Kailua – Best Small Town in America?

Take a beach that is regularly voted as one of the top ten best beaches in the world.

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Kailua Beach

Mix in a dash of water sports. Sprinkle the bay with a few islands. Add a Polynesian dream mountain background. Let a refreshing steady breeze blow through. And top the whole thing off with a small town and a laid back vibe.

The dog seems happy. Kailua Beach.

The dog seems happy. Kailua Beach.

Sound like the best small town in America? It just might be.

With a setting like this, it is hard to go wrong.

What Kailua lacks in architectural splendor, it more than makes up for with the beauty of its surroundings and the vibe of its residents.


Kailua Town

The beach is perfection – not too crowded, soft white sand, turquoise waters, and home to as many water sports as you can desire – body boarding, surfing, paddle boarding, kite surfing and general water frolicking all abound.   As if that was not enough, two islands are located off the coast near neighboring small town Lanikai, and adventurous types can swim or paddle to them when conditions are right.

If the beach is not your cup of tea, then you can find plenty of hiking to do in the surrounding mountains, much of which is covered in vegetation resembling a tropical jungle paradise and always offering stunning views from their peaks. And because Kailua is located on the windward side of Oahu, there is very likely to be a refreshing breeze cooling you the entire time.


Yes, that is really a rocking chair on top of a hill overlooking Kailua Beach.

The town of Kailua itself has the feel of a one-streetlight town in 1950s America, but with enough amenities (read: Whole Foods and Target) to make it easy to meet basic needs with no real hassle.   You can technically walk or ride your bike anywhere, though obviously a car is helpful for taking trips outside of town. The locals are friendly, casual, and beachy. Families and Japanese couples on vacation are everywhere.

Outside of the beaches, there is not a lot happening in tiny Kailua. That being said, on Sunday mornings the town is host to one of the best farmer’s markets I have ever attended.   The market is small and the offerings are foodie-centric.   The quality of the food is out of this world good, and will more-than-easily satisfy the most discerning foodie critics. Live Hawaiian tunes add to atmosphere. And for the families, a nearby playground keeps kids busy, in addition to an adorable table set up for kids to do crafts inside of the market itself.   On Thursday nights, Kailua plays host to another outdoor market, which is also heavily food focused. The feel of the market is a bit different, but it is still excellent, extremely popular, and worth checking out.  If you are coming with small children, consider bringing a mat to sit on. Each week a very large gathering of families forms around the live musician, everyone spread out on mats and lawn chairs, making for a very kid friendly scene.


Saturday morning market Kailua.

Kailua farmer's market.

Kailua farmer’s market.

The drive to Kailua from Honolulu is short, thirty minutes or less (except in rush hour, which like in all of Oahu, can be epically bad). To get there you traverse an incredible mountain range, passing over and through jungle covered vertical ridges that are covered in more waterfalls than you can count during rainstorms. The drive is so beautiful that I actually consider the commute to be one of the highlights of visiting Kailua!

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Mountain commute to Kailua. Get ready to break on through to the other side.

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Drive to Kailua. Just add waterfalls.

Is Kailua the best small town in America? Perhaps, perhaps, perhaps.







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