Oahu, Hawaii: Five Day Adventure Itinerary on Hawaii’s Capital Island

Breathtaking views, great food, cultural diversity, iconic beaches, paradise. These phrases barely begin to scratch the surface of how incredible the island of Oahu is and the amazing experiences it has to offer. The third largest island of Hawaii, Oahu is known as a perfect destination for any kind of traveler. Whether you’re looking for a quiet retreat where you can relax on a beach sipping a tropical beverage, or you’re ready to hike the remnants of a volcano and swim with sea turtles, this beautiful island is the place you need to visit! From Honolulu to the famous North Shore, this five-day travel itinerary’s goal is to introduce ideas for where to stay, where to eat and of course, what to do while on the island properly known as “The Gathering Place.”

Arriving in Oahu & Where to Stay in Honolulu:

Unless you are a resident of Hawaii on one of the other islands, then most likely you will be flying into Honolulu’s international airport. Many flights from the continental United States tend to arrive in the mid-afternoon timeframe, which does give you the opportunity to explore a little bit on your first official day on Oahu. However, you will be a little jet-lagged, which is why this particular itinerary will begin with your first full day on the island. 
For lodging, we chose to stay at the Ala Moana Hotel in downtown Honolulu. The prices were reasonable, and the location was convenient to everything we wanted to do. Not to mention, it is connected to the Ala Moana Shopping Center, which is the largest open-air mall in the United States! This makes for a perfect first evening in this amazing city due to the many shops and restaurants located here. So, for a quick bonus on where to get dinner on your first night, check out Mai Tai’s in the shopping center. While it’s a super touristy restaurant, the food was amazing, and it was perfect walking distance from our hotel stay! What more could you ask for?

Quick Day-to-Day Summary:

  • Day 1: Sea Turtles and Waikiki
  • Day 2: Honolulu Sightseeing
  • Day 3: Pearl Harbor and Chinatown
  • Day 4: Road Trip to the North Shore
  • Day 5: Waimea Valley and Toa Lua

Day 1: Honolulu & Waikiki

  • Island Brew Coffeehouse, Honolulu, Hawaii – It’s your first breakfast in Hawaii and you deserve the best French toast you’ve ever had (in my opinion at least). This coffeehouse has a few locations around Honolulu and one of them is located in the Ala Moana Shopping Center. Remember that thing I said about perfect walking distance? The vibes in this coffeehouse are perfect for getting your morning off to a good start. Make sure to fuel up on coffee, because it’s about to be time for a swimming adventure!
  • Turtle Canyon, Hanauma Bay Tours – Now that you’re fueled up, it’s time to throw on flippers, strap on a mask and dive in the perfectly blue waters of the Pacific Ocean. Snorkeling with sea turtles is one of the most suggested activities when visiting the Honolulu area and those suggestions are so correct! Being up close to these awesome creatures was such a treat! We chose Hanauma Bay Tours for our snorkeling excursion and we cannot say enough good things about these guides. They were extremely knowledgeable, insanely kind and just simply welcoming. After the snorkeling experience, they also take you to see epic views of the famous Diamond Head.
  • Honolulu Beerworks, Honolulu, Hawaii – After adventuring during the morning hours, it’s time to try the local brews and re-fuel with a good lunch. A short walk from where your tour guides will dock up and drop you off, is Honolulu Beerworks. This was the perfect place to hang out and recuperate from swimming in the choppy water. Highly recommend ordering a beer flight, because they were all simply too good to just pick one!
  • Kaka’ako Neighborhood, Honolulu, Hawaii – The neighborhood where Honolulu Beerworks is located is famous for the many murals that line its building walls. Not to mention even more breweries, shops and restaurants to explore if time allows.
  • Waikiki Area – Famous for its beaches, nightlife, shopping and more, you could spend days exploring everything this area has to offer. But for this evening of your trip, pick one of the many bars to have a relaxing drink or a store to shop for souvenirs until you drop!
  • Kuhio Beach Hula Show – This unique hula show takes place on Kuhio Beach in Waikiki every Tuesday and Saturday night. It’s a great insight to some of the culture that makes Hawaii so great. The show is put on by a local hula school and lasts around 45 minutes and the best part is that show is free for anyone to enjoy! Make sure to arrive a little early to get a seat, as many people attend this one-of-a-kind experience.
  • Marugame Udon, Honolulu, Hawaii – Ever had handmade udon noodles? Ever watched them be made and prepared right in front of you? If the answer is no, go here and taste the deliciousness that is this restaurant! Be prepared for a long line and wait, but it is totally worth it.

Day 2: Honolulu Beaches & Sightseeing

Holona Beach Cove in Honolulu County, Hawaii.

  • Holona Beach Cove, Honolulu County – First stop this morning, a famous landmark and filming location. Not only is Holona Beach adjacent to the Holona Blowhole, but it also happens to be where scenes from the Pirates of the Caribbean movies were filmed! This less crowded beach is perfect for laying out a towel and just relaxing as the waves crash into the rock walls surrounding the cove.
  • Kona Brewing Co., Honolulu, Hawaii – A short distance from Holona, is the brewery that almost everyone knows from Hawaii. Kona Brewing in Honolulu offers fantastic waterway views and an excellent menu of their craft beers and food.
  • Leonard’s Bakery Malasada Truck, Honolulu, Hawaii – Now it’s time for dessert. One of the best things you’ll ever have is a hot malasada. These Portuguese Donut was delicious, and I couldn’t get enough! You’re definitely going to want seconds and probably thirds.
  • Makapu’u Beach & Lighthouse, Honolulu County – After refreshing yourself at Kona Brewing and with sweets, it’s time to head back to the beach, but this time it’s an epic one that also features a scenic hike to an old lighthouse. The Lighthouse Trail at Makapu’u Beach is an easy to moderate hike that takes you through views of tidepools, blowholes, old military sites and of course the famous lighthouse point. Once you’ve completed this out and back hike, make sure to cool off on the beach before heading back to your hotel room to freshen up for another amazing dinner!
  • NatuRe Waikiki, Honolulu, Hawaii – Dress a little fancier and head back to Waikiki for dinner at this unique farm to table French restaurant. NatuRe Waikiki offers dishes prepared with classic French techniques while also being influenced by the local Hawaiian culture that surrounds it. Make sure to make a reservation on their website, as this place books up quickly!

Day 3: Pearl Harbor & Chinatown

Inside the Hangar at Pearl Harbor National Memorial.

  • Island Vintage Coffee, Honolulu, Hawaii – Another morning, another coffee shop. This particular shop specializes in breakfast bowls, which is one of the best ways to start your day off. Add a Kona brewed coffee to that, and the day is perfect already.
  • Pearl Harbor National Memorial, Honolulu, Hawaii – No trip to Hawaii is complete without visiting the site of one of the most famous days in American History. Pearl Harbor is an amazing experience, and you can expect to spend most of your day here. Here are the highlights of what to make sure and experience while at the memorial.
    • U.S.S. Arizona Memorial: a quick ferry ride takes you to the somber memorial where the lost ship still lies on the seafloor. Admission for this experience is $2.00.
    • Pacific Fleet Submarine Museum: features a self-guided tour inside a now de-commissioned submarine and a museum with extensive information about submarines roles in World War II and beyond. Admission is $30.00.
    • Battleship Missouri Memorial: features a self-guided tour of the battleship where the famous peace treaty with Japan was signed, officially ending World War II. Admission is $30.00
    • Pearl Harbor Aviation Museum: features several military planes from various time periods, as well as the hangars where you can still see bullet holes from the attack. Admission is $30.00.
  • Smith & Kings, Honolulu, Hawaii – Once again it’s time to fuel up, and this low-key bar and restaurant is the perfect place since probably been surrounded by people at Pearl Harbor all day. With excellent mixed drinks and an amazing appetizer menu, this is must stop in Honolulu’s Chinatown district.
  • Cindy’s Lei Shop, Honolulu, Hawaii – A short distance away, you’ll find what a local told us was the best lei shop on the island. Here you can pick out your own lei from the hundreds of choices they have or have a special one made just for you! That tends to be a little bit more in the pricey side though. You’ve been warned!
  • Chinatown District, Honolulu, Hawaii – This area has several stores and many uniquely designed buildings and is worth taking a stroll through. One thing to keep in mind with this location is to be aware of your surroundings. As in many places, tourists are prime targets for crime and being taken advantage of.
  • Wagaya, Honolulu, Hawaii – Remember those days of eating ramen out of a cup for every meal while in college? Well all that was leading to Wagaya in Honolulu, you just didn’t know it yet. Hands down the best ramen bowls you can find and a must eat destination while visiting the island of Oahu. Make sure to add yourself to the waitlist, I’m not the only one who loves this place!

Traveling to the North Shore of Oahu:

You may have noticed that I mentioned walking distance in a lot of the above sections. While staying in Honolulu, we chose to walk or use a ride-share service everywhere we went due to how expensive it would be to park a car, as well as the insane amount of traffic in Honolulu. When it came to travel to the North Shore, that is when we picked up a rental car for the remainder of our time on Oahu.

Day 4: Road Trip to the North Shore

Sunset at Ehukai Beah Park on the North Shore of Oahu.

Café Kopi, Kailua, Hawaii – Shortly after your departure from Honolulu, you come across this small town with a café known for its specialty of Singapore Laksa, a traditional Singapore broth dish that you just have to try! 
Kualoa Ranch, Kaneohe, Hawaii – With your energy revamped, are you ready to take a safari through the Jurassic Valley? That’s right, much of the Jurassic Park film was shot here on Oahu and at Kualoa Ranch, you can take several types of tours to witness film locations and the beautiful scenery you see in the movies.
• Ka’a’awa Beach, Honolulu County – As you’re traveling down the Kamehameha Highway, this beach park is a must stop for spectacular photo-ops.
Seven Brothers, Kahuku, Hawaii – Possibly the best burger you can have on the North Shore, this Hawaiian chain has now come to the mainland of the US, however it still embraces the Aloha culture that it comes from, which makes it a great lunch spot.
• Kuilima Cove, Kawela Bay, Hawaii – By this time, you are officially in the heart of the North Shore and it’s time for another snorkeling adventure. This cove is famous for being able to see sea turtles and other marine life and tends to have calmer waters than much of the rest of the North Shore beaches. For this adventure, make sure to bring your own snorkeling gear or you can rent from Turtle Bay Resort next door!
• Ehukai Beach, Pupukea, Hawaii – As the day starts to come to an end, there is no better place than Ehukai Beah Park to watch the sun as it sets over Oahu’s North Shore Beaches. Bring a towel and bask in the natural beauty of the golden glow as the waves crash around you.
Elephant Food Truck, Haleiwa, Hawaii – Down the road from Ehukai Beach is one of the best food trucks on the North Shore in my opinion! This unique food truck experience offers you Thai dishes with a Hawaiian twist. Get the Pad Thai and thank us later…
Turtle Bay Resort, Kahuku, Hawaii – As mentioned in a few lines above, the famous Turtle Bay Resort is located on the North Shore and what better place to stay than where “Forgetting Sarah Marshall” was filmed? This resort offers private rooms, condos and oceanside villas. You cannot go wrong with whatever accommodations you choose, as the resort is one of a kind and a must stay and we already want to go back as soon as possible!

Day 5: Waimea Valley & Toa Lua

Waimea Falls within the Waimea Valley in Haleiwa, Hawaii.

Da Bald Guy, Kahuku, Hawaii – Food trucks are synonymous with the North Shore of Oahu and you cannot miss the traditional Hawaiian style breakfasts that are served up at Da Bald Guy food truck. Steak, rice, and egg for breakfast? Tell us no more, we are there! 
• Waimea Bay Beach, Haleiwa, Hawaii – Want to see huge legendary waves? Maybe catch the surf (if you’re good enough) at a famous Hawaii Beach. Then Waimea Bay is a must stop where you could spend all day. Come here to surf, to relax and to witness what the North Shore is truly known for. Killer 30-foot waves!
• Waimea Valley & Falls, Haleiwa, Hawaii – Across from the beach, this park offers an epic hike to the 45ft. Waimea Falls. Surrounded by beautiful flowers and vegetation, these falls are perfect for photo ops and a relaxing swim.
Toa Lua, Haleiwa, Hawaii – After a long day on the beach and a decent hike and swim at the waterfall, it’s time to stay in the Waimea Valley for one of the best Lua experiences you can have on the island of Oahu. Happening seven days a week, the Toa Lua offers cultural dances from all over Polynesia, amazingly traditional prepared food, and informative cultural demonstrations that will truly give you a feel for what makes Hawaii so unique and unforgettable. Make sure to book in advance and we highly recommend the nighttime Lua due to being able to witness the fire dances. There truly is no better way to spend your last evening on the island of Oahu.

The next morning it will be time to pack up your things and begin the drive back to Honolulu and board your flight back home. On this drive, you may be thinking that five days is totally not enough time to visit Oahu and well, we couldn’t agree more! Oahu and Hawaii in general is an amazing, beautiful place and we should all aim to travel there as many times as life allows us to do so. Until next time my fellow wanderers!
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