Oahu, Hawaii

Our first stop after landing in Oahu and picking up the car rental was Leonard’s Bakery of course! We visited a “Maladasmobile” in Koko Marina Shopping Center on our way to hike Koko Crater. Known for their malasadas, warm delicious donuts without a hole, we knew we had to stop here, and we are so glad we did! Try one of their many delicious flavors but be sure to get the original.  

After devouring malasadas, we made our way to our first hike – Koko Crater Trail, largely referred to as the train track hike in Oahu. Parking was easy with the trailhead located just beyond the baseball field. This hike largely consists of climbing old train tracks to the top so be prepared for a steep incline. Remember to stop every so often and take in the view behind you, including Hanauma Bay – it’s absolutely breathtaking! When you do ascend to the top, you will be rewarded with panoramic views of Oahu and the challenge to get to the top will be worth it! We spent about 30 minutes at the top – taking pictures, exploring the pillbox (an old bunker), and breathing in the fresh island air.  

Tip: Definitely wear sneakers or hiking shoes! There are some points where balance and footing are key to crossing the stairs safely.  

On the way to our hotel, we stopped at Lana’i Lookout and Halona Blowout Lookout – two beautiful vistas accessible via Kalaniana ole highway. The water at Halona Blowout Lookout is crystal blue and mesmerizing. We enjoyed the ease of driving straight to the view after the long hike up Koko Stairs.  For dinner, we went to Chiba-ken, an authentic Japanese restaurant tucked away from the hustle and bustle of Waikiki. We didn’t find dining in Waikiki to be that delectable but this place was the exception!  Tip: During our trip (August), lines for dinner, coffee, and more were outrageous. Be sure to make reservations in advance where possible and venture beyond Waikiki for real, delicious food. 

We woke up early to head to Kailua, a quaint beach town, home to Lanakai Beach. Kailua state beach is just gorgeous, but parking is quite difficult (we skipped this due to the crowds). Wake up early to get a parking spot or be prepared to drive around a bit. Parking for Lanakai Pillbox was no different as the trailhead is in a residential area. We parked in the surrounding neighborhood (make sure to read street signs) and walked a bit to the trailhead.   

Lanakai Pillbox hike starts out with a climb through thick sand, but this is actually the hardest part! There’s also ropes for support as needed. Once you finish this portion, the rest is fairly easy, following an exposed ridge so you get to marvel at the scenic ocean views for most of the hike. There isn’t much of a summit but the views along the way are what make it worth it!  

The town of Kailua has a much more local feel and we loved it! We had lunch at Easy ‘Que (highly recommend even for vegetarians!) before continuing our journey around the island. We headed north hugging the coast, passing the entrance for Jurassic Park and the Dole Plantation (although we didn’t stop for either) during this trip.   

One of our favorite spots was Kaaawa Beach, just north of the Jurassic Park entrance. With crystal blue waters and mountain views, this remote beach had just a few people on it and was so serene. It was really amazing that so many people stick to Waikiki Beach or Kailua Beach and this beach was so quiet. As we continued north, we stopped at Ted’s Bakery for their famous Haupia Crème Pie. This no-frills joint is the perfect stop after hiking and exploring – just be ready to wait (it’s worth it!). We eventually made it to the North Shore, pulling over to experience Banzai Beach. Parking was quite tough, so we had to hike a bit down the cliffs to get there.   

We made our way back taking the inland route (rather than the coastal route) towards Honolulu so we could make it back in time for sunset. To watch the sunset, we drove up Round Top Drive through Puu Ualakaa State Park, stopping at different viewpoints including Tantalus Lookout. Here we enjoyed the magical sunset over Honolulu.  

Diamond Head Trail was the first item on the agenda for our last full day in Oahu. Arrive here early as parking is limited to the state-run parking lot located near the trailhead. The parking lot is huge, and they have traffic attendants keeping the lot safe and fair. You have to pay a fee for parking and for entrance so make sure you bring your credit card. This hike is probably the most crowded hike due to its proximity to Waikiki and level of difficulty (easy). The views are pretty incredible so if you can ignore the crowds and focus on the views, you will enjoy this hiking experience!  

After the hike, we ventured towards the crowds in Waikiki Beach. We rented a chaise lounge chair (it’s almost impossible not to if you don’t get there extremely early). We enjoyed Happy Hour at The Beach Bar, an outdoor, expansive restaurant and bar right on the water and part of Moana Surfrider.  

We woke up early to Stand Up Paddle Board at Waikiki Beach. Check out Moku Hawaii (2446 Koa Ave). Going early was definitely the move and the waters were quite calm and easy to navigate in the morning. Our flight was at noon, so we paddled for an hour and headed back to shore. This was a wonderful adventure to experience at the end and the view of Diamond head and shores of Honolulu was quite beautiful.  

Other things to do in Oahu that we skipped due to time/interest: Shopping in Waikiki, Jurassic Park, Dole Plantation, North Shore, Pearl Harbor Memorial, Surf lessons