Skip to content


    5 day Adventure trip Oahu

    5 day Adventure trip Oahu

    Hello All, Last year we finally decided to visit Oahu.  I say this since most of the people we spoke to mention how busy it is.  We combined Oahu with Kauai and split the trip in two, 5 days in Kauai and the other 5 days in Oahu.

    We saved Oahu for last since we wanted to make sure we get a good experience and enjoy Kauai if Oahu didn’t end up meeting our expectation.  However, we were in for a surprise.  The time we spent on this island was incredible. It was a lot of fun, views were Epic and the people were so friendly.

    I must say the people that you interact with have a great impact on your experience.  They can make your experience amazing or unenjoyable.  For me, when I travel I like to immerse myself in the culture and the place.  I don’t like doing too much touristy stuff.  I want to do the things the locals love and enjoy.  I’m also in for the experience.  Its an adventure and I want to enjoy every part of it. 

    So, we went with low expectation based on others experience and came out with a new perspective.

    Here is our itinerary of the things we did.  I must say we avoided Waikiki during the day and didn’t do much sightseeing here.

    We landed at the airport in Oahu mid-afternoon.

    Picked up our rental and headed to Sam’s.  I love this place!  Sam’s had a little bit of everything. They had fresh poke and kalua pork sandwich.  I enjoyed walking around and finding new things.  Wish I could have picked up one of everything :)  Alas, I can enjoy taking it all in.  We grabbed dinner here and headed to our hotel for the evening.

    We checked into Hilton Hawaiian Village Waikiki Beach Resort.  Not sure if it was part of the package from Costco but we got a upgrade to The Ali'I Tower.  This was Awesome!  The Tower has its own pool facing the beach.  How cool is that.  Our room was facing the resort pool and the room in the Ali’l tower was furnished well.  A lot of reviews on Hilton Hawaiian Village mentioned the rooms needed updating.

    After settling in, we went out for a walk around the Resort.  I must say this hotel has a little bit of everything.  It was like a town in itself.  The place was huge.  Lots of restaurants, shopping center, and pools.

    We loved the ABC stores.  You can even pick up a bite to eat here.  On the beach there were artist playing music, painting, and fire dancers. 

    Waikiki Beach Resort

     hilton hawaiian village

    Day 2 – Some of the highlights of this days

    Woke up early and went for a walk around the beach.  It wasn’t crowded so we enjoyed walking along the beach.

    Today we planned a hike at the Diamond Head.  Its good to have some cash on hand, since some locations only accept cash. 

    We had breakfast at Koko Head Café. Finding parking can be difficult when busy.  You may have to pay for parking. However, their breakfast is delicious.  There are other great places to eat at as well.

    Place to eat near Diamond Head

    Koko Crater Cafe

    Diamond Head is not too far from here.  The 1.6 mile hike can take anywhere from 1.5 to 2 hours.  Make sure you go prepared.  Take plenty of water. 

    The views of Waikki and the water are just out of the world.  

    Diamond Head Hike

    Waikiki View

    Link to the Diamond State Park site,

    Division of State Parks | Diamond Head State Monument (

    We grabbed a bite at Costco near 333A Keahole St.   This was a great spot to walk along the water.

    Some places we stopped along were Halona Blowhole, Halona Beach Cove.  We also ended up walking up to Makapu'u lighthouse. The path is paved but some of the path going up can be hilly.  Go at a comfortable pace and know your limits.  Again, I’d like to stress the point, stay hydrated and take plenty of water.

    It was neat to see whale at a distance. Our trip to Oahu was in February.

    makapu'u lighthouse

    Obama Trail

    Oahu Vacation


    Day 3 – We enjoyed hiking up Koko Crater Railway Trail. Also known as “Koko Head Stairs”. This is not a hike for everyone.  You have to have some form of hiking experience for this. It will test your strength and endurance.

    Hiking the Koko Crater Trail (

    I found a Video example of what this hike looks like from YouTube by


    Its tough going up due to the elevation.  We took a lot of breaks and took our time.  The views are amazing.  Coming down is daunting due to the straight drop.  As you look down, its can be scary.  Go at your own pace.

    Be mindful of other hikers as well. If you’re afraid of heights, then this may not be for you.  Its like climbing stairs.

    Koko Crater trail

    koko crater railway hike

    Hiking the Koko Crater Trail

    We planned to go snorkeling at Hanauma Bay. However, by the time we got there the parking lot was full. Most people were parking on the side.  We didn’t want to do the same since it was a rental car so we decided to drive along towards North Shore.

    We enjoyed stopping at Byodo-in Temple and Hoomaluhia  Botanical Gardens.  The place is beautiful. I felt a sense of peace and calmness come over me.

    The views of the mountains in the background were breathtaking. It rained a bit that day and we could see some waterfalls on the mountains.  The staff at the Botanical Gardens mentioned that when they get a day or two of heavy rains then you can catch multiple waterfalls on the Mountain View.

    There is a fee for the Byodo-in Temple.  This was great to check out as well. You pass through a few cemeteries to get here.  Be respectful of the locals and any funeral services.

    Best of Oahu

    Byodo-In Temple

    It can take couple hours here if this interest you.  Along the way when we got closer to North Shore we stopped by Kualoa Ranch briefly at the gift shop.  They have a lot of activities and you could spend a day here.

    kualoa ranch

    Our goal was North Shore so we pushed along.  A great spot to grab a bite was Ted's Bakery.  We loved this little spot. They have great pies and foods delicious.

    Our next stop was Ehukai Beach aka Pipeline Banzai Pipeline. Finding Parking can get tough but be patient and spots do open up when others leave.

    We got to see the tail end of a surfing competition.  The waves got rough later on.  Its just amazing to see the huge waves coming in.  I could spend hours just watching.

    The Banzai Pipeline - Best waves to surf

    north shore pipeline

    It was getting late in the day and since we were passing through Haleiwa we decided to stop by Matsumoto Shave Ice.  They are quite famous for their shave ice and its well deserved.  The staff was very friendly and polite.  We grabbed ours  and headed to the closest beach to watch the sunset.

    What a day, we drove through most of the island in one day!  If you had plenty of time then you could also explore the town of Haleiwa.


    Day 3  - We grabbed breakfast at ABC and headed to Hanauma Bay first thing in the morning.  There is a fee for parking and entrance.  They also have a short presentation video before heading down to the bay.  Please be mindful of where you snorkel and respect your surroundings.  I love the Hawaii culture since they are very respectful of nature.  Enjoy the water and all it has to offer but be aware of your surrounding and coral life.

    Snorkeling here was out of this world.  The water was cold since we were here in February but once you’re in the water, your body acclimates.  The fish just swim by you without a care in the world.  I had a tinny fish come right up to my face and watch me.  The bay is a marine sanctuary and you will find different species of fish here.

    Hanauma Bay

    We also had reserved tickets to visit  Pearl Harbor.  It was great to pay respects to the men and women before us.  You can spend hours here learn more about its history at the exhibits.  The USS Arizona Memorial was closed for repairs but the boat ride tour passed through USS Arizona Memorial and the Battleship Missouri Memorial.  The emotions you go through seeing this is unexplainable.

     Pearl harbor boat tour


    Day 4  - We decided to have breakfast at Cinnamon's located within Ilikai Hotel & Luxury Suites.  Note of caution, if you decide to order pancakes, get the half stack. In my opinion the full stack is enough to feed 3 - 4 people.  

    I had directions for this restaurant and as soon as we got close to the Hotel we weren't sure where the restaurant was located.  I guess I had a clueless / tourist here look.  A lady on the sidewalk looked at us and asked if she could help.  I mentioned we were looking for the restaurant and she smiled and pointed us in the direction of the hotel and how to get there. 

    I was speechless, this person took the time to approach us and help us with directions. How cool was that.  All I could say at the time was Thank you! You made my day.

    We drove back to North Shore so we could catch more of the waves.  This place is just breathtaking.  We spent most of the morning here and grabbed lunch at Teds Bakery.  Next time I’d like to stay in North Shore for a day or two.  We spent some time at Turtle Beach and Dole Plantation. The Hilton Hotel had fireworks planned Friday night so we headed back to the hotel to get a glimpse of the fireworks.


    Day 5 - We lounged around the hotel and checked out at 11 am. We did stop by at the Swap Meet for some souvenirs before heading to the airport.

    If your headed to Oahu, I hope this itinerary is helpful to you.  Enjoy your Vacation and be safe.  If there are other things you did and had a blast with, do let me know.  I’d love to hear about new things and places to visit.

    Check out our Jewelry Collection if your looking for earrings, rings, and accessories for your trip.