A Complete 5 Day Itinerary to Oahu, Hawaii: See the Whole Island!

To be honest with you when we went to Oahu, Hawaii last year, I didn’t think I was going to like it (we had to go for a wedding). I wasn’t that into a Honolulu / Waikiki type of vacation, it seemed to lux and tourist driven for me. But boy was I wrong because we loved it. It was because instead of staying in the Honolulu core, we treated ourselves with your credit card points (shoutout to RBC’s Points System) to a car rental and got to see the entire island in all its glory. Honolulu wasn’t my favourite, it did, however, host some of the best places to eat, but regarding things to do and things it sees in Oahu, Hawaii – your better off doing a bit of traveling around the island.

Oahu, Hawaii was probably one of my best-planned vacations because we were going for 8 days for a wedding. I didn’t think I was going to have that great of a time, so I ultra planned it to make sure we did, and I am glad I did because that got me to discovering some of the less touristy places on Oahu, Hawaii.

Here is my Complete Guide to Oahu, Hawaii: How to see the island in 5 Days, eat at the best places and do the coolest things!

Oahu, Hawaii Day 1: THE EAST SIDE

Have a Wonderous Breakfast on the East Side at Over Easy

Address: 418 KUULEI ROAD 103, KAILUA, HAWAII 96734

Shoutout to the best breakfast place name and to the fact that I can’t make my eggs over easy. My biggest recommendations for Hawaii is get up with the locals, get up early, this place opens at 7 am and is undoubtedly busy during peak times.

 Lanikai pillbox hike view point oahu, hawaii

Work off Breakfast with a Moderate Hike Up the Lanikai Pillbox Hike

Address: Pillbox Hike, 265 Kaelepulu Dr, Kailua, HI 96734, USA

Be warned, it’s either a drop-off or street parking that can be semi-hard to find if you are going during a peak period. But like all hikes you can do in Oahu, you won’t regret it, the view was spectacular. This was easily the best value for effort hike we did. Meaning that it was the best amount of effort for the best view imaginable.

Reward Yourself With Brunch at Cinnamons

Address: 306 S Kalaheo Ave, Kailua, HI 96734, USA

If you are still digesting breakfast, then first you might want to reconsider all the food stops I put you for on this itinerary. But you gotta eat a Cinnamon’s and you

Go To Oahu Prettiest Beach, Lanikai Beach

kanikai beach oahu hawaii

Address: Lanikai Beach, Kailua, HI 96734, USA

The mistake we made was going here first and comparing every other beach we went to, to this one. Actually no it wasn’t a mistake, cause knowing how pretty it was had us going back over and over again.

Opt For A Lighter Lunch at Kalapawai Market

Address: 270 Kuulei Rd #105, Kailua, HI 96734, USA

You might not even be hungry from the heavier breakfast and brunch options I provided, but you might be hungrier a little later during the next activity! So grab some sandwiches and sweets and be on your way.

Check out Bellows Field Beach Park

Address: 220 Tinker Road Waimanalo, Hawaii 96795

You could go back to the gorgeous Lanikai, or you can check out something new and go to Bellos Field Beach Park.

After a Day of Beach Have Dinner at Rai Rai Ramen on the East Side of Oahu, Hawaii

Address: 124 Oneawa St # 1, Kailua, HI 96734, USA

Indulge in some rich broths for dinner to warm your insides.

For a Sunset Walk

Either pick one of the previous beaches or try to race you way back up the pillbox height, your in Hawaii so make sure you take the extra time to enjoy the sunset!

Oahu, Hawaii Day 2: The North Shore

Grab Some Sort of Acai Bowl from Banzai Bowls

Address: 59-186 Kamehameha Hwy, Haleiwa, HI 96712, USA

Acai bowls are the staple of Hawaii and to be real eating them for breakfast makes be feel like I started my day off right!

Just Walk Around Haleiwa Town and Watch Them Surf

Go for a stroll around the town that is known worldwide for it’s surfing.

Indulge for Brunch at Dat Cajun Guy

Address: 66-472 Kamehameha Hwy, Haleiwa, HI 96712, USA

Since we ate a healthy breakfast, it’s time to indulge at brunch at Dat Cajun Guy, not that you need a reason to indulge you on Vacation. But some people I get don’t like to eat too heavy until later in the day. And later in the day it is 😀

Ethier Learn to Surf or Go Snorkeling at Sharks Cove

Go to the beach, rent a board and ask someone to teach you the basics of riding. It’s gonna be hard, you might hate it but at the end of the day, at least you can say you did it. But if that’s really not your thing, opt to snorkel at Sharks Cove instead.

giovanni shrimp truck north shure

Eat a pound of garlic butter shrimp from Giovanni’s Shrimp Trucks

Address: 66-472 Kamehameha Hwy, Haleiwa, HI 96712, USA

Drive there, stop there and eat. Even if your still full, you’ll somehow make room. I believe in you.

Activity Swim under Waimea Falls

Address: 59-864 Kamehameha Hwy, Haleiwa, HI 96712, USA

I hope you were able to rest a tad, but hike through the Waimea Falls to be met with a dip in the fresh water is the ultimate way to end the day.

Grab Some Poke Bowls from a Local Place

I don’t really think you can go wrong with Poke Bowls, well if the fish smells off you probably shouldn’t. Anyway, your gonna be smelling and sticky from your hike so grab some bowls to go and head off to a beach or home or whatever.

Wash off the Day at Sunset Beach

Address: Pupukea, HI 96712

Wash off the day and end your day my watching the sunset at Sunset beach, I could picture a better ending to the day.

Oahu, Hawaii Day 3: The South Bay

Have Breakfast at the Hotel or Local Coffee Shop

You’re waking up early, depending on where you are on the island you want to leave your hotel at 6 am to get to your destination before 7 am. So order breakfast in or buy something the night before at the ABC market.

hanauma bay oahu hawaii

Start Your Day Snorkeling at Hanauma Bay

Address: Hanauma Bay, Hawaii 96825, USA

It’s early and hopefully, it’s not Tuesday, cause they are closed on Tuesday. Getting here before 7 am has many benefits, one being its free to enter and two is that you get parking and three it’s not as crowded. Also, pro tip is that go all the way to the end of the beach.

Brunch Island Brew Coffeehouse

island brew house coffee oahu hawaii

Address: Hawaii Kai Shopping Center, 377 Keahole St, Honolulu, HI 96825, USA

The food is tasty here and the options are great, you can grab away filling acai bowl to keep you feeling healthy or a waffle spread just because you can!

Climb Up a Million Stairs on the Koko Head Trail

koko head trail oahu hawaii

Address: 7602-, 7604 Koko Head Park Rd, Honolulu, HI 96825, United States

This is nature’s stairs on a whole new level. It’s nothing but stairs and it goes on and on and on, but let me tell you, the view was incredible so if you just power through it, you’ll be facing a great reward.

Grab Some Poke Bowls from Ono Seafood

Address: 747 Kapahulu Ave, Honolulu, HI 96816, USA

Chances are you are already wipe out from the day, but it’s far from over you productive people you. Grab some poke bowls and head to the beach to take a nap.

Go to The Closet Beach

Check out: Waialae Beach Park Address: 4925 Kahala Ave, Honolulu, HI 96816, USA

Find you yourself the near beach to nap on, just don’t forget sunblock!

Eat at an American Classic: The Cheesecake Factory

Address: Royal Hawaiian Center, 2301 Kalakaua Ave, Honolulu, HI 96815, USA

The one on the strip gets busy, yes I realized that there are a million other better restaurants but if are visiting Hawaii and you aren’t from the states then like me you don’t get Cheesecake Factory and it’s millions of options at home.

After Dinner Just Stroll Around the Strip

One of the favorite things to do on vacation is just walking around and people watching. Watch the street performs, window shop, grab dessert, and watch a live show.

Oahu, Hawaii Day 4: Honolulu, Hawaii

Stop by the Classic Honolulu Coffee for Breakfast and Coffee.

Honolulu Coffee has gone international, I know they just opened a few locations here in Vancouver, so make sure to visit the spot that everyone raves about!

Make a Visit to Pearl Harbour

Address: 1 Arizona Memorial Pl, Honolulu, HI 96818

Because you can’t go and not visit.

Head Back to Honolulu’s for Brunch Goofy’s

Address: 1831 Ala Moana Blvd., Suite 201 Honolulu, Hawaii 96815

Deliciousness, pure and amazing deliciousness. Make sure you add this to your must eat in Honolulu list.

Beach it to Waikiki Bay

Waikiku beach honolulu oahu hawaii

Address: Waikiki Beach, Honolulu, HI 96815, USA

There are a bunch of beaches, so walk the water, set down your towels and bask in the sun!

Eat Lunch at Marukame Udon

udon honolulu oahu hawaii

Address: 2310 Kuhio Ave #124, Honolulu, HI 96815, USA

This place gets a nice long nice, that’s how we knew it would b good, because we shall them bring out the velvet ropes, we wanted to have lunch at heavenly but they already had a super long line so we opted to go here instead, I guess not everyone see udon has the perfect lunch meal

Mall Shopping and Shopping on the Strip

Address: 1450 Ala Moana Blvd, Honolulu, HI 96814, USA

After days filled out adventure, it’s time to fill your materialistic soul, I am not one to judge because mine is here and thriving. Either shop on the strip or hit up the Ala Moana Center for some amazing shopping. PS rumor has it, designer goods are slightly cheaper in Hawaii compared to other places in the USA!

Find Your Favorite On The Strip to Have Dinner At

After a nice afternoon of shopping drop your bags off at the hotel and head over to the strip and pick a place that looks good. Make sure you read the review because some places can be tourist traps but for the most part we enjoyed our random pick!

If It’s Friday Watch the Fireworks on boardwalk

Address: 2005 Kalia Road, Honolulu, Hawaii, 96815, USA

I really hope it’s a Friday the night you find yourself on the strip because you can now just mosey on over to the Hilton Hawaiian Village and watch the fireworks with your ice cream in hand.

Oahu, Hawaii Day 5: End on The West Side

Have Breakfast at Heavenly Island Lifestyle

Address: 342 Seaside Ave, Honolulu, HI 96815, USA

We ate here the most because it was so good. Breakfast, Lunch or Dinner Heavenly has you covered if you are looking for a food spot in Oahu, Hawaii!

Go for a drive and Check all the View Points Drive Along the Way

oahu hawaii lookout point

All the viewpoints are amazing, so make sure you drive around the entire island (it’s not that big) and stop at all the view points, you are either going to met with endless ocean or a lush terrain, either way, you won’t be disappointed to what Oahu, Hawaii has to offer. Since are are ending on the West side, make sure your driving eastward.

Have Pie for Brunch Ted’s Bakery

Address: 59-024 Kamehameha Hwy, Haleiwa, HI 96712, USA

Get some chocolate pie, you deserved it.

Swim or See The Turtles at Laniakea (or Turtle) Beach:

Address: 574, 61-574 Pohaku Loa Way, Haleiwa, HI 96712, United States

I like turtles.

For Lunch Grab Burgers at Seven Brother at the Mill

seven brothers on the mill oahu hawaii

Address: 56-565 Kamehameha Hwy, Kahuku, HI 96731, USA

Burgers are my favorite food, and if they are yours as well then eat here, because it’s amazing. And also Oahu, Hawaii’s best burger spot.

Go Kayaking

You have explored a lot of the land, now it’s time to explore the waters so go Kayaking and have some FUN!

Grab Dinner Somewhere on the Beach

dinner views oahu hawaii

So as you continue your drive around the island, stop for dinner somewhere along the beach.

End The Day At KO’OLINA LAGOONS for an Epic Sunset

Address: 92-100 Waipahe Pl, Kapolei, HI 96707, USA

Bask in the glory that is Oahu, Hawaii and don’t forget your dessert!

And that brings me to the end of my Complete Guide to Oahu, Hawaii – I hope you enjoyed, I really love writing this post because it really let me reflect on all the places we went last year! If are headed to London, England by any chance, check out my Complete Guide to London, England: Free Things to Do and Cheap Places to Eat!

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8 Comments

  1. February 6, 2017 / 9:29 pm

    This is a great guide to Oahu! You went up to the Lanikai Pillboxes! I want to do that so badly! I haven’t spent much time on Oahu, but you really created a fantastic itinerary on how to make the most during a short stay. <3

    • Jennifer
      February 8, 2017 / 8:15 am

      Thank you, I before I went I was determined to make the most out of the trip and tried to plan everything down to a T!

      I really hope you get to visit the Lanikai boxes one day soon it was defs the highlight of the trip!

  2. February 7, 2017 / 1:40 pm

    Looks and sounds amazing! Love all the food recommendations too – I base all my itineraries around food. 🙂

    • Jennifer
      February 8, 2017 / 8:16 am

      Is there anything other way to plan any trip 😀

      good food = food mood!

    • Jennifer
      February 8, 2017 / 8:16 am

      I am happy to have helped, thank you for stopping by, & I like your blog too!

  3. Megan
    July 17, 2017 / 4:56 pm

    Thanks so much for the guide, I’m using a lot of these for a trip this fall! Question for you: where did you stay during the week? Did you hop from town to town or stay in Honolulu and drive around?

    • Jennifer Bui
      August 12, 2017 / 4:48 pm

      Hey Megan!

      We stayed in Honolulu at the Hawaiian Prince Hotel and rented a car to drive around! Send me pics on your adventures!

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