oahu - A Complete 5-Day Itinerary for Oahu.

These are unusual times we find ourselves living in, with restrictions being put in place and lifted with little notice, so please be sure to confirm operating hours before visiting any of the attractions or venues mentioned in this article.

There are so many reasons to visit Oahu. Big-waves, beautiful beaches, historic palaces, great dining and luaus (you have to visit a luau when you come to Oahu). This - Complete 5-Day Itinerary for Oahu - will take you through each day of your Hawaiian vacation - walking or driving you from one top attraction to another - so you don’t miss anything.

Our latest Oahu Travel Blog article, ‘Visit Oahu: A Complete 5-Day Itinerary for Oahu,’ will help you plan the ultimate trip to Oahu - our island paradise.

Rich culture, mild temperatures and generous people. All of these and more await on your next adventure on Oahu.

Oahu is filled with many fun and memorable things to do, see and experience - so use this Guide to 5 Days on Oahu to help you get the most out of your time here.

Day 1 - Honolulu & Waikiki

For your first day on Oahu, wake up from your cozy bed at Ambassador Hotel Waikiki and head to Alii Coffee (closed on Sundays) for some fuel to start your day.

When you’re caffeinated, stroll to Sweet E’s Cafe for a traditional Hawaiian breakfast at an affordable price.

Since you’ve likely just eaten your weight in pastries and other morning goodies at Sweet E’s, you’ll want to walk off the calories on the way to your first attraction: Diamond Head.

Diamond Head Crater is a 300,000-year-old volcanic crater that features a 1.8-mile round-trip hike on a trail gaining 452 feet from base to end. The prize at the end of the trail is an awesome view of Honolulu and the eastern side of Waikiki.

You’ll be ready for lunch after your Diamond Head trail workout, so head to Helena’s Hawaiian Food or Rainbow Drive-In, both of which are great options in Waikiki. Stop by Waiola Shave Ice for an after-lunch treat.

Next you’re off to view the King Kamehameha Statue and wander the grounds of Iolani Palace. These 2 landmarks will provide a bit of background on the history of Hawaii.

Shop for an hour or so at the inexpensive ABC Store in Waikiki and hit the high-end retailers in downtown Honolulu for bit of window shopping (or a splurge).

A trip to Oahu has to include an afternoon on Waikiki Beach. Grab a towel or blanket, and relax on the sand as you watch the windsurfers and body boarders playing in the mild swells. Go for a swim, paddle board and catch a memorable sunset on this top Oahu beach.

Finish your day in Waikiki at Duke’s, a famous dinner spot that is complete with a barefoot beach bar.

Oahu is an amazing island paradise where you could spend months, or even a lifetime discovering all there is to do and see on the island. This sample 5-Day Itinerary gives you just a few ideas for how to spend your time on Oahu...the best itinerary is the one that you create for yourself. Do the research. Do the planning. In the end the itinerary you create will be the perfect plan.


Day 2 - The North Shore & Dole Plantation

Wake up early because you’re headed to the North Shore, famous for its big waves and daring surfers. Grab coffee on the North Shore from Brew & Foam, and stop by Haleiwa Bowls for a nourishing acai bowl.

The rest of your morning will be spent at Laniakea Beach where you’ll enjoy stunning scenery and maybe even a glimpse of some sea turtles. Relax for a few hours and then explore Haleiwa, a charming surfer’s town with quaint little shops.

Lunch at Kono’s in Haleiwa is a must, followed by shave ice at Matsumoto Shave Ice. 

Head to Banzai Pipeline for an afternoon of superior surf or just surf-watching. You don’t have to get into the water to enjoy the special experience the Banzai Pipeline offers. Just sit on the shore and be amazed at the locals who make riding the gigantic waves of Pipeline look like child’s play.

Next, drive inland to the Dole Plantation to experience the Pineapple Garden Maze, the Plantation Garden Tour and a ride on the Pineapple Express. Plantation Grille is the perfect place for dinner on Day 2 of your Oahu adventure.


Day 3 - North Shore - Pearl Harbor - Polynesian Cultural Center

It’s back to the North Shore for Day 3 of your Oahu adventure. Begin the day with coffee and breakfast at The Sunrise Shack. 

After you’ve fueled up, go for a hike up to the Ehukai Pillbox. This 2.1-mile round-trip hike brings you 675 feet above sea level to view the North Shore from a special vantage point.

You’ll probably be hungry after your mega hike, so sit down to lunch at Ted’s Bakery. Celebrate the day with a piece of pie for dessert.

Spend an hour or so at Sunset Beach and say ‘goodbye’ to the North Shore as you head to the USS Arizona Memorial to pay tribute to our fallen heroes.

For a memorable end to Day 3 on Oahu, attend a luau at the Polynesian Cultural Center located just about an hour from your hotel in Waikiki. The spectacular show at this popular luau is just one of the ways the Polynesian Cultural Center preserves and portrays Polynesian life on the island of Oahu.


Day 4 - The Windward Side

Get an extra-early start on your morning on Day 4 so you can hike up to the Lanikai Pillboxes before sunrise. Bring a headlamp or flashlight, and prepare for a challenge because the trail entrance sits in a residential area with limited parking spots. Remember why you came, though, and persevere. The views from the top of the trail are nearly otherworldly and you won’t want to miss them.

An energizing breakfast is in order after your hike up the Lanikai Pillboxes, so head to Kailua for an acai bowl and then pick up coffee at ChadLou’s Coffee Roasters.

Next, it’s time to experience the Nuuanu Pali Lookout. You’ll travel along the scenic Pali Highway, through mountains and tunnels, to arrive at Lookout where you can view sparkling seas and many charming Hawaiian towns. The entrance fee to the park is $3 and the views are amazing.

We’re off and running on Day 4, on the Windward side of Oahu, fitting as much adventure in as we can. Photograph the cascading water of nearby Lulumahu Falls (you’ll need a $2.50 permit to enter) and then sit waterside for a relaxing picnic lunch.

Ready for a mid-afternoon treat? Go back to Kailua to Island Snow for more shave ice or a scoop of ice cream.

Play the rest of the day away on Lanikai Beach. Build a sand castle or go for dip in the crystal blue water. Lanikai Beach is one of the world’s best beaches and it’s famous for its powdery white sand.

As an alternative, enjoy the sun and sand at Kailua Beach Park, one of Oahu’s most beautiful beaches. This beach offers excellent kayaking, swimming and windsurfing. Kailua Beach rarely experiences the big waves that are frequent on the North Shore, so it’s a great beach for families.

Dinnertime in Kailua is always a good idea. Relax over a meal at Kalapawai Cafe & Deli, then head back to your hotel to rest up for Day 5 - your last day - on beautiful Oahu.


Day 5 - The Southeast Shore

Rise and shine. It’s Day 5 on your Oahu adventure and you’re headed to Koko Head Crater for a sunrise hike. Bring your flashlight or headlamp, and be prepared to burn some muscles on this strenuous hike. Your legs are going to ache tomorrow, but today enjoy the spectacular view that awaits atop the 1,048 stairs.

Sit down to breakfast at Island Brew Coffeehouse and reflect on how much of Oahu you’ve experienced on this amazing and memorable trip. The fun’s not over yet, though!

The rest of your morning will include snorkeling at Hanauma Bay. This striking bay is the most popular snorkeling spot on Oahu, which means it might be crowded, but the view you’ll have of Oahu’s marine life is well worth it. *Hanauma Bay is closed on Thursdays

Drive to Halona Beach Cove, the backdrop for the Pirates of the Caribbean movie, and explore the beach cave as well as the cool blowhole.

Up the road just a bit, take pictures of the Makapuu Lighthouse, a beautiful lighthouse with an authentic red pointed roof. Enjoy a picnic lunch while enjoying the scenery.

Spend the remainder of the day at Waimalola Beach.

On the way back to your hotel, pick up groceries so you can cook an authentic Hawaiian meal in your room. End the evening looking through your digital photos and remembering all of the special moments you spent on Oahu.


Closing Note: Of course there are many more activities, attractions and adventures you could include in a 5-Day Itinerary, Hikes, Waterfalls, Luau's, Live Music, Beaches...and more Beaches, but this is just one, 5-Day Itinerary that will be followed up with other versions in the near future so check back!

We hope our latest Oahu Travel Blog article, ‘Visit Oahu: A Complete 5-Day Itinerary for Oahu,’ has helped you organize your days so you can make the most of your visit to Oahu.

You may also enjoy this article; 'Swim with Sharks off Oahu.'

Visit our Oahu Travel Guide for more recommendations for all there is to do, see and experience when visiting Oahu.

For the 'Best Rates Guaranteed' at our Waikiki Hotel go here to Check Rates, Book Now or call: 808-941-7777