Oahu Itinerary – The Ultimate Oahu Travel Guide For 2019

The Hawaii dream became a reality for me when I visited the Island of Oahu for a friends Wedding. We spent 2 weeks exploring this wonderland by car, finding epic hikes, hidden bays and amazing food!

Hanging out on the North Shore, Surfing, Hiking the likes of Diamond Head and eating from food trucks are amongst the best things to do on Oahu. Oahu is the most popular of the Hawaiian Islands, although not the biggest it has a lot to offer!

In this Oahu itinerary i’ve mapped out 12 days of adventure, foodie delights and relaxing in Waikiki.

Related: “New York itinerary for 4 days- Perfect Guide for your First Time to NYC!


Oahu Itinerary – The Ultimate Oahu Travel Guide For 2019

Things you should know for your Oahu Itinerary

Getting there: Jetstar often has sale fares to Honolulu and takes around 9 hours from the East Coast of Australia. If you are coming from someone other than Australia I would recommend searching on Skyscanner.com for your cheapest route. 

On arrival: You will need a passport and Visa(Esta) to get to Hawaii, unless you are a US citizen. Learn more about entry requirements HERE.

Population: Over 953,207

Capital: Honolulu

Currency: US Dollar

Exchange Rate: 0.72 USD to 1.00 AUD (Nov 2018)

Language: English and Hawaiian.

When to visit:  Any time of year is a good time to visit Hawaii. The average temperature here is between 24°-29.5° C. Summer, between April and November, is warmer and drier (average temperature is 24°-31° C) while winter, between December and March, is a bit cooler (20°-26° C). Trade winds keep things comfortable year-round. Whale watching season begins in late December and ends in early May. Peak whale watching months are between January and early April. November through February is big wave surf season on Hawaii’s north shores.

Getting Around: Many visitors enjoy taking guided bus tours to conveniently explore the Islands. Shuttles, taxis and public transport are available on the majority of islands. You may also consider renting a car. Reserve your rental vehicles in advance because quantities can be limited on some islands. Australian travellers don’t need an international driver’s licence as major car hire companies accept an Australian licence. In some cases, drivers will need to be more than 25 years of age and in possession of a major credit card.

Days 1-4  Explore the North Shore

Driving along the North Shore of Oahu each morning to check the surf lead to endless inspiration and surreal scenery. I am so glad we spent the majority of our time exploring the North, the mornings consisted of surf checks, followed by acai bowls, admiring the friendly turtles before going on late afternoon hikes. There are so many things to do on the North Shore including hikes, surfing and eating!
We stayed in a beach house with the most incredible view perfect for sunset swims and late afternoon beers- you can find similar accommodation here.
I would also suggest going to Pupukea Grill at least once a day, exploring the magical Waimea Bay and the famous Haleiwa.

TIP: Explore Oahu like a local with these insider tips! 

Crystal clear water against clean white sands makes Oahu beaches some of my favourites. Although North Shore brings in enormous swell making swimming sometimes impossible, it was still wonderful to sit and bask in its presence, appreciating the fierceness and all its beauty. Instead, venture close by to beaches like Lanikai, Waimea Bay and Haleiwa Beach Park for swimming.

The island’s coast boasts rewarding panoramic views of the hills and the waves which are not to be missed. For something, a little extra special be sure you visit Hanauma Bay the islands well-known snorkel beach.

Tip: Because parking is limited, you should arrive as early as possible because after the lot is full, they just turn people away.

When someone asks me how Hawaii was, I immediately start ranting on about the food. In particular my poke bowl from Pupukea Grill, I had on the North Shore. My partner and I loved it so much, we have replicated the poke bowl recipe and it is now a dinner favourite. Fresh produce, variety and large serves are something to appreciate in Hawaii. Make sure you try the ‘fish tacos’ on the North Shore, the Acai bowl from the Purple Food Truck, and the Ramen in Waikiki.

Days 4-6  Head to the East

Oahu’s East Side is an understated paradise that is full of adventure and gorgeous beaches. There are not large hotels or small but instead, you get to see Hawaii in its local and calmer state. The East Coast, also known as Windward Oahu, is located 30 minutes from Waikiki and Honolulu and is well worth touring by car as the coastal drive is scenic and varied.  The region is largely made up of quiet, coastal neighbourhoods and towns nestled between stunning 3000ft mountain ranges and the sea, it is also home to the famous Hanauma Bay and other magical places like Makapuu Point, Chinaman’s Hat, and Lanikai Beach.

STAY: Kailua GuesthouseParadise Palms B & B,

If you like a bit of a challenge, aren’t afraid of heights and can appreciate some moderate rock climbing, then the Olomana hike should be at the top of your list. For something a little less deadly try Hau’ula Loop Trail or Diamond Head. Here are the best Oahu hikes.

They say that it is the journey that matters, not the destination. I find that the truest when venturing on a hike. Hawaii is home to some incredible walks that suit all fitness levels and ages. With My favourite was the challenging Olomana Hike it is easily one of the best things to do on Oahu. I’ll be honest if I had of researched this hike before my trip I probably would have been too scared to part take. Instead, I was travelling with 3 males and pretty much just tagged along with whatever they had planned for the day; something I am thankful for. The Olomana 3 peak hike was my favourite experience in Hawaii.

Although a challenging and dangerous hike, you are rewarded with the most unbelievable view. It is around 2.5 km to the first and highest peak (there are three in total), we only did the first one as the course becomes a bit sketchy.

Hawaii is one of the most geographically isolated places on the planet. For some, that means only one thing: groundswell. Everywhere, in every direction, the currents of the Pacific are churning up the winds, storms and fetch that give these islands their world-class waves. Below is a list of the best places to enjoy them.

Oahu itinerary

Day 6  Discover Hanuma Bay

Scuba diving in Hawaii offers some of the best underwater sights, thanks to the protected marine areas surrounding the islands. The best spots for scuba diving in Oahu are Kahuna Canyon, Mahi and Sea Cove

On Oahu’s east side you will find the magnificent Hanauma Bay Nature Preserve where you can snorkel! This volcanic crater is a marine life conservation area sheltered from ocean swells and packed full of fish. Needless to say, it’s wildly popular, so be prepared for crowds. The tropical fish, coral and turtles amongst clear blue water make it worth though.

Days 7-10  Relax at Waikiki

Although Waikiki is the main destination for tourist with crowds consuming every inch of sand possible the beauty is still not lost. We spent the majority of our time exploring other parts of the islands and ended our trip with 4 nights in Waikiki- which was plenty of time.

Waikiki, unlike the North Shore, has gentle waves and is home to water sports and sparkling turquoise ocean.
Stay at the amazing The Royal Hawaiian, Oahu’s Most Iconic Hotel that’s right on the beach! Amazing food and shopping are plenty in Waikiki and are surround by your hotel making it the perfect family-friendly destination.

My favourite part though is the walk up Diamond Head. The picture below is the view from the top overlooking the city of Waikiki and its pristine waters. Tip: For a little extra challenge when hiking diamond head start your hike from your hotel instead of getting a bus to the start.

STAY: Alohilani Resort Waikiki BeachHyatt Regency Waikiki Beach Resort & Spa, Hilton Hawaiian Village Waikiki Beach ResortThe Royal Hawaiian

If a little retail therapy is on your vacation to-do list, Oahu’s diverse shopping centres have you covered. There’s something for everyone and every budget, whether you’re looking to splurge on luxury goods, need locally made souvenirs for family and friends back home or you’re a bargain shopper on the hunt. With its mix of outlet stores, cool local boutiques, discount shopping, US chain and department stores you won’t be disappointed. Try Ala Moana Center, the largest and best shopping centre in Hawaii!

Day 10  Day trip to the West Coast

The western side of Oahu, known as the Leeward Coast, is home to beautiful beaches and quieter atmosphere than the bustling areas of Honolulu and Waikiki. There are a wide range of water sports and beautiful beaches and is a short drive to Waikiki and Pearl Harbour. Although there are fewer shops and restaurants than Waikiki the charm lays in its unspoilt coast and rugged mountain ranges.

STAY: Marriott’s Ko Olina Beach Club,  Makaha Beach Cottage, Four Season Resort Ko Olina

Day 11-12  Back to Waikiki

The western side of Oahu, known as the Leeward Coast, is home to beautiful beaches and quieter atmosphere than the bustling areas of Honolulu and Waikiki. There are a wide range of water sports and beautiful beaches and is a short drive to Waikiki and Pearl Harbour. Although there are fewer shops and restaurants than Waikiki the charm lays in its unspoilt coast and rugged mountain ranges.

STAY: Marriott’s Ko Olina Beach Club,  Makaha Beach Cottage, Four Season Resort Ko Olina

That was our Oahu itinerary for 12 days. If you are planning to visit the other Hawaiian Island check out The Ultimate Hawaii Bucket List with lots of amazing things to do!

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53 thoughts on “Oahu Itinerary – The Ultimate Oahu Travel Guide For 2019

  1. I really want to try an acai bowl! I’ve had acai berries, and chocolate covered one’s too, but never one of those fancy looking (ready to Instagram) looking breakfast bowls. I’m also hoping we get to go to Hawaii soon. I don’t even care what island! But my husband is training for his 6th Ironman Triathlon (in 2 wks time!) and if he qualifies, we get to go to KONA so he can race there. I’ve just heard so many awesome things about Hawaii!

    1. That’s so cool Nancy, I never seen choc covered acai berries! I’ll be on the hunt for them in the future! Haha I am always making acai breakfast bowls, some our Instagram ready 😉 Goodluck to your husbands and thanks for commenting 🙂

  2. I’ve always wanted to visit Hawaii and this makes me want to go even worse! That food looks delicious, I would actually be willing to try it and that’s saying a lot as I’m super picky.

  3. Wow, what an amazing trip (and when it’s for a wedding, it’s practically selfless, right?)
    Thanks for the food recommendations – I love smoothie and acai bowls, but we don’t really have them here – looking forward to scoping out the Purple Food Truck.

      1. I’m near Toronto (2hrs away), and the closest I can get is buying the powder or dried fruit from a health store, lol. Looking forward to exploring your site a bit more 🙂

  4. I will be visiting Hawaii for the first time (I usually go to the Caribbean every year since I’m on the east coast) in the spring and I’m so excited. I’ll keep this post for references on where to eat and what to see.

    1. Wow Alli, how is the Caribbean? I would love to visit there! Let me know if you have any questions or would like more suggestions on restaurants or things to do- would love to help 🙂

  5. I am going to Hawaii next year on vacation for 14 days. Your pictures are beautiful, I’m so looking forward to seeing all the beauty and tasting all the flavors of the islands.

    1. Thanks for commenting Rachel. It seriously was blissful 🙂 If you make that leap and book a flight email me with any questions you might have 🙂

  6. Love love love your photos ,such amazing views and the scenery is so beautiful. I really want to go back to Hawaii and explore more othe other ISlands. Thank you for the great post.

    1. Haha is that you mum? Thanks for commenting 🙂 I knew you would love this posts! We should definitely organise a trip to the other islands asap! Xxx

  7. Your photos and tales make me nostalgic for the islands. Make sure you get Matsumoto shave ice on North Shore next trip.

    1. I know what you mean Jaime, I was feeling seriously nostalgic when I was writing this post! I actually can’t believe I missed the shaved ice, good excuse to go again though? Hehe 🙂

    1. You are so right Franc, Hawaii is just filled with natural beauty. I love driving around the island looking one way and seeing glorious mountains and then turning your head and seeing those crystal waters!

    1. Stefany, thanks for reading. It is seriously beautiful. And although I didn’t mention it above the people have a lot to do with that. Such an amazing spirited island. Xx

  8. Wow! And Wow! At those amazing photos!
    What a fantastic adventure!
    I”m so very glad you got to have this experience!
    Thanks for sharing.

    1. Thanks for reading and taking the time out to comment.
      Glad you liked our post and was inspired. Our main mission is too simply inspire 🙂
      Love you! x

  9. Wow – I can see why that is a dream vacation. I am an amateur photographer, so that visit would be like a dream to me. It’s absolutely gorgeous! I definitely need to go there!

  10. Loved reading this and seeing those beautiful pictures. I lived on Oahu for about a year when I was 11 so the pics brought back a host of memories.

  11. Ooo you make me want to go back and try out your food suggestions. We have been to Maui a couple of times also and I absolutely love it. It is a totally different feel to Waikiki, so much slower and relaxing. Not a huge amount to do but chill – perfect.

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