A Complete 5 Day Itinerary to Oahu, Hawaii

Updated September 2019

To be honest with you when we first went to Oahu, Hawaii in 2016 I didn’t think I was going to like it but we “had” to go for a wedding. I wasn’t that I was against having a beach vacation, but rather Honolulu/Waikiki seemed over-hyped, extremely luxurious and very tourist-driven for me. I can be the first to admit that I wrongfully judged a book by its cover – a covered I gave it may I add.

pinterest image - "5 days in Oahu"

But I so glad to tell you how wrong I was because we loved it. Every single part of it. We went back again in 2018 and are planning another trip in 2020. One of the reasons I think we loved it so much is because instead of staying in the Honolulu core, we rented a car got to see the entire island in all its glory. Honolulu wasn’t my favourite area, but it did, however, host some of the best places to eat. Regarding things to do and things to see in Oahu, Hawaii – your better off doing a bit of travelling around the island.

Oahu, Hawaii was probably one of my best-planned vacations because I really didn’t think I was going to like it so I made sure to really dig into things we could do. We were here for 1 week with 5 days of explore (plus 1 travel day, 1 wedding day).

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!

A Complete 5 Day Itinerary to Oahu, Hawaii

Day 1 in Oahu, Hawaii: Exploring the East Side

Lanikai pillbox hike view point oahu, hawaii

  • Breakfast at Over Easy Address: 418 KUULEI ROAD 103, KAILUA, HAWAII 96734
  • Lanikai Pillbox Hike  Address: Pillbox Hike, 265 Kaelepulu Dr, Kailua, HI 96734, USA – Hike Up the Lanikai Pillbox Hike –  Be warned, it’s either get dropped off or get there early for street parking that can be semi-hard to find. 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.
  • Brunch at Cinnamons Address: 306 S Kalaheo Ave, Kailua, HI 96734, USA
  • Lanikai Beach Address: Lanikai Beach, Kailua, HI 96734, USA – Go To Oahu Prettiest Beach, Lanikai Beach 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.
  • Kalapawai Market Address: 270 Kuulei Rd #105, Kailua, HI 96734, USA It’s cute and you can grab some snacks.
  • Field Beach Park Address: 220 Tinker Road Waimanalo, Hawaii 96795 – Check out Bellows Field Beach Park or you can go back to the gorgeous Lanikai. Check out something new and go to Bellos Field Beach Park.
  • Dinner at Rai Rai Ramen Address: 124 Oneawa St # 1, Kailua, HI 96734, USA
  • Sunset Walk Address: Any Beach 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!

Day 2 in Oahu, Hawaii: The North Shore

giovanni shrimp truck north shure

  • Breakfast Acai Bowl from Banzai Bowls Address: 59-186 Kamehameha Hwy, Haleiwa, HI 96712, USA
  • Walk Around Haleiwa Town
  • 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 πŸ˜€
  • 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.
  • 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.
  • 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 freshwater 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.

Day 3 in Oahu, Hawaii: The South Bay

koko head trail oahu hawaii

  • Snorkeling at Hanauma Bay Address: Hanauma Bay, Hawaii 96825, USA – It’s early and hopefully, it’s not Tuesday, because they are closed on Tuesdays. Getting here before 7 am has many benefits, one being it is free to enter and two is that you get parking and three it’s not as crowded. Also, a pro tip is that go all the way to the end of the beach there will be less people set up here as the day goes on.
  • Brunch Island Brew Coffeehouse 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 up the Koko Head Trail Address: 7602-, 7604 Koko Head Park Rd, Honolulu, HI 96825, United StatesThis 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.
  • 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 Waialae Beach Park Address: 4925 Kahala Ave, Honolulu, HI 96816, USA Find you yourself the near beach to nap on, just don’t forget the 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.
  • Explore 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.

Day 4 in Oahu, Hawaii: Honolulu, Hawaii

Waikiku beach honolulu oahu hawaii

  • Honolulu Coffee or Island Vintage Coffee for Coffee, they’re everywhere and its a staple
  • Visit to Pearl Harbour Address: 1 Arizona Memorial Pl, Honolulu, HI 96818
  • Brunch at 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 Beach Bay Address: Waikiki Beach, Honolulu, HI 96815, USA
  • Eat Lunch at Marukame Udon Address: 2310 Kuhio Ave #124, Honolulu, HI 96815, USA
  • Shop at Ala Moana Center 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!
  • Dinner on the Strip – 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.

Day 5 in Oahu, Hawaii: The West Side

oahu hawaii lookout point

  • 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 Along the Way – 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 at Ted’s Bakery Address: 59-024 Kamehameha Hwy, Haleiwa, HI 96712, USA – Get the chocolate pie, you deserved it.
  • Swim or See The Turtles at Laniakea Beach aka Turtle Beach Address: 574, 61-574 Pohaku Loa Way, Haleiwa, HI 96712, United States
  • For Lunch Grab Burgers at Seven Brother at the Mill 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!
  • 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!
  • Grab Dinner Somewhere on the Beach – So as you continue your drive around the island, stop for dinner somewhere along the beach.

Where to Stay in Oahu, Hawaii

pinterest image - where to stay in oahu - best hotels 2019

Best Neighbourhood for Hotels in Oahu, Hawaii

In all honesty, if you book a hotel the best bang for you buck would definitely be in the Honolulu/Waikiki area, I notice that Airbnb’s in the area for the tendency to be pretty competitively priced against hotels without all the amenities/security. If you wanted to stay in the North Shore however then I would recommend looking into Airbnb.

Best Hotels in Oahu 2019

My favourite website to book hotels is Agoda, I have been using it for years and have used it to book our previous two stays and will most likely use it to book our next stay unless I can rack up enough credit card points and therefore I will be using my credit cards booking site. In 2016 we had a pretty good stay in Prince Waikiki (offered free parking) and in 2018 we had an amazing stay at the Modern Honolulu and my dream stay would have to be at the Kahala Hotel & Resort – it’s actually where the wedding was held and fun fact we actually saw Pierce Brosnan here too!

Here are a few best mid-luxury / luxury hotels  in Honolulu

  1. Moana Surfrider, A Westin Resort & Spa
  2. The Laylow, Autograph Collection
  3. ‘Alohilani Resort Waikiki Beach

Should You Rent a Car Oahu, Hawaii?

My answer, in short, is yes, but not for the entire time you are there, especially if you are staying in Honolulu. Hotels can often charge $25-$35 dollars a night for parking, with only a few hotels offering overnight parking for free. On top of that free/cheap street parking is extremely hard to find, however, if you are staying at near the Marina you can find parking at $1 an hour but that cost can really add up especially if you having a pool day.

If you add the cost of a car rental, insurance (check to see if your credit card includes it), gas and parking, it might just be cheaper to uber places. The first 2 times we went we rented a car for the entire trip, but when we go back in 2020 I think we are just going to uber to most places and potentially just rent a car for 2-3 days rather than the entire trip.

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 5 Day London Itinerary or if you are going to Paris check out my 3 day Paris Itinerary!



  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. πŸ™‚

    • Jennifer
      February 8, 2017 / 8:16 am

      Is there anything other way to plan any trip πŸ˜€

      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!

  4. Lorena
    April 24, 2018 / 9:06 pm

    Omg!! Really enjoy all your eating places,we are going in couple of weeks we are staying in Waikiki.wish us luck

    • Jennifer Bui
      September 2, 2019 / 9:56 am


  5. Jenny
    October 21, 2018 / 10:22 pm

    I use to work at Cinnamons! Love the owners love the restaurant!

    • Jennifer Bui
      September 2, 2019 / 9:56 am

      what a small world!

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