Oahu Five Day Itinerary

Explore Oahu in 5 Days

Oahu Five-Day Itinerary Suggestions

At some point in planning your vacation to Oahu, it’s probably going to hit you, “Wow, this is a lot harder than I thought it’d be... there’s so much to do.”  Welcome to the state where the possibilities for activities and adventures are limitless, to where you’ll likely never find yourself bored unless you refuse to leave your hotel room. This portion of our website is here to help you focus on planning your trip and should allow you to organize what you want to do into simple itineraries.  Planning your vacation doesn’t have to be a chore, and hopefully, our recommendations will be of assistance in your preparation.

We’ve designed our Oahu itineraries around a set number of on-island Oahu days: offering one, three, five, and seven-day itineraries for exploring the island, soaking in the best sights, and ensuring your precious time (and potentially money) on Oahu is spent wisely. We’ve tried to balance our itineraries between those who seek adventure and those looking to find a good beach and relax. Overall, we want your experience to be exactly what you’ve dreamed of when planning your Oahu trip.

We’ve provided all Oahu directions via Google Maps when possible, as Google Maps works on all platforms and across all devices. You should be able to pop the directions into your phone or tablet and go. To help you visualize each day’s itinerary, we’ve also provided overview maps that help you get your bearings.

Our five-day Oahu itinerary below includes many of the recommendations in our three-day Oahu itinerary, plus some other must-see sights, attractions, and activities for the extra two days on the island. Skip ahead to the 5-day itinerary now →

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Overview of Oahu - the 'Gathering Place"

There's a reason Oahu is known as The Gathering Place, as it offers so much to attract- and keep- the attention of locals and tourists alike. Oahu may be number three in size among its fellow islands in the Hawaiian chain, but it is first in population. Nearly 900,000 people share Oahu's 600 square miles of mountains and beaches - that's a full three-quarters of the state's population. Oahu is primarily defined by the state capital of Honolulu, Pearl Harbor, and the world-famous Waikiki Beach. These areas host thousands of tourists daily.

Honolulu is the state's capital and major financial center. It is also home to the main campus of the University of Hawaii. However, Honolulu wasn't always the main seat. Until 1845 the capital of the Hawaiian Kingdom was located on the island of Maui. King Kamehameha III ordered the move, and the Iolani Palace was built later.

But Oahu is much more than Honolulu or Waikiki - it may well be the most beautiful of all the major islands. You simply have to know where to go to experience the beauty that is Oahu. We'll attempt to introduce you to as much of Oahu beyond Waikiki and Honolulu as possible in our daily itineraries.

Geographically speaking, Oahu is made up of two separate but overlapping volcanoes, known as a volcanic doublet. Its asymmetrical butterfly shape is formed by two mountain ranges: the Waianae Range in the west and the Ko'olau Range in the east. Slicing through the center is the flat Leilehua Plateau. Recent (geologically anyway) volcanic eruptions in the southeastern portion of the island which formed the Diamond Head, Koko Head, and Punchbowl craters can be blamed for Oahu's uneven shape.

The eastern coast of Oahu is hemmed in by a gorgeous mountain range and boasts a trifecta of the island's best beaches. The eastern region offers many visitors an escape from the bustling Waikiki scene while still offering the proximity to the shopping and activities of the nearby city just a half-hour drive away.

The famous north shore of Oahu is a surfer's paradise, especially in the winter months when the surf is up. The monster waves and laid-back atmosphere have professional surfers flocking to Banzai Pipeline and Waimea Bay to ride some of the most killer waves in the Pacific. About an hour's drive from Honolulu, this region has a surprisingly unpopulated feel to it. Many miles of beaches stretch along this portion of Oahu, making it a popular haven for those looking to relax in the sun.

The central region is where a large portion of the island's residents live. For the most part, there isn't much here for the typical island visitors - just a few scattered beaches. However, Central Oahu has one of the island's most significant attractions: Pearl Harbor and the U.S.S. Arizona Memorial. More than one million people a year pay their respects to the many military personnel who lost their lives during the Japanese attack. Many of these men and women and veterans of many wars are laid to rest in Punchbowl National Cemetery at Pu'owaina Crater (Punchbowl).

The leeward or west side of Oahu is called Wai'anae and is filled with pineapple fields.

Beyond the skyscrapers and decidedly urban nature of the southern tip of the island in Waikiki & Honolulu is an Oahu of outstanding natural beauty and old-time charm. For the traveler looking to experience a modern paradise, Oahu has it all - the excitement and culture of a large metropolitan city, the unspoiled beauty of tropical coastlines and verdant mountains... plus everything in between. Hopefully, our daily itineraries for Oahu will help you experience the very best that Oahu has to offer, regardless of how long your stay is.

Accommodations on Oahu & Where to Stay Summary

On Oahu, you’re probably staying in Waikiki; it’s where the vast majority of travelers book their rooms. If you haven’t yet decided where to stay on Oahu, we can help with that too, be sure to check out our Where to Stay on Oahu article for the best tips and suggestions on where to book your stay. Don’t worry if Waikiki isn’t you’re starting point, as there are several accommodations, b&bs, inns, etc. scattered across the island. Regardless of where you’re staying, we’ll still help you plan accordingly.

Be sure to also read our Best time to Visit Oahu article for an in-depth look at when the best time to visit Oahu is for your travel party.

Getting Around Oahu

On Oahu, even with the public transit options, like ‘TheBus’ available, a rental car is still one of the best options for getting around the island and viewing all the sights we detail in our itineraries. The rental rates in Hawaii are often some of the cheapest anywhere in the world because the competition is typically fierce.

Summary of what to pack on your Oahu trip

Regardless of how much you’ve traveled in the past and where you’ve been, there is one good rule to follow when coming to Hawaii, leave as much as you can at home. Seriously, bring only what you’ll need during your stay and nothing more. For starters, schlepping around three suitcases is NOT what you want to be doing after getting off a long plane ride. Next, consider that long pants, dress clothes, and anything else formal really have no use in Hawai‘i (unless you are staying in a very exclusive resort). Chances are a pair of shorts and an old Aloha shirt are all you’ll need for even some fine dining.

As far as clothing goes, that’s usually a few pairs of shorts, several T-shirts, sandals or flip-flops (slippahs as Hawaii residents call them), and a good visor or hat, anything made of a cotton blend is usually good. A light jacket might also be nice for those visits to higher elevations.

With the motto, “less is more” in mind, here are a few other items to bring. Sunblock (the UV on Hawai‘i is typically 10+ in the spring, summer, and fall), a backpack (for any hikes) and a water bottle, slippers (flip flops, shower shoes, zoris), mask, snorkel, and fins (or rent locally instead), two bathing suits (one to wear while the other dries) and a cover-up, your phone or a camera, lightweight raincoat or poncho (for mountain/rain forest hiking), bug spray with DEET (for any forest hikes), flashlight (if the sun goes down before your hike ends or for night walks on the beach), hiking boots and hiking rods, and most importantly a list of all your troubles to leave behind.  For more information on what to pack, seeing our What to Pack When Visiting Hawaii article.

Five Day Itinerary for Oahu

5-Day Oahu Wayfinder Guide

We'll officially kick off our itinerary suggestions by quickly covering the days you both arrive and depart. While they are not completely a wash in terms of planning something to actively do or participate in those days, we like to keep them open and use them for relaxing after we arrive and before we depart.

Arrival Day on Oahu

Let the first day you arrive be a day to adjust to the islands. Grab a bite to eat, pick up supplies and/or groceries, enjoy your first Hawaiian sunset that evening, and get to bed early as it has likely been a long day. If you’re flying in from another island, as we often do, then some light sightseeing probably won’t be a problem once you’re set up with your new rental, etc. But generally, we advise people to take it easy the first day, soak in their local surroundings, and acclimate to Hawaiian time.

Departure Day from Oahu

Like your arrival day, this day is meant to wind down from your trip and prepare for your jump to another island or for the journey home. We suggest grabbing a bite to eat from one of your favorite local restaurants near your accommodation and maybe some final souvenir shopping at some of the many stores and local shops around the island. Undoubtedly, the local community would appreciate your business. In Hawaii there are no “Goodbye’s” - so we’ll say A Hui Hou, which in Hawaiian means ‘Until we meet again.’ Aloha!

Oahu 5-Day Essentials Itinerary 

We're working on our more advanced modular itinerary for Oahu, similar to how we've set up our Maui ItinerariesUntil we have that ready, check out our Essentials Oahu itinerary to get you started.

Oahu is the proverbial heart of Hawaii and the gateway to the Aloha State. Known as "The Gathering Place," Oahu seamlessly blends urban sophistication with natural beauty, making it an incredible destination for visitors from around the world.

Here, you will discover a vibrant mix of unique experiences that blend historic landmarks, bustling city life, and breathtaking landscapes. From the iconic Waikiki Beach, the solemn and historic Pearl Harbor, to the world-famous surf on the North Shore, and the rugged cliffs of the Koolau Mountains, Oahu offers something for everyone.

Immerse yourself in the rich heritage of the islands by exploring Iolani Palace, the only royal palace on US soil, and learn about the Pacific Island cultures at the Polynesian Cultural Center. Dive into crystal-clear waters of Hanauma Bay for a mesmerizing snorkeling experience, and explore Kualoa Ranch, a popular film location for numerous Hollywood blockbusters.

Get ready to experience a lively blend of Polynesian culture, delectable Hawaiian cuisine, and the island's 'aloha' spirit during your 5-day adventure on this beautiful island. Whether you're a beach lover, history enthusiast, foodie, or outdoor adventurer, Oahu promises an unforgettable journey that will leave you longing to return.

Day 1: Explore Waikiki Beach

  • Check into your hotel in Waikiki and spend the rest of the day on Waikiki Beach, exploring nearby shops and restaurants.

Day 2: Pearl Harbor & Honolulu

  • Spend your morning at the Pearl Harbor National Memorial.
  • In the afternoon, explore downtown Honolulu, visiting landmarks such as the Iolani Palace, the Kamehameha Statue, and the Hawaii State Capitol.

Day 3: Diamond Head & Hanauma Bay

  • Morning hike to the top of Diamond Head. Don't forget to make a reservation in advance; a reservation is now required to visit and hike the trail.
  • Drive to Hanauma Bay for an afternoon of snorkeling and relaxation. Advanced reservations are highly recommended.

Day 4: North Shore & Polynesian Cultural Center

  • Start with a morning road trip to Oahu’s North Shore.
  • After lunch, visit the Polynesian Cultural Center to learn about Pacific Island cultures, enjoy traditional meals, and watch performances.

Day 5: Kualoa Ranch on Oahu's East Coast

  • Spend your morning at Kualoa Ranch. You can take an ATV tour or a movie site tour.
  • If time allows, be sure to stop by and check out Mokoli'i Island at Kualoa Point

Itinerary Conclusion

This 5-day itinerary is quite condensed, and you'll be moving at a quicker pace. Don't forget to take some time to relax, enjoy the Hawaiian cuisine, and soak in the natural beauty of Oahu!

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