Hawaii is our favorite place in the world, and Oahu is my favorite island. (Yes, I’m an Oahu stan.) It has everything: beautiful beaches, lush hikes, quieter scenery once you leave Waikiki, and some of the best food anywhere. After numerous trips, we’ve landed on an Oahu itinerary we keep coming back to. Here’s our five-day plan, plus where to stay, where to eat, and what to pack.
Where to Stay in Waikiki: The Halepuna
Our favorite hotel on Oahu is the Halepuna Waikiki, the sister hotel to the storied Halekulani. It’s an easy walk to everything in Waikiki, which makes it a perfect home base for exploring the island.
This hotel is quiet, unlike many hotels in Waikiki, classy, and has more of an adult vibe. It’s owned by a Japanese company, so the service is very good as well. The pool is on the smaller side but has nice views of the city and ocean, since it’s on the 8th floor, and there is a large, hot Jacuzzi that we love to soak in after coming back from the beach. There’s also a nice pool bar where you can get cocktails and snacks.
We actually found the Halepuna by accident. On one trip we booked the Hyatt Regency Waikiki, and the stay was so bad that we checked out after two nights and moved to the Halepuna for the rest of the trip. We’ve been going back ever since.
We’ve also stayed at the Royal Hawaiian and the Outrigger Reef, and would happily recommend both.
Getting Around Oahu
You can walk almost everywhere in Waikiki, but rent a car for the road trip days. On one trip we rented a Jeep for a few days, which made the North Shore and windward side easy. If you only need a car part of the trip, pick it up in Waikiki rather than at the airport.
Day 1: Waikiki
Ease into the trip with a slow day in Waikiki.
- Morning: Coffee and an açaí bowl (I recommend the Liliko’i Moana Bowl) at Island Vintage Coffee. It’s our first stop every single trip.
- Optional early hike: Diamond Head. Go early to beat the heat. I’d read to expect it to take 2-3 hours, but we did it in about 90 minutes, at a moderate pace and in the rain.
- Midday: Explore Waikiki, shop, and hit the beach. Kahanamoku and Sans Souci beaches are calmer alternatives to the main stretch.
- Afternoon: Drinks and live music on the veranda at the Moana Surfrider, or a mai tai at the Mai Tai Bar at the Royal Hawaiian.
- Happy hour: Monkeypod Kitchen in Waikiki runs happy hour in the afternoon.
Day 2: Southeast Oahu Road Trip
This scenic drive along the southeast coast is one of my favorite days on the island.
- Morning: Book a snorkel excursion, or snorkel at Hanauma Bay. Hanauma Bay requires reservations, and they go fast, so book as soon as they open. If you want to do an excursion I recommend Holokai Catamaran’s Turtle Canyon Snorkel. We’ve done it twice and have seen dozens of turtles each time, which is so magical! The boat leaves from Waikiki Beach, so it is very convenient as well.
- Lunch: Kono’s for pork burritos and sliders.
- Lanai Lookout for dramatic coastline views.
- China Walls and Spitting Cave if the surf is calm enough to visit safely. China Walls is one of my favorite places in the world to sit and watch the ocean. There are usually some people jumping into the ocean from there as well, which I would not recommend unless you are a very proficient swimmer, but it’s fun to watch.
- Halona Blowhole and Halona Cove, two quick stops right next to each other.
- Makapuʻu Point Lighthouse Trail, an easy paved hike with big ocean views. It is unshaded and can get very hot so be careful when you go.
- Makapuʻu Beach and tide pools.
- Waimānalo Beach if you want a swim.
- Sunset: Tantalus Lookout at Puʻu ʻUalakaʻa, about 15 minutes from Waikiki.
- Dinner: Rigo in Honolulu. It’s a must for us every time. A Japanese-owned restaurant serving Spanish-Italian cuisine, what could be better?
Day 3: North Shore
The North Shore is laid-back surf towns, shrimp trucks, and turtles. Leave early and make a full day of it.
- Breakfast: Green World Coffee Farm in Wahiawa, on the way up.
- Optional stop: the Dole Plantation, also on the drive north. Touristy but cute, especially if you have kids.
- Waimea Valley: walk the trail through the botanical garden to the waterfall. Reservations were required when we went, and it was $25 per person.
- Lunch: You have to visit a North Shore shrimp truck. We tried Jenny’s Shrimp Truck on our last visit and I’m still dreaming about it.
- Haleiwa town: wander the shops and get shave ice at Matsumoto (as long as the line’s not too long).
- Laniakea Beach: known as Turtle Beach, and a good spot to see green sea turtles resting on the sand. Give them plenty of space.
- Shark’s Cove: tide pooling and snorkeling when the water is calm, usually in summer.
- Sunset drinks: Roy’s Beach House at Turtle Bay. Make a reservation or get on the waitlist. We like to walk around the tidepools at the resort after dinner. I hope to stay here some day!
Day 4: Kualoa Ranch and Ko Olina
- Breakfast: Kona Coffee Purveyors in Waikiki. The line gets long, so go early (or send someone ahead).
- Ko Olina: visit Aulani and the Ko Olina lagoons on the west side.
- Lunch: Rainbow Drive-In for a classic Hawaiian plate lunch, or poke.
- Afternoon: the Kualoa Ranch movie sites tour. It’s about 90 minutes and takes you through the valley where Jurassic Park and dozens of other films were shot. Book ahead.
- Evening: pool time back at the hotel.
Day 5: Windward Side
The windward (east) side is lush, green, and home to some of the prettiest beaches on the island.
- Nuʻuanu Pali Lookout on the drive over.
- Kailua farmers market on Sundays for an Aiwi waffle, or a snack from Kalapawai Market.
- Pillbox Hike for views over Kailua and Lanikai.
- Brunch in Kailua: Boots & Kimo’s, Moke’s Bread and Breakfast, or Over Easy.
- Kailua and Lanikai beaches. At Lanikai you can rent a kayak and paddle out to the Mokulua Islands. We’ve never done this, as I am a little nervous going so far into the ocean, but it looks beautiful. Lanikai is my favorite beach I’ve ever been to. The water is so clear and beautiful, with super gentle waves. Parking can be tough though, so be prepared to circle.
- Hoʻomaluhia Botanical Garden, which is free.
- Byodo-In Temple, a replica of a Japanese temple in the Valley of the Temples.
- Dinner: Haleiwa Joe’s at Haiku Gardens. They don’t take reservations, so get there early.
- Nightcap: Skull & Crown, a tiki bar in Honolulu.
This is a packed day, so I would prioritize a few stops instead of trying to hit them all! Personally, I will always choose a few hours on Lanikai Beach over anything else.
Where to Eat on Oahu
Coffee and Breakfast
- Island Vintage Coffee: coffee and açaí bowls. Our first stop every trip.
- Halekulani Bakery: coffee and pastries, in the same building as the Halepuna.
- Kona Coffee Purveyors: worth the line, with pastries from B Patisserie in San Francisco. The black sesame kouign amann is what dreams are made of.
- Kai Coffee Roasters and Knott’s Coffee Roasters in Waikiki.
- Leonard’s Bakery for malasadas.
- Arvo for brunch in Honolulu.
- Aloha Kitchen for soufflé pancakes.
Casual Eats
- Marukame Udon in Waikiki. Expect a line, but it moves fast.
- TsuruTonTan for udon.
- Kono’s for pork burritos and sliders.
- Rainbow Drive-In for a Hawaiian plate lunch.
- Helena’s Hawaiian Food or Highway Inn for traditional Hawaiian food.
- Sam’s Kitchen in Waikiki for garlic shrimp.
- Kamitoku Ramen at Ward Center for beef ramen and fantastic gyoza.
- Gyoza Studio Kubota for gyoza and ramen.
- Aloha Melt for grilled cheese, open late.
- Paia Fish Market Waikiki for fish tacos.
Poke
- Maguro Spot in Waikiki
- Maguro Brothers in downtown Honolulu
- Morning Catch Poke in downtown Honolulu (open until 2 p.m.)
Dinner
- Rigo in Honolulu. A repeat favorite. The papaya, mascarpone, and prosciutto crostini (pictured) ranks in the top dishes I’ve ever eaten. We go literally every time, even if we’re just on a quick one or two night stopover on the way home from Japan. Spanish-Italian fusion. I recommend any of the pastas or pizzas, the garlic bread, and the gazpacho.
- Sushi Murayama
- Taormina in Waikiki. Japanese-style Italian pasta. A bit more upscale for a nice evening out.
- Duke’s and Hula Grill in Waikiki, both classics.
Drinks
- Mai Tai Bar at the Royal Hawaiian for the classic Waikiki mai tai.
- The Moana Surfrider for drinks and live music on the veranda.
- House Without a Key at the Halekulani. Great drinks and a beautiful setting. Go for a cocktail, not dinner. The coconut cake martini is on my all-time favorite drinks list. They’ve had hula performances before too, usually starting around sunset. You can also order the famous Halekulani coconut cake!
- Lewers Lounge at the Halekulani for live jazz.
- Roy’s Beach House on the North Shore at sunset. Eat a dinner of various appetizers here. The entrées are extremely expensive, but the starters are generously sized and delicious.
- Skull & Crown for tiki drinks. This is such a cool, haunted ship-themed bar in Chinatown. We were very impressed by the decor inside and had a fabulous server as well.
- The Honey Bar in Kaimukī for mead and honey-based drinks. They also have a new location in Manoa, which is a bit more convenient to Waikiki. Get the tasting flight!
Shave Ice
- Matsumoto Shave Ice in Haleiwa
- Island Vintage Shave Ice in Waikiki
- Waiola Shave Ice
- Shimazu Shave Ice
- Uncle Clay’s House of Pure Aloha
It’s tough to narrow down my favorites, but if you only eat at three places:
- Rigo
- Gyoza Studio Kubota
- Maguro Spot
More Things to Do on Oahu
- ʻIolani Palace: book a tour in advance.
- Queen Emma Summer Palace: tours require reservations.
- Manoa Falls hike: a short rainforest hike close to Honolulu.
- Foster Botanical Garden in Honolulu.
- Ala Moana Center for shopping, and Yomi’s yogurt with black rice.
- A sunset catamaran cruise off Waikiki.
- Waimānalo Bay for easy boogie boarding waves.
Best Time to Visit Oahu
We’ve been in January, March, May, June, August, and September. Spring and winter can be windy and cloudy, which has cut into our beach time on a few trips. For the best chance of good weather, I recommend visiting between May to October.
Add On a Few Days on the Big Island
My aunt and uncle live on the Big Island, so I grew up visiting, and we often end a trip with a short hop over to Kona. On our last visit we saw sea turtles, dolphins, and even a whale, ate fresh-caught mahi mahi and ono, and had the best snorkeling we’ve ever done together at Two Steps. The water there is warmer than on Oahu. The flight is a bit less than an hour, you basically ascend, cruise for fifteen minutes, and then descend, so it’s an easy hop.
What to Pack for Hawaii
- A packable beach bag (we love the classic ABC Stores bag or something like this would serve you well)
- Flip flops (I always take my trusty Rainbows)
- A couple of nicer outfits for dinner
- At least one swimsuit for each day (shop my favorite swimsuits and vacation outfits here)
Our Oahu Itinerary at a Glance
- Day 1: Waikiki
- Day 2: Southeast Oahu road trip
- Day 3: North Shore
- Day 4: Kualoa Ranch and Ko Olina
- Day 5: Windward side
Stories from my LA life. Golden hour drives, good food, cozy corners at home, and trips near and far.
Leave a Reply