O’ahu 5-day Travel Guide

Have you always dreamed of traveling to O’ahu, Hawaii? Are you not a fan of planning? Or perhaps, you don’t mind planning but you simply don’t know where to start? No worries! I got you fam!

I had the most amazing experience in Hawaii. I spent five days in O’ahu before heading off to Maui and spending four days there. It was a dream and there was definitely much more to see and do on the island that I was unable to get around to. If you have about as much time as I had, I highly recommend the following itinerary. If you have more time, feel free to use my guide as a baseline and add to it!


Where to fly?

The major airport on the island is Daniel K. Inouye International Airport, code HNL located in Honolulu.

When to go?

The weather in Hawaii is always warm due to its tropical climate so you can never really go wrong on the temperature front. I wanted to beat the summer crowds that tend to flock in July and August as well as avoid both the hurricane and rainy seasons so I visited in May. The weather was perfect almost the entire time with the exception of one afternoon of showers which ended up being the perfect time to sleep off some of my jet lag.

Where to stay?

I recommend staying in one of the many hotels in Waikiki. There’s so much to do in O’ahu, I rarely spent time in the hotel room so I think paying extra to stay in a resort is unnecessary. It is super important to rent a car so you can explore other parts of the island. However, I enjoyed spending evenings bar hopping and dining in Waikiki. There are many options for great seafood, live music, and drink specials all within walking distance of each other.

What to do?

Here’s my recommended five-day itinerary:


Day One:

  • Fly into HNL airport
  • Rent a car from the airport
  • Drive to Waikiki
  • Check into hotel
  • Walk to the beach to catch a quick view
  • Go to ABC store to stock up on Gatorade and alcohol (obviously)
  • Relax to recover from the long day of travel
  • Go to a Happy Hour
  • Recommendation: Sky Waikiki
    • Amazing rooftop location!
    • Only had drinks here, Happy Hour prices are good and drinks are tasty!
    • Amazing view!


  • Grab dinner
  • Recommendation: Buho Cocina y Cantina
    • This place is right beside Sky Waikiki
  • Head back to the hotel


Day Two:

  • Eat a big breakfast
  • Visit The Pearl Harbor National Memorial first thing in the morning 
    • Opens at 7am
    • Budget 2.5 hours for your visit
    • Free entry
    • No bags or purses allowed! Lockers provided for a $5 fee
  • Drive to Nānākuli to visit the Mermaid Caves and relax on the beach


  • Drive back to Waikiki and grab lunch at Ono Seafood for a delicious poke bowl. Ono Seafood is a local, super casual, takeaway spot with a few picnic tables out front, but no indoor seating. This is a MUST!

Ono Seafood

  • Take a break or a walk along the beach in Waikiki
  • Grab dinner
  • Recommendation: Explore The Street Food Hall
    • Try one or more of the restaurants inside to keep day two casual.
    • Look out for drink specials during happy hour and late night hours.
  • Head back to the hotel


Day Three:

  • Eat a small breakfast
  • Head to Diamond Head Crater to hike the summit (arrive before 8:00 am)
  • Drive to Hale’iwa in North Shore
  • Grab an early lunch
  • Recommendation: Farm to Barn
    • This is the cutest place EVER!
    • Charming cafe with a relaxing atmosphere and a healthy menu.
    • Try the Vegan Poke Bowl.
    • Note: Farm to Barn is closed on Monday, open from 9am to 3pm from Tuesday to Saturday and 9am – 2pm on Sunday.

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  • Head to Hale’iwa Beach Park
    • Note: there are rip tides in this area of the beach, therefore, we did not swim and there are signs urging people not to swim here. This beach is perfect for laying out and feeling the breeze. If you’d like to swim, consider another beach. There are other areas of Hale’iwa and North Shore good for surfing and other water sports. Please read the signs and be cautious to ensure you are in the right section for the activities you want to do.
  • Grab a late lunch
  • Recommendation: The Beet Box Cafe Hale’iwa
    • Delicious organic vegetarian restaurant with fresh healthy warm food options as well as smoothies and acai bowls.
    • Breakfast served all day!
    • Open every day from 7am to 4pm.
    • Try the Portabella Stache’wich with a Ginger Lemonade 
  • Grab Hawaiian Shave Ice from Matsumoto Cafe to satisfy your sweet tooth!


  • Drive back to Waikiki to rest
  • Grab a late dinner
  • Recommendation: Duke’s Waikiki
    • Try the fish sandwich or the sauteed mac nut and herb crusted fish of the day
  • Head back to the hotel


Day Four:

  • Eat a large breakfast
  • Hike Koko Crater Railway Trailhead (begin before 7:30 am)
  • Drive to Kailua
  • Grab a big brunch
  • Recommendation: Cinnamon’s
    • Open every day from 7am – 2pm
    • Grab a table in the gazebo or in the courtyard
  • Go to Kailua Beach Park Calm, beautiful, clear water, safe for swimming, soft sand


  • Drive to the Makapu’u Lookout
    • If you have energy, walk the lighthouse trail
  • Drive back to the hotel, relax for a bit
  • Grab dinner
  • Recommendation: Hula Grill Waikiki
    • Live music, nice beach view, good cocktails, good fish tacos, good service
  • Go back to the hotel


Day Five:

  • Grab breakfast
  • Head to Kaka’ako Waterfront Park
  • Walk around SALT shopping center
    • A very hip and highly rated shopping center
  • Grab lunch in SALT shopping center
  • Recommendation: FISH
    • Cool industrial style outdoor restaurant
  • Do a chocolate tasting at Lonohana Chocolate Tasting Bar
  • Enjoy a beer flight at one of the many breweries
  • Recommendation: Village Bottle Shop and Tasting Room

Beer Flight

  • Head back to Waikiki
  • Take a sunset booze cruise
  • Recommendation: Na Hoku II Catamaran
    • Open bar
    • Gorgeous sunset views
  • Grab dinner
  • Recommendation: Find a random local and ask them where you should eat! Try whatever they recommend!
  • Head out for drinks or back to the hotel to end your trip in O’ahu


For more information and tips on O’ahu, visit my post: “5 Tips for an Unforgettable Trip to O’ahu”

For more information on the Diamond Head Crater Hike click here!

For more information on the Koko Crater Railway Trailhead click here!

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