The Ideal Oahu Itinerary for 5 Days in Paradise

Sun, sand, and surf – what a magical combination. Hawaii has all three in excess, which is why people love to flock there for tropical vacations. The most popular island to visit is Oahu, which is also home to the largest population of locals. But between the crowds and the city buzz, is Oahu really worth the trip? Absolutely!

Oahu is a great Hawaiian destination, especially for your first trip to Hawaii. It has everything: city amenities, culture and history, and even outdoor adventure like waterfalls, hiking, and – of course – surfing.

In early 2021, Mr. V and I made the decision to reschedule a trip to Hawaii that we had planned in 2020 – and obviously cancelled. (It was supposed to be his bachelor party and I was going to tag along to explore on my own.) Instead of our original destination of Maui, we chose Oahu: he had never been, and it had been over a decade since my last trip to this particular Hawaiian island. This Oahu itinerary you’re about to read was informed by our trip and some of my own knowledge about traveling in Hawaii in general.

I’ve checked out the rest of the 5-day Oahu itineraries my fellow travelers suggest, and I’m gonna be honest: there is nowhere enough beach time. Part of the reason you go to Hawaii is to relax and unwind on the beach, right? It certainly was for us! So in my itinerary, I’ve given you busy days of exploring Oahu mixed with time enjoying those pristine Waikiki beaches everyone comes to Oahu to enjoy.

So if you’re ready to head to Hawaii and want plenty of beach time mixed in with your explorations and adventures, read on. By the end of this post, you’ll know how to spend 5 days in Oahu, where to eat and stay, and a few other handy pieces of advice to plan the ultimate Oahu itinerary.

In this post, I promote travel to a destination that is the traditional lands of the Kō Hawaiʻi Paeʻāina (Hawaiian Kingdom) people. With respect, I make a formal land acknowledgment, extending my appreciation and respect to the past and present people of these lands. To learn more about the people who call these lands home, I invite you to explore Native Land.

Oahu Travel Tips

Before jumping into the itinerary, there are a few topics I want to cover first. This section helps answer some common questions so that when you reach the end of my post, pretty much all of your questions are answered! (You can, of course, comment with any other questions you have.)

Oahu vs. Honolulu vs. Waikiki

When planning a trip to Oahu, you might confuse some of the geography, so it’s helpful to clear that up first.

• Oahu is the island. It’s traditionally called “The Gathering Place” since it’s where the ali’i (nobility) used to gather when Hawaii was ruled by Hawaiians.
• Honolulu is the biggest city on Oahu, and the capital of Hawaii. About 35% of Oahu residents live in Honolulu.
• Waikiki is the main neighborhood (basically its own small city) within Honolulu, where you can find most of the tourism infrastructure (hotels, tours) and some of the island’s nicest beaches.

To be clear: Waikiki is not Honolulu; it is part of Honolulu. As you’ll see in my itinerary, there’s more to Honolulu than just Waikiki, and you should get out to explore that part of the city too. And of course, there’s more to Oahu than just Honolulu, so I recommend getting out to explore more of the island too!

When to Visit Oahu

Maybe you already grabbed a good deal on flights to Hawaii, or maybe you are totally flexible on dates up to this point and want to know when to visit Oahu.

In terms of weather, Hawaii and Oahu’s rainy season is between November and March, whereas the sunny season is between April and October. However you might also want to keep crowds in mind when booking: most people visit during the winter months on the Mainland, which are from January to March.

Between the weather improving and escaping the crowds, the best time to visit Oahu is between April and May or between October and November. We might call these shoulder seasons, but they’re actually ideal and the word is getting out that those are great times to visit too. (We made our most recent visit in April 2021, and it was definitely not empty of crowds during that time!)

Getting Around Oahu

Oahu – especially big-city Honolulu – has all the main infrastructure for getting around, including public transportation and private options too. In this post, I recommend the following transportation:

1. TheBus – TheBus is Honolulu’s mass transit system is pretty good for getting around if you’re going somewhere along the main lines.
2. Taxis or Uber – If you need to get around by car and don’t want to take the bus, getting a taxi or Uber is a good option, though can be expensive! Do not use Lyft! We had a terrible time every time we tried to use Lyft and while it was always cheaper, we literally never got connected with a driver any time we tried to use it.
3. Hui or Turo for rental cars – In addition to Turo, the car-sharing service I love, Oahu also has Hui – a local per-hour car rental service similar to Zipcar. This is a great option for renting a car since they have pick-up lots scattered across the city. Hui rentals start from $10/hour and you should reserve at least four weeks in advance. (The major rental car agencies all operate in Honolulu, too.)
4. Biki Bikes for bike sharing – For shorter distances, such as running to Foodland for their delicious poké or riding up to Diamond Head, consider grabbing a Biki Bike. We used this service several times to zip around town during our trip and it’s super easy.

You’ve got plenty of options for getting around Oahu and Honolulu, however you prefer!

What to Pack for Oahu

I already have a specific packing list for Hawaii and you don’t need anything special for Oahu. In addition to clothes and swimsuits and sunglasses, consider packing:

• Reef-safe sunscreen – Hawaii’s reefs are a vital natural resource and normal sunscreen kills them!
• A hat to help protect you even more from the sun
• Water-proof shoes or sandals
• Reusable bags, straws, and water bottles (Hawaii is very strict on single-use plastics!)

Did I forget anything? Oh yeah: be sure to leave space in your luggage for souvenirs!

How to Spend 5 Days in Oahu

To give you a brief glimpse of what my recommended Oahu itinerary looks like, here are the basics:

• Day 1: Arrive & Beach Time
• Day 2: Explore Oahu by Car
• Day 3: Dimond Head Hike & Beach Half-Day (with Optional Parasailing)
• Day 4: Explore Honolulu Beyond Waikiki
• Day 5: Beach Day Before Departure

Ready to dive into the details? Throw on that swimsuit and let’s do it!

Day 1: Arrive & Beach Time

On your arrival date, it’s hard to plan – so let’s make it simple! Once you arrive in Oahu, get an airport transfer, taxi, or Uber to your hotel. Once you’ve settled in, switch into your swimsuit and head to the beach for a bit. You can dig your toes in the soft sand, take your first dip in the Pacific, and watch a gorgeous Hawaiian sunset. (How are they so much prettier than at home?!)

As you start to get hungry, you have a choice for dinner: luau or local. There are several luaus offered in Waikiki pretty much every night, but to be honest, I’ve never done one, I’m not sure they’re worth the money, and I’m not sure about the cultural accuracy of mass-marketing Hawaiian culture. So obviously my vote is local! In this case: local craft beer. There are some great craft breweries across the Hawaiian islands, so pick one for dinner: Maui Brewing Co. has a location in the heart of Waikiki, or you can escape some of the crowds at Waikiki Brewing Company a bit further from “downtown” Waikiki.

Day 2: Explore Oahu by Car

Ready to get out and explore more of Oahu? Some folks recommend doing what I suggest today in 2-3 days but A) that eats into beach time and B) that costs a lot more in rental car expenses! So let’s pack today full and then you can relax in the sand a bit more through the rest of this Oahu itinerary…

Start by picking up your rental car. You could use Turo or Hui; most of the major rental agencies are located out at the airport and not super convenient for daily rentals.

For the first part of this drive, you have some options:

1. If you just want to drive, head east out of Waikiki and drive highway H1 to loop around the southeast part of the island. You’ll pass some cool natural spots if you want to stop, including China Walls and Halona Blowhole.
2. If you want some Hawaiian culture, head north on state highway HI-83 to the Polynesian Cultural Center. You’ll bypass the southeast part of the island.

In either case, you want to end up on the North Shore for lunch. This is Oahu’s top surfing spot, but stick to the shore and seek out lunch instead. A lot of guides recommend one of the North Shore shrimp trucks (there are several), but I recommend Pupukea Grill instead. This food truck makes incredible Hawaiian food with zero tourist-accommodating fuss. I had an insanely good poké bowl and Mr. V had a bowl with poi and kalua pork; we ate at the park overlooking Shark’s Cove and it was pretty much a perfect meal.

A short drive further around the island takes you to the turnout for Waimea Falls. If you enjoy easy hiking/hilly walking, this is a must-do. The Waimea Valley is a tourist attraction: it includes a natural botanical garden, cultural presentations, and a swimming hole at the base of the falls. We didn’t dip in the water (we didn’t realize you could swim there!) but did spend a really nice hour walking around. Give yourself 60-90 minutes for this stop.

Okay, you have a choice now: shave ice or Dole whip? Or maybe both! If you want shave ice, make the drive to Matsumoto Shave Ice in Hale’iwa. This shop is over 70 years old and still serves up some of the best shave ice in the state. (That says a lot because “Hawaiian shave ice” is such a ubiquitous concept!) Be sure to add the condensed milk as that makes it even better.

If you want Dole Whip, plug the Dole Plantation into your phone map. You’ll probably need to queue up to get in the shop and wait again to order this tasty treat, so give yourself plenty of time. If you want, you can spend even more time, they offer tours of the pineapple plantation.

Then it’s time to make your way south across the island, back toward Honolulu. There is no road that circumnavigates the entire island, so heading further west will require backtracking; there are some good hikes on that part of the island though.

As you get closer to Honolulu, you again have a choice: take it easy or, if you’re feeling amibitious, drive the leeward coast. There aren’t many tourist attractions on the west coast of Oahu, and you’ll get a view of how locals live on the island (I’ve never seen so many Hawaiian sovereignty flags!). Again, there are some great views and a few good hikes, but this isn’t a must-do if you’re already tired by this point in the day.

Either way, it’s back to seek out dinner in Waikiki. Grab a reservation for the Hau Tree this night; this restaurant is fabulous and has gorgeous sunset views from the lower patio if you can get a table down there.

Day 3: Dimond Head Hike & Beach Half-Day (with Optional Parasailing)

Rise and shine, sunshine! In Hawaii, the sun is up so you should be up too!

Start the day by making your way to Diamond Head, the cinder cone volcano that looms over the Honolulu area. You can get here by Uber, TheBus, or by grabbing a Biki bike rental (which is what Mr. V and I did). Once you arrive at the Diamond Head entrance area (which will also require walking if you take the bus or bike), you can hit the main trail and start your ascent inside the cone of this sleeping giant.

At the top of Diamond Head, you’ll have 360-degree views of Waikiki, Honolulu, and the southern windward coast of Oahu. This is seriously one of the best views on the island and well worth the effort. Just be sure to get started early in the day because it can get really hot climbing inside the inside walls of the cinder cone as the day progresses.

Next, head back down, grab some lunch; Tiki’s Bar & Grill is kitschy but convenient and has surprisingly good food for lunch. Then set yourself up on the beach. (You might actually want to go reserve your beach chairs before hiking Diamond Head, to ensure you get a good spot.) The rest of the day is at your leisure to relax in the sun, cool off under an umbrella, and take a few dips in the ocean. Don’t forget to stay hydrated, especially after hiking in the morning!

If you want to kick it up a notch, you could also try parasailing at some point during the afternoon. This was on my 40 Before 40 list and so Mr. V and I decided to splurge and do this on one day of our Oahu itinerary. We were staying at the west end of Waikiki so right near the marina where parasailing tours leave.

Parasailing was easily one of the highlights during a great trip. Riding the boat gives you great views of Waikiki and Diamond Head (hey, you were up on top of that earlier today!) and the parasailing ride is really thrilling. I was definitely hooked – I’d go again in a heartbeat!

After the sun goes down, it’s time for dinner; I recommend grabbing food somewhere in Waikiki. Hideout at The Laylow is a perfect spot for a casual dinner that’s centrally located but not a tourist chain.

Day 4: Explore Honolulu Beyond Waikiki

After an adventurous morning and relaxing afternoon on the beach (possibly punctuated by more adventure!), it’s time to get out and explore the rest of Honolulu. So far, most of your time in Honolulu has been spent in Waikiki, but as I mentioned earlier, that’s one small part of this big metropolitan city.

Note: This day’s plan is best if you see a rainy day forecast. You can certainly re-order the days in this Oahu itinerary to accommodate rain in the forecast!

Experience History & Solemnity at Pearl Harbor

Rise and shine to make your way to the historic site of Pearl Harbor; I recommend booking another Hui rental car for this day, as it makes the logistics way easier. You need 12 hours of rental.

The Pearl Harbor National Memorial opens at 7am daily and is one of the most-visited attractions on Oahu, so I recommend arriving early. Additionally, about half of the Pearl Harbor memorial is exposed to the sun and it can get hot fast, so starting early will help you escape the heat of the day.

It takes about 3-4 hours to visit Pearl Harbor, including a ferry ride to and from the USS Arizona Memorial. Definitely grab a reservation for the USS Arizona Memorial program, as you can end up wasting a lot of time waiting for a spot on the ferry otherwise (we had to wait about 45 minutes). The National Park Service has a handy page that answers all your questions about this part of visiting Pearl Harbor. Visiting Pearl Harbor is a solemn place – the USS Arizona is considered a national cemetery and human remains are still located on-site –, so remember to be respectful.

Visit The Bishop Museum

From Pearl Harbor, drive to The Bishop Museum. Along the way, make a stop at Fresh Catch, which is near Pearl Harbor. I was recommended this poké spot by local Hawaiian blogger friend Rachel and she was right that they have some of the best poké in town. You can eat your food right in the tiny takeaway shop or out by your car, or head down the street to Neal S. Blaisdell Park for a short picnic.

The full name of The Bishop Museum is The Bernice Pauahi Bishop Museum, and it’s also the Hawaiʻi State Museum of Natural and Cultural History. Basically, it’s the museum to visit on Oahu if you’re going to spend any time at a museum. And I get it – spending time at a museum during your paradisical vacay may not interest you. But as a traveler in Hawaii, you have an obligation to learn about the land you’re visiting; there’s literally no better place to do this than The Bishop Museum.

Explore the galleries to learn more about Hawaiian history, culture, and society; there are some incredible artifacts here including carvings, artworks, traditional clothing, and so much more. Additionally, there are exhibits focused on science, including a kid’s building and a planetarium. Y’all know how much I love a good planetarium!

Dinner & Drinks in Downtown Honolulu

No, I don’t mean you should head back to Waikiki for dinner. Let’s go to the real Honolulu, the neighborhood where locals dine and enjoy living on this awesome island. To get here, you probably want to catch another Uber or use your Hui rental car.

For dinner, there are some great options; Mr. V and I went to Lucky Belly (it was actually my birthday dinner, so I got to pick!). They had great ramen and delicious, inventive cocktails – you will feel like you’re sitting in a posh SF or NYC restaurant and almost forget that Hawaii is so far from the Mainland. There are plenty of other good options in the area too if ramen isn’t your thing; I used Yelp to explore options.

After dinner, head down the street to Skull & Crown Trading Co. This is one of Hawaii’s new-age tiki bars (and one of only two in Honolulu, the other being the historic La Mariana Sailing Club). I recommend getting reservations (inside not outside) if you can; Skull & Crown is a popular spot and the drinks are freakin’ awesome. The decor and experience add on top of that making this a really unique experience to have during your Oahu itinerary.

Day 5: Beach Day Before Departure

Assuming you depart at some point on today – your final day in Oahu – I’d lay low and enjoy a last little bit of sun before you have to head to the airport. Grab a spot on the beach or rent a few chairs again (literally always worth the money!) and let the world wake up around you.

Or you could be like Mr. V and I and go for a long walk on the beach. We spent the time reminiscing about our trip and starting to plan the next one. 😂

You may have time for lunch before leaving; if you do, I’d grab something good near your hotel or vacation rental. Then it’s back to your accommodation to grab your luggage and head to the airport. We used the same driver (a taxi who also offered private transfers) to get back to the airport for a flat rate. The Oahu airport is pretty big so there are also food options here if you didn’t get lunch before heading out.

Leaving Hawaii is always hard – it’s easy to see why people fall in love with this place and move here. So don’t be surprised if you spend takeoff with your face pressed against the window, looking down on the islands as they pass beneath the plane. Just remember: now that you’ve been once, you can definitely plan a return trip to Hawaii!

Where to Stay for 5 Days in Oahu (4 Nights)

For your four nights in Oahu, I recommend staying in Waikiki. There is literally every hotel brand you can think of in Waikiki, but after my visit, I feel comfortable recommending:

• The Hilton Hawaiian Village – Right on the beach, this huge hotel complex has everything you need. From $221 per night; book on Booking.com or Hotels.com.
• The Royal Hawaiian Hotel – A beautiful pink hotel on the beach, this luxury throwback is worth the splurge. From $369 per night; book on Booking.com or Hotels.com.
• Kaimana Beach Hotel – Another spot right on the beach, this hotel has the best beach-y vibes and the Hau tree restaurant is in the lobby. From $134 per night; book on Booking.com or Hotels.com.

There are also tons of vacation rentals. We stayed at this Airbnb, which was a decent option, and here are a few others I like the look of:

• This one-bedroom apartment is in the building next to where we stayed and has a fantastic balcony view. From $113/night; book on VRBO.com.
• This 14th floor beachfront flat is cozy but you can’t find a better location. From $229/night; book on VRBO.
• At the higher end, this 2-bedroom apartment has stunner views and fits a full family. From $349/night; book on VRBO.com.

But in the event none of these are right for your budget or style, there are literally so many other options to choose from. With enough advance planning, you can certainly find something to finalize your Oahu itinerary

And with that, you have everything you need to plan an incredible trip for 5 days in Oahu. Have any questions about planning your Oahu itinerary for 5 days? Let me know in the comments!

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