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Hawaii Kayaking- Kailua Bay offers a Travel Adventure for All Ages

Updated on April 23, 2015

Quality is not Quantity

Life changing experiences are rarely what we think they will be. We plan a trip to an exotic getaway and prepare to be swept off our feet by forces outside of our control; the spectacular glitzy weekender in Chicago, Vegas or Monaco (yeah, you wish,) is supposed to satisfy our every wild impulse. Often we find that we have to put out some effort to realize even a little bit of our vacation vision, and only when we search deep inside ourselves to push past the beaten path do we find out what we are really made of.

Just think back to that last non-stop morning to morning alcohol-soaked binger you thought you were way too old for; the “easy to moderate” hike that ended up grinding your knees to the bone, or the last time you had to average 2 hours of sleep a night for days on end because the baby was sick. If you ever stopped to wonder if you could do it and threw those doubts aside to get it done, you came out a changed person (maybe with a pickled liver.)

These experiences don’t have to be long or debilitating, though; especially when you have kids. For my son Austin, he realized a new level of confidence in the ocean with a short but exciting paddle to another world.

View of the Mokulua Islands from the shore.
View of the Mokulua Islands from the shore. | Source

Trip Log: Kailua Day Trip

Kailua, once our hometown on the windward side of O’ahu, Hawaii, is a small town with impossibly fine sand and gentle blue waters. It almost doesn’t belong in the same neighborhood as the rest of the island, and for a long time it was like the other side of the moon.

Before the Pali Highway was blasted through the mountains in the 1950s, the Old Pali Hwy., a narrow cobblestone road which hugged the treacherous cliffs around every turn, was the only means of crossing over the Ko'olau Mountain Range to this side from Honolulu.

Heading through the tunnel and emerging on the other side is like crossing the border into a different country. Broad expanses of multi-hued blue ocean, the green of the jungle everywhere, and a landscape blissfully ignorant of monolithic concrete towers.

We have managed to back to our old hometown by day three of our return to paradise. We packed the ten day trip full, so every hour counts. Our goal here today was simple: Hit the beach, get a kayak and paddle to the Mokulua Islands off of Lanikai beach.

Austin loved the idea. For him, this visit held the promise of going out on a boat, possibly seeing sea turtles and visiting a secret island. What more could a young boy want? The Kailua beach we knew had changed little.

Despite online community forum gripes about how the area had become crowded and lost its small town feel, we arrived to a dramatic partly cloudy sky, the same beautiful views we had known and a sparsely populated parking lot. The only thing that was different was the kayak scalpers.

He sat in the open driver’s side of a white cargo van, waiting to intercept people as they headed to the beach. The side doors were open to reveal boogie boards, kayaking gear and a few well worn surfboards.

With his mellow approach and matter of fact demeanor, we didn’t mind getting his short sales pitch, especially when he was charging about 30 percent less than the local commercial outfitter: $40 dollars for an all day kayak rental This man’s business had an added advantage, as well; it was at the beach, saving us the block long walk from up the street with a kayak over our heads.

Looking out from Kailua Beach Park proper, I had forgotten just how far the Moks (an easy abbreviation) were from the shore. I could handle the 30-40-ish minute paddle, but I knew my Austin would get exhausted. Worse than that, there was a surf break at Flat Island, about a quarter to a half mile out.

Usually an easy break to get past, all I could see were non-stop sets of three and four waves at a time. Having been rolled in the past with swells that were barely ripples, these were not the ripe conditions I was hoping for on my son’s first trip out.

Rolling over was not an option, but the shorter trip to Flat Island was. Truth be told, I’d only been to the Mokulua islands, having shunned the closer Flat Island as too easy to get too and too boring. However, it was the perfect place to start with a child in tow.

Having toured these waters many times before, I opted for the kayak scalper in the beach parking lot. I had no desire to haul the thick plastic two-seater plus paddles a block in the hot sun.

After checking to make sure there were no gaping holes in the craft and that the life vests fit us both, I handed over my $40 dollars and he disappeared. “Just haul it up on the beach somewhere over here when you’re through” he told me, gesturing to a grassy area near the canal we would launch from.

The view from Flat Island
The view from Flat Island | Source
Austin discovered strange footprints as we explored the area.
Austin discovered strange footprints as we explored the area. | Source
Exploring the landscape of Flat Island
Exploring the landscape of Flat Island | Source

3,2,1 Launch!

We pulled the boat along the shallow water of the canal, left over from the high tide, then dragged it another hundred feet or so to the water’s edge. The wife snapped a picture of us grinning next to our craft, and we launched our voyager right there on the beach. From the word go Austin’s attitude never changed; excited yet composed, a tad nervous but determined, and never once failing to hear or follow my instructions. As we began to paddle over the gentle ripples of the open ocean, both paddles moving in sync, it dawned on me. Whether this outing lasting 15 minutes or 2 hours, I had just initiated one of those life-changing experiences for my son He was not only trying something completely foreign to him, but he was embracing it with an open mind and succeeding at it.

The plan had been to head out to Flat Island and consider the possibility of journeying to the Mokulua Islands from there. We were challenged by some fun breakers as we muscled our way out to the broad circular expanse of green ice plant covered coral rock that was Flat Island. Parking the kayak on a small stretch of sand, we explored over the sharp ground of the island for a time, enjoying the views on all sides and marveling at the various inlets carved out by the water over hundreds of years.

From our close up view of the waves breaking over the reef, the Moks were not going to be in the cards on this day. But it didn’t matter. However short it was, this had been a full journey. Austin displayed a smile full of wonder and said little the entire time. When we finally left, he sat in the front of the kayak, paddling with more confidence and continually scanning his surroundings; the deep blue waters, the frenetically paddled outrigger canoes, the thunderhead stalling beyond the beach to let everyone enjoy their time here just a little longer.

When we finally arrived, riding a wave on to the beach, Austin was beaming. I looked over at my wife and we both knew he had just grown a little more, in a positive way, never to be the same again.

A great place for all your kayak, paddle boarding and water sports necessities:

Kailua Sailboards and Kayaks

Phone (Local) 808-262-2555
Phone (Toll Free) 1-888-4-KSK-RES (888-457-5737)
Fax 808-261-7341

E-mail Questions:

Address Kailua Sailboards & Kayaks Inc
130 Kailua Rd. Suite 101B
Kailua, HI 96734

Going to O’ahu? Feel free to send me your questions by contacting me through Hubpages, or at

The Mokulua Islands in the distance...
The Mokulua Islands in the distance... | Source
The Mokulua Islands in the distance...
The Mokulua Islands in the distance... | Source

Tips to consider:

-This is an activity everyone should consider during their time on O’ahu. If given the choice between Hanauma Bay, staying at the resort or heading to Kailua, choose Kailua and be rewarded for your wisdom.

-You need to be in reasonable shape and a decent swimmer to attempt either Flat Island or the Mokulua Islands trip. Small waves can roll a kayak with ease and when the swells come in with more frequency, chances of getting tipped over are greater. Ride into the waves at a perpendicular angle to prevent getting rolled, and be prepared for the possibility anyway.

-If the kayak gets tipped over, don’t panic, this isn’t Pipeline where the reef waits to make hamburger of your skin. Get the boat righted, put the children in first, and pull yourself up in one swift motion. If the waves keep coming, swim with the kayak towards the shore. When you have cleared the break, getting back on will be easier.

-Bring a drink if you are going to Flat Island, or even just paddling around the ocean. Pack snacks or a lunch if heading out to the Moks. Take your time and enjoy!

-Don’t forget the sunscreen, and not just for us pale-faced folks; my dark skinned wife managed a burn that day.

-Did I mention sunscreen?

-Our beach side kayak scalper was cheaper, but the licensed commercial outfitters offer newer gear in all sizes, better equipment and guided educational tours that go from Flat Island to the Moks and beyond. Use the beachside renters only if you are comfortable in the kayak and know where you are going.

-Be aware of others on the water. Many people paddle kayaks and outrigger canoes just off shore. Live Aloha and give others the right of way. When you are closer to the break, paddle well away from surfers and stand up paddle boarders riding waves. That being said, there is plenty of ocean for you to find your own private slice.

-Don’t even think about leaving your trash anywhere but in a trash can; please and thank you.


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    • MosLadder profile imageAUTHOR

      Chris Montgomery 

      7 years ago from Irvine, CA

      Awesome Natashalh! Hope you had fun.

    • Natashalh profile image


      7 years ago from Hawaii

      Thanks for the great advice! I'm about to head to Hawaii and I love kayaking. I've been tipped out before, but on a lake, so it was a bit different!


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