2016 was apparently the year of Hawaii for us. First, we went to the Big Island in January with my boyfriend’s family and then we went to Oahu in August with my family. Obviously, 2016 wasn’t the worst year for me.

Oahu Island Guide

My father grew up in Kailua, so for our family vacation this year, we all met up in Kailua for a week on the beach. Some of my family stayed for two weeks, but we just spent a week. And what a relaxing week it was! Granted this post is about six months late, but I figured I’d share my Oahu Island Guide with you today.

Also granted, it’s mostly a Kailua guide because we didn’t travel around much, but I’m still calling it an Island Guide. If you’re from Oahu or have been there before, please share your recommendations in the comments … especially if they’re from somewhere other than Kailua.


Where to Stay

My parents rented a house right on Kailua Bay on North Kalaheo Ave. The house was right on the water, walking and driving distance from downtown Kailua and just a 30ish minute drive from the Honolulu airport. Kailua is much smaller and more quiet than Honolulu, so it’s a more relaxing option than the traditional Waikiki Beach vacation.


Where to Eat and Drink
  • Agnes Portuguese Bake Shop – I’m sure everything here is delicious, but we only got the Malasadas. They are perfect for breakfast, lunch and dinner.
  • Thursday Night Kailua Farmer’s Market – This is no normal farmer’s market. Sure, you can pick up some fresh produce, but you can also get Mexican street corn, crepes, pulled pork, pasta and mochi. Plus, there was a nice gentleman and his band making some sweet family-friendly tunes for your listening pleasure.
  • Lanikai Juice – We stopped by Lanikai Juice after sneaking into a senior citizen Zumba class at the local YMCA. Everyone assumed we were there with our grandma, which we weren’t, so we just went with it and Zumba-ed our hearts out.
  • Kailua Whole Foods – Yes I know this is absurd to put here, but this Whole Foods is popping. People come here for happy hour, breakfast, lunch, dinner, snacks and everything in between. It seems to be the hot spot in town and it has a great variety of items you can’t find at other Whole Foods.
  • Island Snow – If you’re in Hawaii, you’ve got to get a cone of shaved ice, no? Stop by Island Snow for all of your shaved ice needs.
  • Uahi Island Grill – It’s a teeny tiny restaurant, but everything at Uahi Island Grill was fresh and delicious. There were nine of us at dinner and there wasn’t a dish we didn’t like.
  • Surf Lanai – The food was good but the best part of this place is the view. You’re right on the beach and can see Diamond Head from most of the tables.


Where to Shop
  • Ala Moana Center – According to Google, this is the world’s largest outdoor mall. It seriously has everything you could possible want and the Nordstrom is fantastic!
  • Industry Boutique – This was an adorable little boutique in Kailua. I walked in just to browse and walked out with a dainty black pearl necklace.
  • Aloha Sunday – This is a men’s store, so bring (or shop for) a fella. It’s kind of urban Hawaiian hipster …. whatever that means.
  • Island Bungalow Hawaii – This is a charming shop in Kailua that’s nice and cozy. I’m not sure if she was the manager, owner or an employee, but the woman who was working when we went in was very sweet as well.

What to See and Do
  • Lanikai Pillbox Hike – This is a relatively short, moderate hike that ends with great views of Kailua Bay, the town and the Mokes.
  • Kayak to the Mokes – Sure I may have freaked out and thought we were going to drown at sea on the trip to and from the Mokes. And sure, I might have allegedly been a horrible kayaker, but being on the Mokes was so much fun. Be warned, it’s a quite long kayak, so only do this if you are confident you won’t cry because you think you’ll never make it home.
  • Waikiki Beach – The famous Waikiki Beach is a must-see if you’re spending time in Honolulu. We didn’t spend time on the beach as actual beach goers (far too over crowded for my liking), but it was a fun place to people watch.
  • Lanai Lookout – We discovered this on our drive back from Honolulu to Kailua. If you (possibly break the law) climb down the cliff wall to the water, you can get some pretty sweet views of waves crashing around you. Just be safe. Also, I don’t (officially) condone breaking the law.

Rumor Has It

We were pretty lazy this trip, unlike when we went to the Big Island, so I don’t have as much to share in the above sections as I would like. So here are recommendations from a friend who lived on Oahu for a few years and my family who was there the full two weeks and actually got their butts off of the beach.

Oahu Island Guide