Oahu Diamond Head Crater Trail

Poochie mama stayed with grandma at our resort at the Hilton Hawaiian Village. We wanted to take her on our hike up the Oahu Diamond Head Crater Trail but we ended up adding this hike to our morning run. This hike is definitely baby and kid friendly. As we were walking up the trail, I noticed a mom carrying an infant in an Ergo baby carrier. I also saw a couple of families with children ranging from five to eight years old hiking this trail.

It’s famous for its historic hiking trail, breath taking coastal views and military history. The hiking trail was built in 1908 as part of Oahu’s coastal defense system. The hike is about a .8 mile from trailhead to the summit.

We began our run at around 6:00 AM hoping to catch the sun rise on Diamond Head.  As it turns out we did not leave ourselves enough time to catch the sun rise.   The sun actually rises behind Diamond Head so you would  have to be at the park when it opens at 6am and make the climb as quickly as you can.

The distance from the our resort at Hilton Hawaiian Village to the park entrance at the center of the crater was just under 4 miles. We decided to make it a scenic run from the beach while making quick stops to snap a pic of the landmarks on the way.  When we run we travel real light and that morning we only brought with us a cell phone, a ten dollar bill for water while on our way and our hotel key card.

The morning run had stunning views of Diamond Head all along the way.  You can actually make it all the way to Diamond Head via the beach area.  On the way we ran past Fort Derussy Beach Park, Waikiki Beach, Kuhio Beach Park and The Honolulu Zoo.

Finding the park entrance was a bit tricky.  Diamond Head is a crater with the only entrance being a tunnel located on the far side of the crater if your coming from Kalakaua Ave and the Waikiki Beach area.  As we got closer to Diamond Head we reached a park with a large open field which sits just at the base of Diamond Head.  This was a great spot to get a close shot of the crater right behind us.  At this point we had the choice to circle the crater to the left on Monsarrat Ave. or circle the crater on the right, up Diamond Head Rd.  The left side of the crater seemed to be the shorter route on Google maps so we took Monsarrat Ave.  Going up Monsarrat Ave. we passed through a residential neighborhood where Monsarrat eventually turns into Diamond Head Rd.  A little further down Diamond Head Rd.  we passed Kapi’Olani Community College and a little past that was the roadway going up into the crater and the tunnel entering the park.

Upon entering the park, you have to pay an admission fee of one dollar per person if you are walking into the park or five dollars per car.  No biggie I thought,  that would leave is with 8 bucks for water and light snacks.  I pulled out my soggy $10 dollar bill from my sports bra only to find out that it was a soggy $5 dollar bill!  Jase asked in bewilderment, why did I not just put it in my pocket.  But I had a perfectly good answer for him: Because it felt safer in my sports bra.  Luckily the people of Hawaii have the most amazing sense of humor and the booth operator just burst into laughter and said its quite alright and I wasn’t the first to do that.

On the downside, we had $3 dollars left, a hike up a crater and about a 4 mile trek back to our resort.

There is a food truck that sells beverages and snacks at the bottom the trail.  A bottle of water is a $1.50 so we decided to ration a bottle of water going up the crater and then get another bottle when we arrive back at the bottom.  I purchased our first bottle of water and which left me with a dollar and two quarters.  Papa Jay said that if I lost one of those quarters he will probably die (he’s so silly). So we took our bottle of water and started our hike up Daimond Head Crater.

The floor starts off paved and eventually turns into a narrow rocky path.  The trail has a good amount of traffic going both directions and  is just barely wide enough to fit people coming and going at times. Luckily the trail does have handrails (which would have been really scary if it didn’t).  There are multiple lookout points along the trail up the crater with the most amazing views of different areas of Honolulu and the ocean.

Some of the SPECTACULAR views up Diamond Head

Luckily the water lasted us both to the top and even on the way down.  When we got to the bottom of the crater I sprung our last $1.50 which got us our last cold bottle of water.  At that moment Papa Jay got all wide eyed, and exclaimed that he had an amazing plan to get us food and drink.  He reminded me that he just recently signed up to the Starbucks reward plan and can make purchases at Starbucks and pay with his iPhone.  I have to admit, that was a pretty amazing plan.  Jase was also really happy at the idea of drinking his half of the water bottle right then and there.  Then again so was I.  That water did not last even five minutes before it was finished.

So we looked up the nearest Starbucks on Google maps and found one right at the entrance to the park at the base of the crater.  There was only one problem.  Papa Jay’s iPhone only had 20% battery left from all the mapping and picture taking from the morning and we still had a good trek to get there.  We decided to take the other route on the way back thinking it was only a little bit longer.  Boy were we wrong.  It’s almost twice as long but the views of the ocean from that side was incomparable.

We were too spent to run back and the walk seemed to take a lifetime but we finally made it to our sanctuary… Starbucks!  I don’t think I’ve ever been happier to see a Starbucks in my life.  Papa Jay grabbed a banana and ate it on the line (But he paid for the banana peel.  Still full price of course).  We grabbed our food and drink, went across the street, and ate it on the beach.  Happy ending for an amazing adventure.

Baby Travel Tips:  If you’re planning on taking baby just drive into the park and leisurely take baby to the top in a carrier.  There’s no shaded areas to the top so bring a hat or some sun cover and bring plenty of water.


There are quite a few look out spots and rest stops as well. It took us about two hours to hike up and down the trail. Next time, I would for sure use our frame child carrier or Ergo baby carrier and bring our poochie mama.

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