5 Days on Oahu: First-Timer’s Itinerary!
So, you’re visiting Oahu for the first time, and you’re super excited! But I bet you’re also overwhelmed with all the awesome things to do in Hawaii, so you’re not quite sure what’s available or which island it’s on. No worries.
That’s why I created this simple 5 day itinerary for Oahu, based in Honolulu. It’s flexible so you can move days around according to when you get reservations, and it leaves room for you to do more of what you love if you have more time on the island.
Oahu has Hawaii’s signature blue waters, dreamy volcanic landscapes, and a wealth of history. There’s plenty to see and do on this island, regardless of your budget.
Let’s look at how to spend your first week on Oahu to see all the sights!
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How to Spend 5 Days on Oahu (Besides Waikiki)
You’re visiting Hawaii, so of course you’re going to spend a lot of time on the beach, but I’m here to tell you that there’s so much more to Oahu than Waikiki.
Waikiki, which is a neighborhood of Honolulu, gets super crowded because that’s where almost all of the tourists stay. It’s a high-rise jungle of hotels competing for ocean views.
So, get outside of Waikiki! Escape the city entirely!
There are many more equally beautiful beaches around Oahu. You just have to get to them. If you don’t want to drive yourself, there are plenty of tours that will take you.
Hawaii also has amazing waterfall hikes and a lot of history to share. Give your skin a break from sunbathing and find a shady hike or visit an air conditioned museum.
Here’s how I spent 5 days based in Honolulu:
- Day 1: Honolulu & Hawaiian History
- Day 2: Pearl Harbor
- Day 3: The North Shore & Polynesian Cultural Center
- Day 4: Diamond Head, Lanikai Pillbox, and More
- Day 5: On the Water
Here’s where we stayed and our two favorite tours:
- Alohilani Resort Waikiki Beach: oceanfront, great location in Waikiki near food, shops, and the beach, easy walk to Diamond Head
- Waimea tour – Kevo’s Beach Bus Tour
- Snorkel tour – Turtle Canyons Snorkel Excursion from Waikiki
Schedule Considerations
Ticket availability will determine your schedule for you. You don’t have to visit in the order listed above. Shuffle as needed.
While it’s free to visit the Arizona Memorial at Pearl Harbor National Memorial, you still have to reserve a ticket for the short boat ride from the shore to the memorial over the wreck.
Those tickets sell out months in advance. Visit Pearl on whichever day you can get tickets to the memorial!
Likewise, the Polynesian Cultural Center’s luau is the most popular one on the island. It also books out months ahead of time.
Now, you don’t have to tour the PCC the same day you attend the luau, but most people do so they don’t have to drive up to the North Shore twice. Trust us. Traffic on Oahu is awful, even if a shuttle bus is driving you.
Summer vs Winter
You can use this itinerary any time of year, but note that some things won’t be available out of season.
If you want to see huge waves on Pipeline Beach or do some whale watching, come in the winter. Neither are here during the summer.
Don’t make the mistake of thinking there will be smaller crowds in the winter, though.
Winter is more peak season in Hawaii than summer is.
Day 1: Honolulu & Hawaiian History
The Hawaiian Islands have a lot of local native history and a lot of unfortunate history once the Europeans showed up. Big surprise.
King Kamehameha the Great united the Hawaiian Islands in 1810. Previously they had been a bunch of separate factions under different chiefs. Eventually the Hawaiian monarchy would fall to the ambitions of American businessmen. Again, big surprise.
Today, you can visit Iolani Palace, the last seat of the Hawaiian monarchy, located right next to the modern-day state capital building. It’s the only former royal palace on American soil.
Don’t miss the King Kamehameha the Great statue across the street in front of the judicial building.
For more Hawaiian history besides just the former monarchy, visit the Bishop Museum, also known as the State of Hawaii Museum of Natural and Cultural History.
This incredible history and science museum covers everything from the arrival of the Polynesian people to the Hawaiian Islands to the incredible natural habitat and volcanic landscapes that make up Hawaii.
If you’re more of a tour person, here’s a great FREE walking tour that’ll give you the highlights in under an hour. (They have food tours, too!)
In the afternoon, take a stroll down Kalakaua Avenue in Waikiki, the main street with tons of shopping. It’s worth your time to see it once if you’re not staying in the area.
(If you do stay here, you’ll walk up and down this street plenty of times throughout your stay and you don’t need to schedule a time to do it.)
You’ll find plenty of entertaining street performers, particularly in the evenings, and shopping for those with deep pockets and/or a sweet tooth.
Pro Tip:
The ABC Stores sell more than alcohol (although they sell a lot of that, too) and they have a reward system if you spend a certain amount at their stores within a specific timeframe.We got a free Hawaii mug just from buying sandwiches, snacks, and drinks for hikes and chillin’ on the beach. Plus, there’s an ABC Store on almost every block in Waikiki, so it’s easy to reach their spend amount.
Make a reservation at Duke’s for lunch or dinner, whichever is available. The Hawaiian monarchy had many dukes, duchesses, princes, and princesses, but The Duke is always Duke Kahanamoku, Olympic swimmer and the father of modern surfing.
End your day with a dip at Waikiki Beach. It’s smaller than you realize, and will certainly be crowded, but it’s worth a chance to cool off.
The sandy part isn’t very wide unless you’re closer to the incredible Royal Hawaiian Resort. They often have surf classes or outrigger boats coming and going at this end of the beach.
For incredible sunset views, walk down to Fort DeRussy Beach.
Good to Know:
All beaches are public property in Hawaii. A hotel, even a fancy oceanfront hotel, cannot stop you from using the beach. Just make sure you stick to public pathways to get there. The hotels CAN stop you from walking through their property if you’re not a guest, so you’ll see gates around their pool areas and outdoor spaces.
Day 2: Pearl Harbor
The infamous attack on Pearl Harbor by the Japanese brought the US into World War II, and it happened here in beautiful Hawaii, before the islands were even a state.
If you’re in Honolulu and don’t have plans to do anything but chill at the beach, make an exception for this.
If you want to see the Arizona Memorial Site, which I highly recommend, then you need to reserve your ticket ahead of time. Months ahead of time.
Good to Know:
They have a standby line for those that don’t have tickets to the Arizona Memorial, but you will be there a while. That line moves very slowly in peak season, and you’re not guaranteed to get a seat. Full disclosure: we used it one July several years ago and we did, eventually, get seats on a boat after about 1.5 hours waiting.If you go this route, get in line early and take turns leaving one member of your group in line while the rest go explore the free exhibits nearby. Just make sure you’re all back in line when it comes your turn, or you’ll have to go to the back of the line and start again.
A lot of visitors misjudge how long they need to see everything at the Pearl Harbor National Memorial Site. They think a half day, just a few hours really, will be enough.
If you’re not a history fan and you don’t plan to visit anything besides the free sites, then that might work for you.
But even the non-history buffs will find climbing through a submarine or a battleship to be a cool experience, and you need more than a couple of hours to do that.
Get the Passport to Pearl Harbor ticket and see the paid attractions, too. Here’s everything you need to know about what’s free, what’s paid, and how to use your time wisely to see it all.
The Naval Museum gives you access to the huge submarine docked right next to the Ford Island Bridge.
Take the bus across to Ford Island and see the USS Oklahoma Memorial, the Mighty Mo (USS Missouri), and the Pearl Harbor Aviation Museum.
The Mighty Mo, the battleship where the articles of surrender were signed to end World War II, is docked a short way down from the Arizona Memorial.
The USS Oklahoma Memorial is right outside the entrance to the Mighty Mo, remembering the thousands of men who couldn’t be rescued from the overturned vessel.
If you or your kids like planes, you don’t want to miss the Pearl Harbor Aviation Museum. It has both a hangar full of World War II-era planes and a hangar full of modern day jets, and you can still see bullet holes in the hangar door glass from the 1941 attack.
Day 3: North Shore
Visiting Oahu’s North Shore is a must for visitors, regardless of the season.
While winter is when you’ll find the enormous waves at Banzai Pipeline Beach that host world surfing competitions, snorkeling in Waimea Bay in summer is more fun for those that prefer to be in the water.
You’ll pass by the famous Dole Plantation on your way up here.
Worth a stop if you want some merch or a tour of the pineapple fields, but you can get pineapple soft serve or a dole whip at pretty much every ice cream shop on Oahu.
The Polynesian Cultural Center in Laie is another enormously popular sight on the North Shore. It’s a very interesting history and culture tour, but their most popular for their luau.
This luau books out months in advance, so if you find tickets available, jump on them!
None of these sights are very far apart. The Dole Plantation is about 45 minutes from Waikiki. Waimea Bay is 20 minutes from Dole, and the Polynesian Cultural Center is another 30 minutes from Waimea.
The not fun part is driving back to Waikiki at the end of the day. It’s only a little over an hour’s drive, without traffic, but there’s always traffic if you’re trying to get back in time for dinner in Waikiki.
Good to Know:
If you don’t have a rental car, I highly recommend you book a tour, or a couple of tours, for today. It’ll rush you a little, but you’ll get to see and do a lot without having to worry about transportation. Your guide will keep you laughing while the driver worries about the traffic.
We had a lot of fun on this tour when we showed up in Oahu last minute one July.
Circle Island Tours and Grand Tours are a popular way to see everything by bus, but it’s important to note that they don’t stop at everything.
For example, most include pass-bys of Diamond Head Crater, but none stop there. You’d need to return on your own another day if you want to actually go inside the crater or hike it for incredible views.
Pro Tip:
This is a great way to see the whole island in one long, jam-packed day and to choose places to come back to another day.This itinerary is only 5 days, but I bet you’re here for at least 7, maybe 9 days. Take one of the extra days to go back and visit the parks, beaches, or vistas you didn’t get to stop at on your bus tour.
Day 4: Diamond Head, Lanikai Pillbox, and More
Hawaii has some amazing views from the top of its craters, and Oahu is no exception. Today, go take a hike for a stunning view!
Now, fair warning: most of the hikes on Oahu, and in Hawaii in general, have pretty steep sections. They don’t have rolling hills. They have volcanic craters and ridges.
But the views and the waterfalls are always worth the effort!
Diamond Head Crater is within walking distance from Waikiki, but you could take a cab or the bus if you prefer to save your legs for the hike up the craterside.
Check out my full review of this hike, and don’t forget that the state park that maintains Diamond Head requires timed entry tickets for all out-of-state visitors.
Another insta-famous Oahu hike is the Lanikai Pillbox, aka Ka’iwa Ridge. This is a great sunrise hike option on the eastern side of the island, with outstanding views in both directions.
Enjoy the sunrise over the gorgeous blue waters of the sea in front of you, and behind you, the beautiful morning light topping the mountain ridges with gold.
The pillboxes are old observation bunkers, once used to spot enemy ships out at sea and now a favorite canvas for graffiti artists.
If waterfalls are more your speed, try Manoa Falls Hike for Jurassic Park vibes or Waimea Falls Hike out on the North Shore. If you’re not on a tour, I’d add Waimea Falls to your North Shore day. Both are short and easy!
Day 5: On the Water
The Hawaiian Islands have thriving sea life you can’t miss on your first visit!
Humpback whales stop here every winter before moving on to their summer feeding grounds in Alaska. Sea turtles are year-round residents. Colorful fish of all types live near the reefs and along the rocky coastlines.
You are missing half of Hawaii if you never get in the water.
I’m a big fan of snorkeling, but you can also scuba, cage dive with sharks, paddleboard, surf, or try your hand at rowing an outrigger canoe.
If you just want to snorkel, you don’t need a tour. Choose a good snorkeling beach like Waimea Bay or Hanauma Bay, and get out there! You can see a lot in the shallow waters near shore.
If you prefer deeper waters (and bigger animals) then a tour is your best bet.
We took this quick and easy snorkeling tour from Waikiki. It was nice that it was so close, so we could fit it in with other activities that day, but it visits probably the most crowded snorkeling spot around the island. It’s not uncommon to see 10 boat tours all competing to see the same turtle.
This is a well-reviewed shark diving tour. I didn’t have time for it on my whirlwind Oahu trip, but it’s on my list for my next visit!
If you’re interested in learning to surf or to ride in an outrigger, you can do both from Waikiki Beach! Walk up to the vendors, and they’ll sort you out.
Happy travels!
About the Author: Rachel Means
With six-figure student loan debt and only 10 PTO days per year, Rachel started traveling the world. A decade later, she’s paid off her loans, changed careers, and been to 42 US states and 17 countries. She’s an expert at planning and budgeting for travel and loves to help others do it, too! Read her full story here.
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