Guest Post: Favorite Warm-Weather Destination: Kailua, Hawaii by Kit Whelan

Favorite Warm-Weather Destination: Kailua, Hawaii
by Kit Whelan, digital nomad and author of Seek New Travel
Follow Kit on Twitter at @kitwhelan

There’s a mythical land of endless summer and sun, it’s name whispered from the chapped lips of cold city dwellers offering a promise of white sand beaches and fresh pineapple juice even in the depths of winter.

“Hawaii.”

You might think it’s passe for me to pick the most famous Hawaiian island as my ideal warm-weather spot, but hear me out.

On Oahu’s un-touristy windward side, the small town of Kailua has a laid-back feel, even by Hawaiian standards. Even the President comes here to relax, and his job is way more stressful than blogging. Here are some of the many, many reasons to love this idyllic spot:

The Beach
Famous for wind and kitesurfing, Kailua’s beach is a mecca for athletes and those wanting a quieter side of Oahu. If you care to try out your kitesurfing skills, there’s always extra boards and teachers at the main beach entrance – but be prepared for seriously sore arms.

If laying on a towel is more your speed, there’s plenty of wide-open space for that too. Nearby Lanikai beach – rated one of the top beaches in the world – has spectacular views of the Na Mokulua islands and calm coves for paddling around.

The Town
The town itself is mostly residential, filled with houses, schools and snack shops. Which brings me to my favorite thing about Kailua: Island Snow.

In a small shopping center a few blocks from the beach sits the best darn shave ice shoppe on the planet. In case you don’t know, shave ice is NOT the same as a snow cone. A block of ice is shaved, not crushed, by a machine, then formed into a cone or cup and covered in delicious syrup. I recommend the POG juice and snazberry flavors. Though I have no idea what a snazberry is I can tell you it’s delicious. If you’re really doing it up, you should also add a scoop of ice cream and a snow cap – sweetened condensed milk covering the top – to make the whole thing pure heaven.

There are other shave ice places on Oahu, and there may be others who tell you Matsumoto’s on the North Shore is the best, but they are sadly misinformed. President Obama brings his family to Island Snow all the time when they vacation in Kailua each winter, as the photos covering the wall can attest, so I have Presidential authority to tell you I’m right about this.

The Food
There are no fancy-pants restaurants in Kailua, but if you want good local food you’ve come to the right place. There are tons of places to get your munch on – from the amazing Crepes No Ka ‘Oi, where you can (and should) have crepes for breakfast, lunch and dinner, to Moke’s Bread and Breakfast with its no-frills diner fare and amazing POG juice. For the carnivores, there’s Teddy’s Burgers where you can sit your sand-covered body on the patio outside, or Pepper’s Place for a greasy yet amazing cheesesteak. Basically, if you want vacation food, you got it!

Honorable Mention: The Rest of Oahu
It’s easy to forget when lazing in Kailua that the rest of Oahu is right there to explore. You can drive up the coast, stopping off to eat some fresh-caught shrimp from a roadside truck before continuing on to watch the surfers on the famed North Shore. You can spend a morning getting lost in Dole’s pineapple maze (the world’s largest maze) and celebrate your escape with pineapple ice cream, yogurt, juice… you get the idea. You can even go hiking and reenact that scene from Forgetting Sarah Marshall where they jump off the cliff, though I’m not sure I’d recommend it!

In our three week trip to Kailua we took a drive to Honolulu and Waikiki only once to see what we were missing, and happily drove back an hour or so later to our quiet, relaxed little paradise. I’d happily make that choice again anytime.