Day 2 – Kailua

Day 2 – Kailua

Go Kayaking and enjoy the quiet and lovely town of Kailua and Lanikai.

About Today’s Plan

The best thing about Kailua Beach? No crowds. Photo by Patrick Rudolph

People come to Hawaii to experience the beautiful outdoors and there is no area better for this than Kailua. Kailua Beach and neighboring beach, Lanikai, both have white sand and blue water. Kailua is a small, quiet town with a decent selection of food to choose from. Kayaking is an activity that everyone can enjoy. It’s easy to learn and even if you aren’t the most physically-fit, you use a tandem kayak and share the workload with a friend! Kailua Beach also has a reef that stretches far, so you will have calm waters for most of the ride.

A Local's Advice

It gets cold here. Kailua is located on the east-side of the island, also called the “Windward side.” The part of the island is windier, rainier, and cooler than Honolulu. Bring a jacket if you plan on staying at the beach in the evening.


  • Reserve a kayak ahead of time. You can also get a tour package where they pick you up from your hotel and kayak with you.
  • Check the weather report – Kailua is located on the Windward side, which is the rainy side of the island
  • Bring sunscreen, sunglasses, long-sleeved shirts, or anything else to help you deal with the prolonged exposure to the sun during the kayaking trip
  • Use the bathroom before you leave. You will be away from civilization for 3-5 hours.

Bring food and water

You’re going to be kayaking non-stop for a couple of hours, so bring snacks with you. Bring water as well. If you stop by Kailua town, you can find many places to grab food, such as Whole Foods Market or Times Supermarket. If you put your food in a waterproof bag (you can rent these from the kayak shops), you can also have a picnic at the kayaking destinations.

Rent your kayak

There are two places near the beach to rent from:

  1. Mokulua Rentals
  2. Kailua Sailboards and Kayaks

More Info

Kailua Sailboards and Kayaks

  • 808-262-2555
  • online discount
  • double kayak 1/2 day = $69, double kayak full day = $79
  • guided tours/pickup available
  • paddleboard, snorkel, windsurf rentals also available

More Info

Mokulua Rentals • 808-489-6273

  • double kayak, full day = $50
  • guided tour available
  • free delivery of kayak to launch point

Mokulua Rentals is much more convenient because they bring the kayaks to the beach (your launch point), free of charge. Their location relative to the kayaking destinations are closer as well, meaning a shorter trip. Kailua Sailsboards and Kayaks offers rentals for paddle boards, bikes, and snorkel equipment, along with kayaks. I use Kailua Sailsboards and Kayaks when I go kayaking and I enjoy their services. I also don’t mind walking the kayak to the beach (they give you a cart). Both are great. You can also rent life jackets, water-proof bags, and or a tour guide (you can read more about kayaking paddles with this informative guide).

A Local's Advice

Bring a watch. Kayaking rental periods are usually for 1/2 days and full days. Bring a wrist watch to make sure you get your rentals back in time. A watch will also help you know when you need to re-apply sunscreen (do it every 2 hours).

Your Destinations

Destination 1: Flat Island (Popoia)

Flat Island is a short distance from Kailua Beach. Photo by Amanda

Not far from Kailua Beach is flat island, called “Popoia.” It’s a bird sanctuary, so you can see birds nesting in the rocks. The landing spot is the sandy area on the bottom-left side. Flat Island is really small, so you might want to just skip this and go straight to Mokulua Island, our main destination.

A Local's Advice

How to get on a kayak? To board a kayak from deep water, you must use your arms to launch your body out of the water and throw your body over the kayak. This isn’t easy, so practice this near the shore in deep water.

Destination 2: Mokulua Islands

In the distance, you will see a pair of cone-shaped islands. They are the Mokulua Islands. Land on the beach on the island that’s closest to you. You are not allowed on the one further out.

The Mokulua Islands are much further out than Flat Island and will be your main kayaking destination. Photo by ganesha.isis

The ride there is extremely calm because of the long-stretch of reef at Kailua Beach. The reef disappears before you reach the Mokulua Islands, so expect the waves to get rougher as you near the islands.

A Local's Advice

Is a wave coming? If you see a wave coming in your direction, you will need to either slow down, speed up, or avoid it. You don’t want the wave to break over you, so estimating the wave break is important. Most of the time, paddling as hard as you can to go through the wave is the best idea.

On the island, you can enjoy the beach, walk around and take a look at tide pools, or kayak around it (only if the water is calm though). There is also a cove on the back-side, about a 10-minute walk away from the front of the island. This area is much better for relaxing as the water is shielded from waves. You can swim here and if the water is calm, you can go rock-jumping too (see video).

Leaving the island

Be aware of the time so that your rental will be returned before your rental deadline. Going from the Mokulua Islands to Kailua is usually faster than going from Kailua to the Mokulua Islands because you will be paddling with the waves, rather than against them.

Hike The Lanikai Pillboxes

After returning your kayaking gear, you’re probably tired, sore, and your skin should be baked. You can just relax at the beautiful beach, but if you have some energy left, I  recommend a short and worthwhile hike: The Lanikai Pillboxes. It’s located on 382-498 Kaelepulu Drive, a short drive from Kailua Beach. This is street parking only in a residential area. This hike isn’t too popular, so there should be plenty of parking. The Lanikai Pillboxes is steep and rugged – the opposite of Diamond Head. This hike is short though and most people can reach the top in 30 minutes. At the top are two stone bunkers. I hear they were used by the military in World War II. Now, the bunkers are just decor for the hike and canvases for graffiti artists. The view is also amazing for such a short hike.


Food and Entertainment

Kailua is a small town with little to do. A lot of people that live here are older people with families, so there’s no night life here at all. People come to Kailua mostly to enjoy the beach. There’s a decent selection of food here if you decide to stay for dinner.

Big City Diner is incredibly popular with locals and offers a lot of local favorites as well as typical diner food. Photo by Burt Lum


Day 3: Explore the North Shore »

7 thoughts on “Day 2 – Kailua

  1. Great Post! I regularly paddle out to the mokes. Sometimes going out to the Mokulua Islands can be incredibly difficult though. Especially in the wintertime, there are regular tradewinds blowing onshore that range from 15-25mph.

  2. Awesome post! I regularly kayak and SUP out to those islands! While they are usually calm waters out in the summertime, there are regular strong tradewinds that can make getting out to the islands difficult. Check out this post ( ) I found about going out to the Mokes as well as Flat Island ( ) and the Lanikai Pillbox hike ( )

  3. I have a feeling that I am going to need this information in the nearest future (planning next vacation maybe) so I am definitely having this post bookmark just in case. Thank you for posting, you rock!

  4. Hi!
    Great post you have there with some useful information.
    I was just wondering how long it takes to kayak out to the Mokulua islands?

    1. It depends where you go from. If you leave from Kailua Beach Park, it usually takes about 1hr15min. If you leave from Lanikai, it usually take about 35 minutes.

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