Two-and-a-Half Days on Oahu – The Urban Island Guide


The second island on our Hawaiian vacation was Oahu.  Oahu is officially known as The Gathering Place, but I like to refer to it as The Urban Island.  It is home to nearly two-thirds of Hawaii’s population, and it features the very large city of Honolulu.  After the natural landscape of Kauai, we were a bit shocked to find ourselves in the heart of a huge urban area.  We spent just over two days on Oahu, but we were able to see almost everything we wanted due to Brooke’s excellent planning.

Air Travel/Transportation

  • Hawaiian Airlines – $5/ea (Used 4,500 American Airlines miles to island hop)
  • Rental Car, 3 days – $0 (Used 7,238 Citi ThankYou Points)

We used 4,500 American Airline miles to book island-hopper flights on Hawaiian Airlines.  These flights are available on for 5,000 AA miles, and we got a 10% rebate because of our Citi AA Platinum cards.  Availability was a bit spotty for award seats, but we were able to make it work with some careful planning.  If you can’t find award seats, the flights are inexpensive at $80-$100.

Knowing that we wanted to explore as much of the island as possible, we opted to rent a car.  Again, we used our Citi ThankYou points to book a rental car with Thrifty through the Citi Travel website, at a rate of 1.25 cents per point.  This time, we were upgraded to a Buick Verano with a leather interior and “luxury sound system.”


  • Holiday Inn Resort Waikiki Beachcomber, 3 nights – 105,000 IHG points
Very close to Waikiki Beach

We booked three nights at the Holiday Inn “Resort” Waikiki Beachcomber using our IHG points.  I put resort in quotations, because this hotel was nowhere close to a resort… more on that in a minute.  We selected this property, because we did not know much about Oahu, and we assumed Honolulu would be the place to stay.  Most hotels in Honolulu want outrageous point rates, so we settled on 35,000 per night at the Beachcomber.

What we Liked

  • Location – While not directly on the beach, this property sits across the street from world-famous Waikiki Beach.  It is also centrally located on Kalakaua Avenue, a bustling street with high-end shops and nice restaurants.
  • … that’s about it.

What we Did Not Like

  • Room selection – Brooke is an IHG Spire Elite member, so when we saw an upgrade to an “ocean view” room, we expected to be able to, you know, view the ocean.  The Beachcomber’s definition of oceanview means: You can lean over the balcony railing and catch a glimpse of water.
  • Parking – Parking is valet-only and costs $35 per night ($30 for IHG members).  Honolulu parking is expensive, but this is crazy.  There is no additional price break or consideration for Spire Elite guests.  We paid for the first night, after the manager insisted there was no way he could waive the fee.  Fortunately, we learned about FREE street parking along Ala Wai Boulevard (all day) or along the side streets (6pm – 7am).  We were able to skip an extra $60 in parking charges by walking an extra block.  If you park on Ala Wai Blvd, make sure to move your car by 8am on Monday and Friday, because they sweep the streets.  We literally saw the tow trucks lined up at 7:45am waiting.
  • Pool Closure – On our last night, Brooke and I wanted to grab drinks and chill by the rooftop pool.  We walked to the entrance around 8pm to find it closed for a special event.  There had been no indication of this closure, and management was unapologetic.  I spoke with a manger, and he offered to waive one night of parking (which he previously claimed he could do nothing about.)
Standard room

Otherwise, the hotel was ok.  For one of the more expensive IHG properties, this hotel did not meet our expectations.  This is definitely not a “resort.  We would recommend staying elsewhere.


First Night

We arrived at the HNL airport around 5pm, so we met some friends for dinner (they live in Honolulu).  They recommended Nico’s Pier 38, and we were very impressed!  Brooke and I shared the Poke Sampler and the Furikake Pan Seared Ahi (house speciality).  Everything was delicious, and Nico’s is conveniently located between the airport and downtown Honolulu.  Thanks for the great recommendation Amy & Chris!

After dinner, we checked into the hotel and walked through some of the shops along Kalakaua Avenue.  Since we had an early morning planned, we did not stay out too late.

Day 1 – Pearl Harbor & Pillboxes

  • Pearl Harbor

First item on the agenda for Oahu was obviously a trip to the historic Pearl Harbor memorial.  We read a lot of advice about this, because we did not want to miss out.  Many guides and websites recommend arriving very early to get in line.  Other businesses offer to pick up tickets for you for a fee.  We finally discovered that you can reserve tickets in advance through this government website for a $3 fee.  Since the fee is so low, advance tickets often disappear quickly, but there are also 1,300 free walk-up tickets available each day.  We reserved 8:30am tickets, but when we arrived, we were able to grab tickets for the 8am tour.  The day we went, there were literally no lines, despite what other websites had indicated.  We also bought tickets to visit the Bowfin submarine and the Mighty Missouri Battleship.


The free tour included a historic video that provided the background for the attacks on Pearl Harbor and exclusive footage of the actual attack.  After the video, we got onto a ferry to ride out to the sunken Arizona Battleship site.  We were quite surprised to see oil still rising from the sunken ship.  We spent about 30 minutes at the Arizona memorial before returning on the ferry.

Next, we hopped on a bus to ride onto Ford Island and tour the “Mighty Mo.”  Our tour guide was very animated and gave a great, detailed account of the battleship’s history.  We learned that the treaty to end WWII was signed aboard the Missouri.  The Missouri is positioned in the harbor to face the sunken Arizona, creating what our guide called “the bookends of WWII.”  After the tour, we spent a little while roaming through the mess halls, lounges, offices, and bunks of the ship.  It was incredible to imagine what life would be like on such a huge war vessel.

Finally, we grabbed headsets and boarded the Bowfin submarine.  We listened as the audio guide walked us through the lower decks of the submarine.  This tour is simple and quick, no more than 30 minutes.  I definitely gained another level of respect for those who serve our country in such inhospitable environments as battleships and submarines.


Leaving Pearl Harbor, we drove across the eastern part of the island toward Lanakai Beach.  For lunch, we stopped in Kailua at the Uahi Island Grill.  This small cafe was featured on Diners, Drive-ins, and Dives.  We went for the Tamarind Burger and Korean Steak Sandwich, and both were delicious!

  • Lanakai Pillbox Hike


The Pillbox Hike is an absolute must do on Oahu!  It can be tricky to find the trailhead, particularly because the location on Google maps is incorrect.  Use the following address in Google maps: 382-498 Kaelepulu Dr, Kailua, HI 96734.  This will bring you through a residential area, and right to the sign at the trailhead.  You will have to park along one of the streets in a neighborhood.  Also, make sure to wear sunscreen, because the entire trail is exposed to direct sunlight.

Hiking the trail can be a bit challenging due to high winds and loose rocks.  You will follow the edge of a ridge up the side of a cliff.  Some parts are a bit steep, and the trail is not always clear, which makes this a fun hike.  Take your time and pick your own path up the hill.  Continue until you see the first pillbox, or small, flat-topped building.  We reached the pillbox and climbed on top for an incredible view of Lanakai Beach’s clear blue water.  We lingered up here for a while, enjoying the gorgeous scenery and nice breezes.

  • Lanakai Beach

Back at the base of the trail, we walked through the neighborhood to Lanakai Beach.  This may be the most beautiful beach we saw during our trip.  The water is a beautiful shade of blue, and the small islands off the coast really add to the scene.


  • Makapu’u Point Lighthouse Trail

Departing Lanakai Beach, we chose to drive the Kalanianaole Highway around the eastern tip of the island.  The road hugs the coastline and provides great views along the cliffs.  We made one more stop to walk the Makapu’u Point Lighthouse Trail.  I would hardly call this paved walkway a “trail,” but it provided an easy path to the lookout point.  We enjoyed a leisurely 2-mile stroll out and back.

On the way back to Honolulu, we stopped for dinner and beers at Kona Brewing Company.  They featured 14 in-house beers, some only available at the restaurant.  We grabbed a couple beer flights and some dinner.  I highly recommend the Wailua Wheat, Hula Hef, and Lemongrass Luau!


Day 2 – North Shore

On our second day, we drove up to Oahu’s famous north shore.  This area of the island is famous for its intense surf and huge waves.

  • Laniakea Beach (AKA Turtle Beach)

Laniakea Beach (not to be confused with Lanakai Beach) is very well known as being a place where huge sea turtles come to chill.  They can be found hanging out on the sand, catching some rays.  Unfortunately, the turtles were nowhere to be seen on the day of our visit. 😦

  • Waimea Beach Park

Many beach parks can be found along the north shore of the island.  These are usually places with a parking lot off the roadside, some benches, restrooms, and of course, a beach.  We chose to stop at the Waimea Beach Park, because I read about a huge rock where people jump into the waves.  I was not disappointed!  Brooke stood by, shook her head, and videoed me jumping from the top of this rock into the crashing waves below.  It was so much fun that I had to do it twice!

  • Shark’s Cove Snorkeling

Despite the awesome name, there are no actual sharks in Shark’s Cove.  It is a relatively shallow area surrounded by rocks, where water flows in through a channel.  There are some colorful fish to see, and some interesting coral formations.  To fully enjoy this area, you should bring your own snorkel gear and water shoes.  There are sharp rocks and coral, so watch where you step!


  • Lunch – Sandy’s Sandwiches

After we finished snorkeling, we were very hungry.  Thanks to Yelp, we discovered a tiny food truck on the side of the road called Sandy’s Sandwiches.  We had read that the sandwiches are HUGE, so we opted to share one.  This was a great call, because this may have been the largest turkey sandwich I have ever seen!  If you are hungry on the north shore, definitely check out Sandy’s!

  • Bonsai Pipeline

Since the food truck had nowhere to sit and eat, we took our gigantic sandwiches to the nearby beach, labeled Bonsai Pipeline.  Here we sat down and watched surfers catch some gnarly waves.  I had never seen waves this large before, but the surfers really seemed to love it.  We found out that a world surf competition was taking place in the coming days, so apparently we stumbled upon their practice session.

  • Haliewa 

On our return drive toward Honolulu, we followed signs for the town of Haliewa.  Some people we met had mentioned great shopping and shave ice in this area, so we wanted to explore.  Our first stop in Haliewa was at Matsumoto Shave Ice.  If you’ve never had authentic shave ice, you really should try it!  Here, they serve fluffy shave ice on top of ice cream, mocha balls, and azuki beans (boiled in sugar water).  They top the shave ice with your choice of over 30 flavors!  Deeeeelicious!


After nearly putting ourselves into a sugar coma, we strolled through the eclectic Haliewa shops.  Since we didn’t feel like buying anything, and we were getting pretty tired, we grabbed honey lattes from Island Vintage Coffee Company.  Oh wow, their lattes are very tasty and exactly what I needed before driving back across the island.

  • Tantalus Lookout Point

Before returning to Honolulu, we stopped at the Tantalus Lookout Point, on a mountain high above the city.  The vantage point provides an excellent panoramic view of the urban areas of Oahu as well as Diamondhead Crater.  We arrived just in time to watch the sun descend over the western side of the island.


Day 2.5 – Sunrise Hike

  • Diamondhead Crater


Our final day on Oahu started very early!  We arrived at the foot of Diamondhead Crater around 6:30am.  We began the hike to the top in the dark, so we could watch the sunrise from the summit.  Even at the early hour, the trails and pathways were crowded.  We followed the winding trail along along some ledges, through tunnels, up stairways, and eventually to the very top.  At the top, we marveled as the sun crept up over the horizon.  It was B-E-A-utiful!

  • Hanauma Bay Nature Preserve – FAIL

We planned to visit this beautiful snorkeling area before returning to the hotel to shower, and then head to the airport.  Unfortunately, in our research, we missed the fact that it is close only on Tuesdays… so we arrived at a giant CLOSED sign!  Booooo!

  • Lava Tube

Since we had some hours to kill before our flight, and the nature preserve was closed, we decided to explore a bit more.  I had heard about a “secret lava tube” (tunnel created as lava hardened) somewhere near the nature preserve, so I googled it.  There were a few videos on youtube where people went through the lava tube, under the highway, and out to a really cool looking cliff!  I had to find it!  After analyzing the videos, I started to pick up clues.  We followed the clues like a scavenger hunt and found the lava tube, so we decided to make a video as well.  I hope this helps you find the tube for yourself!

After the lava tube adventure, we returned to the hotel to gather our stuff and check out.  We headed to the airport to catch our flight to the last of our three islands, Maui.

Total Trip Cost Breakdown

The following table breaks down our transportation and lodging costs.

Item Points/Miles/Loophole Actual Cost
Airfare x 2 from LIH-HNL 4,500 AA Miles + $5 per ticket on Hawaiian Airlines $10
Rental Car – 3 Days 7,238 Citi ThankYou Points (1.25CPP) $0
Holiday Inn “Resort” Waikiki Beachcomber 105,000 IHG Points $0

Oahu was a mixture of fast-paced city and laid-back island, with a bit of significant history sprinkled in.  I hope you enjoyed our brief tour of The Urban Isle!  What are your favorite parts of Oahu?


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