Our Hawaiian Adventure: Oahu Edition

Meghna and I were figuring out where to spend her holiday break while I had some time off. We tossed ideas back and forth until I pitched the idea of tagging along on part of her family trip—but with a twist. Instead of Maui with her family, we decided to do a week in Oahu beforehand.

This itinerary quickly became one of our most shared trips among friends and family—over a dozen shares already—so now it’s time to share it with everyone!

Here’s the breakdown of our trip, WanderEarth style, with tips and tricks for an unforgettable 6-day adventure on the island of Oahu

Hotel: Sheraton Waikiki Beach Resort

Being the holidays, finding the right hotel was a bit of a struggle. After some searching, I came across the Sheraton Waikiki Beach Resort, and thanks to a good friend, we were able to snag a discounted rate. We stayed here for the entire trip, and I can honestly say this might be one of my favorite hotels yet.

From the amazing bar, infinity pool, all the activities they offer, and even a heated bidet toilet in the room; it felt like the perfect resort. And I have to mention—the pina coladas and mai tais here were the best I’ve ever had.

Day 1 Waikiki

I flew into Oahu the night before, got settled into the Sheraton Waikiki, and had a full morning to myself before Meghna’s flight landed later in the day. I kicked off the day with a cup of coffee from Kona Coffee and made a quick stop at Billabong to grab some swim trunks and a beach blanket—which, as it turns out, became an essential item for our beach-hopping adventures throughout the trip.

Waikiki Beach was just a short walk from our hotel, so I wandered down to check it out. Behind the beach is a lively stretch filled with stores, restaurants, and shops, which I took some time to explore and get familiar with. Once I was done walking around, I headed back to the hotel to enjoy the infinity pool and grab a seat at the hotel bar. While sipping on Mai Tais, I quickly realized the bar is a hot spot, filled with both first-time visitors and returning guests who come back year after year.

Later in the evening, I picked up Meghna from the airport, and we headed straight to Aloha Melt Waikiki for a quick sandwich for dinner by the beach. It was a perfect, low-key start to our Hawaiian adventure.

Waikiki Beach

Day 2 Eastern Shore of Ohau

One of the things I was most excited for was kayaking at Kaneohe Beach, but high winds had other plans—everything was shut down. We decided to make the most of it anyway, using the day to explore the eastern side of Oahu instead.

Byodo-In Temple

We made our way to the Byodo-In Temple, a stunning Buddhist temple tucked away in the lush greenery of the Eastern Shore. Open daily from 8:30 AM to 4:30 PM, it’s definitely worth carving out some time for a visit. The temple grounds are incredibly peaceful, with koi fish ponds scattered throughout, adding to the serene atmosphere.

It was one of those moments where time slowed down, and we could simply take in the beauty and tranquility of the surroundings. If you're ever on the Eastern Shore, make sure this stop is on your list.

Yummy Huli Huli Chicken

📍 49-132 Kamehameha Hwy, Kaneohe, HI 96744

Sometimes, it’s the simple meals that leave the biggest impression, and Yummy Huli Huli Chicken was exactly that. While driving along the Eastern Shore, we spotted a grill on the side of the road with rows of chicken roasting over open flames—we couldn’t resist pulling over.

At first glance, it had a trucker stop vibe with a small shop selling snacks, artisan goods, and a casual dining area in the back. But let me tell you, the chicken was juicy, tender, and packed with flavor.

This spot might be considered a hole-in-the-wall, but it delivered one of my favorite meals in Hawaii.

Yummy Huli Huli Chicken

Macadamia Farm

Right across from Yummy Huli Huli Chicken, we stumbled upon a macadamia farm with chickens and other wildlife roaming around. Inside, they had all sorts of Hawaiian treats, including different local nuts to sample (macadamias, obviously). We ended up grabbing a couple of bags for home.

Kualoa Ranch (Jurassic Park)

Welcome to Jurassic Park—where dinosaurs roam free… or in this case, horses and ATVs.

Kualoa Ranch is an absolute must-visit on Oahu, offering stunning landscapes and iconic movie set backdrops. Whether it’s ATV adventures, horseback riding, or guided tours, there’s something for everyone.

Unfortunately, we didn’t make a reservation in advance, so our visit was limited to walking around the entrance and soaking in what we could from a distance. Pro tip: book your activities early because this spot fills up fast.

Even with just a glimpse, the green valleys and towering peaks made it worth the stop.

Ho’omaluhia Botanical Garden

While driving around this part of the island, we stumbled upon Ho‘omaluhia and decided to check it out. Unfortunately, we didn’t get to fully enjoy the Botanical Garden experience. But as soon as we got out of the car to walk around, the rain started pouring, and we made a break back to Tomato (our trusty rental).

Germaine’s Luau

After much research, Meghna chose Germaine's Luau, and it turned out to be a great pick. They offer transportation from Waikiki, which I’d definitely recommend if you’re planning on having a few drinks—it’s a bit of a drive from the city.

We arrived early and spent some time on the beach nearby, walking around, snapping photos, and even catching a nice view of a lighthouse in the distance.

The luau itself was entertaining, with all the classic elements you’d expect, including a pig roasted in the ground—you even get to watch them pull it out, which was pretty cool.

We enjoyed a few Mai Tais and Piña Coladas alongside an endless dinner spread featuring roasted pig, Huli Huli chicken, macaroni salad, and rolls. While the meal wasn’t the highlight, the overall experience was fun for all ages.

Since it was Christmas time, they even had a Hawaiian Santa making an appearance, which added a festive touch to an already memorable night.

Day 3 North Shore

Green World Coffee

On our way to North Shore, we made a quick stop at Green World Coffee Farm for a fresh brew. This spot isn’t just about coffee—it’s an experience. We wandered through their coffee bean plants, getting a closer look at where it begins.

The coffee is roasted right on-site, and you can enjoy a few samples while you’re there. If you’re planning to bring back a taste of Hawaii for friends and family, this is the place to grab some beans. You’ll see these beans sold throughout the island, but the farm itself offers the freshest selection.

Dole Plantation

"Hop aboard the Pineapple Express!"

This wasn't part of our original plan, but as we were heading toward North Shore, we passed by the Dole Plantation and decided to check it out. It ended up being a fun stop. The human maze is a great way to pass the time, and we did a scavenger hunt that added to the fun.

Afterward, we took the Pineapple Express tour around the plantation. The tour gives you a good look at how the pineapples and other fruits are grown on the plantation. You’ll also see some animals along the way, which adds a nice touch to the experience. This place is one of the largest and most famous pineapple-growing sites in the world. Now, when I buy pineapples, I always check to see if they're from the Dole Plantation in Oahu.

While you’re there, make sure to grab some pineapple soft serve. It’s refreshing and a perfect way to cool down. There are also a variety of pineapple-flavored snacks and treats you can pick up, from candies to other goodies. It’s definitely worth the stop, especially if you’re already in the area, and it’s a nice little break during the drive.

Laniakae Beach

At certain times of the year, you can spot sea turtles and even their nests here, but we weren’t lucky enough to see any this time around. Instead, we had fun watching the surfers catch waves—a classic North Shore sight. The sand at Laniakea is so soft that I actually struggled a bit walking around, thanks to my Achilles still healing. We ended up just laying out our beach blanket, enjoying the breeze, and watching the surfers—simple, but the perfect way to unwind.

Giovannis Shrimp Truck (Cash Only)

The shrimp debate started before we even got to Hawaii—everyone seemed to have an opinion on where to find the best. At Giovanni’s, you’ll see a bunch of food trucks lined up, but Giovanni’s always has the longest line and only takes cash, so we had to hunt down an ATM first.

We tried the shrimp scampi, known for its world-famous garlic flavor, and Meghna opted for the lemon butter. Both were tasty, and the hot sauces on the side took it up a notch. If you’re a fan of a little kick, definitely give those a try.

Sunset Beach

One of the most iconic and picturesque spots on the North Shore, Sunset Beach was just a 10–15 minute drive away from where we were. We almost skipped it to head back to Waikiki, but decided to stay for the sunset—and I’m so glad we did. You’ll see surfers catching waves, people hanging out with a beer in hand, and everyone just enjoying the moment.

As the sun dipped below the horizon, the sky lit up with an array of colors—one of those memories I still look back on and smile. We definitely enjoyed our time here and would recommend making the stop if you’re in the area.

Ted's Bakery

Even though we weren’t particularly hungry, we spotted Ted’s Bakery on our way back and decided calories don’t count on vacation. We were curious to see if it could settle the shrimp debate between Giovanni’s and Ted’s.

As it turns out, the debate rages on. I preferred Ted’s Cajun Shrimp—it was loaded with flavor and already peeled, making it super easy to dig in. Meanwhile, Meghna swore by Giovanni’s. Looks like this one’s up for future couples and travelers to settle for themselves.

"Ted's Bakery or Giovannis Shrimp Truck?"

Day 4 Sunrise Trails, Presitine Beaches and Savory Discovery

Pillbox Hike

Let me start by saying this hike is no joke. Meghna and I wanted to catch the sunrise over the ocean, so we dragged ourselves out of bed at an ungodly hour. Of course, we ended up running late, and parking was tough. The Pillbox trailhead is tucked into a neighborhood with limited spots and plenty of "no parking" signs—definitely get there early if you want that perfect sunrise view.

We finally found a spot for tomato (yes, that’s what we named our red rental car) and started the trail. Almost immediately, I realized my Achilles tear still isn’t fully healed. The trail has loose rocks and parts where you’re practically crawling. I ended up stopping around halfway because my Achilles just wouldn’t have it. Really wish I could’ve finished, but that’s just another reason to come back and tackle it when I’m fully recovered!

Lanikai Beach

Lanikai Beach is often voted one of the world’s best beaches, and after seeing it firsthand, I totally understand why. The sand is unbelievably soft, and there weren’t many tourists around, which made it feel super peaceful. Even in December, the water was crystal clear—with no seaweed in sight. We spread out our trusty beach blanket, took a relaxing stroll, and jumped in for a quick dip (or at least my version of swimming). It was exactly what we needed to recharge after the Pillbox hike.

Makapuu Lighthouse Trail

Before we stopped for lunch, we decided to squeeze in another trail. Thankfully, this path was much more manicured and smooth compared to Pillbox, but the incline and length quickly took a toll. It winds around with steep elevation gains, and let’s just say I’m not in peak physical condition right now—hello, “Achilles weight.”

As we made our way up, we noticed a small break in the paved path that led closer to the lighthouse. It’s marked off for safety reasons (loose rock and gravel), and not recommended, but I have a thing for lighthouses, so I hopped the small barrier anyway. Meghna wasn’t thrilled and stayed behind, but I snapped a few photos and safely rejoined her.

We continued to the top of the main trail, which offered stunning views. Definitely bring water and wear comfortable shoes—while this hike isn’t especially difficult, the steady incline can be tiring. All in all, it was a worthwhile trek, even with my Achilles still on the mend.

Maui Mike's Chicken

If you’re from Dallas, you know Mike’s Chicken is a local staple. Naturally, I had to see if Maui Mike’s in Hawaii could measure up. Honestly, it reminded me more of a Cowboy Chicken chain—decent, but nothing I’d go out of my way for. I wouldn’t necessarily put this on the must-visit list.

We spent the rest of the day hanging poolside at the Sheraton Waikiki and going down to Waikiki shopping. Some of the designer stores do offer no tax or better deals compared to being home in Dallas. If you're looking for a fancy bag, wallet or something designer look while here- you may find a better deal than Texas.

Spice Up In keeping with my tradition of trying Indian restaurants wherever I go, we stopped by Spice Up for a change of pace. After days of Huli Huli Chicken and garlic shrimp, it was time for some haldi and garam masala. The food was great, and the service was fantastic. I also noticed a few locals dining in, which made it feel like more than just a tourist spot. All in all, it was a comforting break from the usual island flavors.

Spice Up

Day 5: Sluggish Morning, Scenic Hike and a Step Back in Time

We woke up sluggish and took a slow start to the day. Sheraton Waikiki had a great coffee shop serving local beans and options. I have probably mentioned the hotel a few times, if you can't tell I very much enjoyed our stay here.

Diamond Head Hike

Diamond Head Crater is that iconic landmark you’ll spot as soon as you arrive at Waikiki Beach—towering over everything and practically begging you to explore it. It’s just a quick drive from Waikiki, although there is a small admission fee to start the hike. The path winds through tight tunnels and stairways, and overall, it took us about an hour to reach the top. The payoff? Stunning panoramic views of Waikiki and its shoreline.

We capped off the hike by sipping pineapple juice straight from a freshly cut pineapple—definitely a highlight of the day. It’s a fun, refreshing way to celebrate conquering the summit.

Leonard's Bakery

Get ready to indulge in malasadas—if you’ve watched any travel vlog or scrolled TikTok for Hawaii recommendations, you’ve probably come across Leonard’s Bakery. We ended up ordering one of each flavor, which might’ve been overkill, but honestly, they were all amazing. My favorite was the sweet and sour, a perfect balance that kept me coming back for more.

Waikiki Food Court

We stumbled upon the Waikiki Food Court near our hotel—super convenient for a quick bite, but nothing mind-blowing. Think of it like a mall food court, just with a few more Hawaiian and Asian options thrown in.

Pearl Harbor

Visiting Pearl Harbor comes with a tangible sense of history. Unfortunately, the USS Arizona boat tour was shut down during our visit, so we didn’t get to explore that. We did spend time in the museum, learning more about the events that unfolded here. It’s not a very long visit, but definitely worth it—this place is a significant chapter of American history.

Day 6: Easy Bites, Sky-High Thrills and a Sunset Farewell

Hula Grill Waikiki Breakfast Early on, I spotted Hula Grill while hunting for new swim trunks and mentally bookmarked it for a breakfast spot later in the trip. I finally made it there and went with my usual veggie omelet—it was delicious. They offer a good mix of breakfast and lunch dishes, so there’s something for everyone. If you’re in Waikiki, definitely consider walking over.

Parasailing

I love a good adventure, but I have a fear of heights and deep water (and, well, I can’t swim). Naturally, parasailing seemed like the perfect thrill. It was my first time, but Meghna had done it before, so she helped keep me calm. We got an incredible view of Waikiki from out on the water. If you’re looking for something fun and relatively affordable, parasailing is a great option.

Manu Kai Catamaran

Later, we ended our night with a sunset catamaran tour. We boarded right off Waikiki Beach, just a short walk from our hotel. The tour included three drink tickets, but we found out it was actually unlimited. Unfortunately, the boat was a bit rockier than I expected, so I skipped most of the drinks and just enjoyed the views and time with Meghna. It was a beautiful way to see Waikiki from the water.

Paia Fish Market Waikiki

For our last dinner, Meghna chose Paia Fish Market, driven by her love for seafood. The food was amazing all around, and I’d definitely call this a must-visit spot in Oahu. It was the perfect cap to our trip.

Paia Fish Market

Reflection

Hawaii turned out to be the trip where Meghna and I truly got to know each other on a deeper level. We realized we can enjoy each other’s company anywhere in the world, no matter what we’re doing. From hiking and exploring different beaches to indulging in local food and shopping in Waikiki, we made the most of our time there. And yes, there was that chlorine pool water that flared up my eczema—but that’s a story for another day.

Oahu itself has a lot to offer. You could easily spend weeks there, trying different things every day. But if you’re a go-getter, it’s totally possible to cover the key highlights in just 3–4 days.

Travel Tips

• Beach Blanket – I grabbed one from Billabong and it went everywhere with us. Most beaches don’t provide towels or chairs, so having something sand-resistant to lay on was a game-changer.

• Keep Some Cash On Hand – Some mom-and-pop places are cash-only. You don’t need a ton—$100–$200 should be plenty for a couple.

• Hotel Location – At first, I considered booking different hotels around the island for convenience. I’m glad I stuck with Waikiki. Once the sun sets, most of the island winds down, while Waikiki stays lively. We were still able to grab a snack, enjoy a drink, or do a little shopping after dark.
  

Thanks for reading all the way through—or even if you just scrolled to the bottom. I appreciate your support, and I hope this helps you plan your own Hawaiian adventure!