If it’s your first time visiting Hawaii and you’ve traveled all that way, I think it’s a must-do to spend at least a couple of days in Oahu. On our first visit to Hawaii, we spent 4 days on Oahu and then 4 days on Hawaii (The Big Island). I will cover the Hawaii itinerary separately, but this is a great combination that allows you to experience all of the best things that Hawaii has to offer. I recommend flying in to Honolulu (HNL) to start your trip, and then taking one of the quick flights on Hawaiian Airlines to the next island. I would do Maui on a separate trip (see my week-long itinerary in this post), because there is so much to do there. The weather in Hawaii is pretty much the same year-round (rainy season is November through March), so any time of year is good to travel there. For this Oahu itinerary, we were traveling as a family (my kids were 11 and 8), plus my parents were along, so it’s a good one for all ages!
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Here is a sample 4-day itinerary for Oahu based on our family trip in the spring:
DAY 1: ADJUST TO TIME ZONE AND EXPLORE WAIKIKI
First, where to stay? Since we were going to be on Oahu for a pretty short time and wanted to hit the popular spots like Pearl Harbor and Diamond Head, we decided to base right in the Waikiki Beach area. We had a beach resort booked for the second half of our stay on Hawaii, so we kept the cost lower by staying at a the Hyatt Place Waikiki Beach, just a short walk from Waikiki Beach. It’s a great hotel (try to get a room with a balcony overlooking Diamond Head) with all the bases covered…free breakfast, outdoor pool, gym, etc. If you’re staying for a week and want to stay away from the hustle and bustle, friends of mine have stayed at Turtle Bay Resort, and absolutely loved it. Just keep in mind that it is on the North Shore which is 1 hour and 15 minutes from Waikiki, and traffic on Oahu can be really bad. But in spite of the traffic situation, I do recommend renting a car so that you can fully explore the island.
For most travelers, you’ll probably arrive in Honolulu pretty late in the day (especially in whatever time zone you’ve come from). The goal is to stay awake until a normal bed time in Hawaii so that you can sleep as late as possible. The first morning you will probably wake up really early either way, and will get pretty tired by dinner time. For the first day I’d suggest spending the day exploring the Waikiki Beach area. The public beaches can be a little crowded, but you don’t have to worry about parking and there are plenty of facilities and food options nearby. And beautiful sunsets! If you’re in Waikiki on a Monday or Wednesday be sure to check out the Waikiki Farmer’s Market (just a short walk from the beach, currently open 4-8PM). They have lots of unique drinks, food, and other Hawaiian products to try (or take home), including one of my absolute favorite finds, the coconut peanut butter from North Shore Goodies. If you’re not able to make it to the Farmer’s Market, do yourself a favor and find one of their stores and buy some…you won’t regret it!
DAY 2: DOLE PLANTATION, HALEIWA, AND NORTH SHORE SURFERS
Grab breakfast at the hotel, pack your beach gear and some snacks, and get ready for a day of exploring. If you haven’t done the Dole Plantation before it’s a bit touristy, but still a pretty fun way to spend an hour or two, especially if you have the kids in tow. It’s about a 45 minute drive North of Waikiki. You can explore their gardens, do a pineapple maze, take the Pineapple Express train ride through the grounds, have some Dole Whip, and shop for some pretty neat souvenirs. My daughter harvested her own pearl from an oyster and had it made in to a really cute gold necklace right on site! They have a full restaurant there as well if you want to have lunch during your visit, but if you can hold off for a bit, I’d recommend getting lunch in Haleiwa, just another 15 minutes up the road from the Dole Plantation.
Haleiwa is a great little surf town that’s about an hour Northwest of Waikiki. It’s at the South end of the North Shore. We found this great food truck with amazing fish tacos…not sure if this particular one is still around, but keep your eye out for the casual seafood places in this area. Everything is so fresh!
After lunch, head up North a little further to Laniakea Beach (sea turtle sightings and surfer watching) or Waimea Bay (surfer watching and visit Waimea Falls, a 3.5 mile hike in total). You can also just hang at the beach and stay to watch the sunset before heading back to Waikiki. Just a warning that parking at these public beaches gets very full, especially on weekends, and you are pretty much stuck waiting for a spot to open. The weather became pretty hairy for our ride home, so always good to have a change of clothes and a rain jacket in case of a sudden weather change. With that said, after the rain you’ll often see a rainbow!
DAY 3: PEARL HARBOR AND OCEANSIDE DINNER
In my opinion, one of the main reasons to make a stop in Oahu on your Hawaiian vacation is to visit Pearl Harbor, since it is such a significant part of US history. My dad was stationed at Pearl Harbor during the Vietnam War and my mom was a nurse in Honolulu, and this was their first time back to Hawaii in nearly 40 years. It’s a surreal and somber experience to tour Pearl Harbor, but definitely worth it. You’ll want to plan to spend the entire day there; do the full experience that includes all the options, including the boat tour that takes you out to the USS Arizona. I highly recommend booking your tickets in advance and make sure the USS Arizona is included, because the number of people that can tour each day is quite limited. As another option, if you want to take the stress out of booking a self-guided tour and getting tickets, you can arrange for a tour through companies like Trip Advisor as well.
After a long day of touring, get cleaned up and book a nice dinner along the beach and catch the sunset. Since there’s a Duke’s on Waikiki Beach, you know I have to recommend going there! The mai tais, fresh fish, and hula pie for dessert are not to be missed!
DAY 4: DIAMOND HEAD, NU’UANU PALI, AND KAILUA
For this last full day on Oahu, we will head to the East side of the island. Be sure to have a hearty breakfast, and pack some hiking shoes, beach gear, and an extra change of clothing. The hike up Diamond Head is a must-do on Oahu. It’s fairly steep at 560 feet of elevation gain (including 175 steps!), but short at 0.8 miles each way. It will likely be crowded, but the views at the top are pretty amazing and well worth it. And it’s only about 15 minutes from Waikiki Beach!
After the Diamond Head hike, drive about 25 miles North to the Nu’uanu Pali Lookout. It’s a beautiful spot to see a completely different part of the island – the lush windward side, and cliffs all around. You just need about 20-30 minutes here to take in the views…and experience some serious wind!
From Nu’uanu Pali, head another 15 minutes Northeast to the town of Kailua, which has some of the most beautiful white sand beaches in all of Hawaii. Grab lunch at one of the restaurants in Kailua, and then head to the beach! We spent our time at Kailua Beach Park, but there are others nearby including Kalama Beach Park and Lanikai Beach that are equally beautiful. The day we were there it was pretty breezy, so there were plenty of waves to play in, and wind surfers galore! It was also very quiet along this entire stretch of beach. A wonderful place to spend the afternoon.
DAY 4.5: DOWNTOWN HONOLULU LANDMARKS AND TRAVEL DAY
Most flights tend to leave Hawaii in the evening, so you might have a half-day left in Oahu. Our flight to the Big Island was in the late afternoon, so we stopped in downtown Honolulu for a couple of hours on our way to the airport. We visited the Iolani Palace, where King Kamehameha and other Hawaiian royalty have lived over the years, the courthouse where my parents were married, the King Kamehameha statue, and explored the gardens in the area full of huge banyan trees. It’s a nice way to spend your last few hours in Oahu before heading home, or to your next island.
Great trip , trip of a lifetime , thanks Fred
It was such a great trip! My next post will be on the second half of our trip when we went to the Big Island…