Kailua and the Windward Side

Waikiki is great, a kind of theme park for families and beaches and the issues that confront them both. We have had many, many pleasant sandy experiences in Waikiki and still spend time there whenever we visit Hawaii.

However, when you are interested in graduating to something a bit more sophisticated, a bit mellower and more Hawaiian, but still convenient and on Oahu, we suggest the Windward side.

Windward is a generic description for the “other” side of Oahu, sort of opposite from Waikiki. You can get there by bus, but it takes a long time and leaves you without many options for exploring except more long bus rides. A rental car is close to required, especially with kids, their maintenance supplies and swim tackle.

Kailua (yes, it has a web site) is sort of the center of the Windward side, and makes an excellent base for enjoying the whole “other” side of the island. Reachable by car from Waikiki in about 40 minutes outside of rush hour (when commuting traffic can change the trip into a two hour slow crawl), this is a small, laid back town with all the restaurants and small shops you need, right next to a lovely beach. The whole smell of the place is calm, peaceful, small-town-in-Paradise, the Truman Show without the scary edge. When the Keys get too tight for Jimmy Buffet, I bet he comes here.

There are no hotels that we saw in Kailua, but plenty of nice cottages, cabins and bed and breakfast places in a lot of price ranges. Expect to pay about or a bit more than a hotel, varying a lot based on how close you are to the beach and how much space you get. If you are thinking here or Waikiki, Kailua is most certainly more expensive than the mid-priced places in Waikiki. In return, however, you get a kitchen, maybe some extra room, a lot more privacy and those other three important real estate things.1

1 The three most important things are location, location and location.

There are a number of places to track down cottage rentals. Go to Google and search under “Kailua cottage” or “Lanikai cottage” to get started. Lanikai is either an extension of Kailua or a special, magical place right attached to Kailua depending on whether you are a real estate agent or a regular person.

Note that most of these cottages are owned and run by individuals, so things can take time and be less formal than a megahotel. For example, in our case, checking availability involved the exchange of a few emails, and I had to pay by mailing a check to the guy. He wrote back telling me that when I showed up at the cottage, the key would be under the doormat, which it actually was. No credit card, secure web site stuff here.

Where ever you find your key, the beach at Kailua is nearby and wonderful, like back when wonderful meant something. Graced with fine, soft sand, the beach gives way to a smooth bottom with few rocks, and gentle waves. There are showers and a snack bar available, but bring your own towels, chairs, sun lotion and that kind of stuff. We just left our things on the beach for hours without a problem.


One cool thing popular on the beach is kayaking, which is easier and more fun than it sounds. Unless you are a seriously heavy packer, you probably need to rent a kayak. They seat one or two people, and come with life jackets and paddles. The most visible place to rent kayaks is Hawaiian Water Sports, which is up the street from the beach and requires a hot and unpleasant 10 minutes walk pulling your kayak alongside the road. Not recommended for small kids or those with them. The shop does offer some advantages, however, in that they will take phone reservations, have set prices, accept credit cards and everything was neat and clean and safe.

If you want to save the hot walk and maybe save a few dollars, ask around at the concessions stand. Individuals (in New York they would be called entreprneaurs) hang out there who will rent you a kayak. Technically they are not supposed to do so because of some laws on concessioning. If this is within your moral compass, you can negotiate a price and terms, like how long you can keep the kayak, that are better than the shop prices. Sales are in cash only.

Once geared up on whichever side of the law you prefer, the only hard part is next. The kayaks need some decent effort to get them out a few yards past the small surf break, so a spunky parent needs to do this while the kids wade alongside. We found it easiest then for the parent to hoist the kid into the kayak and then board him/herself without committing any comical (small kids) or sooooooooo embarassing (teens) acts such as falling into the water. Every rental comes with a life vest and this is a good time to make sure small ones and weak swimmers have the vest on.

If two people are paddling then they have to synch themselves up, like the slaves on the old Roman ships. We failed totally at this and discovered that one Dad paddling earnestly while one kid stayed the hell out of the water was more efficient than two people randomly flailing away. Your mileage of course may vary.

Flat Top Island

An easy destination is nearby flat top island, visible from everywhere on the beach. With no idea what we were doing and a completely useless eight year old aboard, we got out to the island in about 45 minutes of mild profanity and effort. The bigger, distant islands which evoke tropical survival fantasies among consenting adults take about 90 minutes of paddling, and remember it takes about that much time to get back.

The flat top island we recommend is actually a bird sanctuary. You can beach the kayaks on the right side of the island and climb up easily. Once atop, look down. You want to make sure you step only on exposed rock, never on greenery. There are two reasons; the green undergrowth often hides bird eggs which you do not want to crush and the greenery often hides nasty holes in the rock, into which your foot will slip crushing your ankle. Both are to be avoiding, so tread carefully. The island is small, but our kids treated it as if they were the first humans to ever set foot there, becoming excited when we saw a tide pool, and pointing out bird nests and found eggs for an hour. There is nothing on the island but you and birds, so bring water, sunscreen and anything else you need. There are no toilets or trash cans either, so plan ahead on those goodies.

User Feedback

I love swimming on this side at Kailua Beach Park. But, beware the jelly fish…

Melissa Davis

We recently moved to Hawaii and have appreciated the tidbits about our new home on this website. However, I would like to say something about the kayaking. We went to Hawaiian Water Sports and the other shops in town and were unimpressed with the operations. Through a websearch we discovered Mokulua Kayak Guides (spelling?) and went with them. From the very beginning we were treated very professionally and felt very safe. We have 2 small kids so this was a big issue for us. We learned more about Hawaii than we ever thought was possible and we’re planning to go out again with these guys. They dont have a retail shop, but operate fully within the permit system, if thats a worry for you.

Scott Steward

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