My Oahu Hawaii Itinerary

My Oahu Book CoverMy 2014 trip was an 8 night 9 day 2 island Hawaii vacation (and to attend my cousins wedding on the Big Island). With just a little over a week in Hawaii, it was going to be a tight trip if we wanted to visit more than 1 island. But because this was going to be my first time in Hawaii, I felt I needed to see Oahu (and to visit a couple things I want to revisit from my Korea trip last year). With that in mind, we ended up with 4 days in Oahu, 5 days on the Big Island, and 1 travel day.

Below is our Oahu 4 Day Itinerary (We left Oahu early in the morning on Day 4 to fly to Big Island). We rented a car via Dollar Car Rental, using our phones as GPS (1 android and 1 iPhone) and covered most of the major attractions in Oahu.

August 26, 2014 to August 29, 2014

Day 1: San Diego to OAHU

After a five hour flight from San Diego to Honolulu we made our way to get our rental car and lucky for us no line and then made our way to our hotel using our trusty cell phones for GPS. As mentioned above, there were a couple things from last years South Korea trip that triggered a couple stops in Oahu. Marukame (Marugame) Udon and Nature Republic. Once we were settled in at our hotel, those were the first things I marked off my “Things To Do” list.

  • Direct flight San Diego to Honolulu (5 hours)
  • Arrive in Honolulu, pick up rental car
  • Hotel: Sheraton Princess Kaiulani Hotel
  • Dinner: Marukame Udon, Musubi Cafe Iyasume
  • Shopping: Pualeilani Atrium Shops at the Hyatt Regency Waikiki Beach Resort and Spa, Ala Moana
Day 2: OAHU – Central Oahu and North Shore

Oahu Day 2 - Itinerary and Map

Our first full day in Hawaii, we were up bright and early spent the day heading up to the North Shore with plenty of stops on the way. We started from our hotel in Waikiki (made a quick stop at Waikiki Beach early in the morning, picked up some musubi for breakfast and started our road trip at about 7:20am. The drive from Waikiki to North Shore takes a little over an hour etc. but with all of the stops we got to Waimea Bay Beach North Shore at about 3:00pm. We headed back to Waikiki after the beach (full 1 hour drive) for dinner and called it a night.

Day 3: OAHU – Wayside Coast and Honolulu

Oahu Day 3

We once again woke up bright and early for a morning hike up Diamond Head which is a relatively easy hike (just beware of the stairs towards the top). After our hike, we headed back to Waikiki (not shown my map) to change and grab breakfast before heading out our drive for the day. We drove to Nu’uanu Pali Lookout/Wayside for a windy view of the Wayside coast Oahu (very different from Diamond Head views), then drove to Byodo-In Temple. After grabbing lunch in lunch at Leonards’s Bakery and Rainbow Drive-In we checked out Chinatown and finally back to Waikiki to go shopping and dinner. We were going to have an even earlier start on day 4 as we head to Big Island.

Day 4: Leaving OAHU

We had a 6:45am flight to Oahu. So we woke up bright an earlier to finish packing up, and check out of the hotel. We returned the car (when it was still dark outside) and took the shuttle bus to the airport and checked-in. For the rest of day 4, check out my Big Island itinerary (Day 1).

  • Check out of hotel
  • Return rental car
  • Fly to Big Island


  1. Seeing so many pictures of that region really gives me the urge to travel there. Sadly I know that me and my family won’t be able at least for the next couple of years 😦

    1. I’m sure you’ll enjoy Hawaii even more when your son is a little older. And if you’re planning to go to Jeju, that is dubbed the Hawaii of South Korea.

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