Oahu, Hawaii- Trip Overview

When I began planning our trip to Hawaii I had no idea where to start, there are so many opinions on islands and so much differentiation between islands that, to be honest, I was quite overwhelmed. Especially since that 9 hour flight kept in the very front of my mind.

Pat had been to Hawaii twice before, in college to play football at the University of Hawaii, so when he suggested we start there I was perfectly happy with his suggestion. Waikiki was supposed to be one of the best places for tourists to visit on the Islands and since he had been there before it would allow us to start somewhere where at least one of us had some kind of comfort in.

Let me preface these posts- we are active adventurers, meaning we have a hard time relaxing, and when I say hard time I mean it's nonexistent. We can't sit on the beach for a full day, and we can't be cooped up in a hotel for too long, either- no matter if a Spa Day is involved. AND another thing is we hate visiting new, exciting areas and just sticking with "what tourists would like". We want to be in with the locals, eating what they eat, doing the activities they do, and surrounding ourselves with the most authentic adventure we can have. This means our vacations aren't going to be for everyone, but their perfect for us, so when reading my vacation/travel posts remind yourself of that.


We flew to Oahu on June 26, visited Pearl Harbor, checked into the Hyatt Regency Waikiki Resort, and immediately began adventuring around the city of Waikiki. To be honest, Waikiki reminded me of a small scale Las Vegas, not in the way of casinos, but in the way of the shopping, the amount of people, and how the city is set up. Our hotel was in the perfect location, nestled into the shops, restaurants, and conveniently twenty steps from the beach. If you want to experience Waikiki I would highly recommend staying at the Hyatt Regency- not only were the prices fair, the customer service was par to none, and the rooms were perfect (and most of you know how picky I am on hotel rooms). To be honest, Pat and I couldn't have been happier with the Hyatt.

The only problem about Waikiki that we realized right away was that we were too close to the mainstream tourism attractions, and not close enough to the local way of life and all of their experiences and food recommendations. Here's another thing, Pat and I don't want to go on vacation and eat at somewhere like The Cheesecake Factory for meals, we want to eat local produce and food! So while Waikiki was perfect for offering that, we quickly found out it wasn't perfect for us. WHICH IS FINE!


On our first full day we got up early, had the buffet breakfast at the hotel then hit Diamond Head State Park, which is a tourist attraction, but one we considered important enough to put up with the crowds and do.

Overall the hike took us a little over two hours to complete, a little bit longer than anyone else will tell you, but that's because you can't take me anywhere and expect me to take just a few pictures... #sorrynotsorry 

The hike was a perfect mix of enjoyable and a little challenging, but it's a hike almost everyone can easily complete. The best part is that after you've completed the hike there's a food truck/stand with fresh fruits, quick snacks, and coconuts! We bought a bag of fresh cut pineapple and enjoyed our own coconuts for quick afternoon snack. (This would be a good place to buy a water bottle if you realize you need an extra one before your hike up.)

The park does fill up quickly and there are very limited parking spots, so I would recommend getting there earlier in the day rather than later. We had to wait about 20 minutes for a parking spot to open up. There are clean bathrooms and a water fountain on the property. 

After we completed the hike Pat found a small local authentic restaurant where we learned all about and ate the staple food of the islanders. It's so amazing to me to experience what other people eat and to learn about their cultures.

Afterwards we relaxed before getting ready so we could get our pictures taken by the amazing SCHYNE Photography! If you're ever out in Oahu I 150% recommend her, not only is she an amazing person but she's such an awesome photographer, too who will make your experience fun and memorable! Plus, she's grown up on the islands, so she can give you a list of her favorite things to do!


On Wednesday we woke up early and headed to the Western side of the island for a snorkeling adventure. One of my old teammates recommended the Best of the West Snorkel Safari by Wild Side and we are so glad we did it! It was one of the best snorkeling and boating experiences we've ever been on! I loved it so much I'll be doing a separate post on it in the future, so be sure to check it out! Be ready to hear about the dolphins, turtles, and a special surprise we got to swim with!

After snorkeling we went back to the hotel to relax before heading to Chief's Luau! Hawaii is known for their cultures and traditions so we knew we wanted to experience a Luau, and what better day than on our anniversary?! Sadly we were so tired from snorkeling and being out in the sun all day that we were dragging by the time we got to the Luau but it was worth every single penny! The food, show, and atmosphere was so amazing and we would definitely do another one when we go back!


Thursday was our last full day on the island of Oahu. Amber had told us some great places to try so we spent the whole day pretending we were locals and chasing new places to get some awesome footage at!

The first thing on our list was Crouching Lion Trail in Kaawa, which is not a trail and more so of a straight up hike. Literal on the straight up. It was a much quicker hike than Diamond Head and the views were unlike anything I've ever seen. Bob got lugged along but when we got to the top it was way too windy for me to trust him to fly.

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This hike was definitely way more challenging than Diamond Head and I would not recommend this for anyone who isn't in shape, sure footed, or the faint of heart. The hike up is vertical and once you get to the top you're practically scaling on the top of a ridge and the drop down is steep on both sides. Even I got a bit overwhelmed at the site of how high up we were with nothing to hold us back- especially with the amount of wind that would rush over the peaks. Even though Bob didn't get to fly we got a lot of good GoPro footage that will be in the short film!

Afterwards we got some footage with Bob before finding the most amazing food on the island, a food truck named Aloha Shrimp that would have scared you away by just the looks of it if it didn't have such amazing reviews by locals and Yelp-ers. I haven't ever, and probably will never again, experience a shrimp meal like the one they served us at Aloha Shrimp. They were so fresh, the seasoning on both of our plates was unbelievable, and the owner/chef was the cutest, kindest person we ran into the whole day. What was really cool was that it was parked next to a small convenivence store/fruit stand where you could get a fresh coconut to go with it! We thoroughly enjoyed our meal, and by the time the trip was over we had a new food comparison scale... "on a scale from 1 to Aloha Shrimp, what would you rate this place?" ;)

 Turtle Bay, this is where we did our pictures with Amber on Tuesday!

Turtle Bay, this is where we did our pictures with Amber on Tuesday!

We continued our drive around the island, along the North Shore, and into Wimea Bay after our scrumptious lunch. There's something special about a beach that has locals on it, it sounds funny, but to us it's so relieving when we come to a beach where the locals are hanging out. It's almost like we know we've picked the right spot. You could tell Wimea Bay was a hidden treasure on the island, far enough from Waikiki to keep all of the tourists out, but close enough to the locals to make it one of the spots where they came to for birthday parties and a relaxing day.

 Wimea Bay

Wimea Bay

After hanging out on the beach on Wimea Bay and taking some shots with my camera and Bob we had had enough fun for the day and decided to grab dinner and head back to the Hyatt before calling it a night. Pat and I knew we wanted one more Oahu inspired dinner so we stopped at Haleiwa Beach House for dinner. Pat is the best for finding hidden gems to eat at while we're on vacation so I always leave that task up to him! It has the cutest outdoor grass play section for kids, an amazing ocean view, and the food was delicious!

We had so much fun exploring and adventuring throughout the island of Oahu and cannot wait to get back someday, it was one of the best vacations we've had together.

 All pictures are property of Bourbon Oak Tree Photography & Films. These images may not be used without permission. For usage contact Brandie at bourbonoaktree(at)outlook.com

Brandie Scales