Oahu Travel Guide

Where do I begin?


To be honest, I wasn’t excited about going to Oahu. I was infected by everyone’s comments – “It’s NY with Tiki Torches” or “It’s too crowded” or “It’s so expensive.” We were traveling for a friends wedding and were only limited to a week away because of a trip through Beachbody the following week. I knew that I preferred to see the other islands, and multiple islands, but it wasn’t in the cards and we had to go.

When I tell you guys I couldn’t have been more wrong – trust me.

This was beautiful and if I had the choice to go back to any destination, this would honestly take the cake – not because of the price, hotel or color of the water, but because of who we are and how we felt being there.

We felt so comfortable and home, yet so far away and exotic. We took a lot of less traveled paths and found some beautiful nooks around the entire island. People were friendly and there was so much to do!

PicMonkey Collage-37We spent the first 3 nights at Turtle Bay Resort. I had so much planned for us and didn’t want to spend hours driving so I figured it would be a good idea to simply split our week in half. The property was beautiful and all of the rooms had an incredible Ocean View. I had plans on eating at the resort, but we honestly didn’t get around to it because there were so many interesting options else where.

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Our first night at the North Shore we visited Kawela Bay and then hit the food trucks for dinner. There’s a bunch of them clustered together on the main road with so many different options. Stop at Food Land (The local grocery) to BYOB, pick a picnic table and you are set!!! Whoever said the food in Hawaii is expensive, simply didn’t go to the right places.

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Our next day was spent exploring the North Shore.

We stopped at Island Vintage Coffee for a morning Latte – and here’s a random fact about me: I hate Coffee!!! I loathe the smell and the taste! But this… this was good! We also got something that was a little more my speed for breakfast at Hale’iwa Bowls! There’s nothing that makes me happy quite like an Acai Bowl!

We had rented a Jeep so we were just driving around checking everything out! It was so laid back and beautiful.

Here’s another random fact – do any of you remember the show LOST? I’m OBSESSED with it. I’ve probably watched the entire series front to back at least 3-4x. This is where it was filmed, so you know I scouted out some of the show locations!!PicMonkey Collage-40

I found the “Others Camp” from the show, which is actually a YMCA, and as we keptdriving along the North Shore, we found a hiking trail to Kaiana Point State Park. Aside from the driving trail, this place was so untouched and beautiful! It was such a nice and peaceful walk.

On our drive back we had to stop at the famous Matsumoto Ice! There were sooooo many flavors to choose from, but we picked Passion Fruit, Pina Colada and Watermelon – delicious!!!PicMonkey Collage-41.jpg

We then hit up the Food Land grocery store for some local Poke and Beer. This giant bowl of Tuna was only $6. Granted, I asked a few locals where to eat, but you don’t have to spend a lot of money to eat well. We had this joke running that everything we ate was out of a bowl.

After Sunset, it was time for more Food Trucks and then sleep because we had a fun day of hiking planned for the next day.

We had a busy Fourth of July!


Pu’u’ohulu Kai was not planned. I had a list of hikes and things I wanted to do, but my husband stumbled upon this place online the night before. It was on the Western most tip of the island, so we figured “why not?”

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This hike was awesome! It felt very natural, and it was really challenging. It was the most perfect day with crystal clear skies. The view was one of the most incredible things I have seen. We ended up just hanging out up there taking it all in! Just thinking that soldiers used to climb these mountains to station at these Pill Boxes in WWII was just surreal.

PicMonkey Collage-45.jpgIt wasn’t crowded and definitely a less popular hike, if your avoiding crowds. Just get there early before it gets too hot!

In the afternoon we hung out at our resort. Only our resort was several acres so you felt like you were completely alone. We found a really neat tide pool and hung out before the Fourth of July festivities.

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That evening our hotel hosted such an incredible party with Food Trucks, a Polynesian Show and Fireworks.

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We spent our “transition day” doing some last minute things at the North Shore and then we had to head down to Waikiki for the second half of our trip. We visited a few shops and Waimanalo Beach before stumbling upon Makapu’u Point State Park.

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The Makapu’u State Park and Lighthouse was another unplanned trip. We literally saw it, parked, got out of the car and started hiking. This was more of a man-made hike, but the views were insane and it was definitely challenging as well.

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While we were hiking we noticed a few colorful specks off the side of the mountain near these tide pools and then we realized they were people. We ended up climbing off the edge and down the mountain to hang out and go for a swim!

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After a long day, we finally arrived at the Surf Jack Hotel in Waikiki, which was our home for the second half our stay.

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I was blown away by how quaint, cute and boutique this hotel was. I stumbled upon it on Trip Advisor and when I saw it in a spread in Williams Sonoma, I knew that I preferred it over all the generic high rise hotels. It had this retro-surfer feel that was unique, that it had you questioning whether you were in the city or not.

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The next morning we hiked the Koko Head Crater, which was >2,000 steps to the top. It was definitely the most challenging of the hikes that we did, but the view was definitely rewarding.

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On our last full day, we did the Diamond Head Crater simply for the EPIC Skyline view! The views were so incredible, but this hike, unlike the others was very touristy. Be sure to arrive no later then 5:30am to ensure you are the first up there to have time for photos. It is a man made hike, easy to do and will FILL UP and stay filled up, the minute the first herd of people make it to the top.

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Hiking TipsDo your research! Some hikes are more challenging then others. Some are actually illegal. Leave early and start early so your not halfway in the blistering sun and heat. Bring plenty of cold water, snacks and sunscreen. I definitely got crispy the one day. Have fun, challenge yourself, take breaks and take lots of photos!

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Restaurant Recommendations

  • Mahina and Suns – honestly, everything is good here. Drinks, breakfast, lunch, dinner – we had it all. We had the Family Feast for dinner – highly recommend!
  • Bevy – this place has the best mixologists and very creatively crafted cocktails. They had a awesome happy hour and even better bar snacks!

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  • Island Vintage Coffee North Shore
  • Hale’iwa Bowls
  • Aji Limo Truck
  • Matsumoto Shave Ice
  • Lemona Hawaii – get the Lychee shaved ice. This is across the street from the Surf Jack Hotel



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Meghan Mosakowski

lifestyle + wellness coach