Oahu 5 Day Itinerary- Beyond Waikiki

Find Hawaiian charm on Oahu, by venturing past Waikiki on this Oahu 5 day itinerary. Explore Honolulu, Kailua, and the North shore with fun activities such as snorkeling, scuba diving, surfing, and hiking. I highlight some of my favorite meals along the way, and the luau you can’t miss.

Where to Stay in Oahu

Being in Hawaii can be all about staying on the beach, but that isn’t essential for Waikiki. In fact, it majorly backfired during our trip due to the hotel workers being on strike from all the beachfront hotels in Waikiki.

Thankfully, we had reserved a room already at the Hyatt Centric Waikiki, and we were able to get another room for the rest of my family that was originally scheduled to stay at the Hyatt Regency Waikiki. We booked both rooms with points, which meant not only a free stay, but it offered the flexibility to change the reservation and rebook when dealing with the situation with the strike.

Many hotels, like the Hyatt Centric, provide beach gear you can use during your stay. Beach chairs and boogie boards are a great way to make up for not being right on the beach.

Waikiki is very walkable, so it fine to walk over to the beach with your things, and enjoy the same beaches as the resorts. The beach gear can also be packed in your car and taken to other further destinations. We enjoyed them on Kailua Beach, and also found Ala Moana beach to be nice, less crowded spot, to swim and do other water sports.

On the other hand, nothing beats waking up to an ocean view. Be sure to read many reviews of the beachfront hotels in Waikiki, because service and furnishings can vary from good to very bad for the same prices. Some of the well rated resorts include the Hyatt Regency Waikiki, Sheraton Waikiki Beach Resort, and the Prince Waikiki. My parents also stayed at the Hilton Hawaiian Village on this trip, which had some nice features, but could use some updating.

Be aware of high daily parking rates and resort fees so you don’t get surprised at the hotel. This is quite standard for the area, even off the beach. When you use points to book with Hyatt and Hilton, resort fees are waived. Review my Hawaii hotel guide to find out which hotels to use your points at. Some might say Waikiki is overrated, and while it wasn’t my favorite, I think it is a great base to explore from for your first visit to Oahu.

We stayed three nights in Waikiki and one night on the North Shore. We stayed at the Ritz Carlton Oahu Turtle Bay, which has some of the best amenities on the north end of Oahu, as described in my full review of the property.

Day 1: Arrive in Oahu, Explore Waikiki

Afternoon: Arrive at Honolulu airport. Expect to take a while to get out of Honolulu airport. It can be difficult to navigate, and the various terminals and services are very far from one another. It was a very far walk from the gate to the rental car area, so if you are impaired, definitely seek assistance.

We arrived to Oahu after 5 amazing days in Kauai. Driving through Waikiki felt like a completely different world. The buzz of the crowds along with the big name brands lining the streets lent a Miami feel to this beachfront city.

Enjoy the convenience of a centrally located hotel to step right out and be surrounded by shops and restaurants. Parking can be a hassle, so leave your car at the hotel while walking around town or use Uber for a quick ride.

Evening: Dinner around Waikiki — there are plenty of options, from casual bites to fine dining. We opted for an authentic Japanese meal at Waikiki Shokudo. We had several stand out dishes there (don’t miss the ichibo steak) and great service both at the bar and seated at a table.

We also heard from locals that House Without a Key is a great oceanfront option. Grab a nightcap nearby at the jazz club Lewers’s Lounge.

Day 2: Scuba Dive in Honolulu/ Hike Diamond Head

Morning: Start with breakfast at Basalt, Heavenly Island Lifestyle, or ALOH Health Bar & Cafe (order ahead). Then choose your own adventure, in the water or on land.

I personally opted for a half day of scuba diving in Honolulu with Trident Adventures. The water was clear, the sites were not too far from shore, and we saw lots of sea turtles. I’m so glad I did this tour, because otherwise I would not have seen sea turtles on this trip. It is definitely worth going out on a boat to see them like on this snorkel tour or this shallow dive tour.

Meanwhile, my brother rented a surfboard to catch some waves in Waikiki. You could, of course, just relax on the beach as well.

Want to check off every signature Hawaiian activity? Then hike Diamond Head for panoramic views over Waikiki. The Diamond Head hike is considered pretty doable for most levels of fitness as it is paved, but does require many steps.

Pro Tip: Book your Diamond Head hike parking in advance. Spots fill up fast! Use a ride share app to catch a ride to the trailhead if you can’t secure a parking permit.

Evening: Catch happy hour at Herringbone Waikiki for great specials on drinks and appetizers. Or line up at Marugame Udon for their famous noodles. For a rooftop bar, stop in at Hideout.

Day 3: Botanical Gardens & Kailua

Morning: Visit Ho’omaluhia Botanical Garden — it’s a peaceful retreat, and best of all, it’s free! It’s a popular place for photos, but keep in mind that you are no longer allowed to stop in the middle of the road for a certain instagram shot. The gardens close at 4, so it is better to schedule this earlier in your day.

Learn about one of Hawaii’s chief products by reserving a coffee tasting at ChadLou’s Coffee Roasters for an educational experience.

Make your own judgement about the best pancakes in Kailua by making the line to dine at Cinnamon’s or at Boots & Kimo’s Homestyle Kitchen. Amazing varieties of pancakes can be found at either, like banana pancakes with macadamia nut sauce (B&K), cinnamon roll pancakes (C), and guava chiffon pancakes (C).

Lunch: Stop in at the Obama’s favorite shaved ice spot, Island Snow in Kailua. The all natural, homemade flavorings make this shaved ice a special treat. Definitely get the ice cream on the bottom as well. In the same shopping center we grabbed a sandwich for lunch at Mala Market.

Afternoon: Spend a few hours at Kailua Beach swimming and watching the kiteboarders. You could also opt for lunch here since great sandwiches are available at Kalapawai Market.

Evening: Have a barbecue dinner at Easy’Que and finish off at a speakeasy style restaurant, Gaslamp.

Alternative: Go the other way around the island to get to Kailua, and instead make reservations to snorkel in Hanauma Bay and then hike the Makapu’u Point Lighthouse Trail.

Day 4: North Shore Beaches & Luau

Spend some time beach hopping — Laniakea Beach is great for spotting sea turtles, Waimea Beach for cliff jumping, and Three Tables or Shark’s Cove for snorkeling. Stop for a refreshing açaí bowl at Hale’iwa Bowls or The Sunrise Shack.

We had gotten a late start this day so after stopping at Laniakea Beach (no turtles when we were there, but heard that others did see them that day) and The Sunrise Shack, we went straight to Ritz Carlton Oahu Turtle Bay Resort to enjoy the facilities.

I did not find the snorkeling impressive at Kuilima Cove (at the Turtle Bay Resort), but it is a pretty popular spot.

Evening: Experience a traditional Hawaiian luau at Toa Luau ($135-$165 per person). The evening starts with cultural activities and demonstrations, followed by dinner and the dance show. The show featured styles of dance from throughout Polynesia and ended with fire dancers.

I really liked the pace, variety, and organization of Toa Luau. It is a beautiful setting in the Waimea Valley, and is family run, so it is supporting locals. We did the gold tier and found the seating and view to be adequate. You are given a number of tickets to use for drinks based on your tier, and there are three cocktails to choose from as well as other beverages.

Pro Tip: The Luau ticket includes entrance to explore Waimea Valley and its stunning waterfall. You can arrive early or return to explore within 7 days before/after the luau you attend. The trail is quite long, and has cultural stops, so get the little train to take you to the end if you are short on time.

We walked at a brisk pace and it took us almost two hours round trip. For this reason we were glad we decided to return the next day to do the trail rather than try to squeeze it in before the luau. Swimming is allowed at the waterfall, but only with a lifejacket, which there are some old ones for rent there.

When scheduling your trip, pay special attention to what days of the week you are where. Luaus do not occur daily, so always check that the time and place line up correctly.

Day 5: Waimea Valley, Haleiwa, Dole Plantation

Morning: Soak in your last Hawaiian sunrise at the Ritz Carlton Turtle Bay, or just hit the breakfast buffet. Today was free day (no plan) so we did several of the things that had eluded us in the prior days.

We walked to the waterfall in Waimea Valley, had Matsumoto Shave Ice in the historic Haleiwa town, and stopped in a at the Dole Plantation. The Dole Plantation was as overrated as I would expect, but it was cool to drive through the pineapple fields.

No matter the destination, it is important to have a flexible day with no plans every few days. This way activities can get rescheduled if need be and it gives time to catch up on places that may have been overlooked. It can also just be a day to relax, sleep in, or cater to a member of the group specifically, or even break up the group entirely.

Fly out in the evening from Honolulu airport. Dining options were limited at the airport, so we ended up with prepackaged sushi. If you have a bit of extra time, the Plumeria Lounge at the airport is a relaxing spot to unwind before your flight, access it with priority pass or a credit card. There’s an entire garden around the lounge area as well that anyone can access.

If you are looking for ways to save on your Hawaii trip, then don’t miss my full guide to using points to book a Hawaiian vacation.