A First-Timer’s Guide to Oahu

When it comes to dreamy vacation destinations, Hawaii is leading the pack. After fantasizing about visiting the islands my entire life, I was finally able to turn this goal into a reality. My Hawaiian travels took me through Maui and Oahu, from 10,000 feet high summits to underwater mazes of coral.

Given the grandiose nature of Hawaii and its many cultural activities, there is a lot to unpack about the islands. I feel as if I barely scratched the surface in my time here. However, I came home with a huge desire to return someday and dig even deeper into the unique culture there. Even though I hope to participate in some more unconventional activities the next time I visit, there are some touristy attractions that every first-time visitor should cross off their bucket list. Included in this guide to Oahu are things that every first-time visitor should do, my top hotel recommendation, and some must-visit restaurants.

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Where to Stay in Oahu: My Top Recommendation

When picturing Oahu, most people immediately think of the famous Waikiki Beach. This hotel zone is where the majority of tourists live and breathe on the island. Between the beachfront hotels with Diamond Head in the distance and the close proximity to downtown shops and restaurants, Waikiki Beach is usually where tourists begin their hotel search. During my trip, I had the opportunity to stay at the Hilton Hawaiian Village Waikiki Beach Resort. Not only did we have the privilege of staying at this beautiful resort situated on Kahanamoku Beach, but we were also upgraded to a room with an oceanfront view in the Rainbow Tower. Opening our curtains only to be greeted by a view of Diamond Head straight ahead was unlike anything I’d ever experienced. If you’re wondering where to stay in Oahu, there is no question about it in my mind. This property was everything I needed after a few action-packed days in Maui. 

View prices and room details here!

Walking through this property made me feel as if I had stepped foot on a private island. Between the luscious greenery, village shops, chic lounges, restaurants and pools, it was hard to imagine that there was a bustling city not too far from the hotel. During my time there, I visited three out of the six pools available on the property. While the chairs at the Super Pool get snagged up early in the morning, the Tapa Pool is an excellent second option if you’re wanting a bit of a calmer atmosphere. The Paradise Pool was fun to visit for an afternoon, as I was able to embrace my inner child on the waterslide a few times. However, as lovely as the pools were, I also spent a large heap of time on the beach. The Hilton Hawaiian Village has a coveted beach area. What makes it stand out from other beachfront hotels on the strip is that the water here looks as if it is sectioned off from the rest of the ocean due to the shape of the coral and the pier of Port Hilton. Thank goodness for photos I took like the ones below to be able to explain what I cannot properly put into words.

The Hilton Hawaiian Village has a variety of restaurants and food markets found throughout the property. We enjoyed multiple meals at the beachside Mexican restaurant, but we also picked up alcohol and other food items from one of the many ABC Stores. I highly recommend saving some money by purchasing your alcohol here and making mixed drinks. We also attended the property’s luau, an experience that has always been on my bucket list. If you’re contemplating whether or not to spend the money on a luau, let me assure you that it is well worth the price!

In addition to all of the aforementioned perks of staying here, the resort also has a mixture of free activities offered throughout the week. I took advantage of the lei-making class and the hula dancing class. Each of these only lasted around 20 minutes or so, but it was a great way to learn more about Hawaiian culture and engage in local activities. I highly recommend participating in these if you stay here.

Where to Eat in Oahu

No matter where I travel, one thing stays the same: my enjoyment of food. Throughout my time in Hawaii, I tried a variety of local dishes and personal favorites, such as the Mexican joint at our hotel. Although our hotel had numerous meal options, I also had a list of must-stop restaurants to try. If you’re curious about where to eat in Oahu, continue reading to discover a few worthwhile spots.

Eggs’ n Things

If the line outside the door isn’t enough to prove just how favored this breakfast spot is, then let the food do the talking. Due to our timeline for the day, we weren’t able to sit through the hour-plus wait time to get in, but we were glad to have the option of ordering takeout. The macadamia nut pancakes are known to be the restaurant’s specialty, but I opted for the banana pancakes. I was astounded by the portion size, as I was only able to finish about ¼ of what was given to me. This is a great brunch spot, not only because of its tasty food but also due to its generous portions and cheap prices.

The Sunrise Shack

The Sunrise Shack is one of the most recognizable acai bowl sites on the island. Located on the North Shore, this yellow shack is a vibrant and unmistakable shop most known for selling bullet coffee and decked-out smoothie bowls. Unfortunately, we weren’t able to make it up to the North Shore, but there is a location in downtown Waikiki we were able to stop by. My smoothie bowl filled my craving and was a refreshing meal after all my indulgence in Mexican food. 

Island Vintage Wine Bar

Located inside a shopping center in downtown Waikiki, Island Vintage Wine Bar is a sophisticated restaurant offering diverse wine selections and a tasty food menu. I decided to add this restaurant to the itinerary after hearing about its notable charcuterie boards. As the sucker for charcuterie boards that I am, I knew I had to indulge in this fare. This charcuterie board especially stuck out to me due to the local additions: macadamia nuts and papaya. If you’re on the hunt for some quality wine and charcuterie boards in Hawaii, Island Vintage Wine Bar will definitely suffice.

Where to Go During Your First Time in Oahu

Pearl Harbor

Pearl Harbor is one of the biggest tourist attractions in Oahu. Over a million visitors come here each year to commemorate the lives that were lost at the site of this horrific attack. Given that we were doing Oahu without a car, we decided the best way to visit Pearl Harbor was by booking a tour through Aloha Sunshine Tours. This five-hour tour cost no more than $45 per person, and it included hotel pickup and drop-off, a downtown tour, and our entrance to the Pearl Harbor National Memorial. Even though I am not huge into this aspect of history, it was still impactful to be standing at the site where everything went down and have a close look at the actual artifacts recovered from the attack.

Waikiki Starlight Luau

If you’re stuck between which luau to attend in Oahu, I can vouch for the Waikiki Starlight Luau located at the Hilton Hawaiian Village. As we entered, we were greeted by two locals dressed in traditional Hawaiian attire, as well as a table full of fresh leis for us to choose from. We were given a complimentary drink before being escorted to our table for the evening. Between the four-course dinner, mini hula lesson, and cultural-immersive show, this experience was well worth the price and should, in my opinion, be experienced by every individual who visits Hawaii!

Learn more about and book your luau here.

Diamond Head

Each Hawaiian island has a plethora of hiking options to choose from. Some have become illegal over the years due to their placement on sacred lands or unsafe conditions, but there are still plenty of legal trails to choose from. While the island has no shortage of hiking trails, Oahu is home to one of the most visited trails in all of Hawaii: Diamond Head. This volcanic crater is a beautiful sight from afar, but it also makes for a great workout. After ascending to the top, you’ll be greeted with wide-ranging views of the island, specifically of the downtown strip. I will have to say that, after experiencing Haleakala National Park on Maui, hiking Diamond Head wasn’t all that impressive to me. I do recommend it for first-time visitors to Oahu, but it is not something I feel I’d have to do again. I much preferred the views of Diamond Head to the views from Diamond Head. Since we were doing Oahu without a car, we had to catch an Uber to and from the trail, but it was still cheaper than it would have been to rent a car for the trip.

“Church on da Beach” - Waikiki Beach Chaplaincy

Regardless of your denomination or religious beliefs, I highly recommend attending the Waikiki Beach Chaplaincy’s church service on the beach, which happened to be adjacent to our resort at the Hilton Hawaiian Village! Each Sunday, from 10 am-11:15 am, this church gathers on the beach to praise God, spread the Word, and have fellowship with one another. I don’t normally attend church while on vacation, but I knew this was a church experience I could not pass up. The service was so impactful from its start. We engaged in multiple praise songs, received Bibles, watched a church member give a hula dance of praise to God, and heard the pastor preach a motivating sermon rooted in the Word and backed up with historical context. It was honestly one of the best sermons I’ve heard in my life. I was so happy to hear that the church has been allowed to operate on the beach for over 50 years, and I pray that it continues for many more years.

I was so sad when it came time to leave our resort in Oahu. Even before leaving, I was already dreaming of returning to the exact same hotel and embracing even more of the local culture. As you embark on your first trip to Oahu, I encourage you to respect the local culture and leave the island’s natural landmarks better than you found them. This is all a part of the “Aloha” spirit that the locals embrace, and I felt so fortunate to be able to experience a small glimpse of the lifestyle they are accustomed to. I’d love to hear about some cultural activities to engage in the next time I visit. Please leave a comment with your suggestions!

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