Perfect 4 Day Itinerary for Oahu, Hawaii

Perfect 4 Day Itinerary for Oahu, Hawaii

March 2021

Perfect 4 Day Itinerary for Oahu, Hawaii

Hawaii was our COVID escape hatch in 2021. After work over 70 days in a row at a COVID Vaccine MEGA site, I was never in more need of a vacation. Originally, our Hawaii vacation was only going to include Maui but as the different iterations came to be – in planning this trip four separate times to do COVID cancellations – we realized this could be a great opportunity to experience Aulani, A Disney Resort and Spa – somewhere we did not think we would be visiting for awhile. It was a fun thing to discuss and when finalizing this itinerary, it made sense to split our time and experience both Maui and Oahu. Since Oahu did not require COVID testing when traveling between islands at the time, we arranged our itinerary to visit Maui first then midweek fly to Oahu.

There is so much to do on all the different Hawaiian Islands so it is definitely worth exploring them. Plus flights between the islands are frequent, easy, and affordable. Now, let’s plan a perfect trip to Oahu!

Know before you go

  • You will most likely want a car for some or all of your time on Oahu. While it is not a huge island, everything is paced on and primarily along the perimeter of the island so you will want a flexible way to get around. Unless you plan on hanging at a resort the entire trip, look into renting a car. Do this early in your trip planning process as island resources are limited – this includes rental cars.
  • Credit cards are accepted everywhere as well and tours can be booked in advance online so your need for cash is limited but always have some for tipping.
  • Plan ahead as excursions, dining reservations, and accommodations fill up quickly.
  • Island hopping is easy and very common! If you have more time off, add another island like Maui to the trip.

Where to stay?

There are many different parts of the island you can stay in. Many people like to stay in Honolulu and there are many Airbnbs and hotels around the area. For those that want to be in the action with access to city and/or night life, Waikiki is very popular. We were looking for something a bit different and stayed at Aulani, A Disney Resort & Spa which was our first “resort” stay experience. And I will say, when we go back, we will 100% be staying here again. This area of the island is also very relaxed and quite so I could definitely recommend the Ko’Olina area.

Get the Free DESKRIB Guide “How to Find the Perfect Airbnb” – sign up here

What is there to do?

  • Beaches – Probably the most obvious thing to do on a Hawaiian vacation! And there are a ton of beaches. Depending on where you are located on the island, you will have a variety of beaches to choose from.
  • Hiking – Hiking on the island is amazing. I wish we had more time to conquer some of the trails. Word of advice – check the weather carefully before you embark on a long trail – it is quite different than that of the coastline!
    • Ka’ena Point Trail
    • Nuʻuanu Pali Lookout
  • Water activities – You must get in the water while in Oahu! There are a ton of options from renting equipment to do it yourself to going with a tour group. Snorkeling at Hanauma Bay is particularly popular but you can swim at any beach.
  • Whale watching – If you are lucky enough to be visiting during whale watching season, this is a must! We went at the end of February and had some incredible whale encounters both from a boat and from a kayak.
  • Pick a tour – there are various tours offered around the island that you can take advantage of.
    • Dole Plantation
    • Go on a coffee tour with companies like Waialua Estate Coffee and Chocolate or Green World Coffee Farm
    • Movie Fan? Visit “Hawaii Backlot Tour” at Kualoa Ranch where you can see filming locations for many famous movies including Jurassic Park.
    • Manoa Chocolate Hawaii for a chocolate tasting
  • Pearl Harbor National Monument is something everyone should visit when traveling to Oahu. There is immense history here and the museum is displayed very well in addition to the boat ride out to the monument itself.
  • Visit Downtown Honolulu
  • Take a drive to the North Shore
    • Watch surfers at Banzai Pipeline or take a surfing lesson yourself
    • Explore the rain forest and waterfalls at Waimea Valley
    • Paddleboat down the ‘Anahulu River
    • Enjoy the towns along the way such as Haleiwa
    • Make sure to stop at some of the epic beaches on this side of the island

What to eat?

I have to say I was so surprised by how good Oahu food was and it remains some of the best food we have had in awhile. While there are many reason to return to Oahu, the food certainly is one of them.

  • The famous Leonard’s Bakery – PRO TIP: there are “Malasadamobiles” scattered throughout Oahu and there is a closer one than driving to downtown Honolulu – you can avoid the crowds there!
  • Helena’s Hawaiian Food is a popular location, with tourist and locals, for authentic Hawaiian cuisine. wish we had time to eat here again but this time we would do double short rib! Kono’s north shore also serves up some great Hawaiian BBQ and an epic burrito. Waiahole Poi Factory is a staple on the island where it served as a poi factory for 70 years before adding BBQ to the menu.
  • Get your acai bowl fix at Island Vintage Coffee and Haleiwa Bowls.
  • Kamehameha Hwy food trucks, especially for Giovanni’s garlic shrimp.
  • Matsumodo Shave Ice is an establishment on Oahu and serves up excellent shave ice.
  • Eighty Chicken Sandwiches where they literally make eighty chicken sandwiches a day – and they sell out fast so get here at open if you want to try this. Nearby is also Da Bald Guy which is a very well rated food truck.
  • Ken’s Fresh Fish for (as the name implies) some of the best fresh seafood.
  • Ted’s Bakery was one spot we did not make it to on this trip that we will definitely hit on the next one.
  • There are also some incredible breweries on the island – Broken Boundary Brewery, Waikiki Brewing Company, Hanale by Islander Sake Brewery to name a few!


Putting it all together, here is an example itinerary of how to structure a five day trip to Maui. As always, feel free to use this as a guide and insert your preferences along the way.

Day 0Arrival to Oahu
Day 1Hike of choice
Diamond Head Crater Trail
Makapu’u Point Lighthouse Trail
Day 2North Shore – water activity
North Shore – Waimea Valley
Day 3Downtown Honolulu
Pearl Harbor National Monument
Day 4Tour of choice
Day 5Depart

To see our complete itinerary – here!

See all blog posts from Hawaii – here!

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