5 Day Oahu Itinerary 🌸: An Expert’s Guide for 2025

Day 1: Kailua and the Windward Side

Kailua is my favourite town on Oahu. It’s a small-ish beach town with lots to do, see, and eat. It’s large enough to have whatever you need, but small enough that everything is easily accessible.

You’ll love Kailua Beach and Lanikai Beach on the Windward Coast – they’re perfect for kayaking, windsurfing, and swimming. It’s a charming town with a relaxed feel, boutique shopping, local eateries, and weekly farmers markets.

Breakfast

Boots & Kimo’s has been a local favourite on the island for 30 years, it a stop here is perfect for your first day. They’ve moved around a bit over the years as their need for space has grown. They’re now located in the Enchanted Lake Shopping Plaza on Keolu Drive.

They’re famous for their Mac Nut Pancakes – it’s all in the sauce. I’m partial to the Strawberry Waffles, which you can also get with the sauce. But they have a big selection of breakfast and lunch items. And lots of parking.

• Hours: 8am – 1pm, 2pm on weekends
• Closed Tuesdays and Wednesdays

There’s a small Safeway grocery store in the shopping plaza, too, if you need supplies.

Morning – Lanikai Pillbox Hike

Lanikai is a small, upscale residential neighbourhood of Kailua. Its Pillbox Hike, also known as the Kaiwa Ridge Trail, is a popular hike in the area.

It’s known for its stunning panoramic views of Lanikai Beach, the Mokulua Islands (“the Mokes”), and the Ko’olau Mountains.

Morning is the best time for the hike before the day gets too hot. If you can get up early enough, it’s a great place to watch the sunrise. But the views are spectacular any time of day.

Trailhead Location:
The trailhead for the Lanikai Pillbox Hike starts directly adjacent to the Mid Pacific Country Club on Kaelepulu Drive. You’ll find the entrance marked by a small sign leading up from the residential streets.

Length of the Hike:
The hike is relatively short but steep, covering about 1.8 miles round trip. It takes about 30 to 60 minutes to reach the first pillbox, depending on your pace.

The second pillbox, if you decide to go on, is another 10 minutes. The trail is moderately challenging due to its elevation gain and the often slippery, dusty path.

And there is no shade, so wear a hat. But the views will make you forget all that.

🏝️ Fun Facts: The pillboxes along this hike are old World War II military bunkers. They were originally built as observation stations to provide strategic views and defence points over the eastern shores of Oahu. Today, they’re known as “pillboxes” due to their shape.

Where to Park:
Like everywhere on the island, parking can be tricky. There is no designated parking lot for the trail so you’ll need to find parking along the residential streets near the trailhead.

Please be mindful of local residents. Don’t block driveways or mailboxes and follow any posted parking restrictions. Parking is usually easier to find early in the morning or later in the afternoon. You can also park at the Kailua Beach Park and walk up.

Additional Tip:

Due to the trail’s lack of shade and often hot, sunny conditions, I recommend that you wear sunscreen, sunglasses, and a hat. Sturdy hiking shoes are recommended, too, as the trail can be rocky and uneven.

And don’t forget to bring water to stay hydrated!

If you’re not too hungry for lunch after your hike, take a drive around the Lanikai loop. It’s a small, pretty residential area with some impressive homes.

There’s a lovely beach in Lanikai, too, with not-bad snorkelling. Parking is an ongoing frustration, though. If you found a spot before your hike, keep it and walk to the beach to have a look.

There are public beach accesses every 100-300 feet.

Dinner

There are a lot of options for dinner in Kailua. If you’d like to eat on the beach again, stop in at Whole Foods or Times Supermarket.

Whole Foods in Kailua has a large selection of hot food, salads, and baked goods. Or do like I do and stop at Fatboys on Kailua Road for some garlic chicken with extra sauce to go.

Pick up what you like, head down Kuulei Road to Kalama Beach, spread out your towel and relax. Kalama Beach is an extension of Kailua Beach and is quite safe. If you’re lucky, you’ll get to watch a full moon rise up out of the water.

For something with chairs and waiters, Buzz’s Original Steak House is just across the street from the beach park. Buzz’s is known for its laid-back, beachside ambiance and traditional Hawaiian hospitality.

The food is good, but it’s a bit pricey for the portion sizes.

They serve up a menu featuring prime steaks, fresh seafood, and island-inspired cocktails. It’s all enjoyed in a Polynesian-style décor and tropical garden setting. If you like Mai Tais, ask about the BFRDs.

Day 2: Explore Waikiki

Breakfast

On your way out of Kailua, stop for an unforgettable breakfast at Cinnamon’s on Uluniu Street. Their menu is full of local flavours and generous portions. The friendly, casual atmosphere is the perfect for start to your day.

Cinnamon’s is known for their famous guava chiffon pancakes, red velvet pancakes, and the loco moco*. You can enjoy these unique dishes alongside traditional breakfast favourites, all prepared with a distinct Hawaiian twist.

Parking options include metered street parking and metered parking in the attached lot. The buildings on the block are built around a large parking lot, but despite the size it can fill up on weekends.

Hours: 7am-2pm every day

* 🍳 Fun Fact: Loco moco is a Hawaiian favourite with rice, hamburger patties (or spam), and fried eggs, all covered in gravy. Yum!

Morning – Whale Watching or Surfing Lessons

If you’re lucky enough to be on Oahu from December through April, you get to go whale watching! This is when humpback whales travel from Alaska to Hawaii to breed and give birth.

The peak of the season, when sightings are most frequent, is from January to March. Seeing these 45-foot whales from a boat in the middle of the ocean is an incredible experience. I go every chance I get. You can find really great tours at Viator.

If you and the whales are visiting Oahu at different times, take the morning to learn how to surf. There are several stands along the beach, especially on the sand in front of the statue of Duke Kahanamoku, the “father of modern surfing”.

Stop in at one of these stands – they should all be the same price – and arrange your lesson with the beach boys. Or if you like to plan in advance, book your lessons online.

SNACKS: If you’re looking for snacks while you’re on Waikiki Beach, I recommend wandering into any of the nearby hotels. Most of them have small shops where you can buy something to nibble on.

If you have time before lunch, head off the beach to Kalakaua Ave, the main road through Waikiki. There are shops all along the street to wander through, from high-end to inexpensive souvenirs.

As well, stop in at the three floors of luxury and local retailers in the beautiful Royal Hawaiian Center. And you can’t miss the upscale International Market Place.

Lunch

Walk down the beach to the Outrigger Waikiki Beach Resort, where you’ll find Duke’s Barefoot Bar. The food is great, and so are the mai tais, but people go to sit in the sun overlooking the beach!

It’s easy to find if you can see the pink Royal Hawaiian Hotel. Facing the Royal Hawaiian, turn right and go past the hotel next door, the Sheraton. The next hotel you come to will be the Outrigger.

You seat yourself here, and will probably have to hover, waiting for someone to leave before you pounce on their table. If that’s not your style, walk across the street from the beach to Cheeseburger in Paradise.

You’ll find it on the corner of Kalakaua Ave (the main road) and Kealohilani Ave. You can’t go wrong with the Mahi Sandwich, but everything else is good, too. Have a drink in memory of the late Jimmy Buffet.

Afternoon – Diamond Head Crater Hike

The Diamond Head Crater Hike is one of Oahu’s most popular trails. It’s all about the panoramic views of downtown Honolulu and the Pacific Ocean from the top.

The trail is about 1.6 miles round trip, with a moderate to challenging climb that includes steep stairs and tunnels.

It takes most people around 1.5 to 2 hours to complete. The park is open from 6:00am, with the last entrance allowed at 4:00pm. Gates close at 6:00pm. During the winter it will get dark at about 6:30.

There’s an entrance fee of $5 per person if you walk in, or $10 per vehicle, which includes parking. Parking is limited and fills up quickly.

The trail can get pretty busy, especially on weekends and holidays. Consider visiting on a weekday morning for smaller crowds if you can.

Be sure to take a hat, sunglasses, sunscreen, and some water with you!

Dinner

Head back to Waikiki for dinner at the Monkeypod Kitchen. They’re known for their creative menu, with things like hand-tossed pizzas and fresh island fish.

You’ll also find unique dishes like pumpkin patch ravioli, an impressive selection of craft beers, organic wines, and handcrafted cocktails. Their specialty is the famous Mai Tai topped with honey-lilikoi foam.

The atmosphere is hopping and welcoming. It’s open to the beach all along the front, with Hawaiian décor and a fun music scene. It’s a popular spot for both locals and visitors looking for some modern Hawaiian hospitality.

Happy Hour – 3:30pm to 5pm

Day 3: North Shore

Breakfast

On your way to the North Shore this morning, stop at Morning Brew on Kailua Road for breakfast. On top of their extensive blends and coffee drinks, their breakfast and lunch menus are tops.

🚙 Driving tip: For the most scenic route to the North Shore, take Kalaheo Ave in Kailua north, past Kalama Beach to Kaneohe Bay Drive. Turn right at the major intersection onto the Kamehameha Hwy (83-Kam Hwy). It’s a longer drive, but you’ll get to see a lot more of Oahu’s beauty.

Stop at Tropical Farms Macadamia Nut Farm Outlet, 10 miles past Kaneohe. It will give you a pretty interesting look into the world of macadamia nuts.

There are free samples (yum), demonstrations of cracking and roasting nuts, and the chance to purchase freshly roasted nuts and other local products. While you’re there, ask about their tours.

You’ll pass the famous Banzai Pipeline surf break off Ehukai Beach Park, about 3 minutes before Shark’s Cove.

Morning – Snorkelling at Shark’s Cove (no sharks!)

This is the best snorkelling spot on Oahu, April through October. Winter water conditions can be rough. Or they might be calm. I’ve had great experiences here in December. Other times I wouldn’t dare go in the water.

Safety tip: Have a look at the surf conditions online at Rocky Point. This is a surf break about 2 miles up the coast from Shark’s Cove. If this site says that there are waves at Rocky Point, or if the water looks rough when you get to Shark’s Cove, don’t attempt to snorkel.

Snorkelling at Shark’s Cove on the North Shore is a fantastic experience. In good conditions, the water is clear, there is a lot of marine life and interesting underwater formations.

You can book a planned excursion, or pile into your rental car and hit the road.

If you head out on your own, here are some tips to help you make the most of your snorkelling trip to Shark’s Cove, including information about parking:

• Bring your snorkelling gear, including a mask, snorkel, and fins. If you don’t own gear, there are places where you can rent equipment. I recommend a rash guard or T-shirt, too, as protection from the sun and the coral.
  
  Stop at Aaron’s Dive Shop in Kailua and rent everything you need. Or you can call Hawaii Beach Time at 808-585-1474, and they’ll actually deliver your gear to you at the cove.

• The entry into the water – and exit from – is rocky, and sea urchins are common. Water shoes or reef shoes can protect your feet from sharp rocks and coral.

• Be careful as you get into the water. You can get pushed around by the surf, so hang on to the rocks until the water’s deep enough to lie flat.

• Don’t go past the cove into open water. There are strong currents and waves past that point.

• Shark’s Cove is part of the Pupukea Marine Life Conservation District. There are a variety of fish, turtles, and possibly even the occasional monk seal in the water. Remember not to touch or harass the marine life, and avoid stepping on the coral.

• Parking at Shark’s Cove is limited and can fill up quickly, especially on weekends and holidays. Try to get there early in the morning to get a spot.
  
  If the little main parking lot is full, additional spots can be found along the highway. Be careful of traffic and park legally to avoid tickets. I’ve always been able to find a spot. Somewhere.

• There are public restrooms and showers available at Shark’s Cove. And nearby, you’ll find food trucks and small shops. You can grab a bite to eat or pick up some last-minute sunblock or water.
  
  There’s a Foodland grocery store just down the road, too. You can rent coolers (and beach chairs and bikes) from North Shore Bike Rentals if you like.

Lunch

If you want to keep snorkelling after lunch, cross the road and get something from one of the trucks or shops. Keep your parking spot.

If you’re ready to pack it in, backtrack about 15 minutes on the Kam Hwy and pull into the Turtle Bay Resort. You’ll have to stop at the guard booth – just let them know you’re here for lunch.

There are several options for lunch at the resort. I recommend the Beach House, a Roy Yamaguchi restaurant. It’s comfortable, casual, and open-air.

And of course, the food is great! Take some time to wander around the grounds while you’re here.

Lunch hours: 11:30am – 2:30pm; get Bar Bites until 4:30pm

Afternoon – Hale’iwa and the Dole Plantation

After lunch, head back in the direction of Shark’s Cove and continue on to Hale’iwa town. On the way, you’ll pass a spot with a lot of cars parked on the side of the highway.

They’re here to visit Laniakea Beach, aka. Turtle Beach. Find a spot to park, and walk across the road to the water. Hawaiian Green Sea turtles (Honu in Hawaiian) often choose this spot to some on the sand and rest.

The turtles in the sand tend to be roped off, with volunteers on guard to be sure no one gets too close. They take their job seriously, and they will protect those turtles.

Please cooperate. I even saw a monk seal on the beach here once.

At the edge of Hale’iwa town you’ll find Hale’iwa Beach, if you feel like a swim or some sun. It’s a great spot to watch the sunset, too.

Further into town, there are many shops to explore and shave ice to sample. Matsumoto’s has long been known as the best on the island, so the line-ups can be long.

I think that Aoki’s farther down is just as good. Honestly, they’re all delicious.

Choose from different flavours and toppings. You can also get yours on a base of ice cream or azuki beans – a sweet bean concoction that locals swear by.

I’m an ice cream girl myself, with condensed milk on top.

If you can’t find parking at the shops, turn right between Island Vintage Coffee anf the GuavaShop. There’s a large parking lot back there that you can walk from.

There are some artsy craftsy shops, galleries, surf shops, and nice boutiques.

If you have time, or if you’re not a shopper, drive through town and turn left on Hwy 99. About 15 minutes down the road is the Dole Plantation.

The Dole Plantation has activities for any age if you’d like to experience a bit of Hawaii’s agricultural history. Here’s an idea of what you can do at the Dole Plantation:

• Pineapple Express Train Tour: Take a ride on the Pineapple Express for a narrated 20-minute train journey through the working plantation. Learn about the history of pineapple cultivation in Hawaii and see different agricultural fields.

• Pineapple Garden Maze: This is one of the world’s largest mazes, and stretches over three acres. It includes nearly two and a half miles of paths created from 14,000 Hawaiian plants. It’s a fun way to explore the plantation.

• Plantation Garden Tour: Walk through eight different gardens that show the variety of agriculture in Hawaii. Each garden focuses on different crops, including cacao, coffee, bananas, and of course, pineapples.

• Shopping and Eating: The Plantation Country Store has unique Hawaii-themed souvenirs, local snacks, and fresh pineapples. The Plantation Grille has a variety of food options, notably their famous Dole Whip, a soft-serve frozen dessert made from pineapple. If nothing else, have a Dole Whip – delicious!

• Educational Displays and Demos: Learn more about the cultivation and harvesting of pineapples and other crops grown on the islands through different educational exhibits and live demos.

Of these options, I recommend the train, the maze, and definitely the Dole Whip the most. There are admission fees only for the train, maze, and gardens.

Plantation Hours: 9:30am to 5:30 daily

Dinner

You can eat at the plantation if you like. Otherwise, turn back to Hale’iwa town and stop at Hale’iwa Joe’s for dinner. It’s a beautiful, casual spot, with great food, and Mai Tai glasses that you can take home with you.

To get back to Kailua, you can take the scenic route, Hwy 83 (Kam Hwy) back. If you’re not up for the long drive, though, you can take Hwy 99 (also Kam Hwy) and Hwy 2, through the middle of the island. It will save about an hour.

Day 4: Historic Pearl Harbor

Breakfast

Over Easy on Kuulei Road is another great breakfast stop. Everything’s good, but I’m partial to the crispy-edge pancakes.

Morning: the USS Arizona Memorial and USS Missouri

These are really interesting stops that give you a deep dive into important historical events. Ones that shaped the United States.

Your best bet is to put the USS Arizona Memorial into your GPS to find it. It’s about a 40-minute drive from your breakfast spot. The earlier you leave the, lighter the traffic. The memorial opens at 7:30am.

Get your tickets for the Pearl Harbor National Memorial in advance online if possible. Try for one of the early tours to the USS Arizona Memorial.

Tours to the Arizona Memorial begin at the Pearl Harbor Visitor Center. There’s a short documentary film about the attack on Pearl Harbor, followed by a boat ride to the Memorial itself.

After the tour, spend some time exploring the Visitor Center’s two excellent museums. The “Road to War” and the “Attack Gallery,” provide detailed historical contexts. I found them riveting.

From the Arizona Memorial, walk to the nearby USS Missouri, which is docked on Ford Island. This walk can take around 10-15 minutes and gives you a good view of the harbour.

Take a guided tour of the Battleship or explore on your own. The “Mighty Mo” is a glimpse into the life at sea during World War II. It’s famously the site where the Japanese surrender was signed, ending the war.

Lunch

For lunch, head back to the main visitor centre area. Walk toward the bridge from the Missouri. The Pearl Harbor Visitor Center has a little snack shop, but for a full meal, take a 6 minute walk to Restaurant 604.

It’s a global fusion restaurant on the waterfront, right next to the Pearl Harbor Visitor Center. It has an impressive menu and a great view of the harbour.

Afternoon: Pacific Aviation Museum and USS Bowfin Submarine

To get to the Pacific Aviation Museum, drive or take the provided shuttle across Ford Island where you spent your morning. This museum is home to an impressive collection of aircraft.

It’s fascinating if you have any interest at all in the aviation history of the Pacific War. I also highly recommend adding on the Tower Tour, which lets you climb the historic Ford Island Control Tower.

This tour gives you a panoramic 360-degree view of Pearl Harbor. You’re able to see the important historical sites from an exceptional vantage point.

Then walk or drive back towards the Visitor Center to tour the USS Bowfin submarine, known as the “Pearl Harbor Avenger”. The museum and park here will give you an amazing look into life aboard a WWII submarine.

Here are some tips for visiting Pearl Harbor:

Exploring Pearl Harbor is a great experience and knowing a few insider travel tips can help enhance your visit:

➦ Book Tickets in Advance: Tickets for the USS Arizona Memorial tickets can be limited. They’re available online 60 days in advance and on a same-day basis, but they can go quickly, especially during peak tourist seasons.

➦ Arrive Early: Pearl Harbor Visitor Center opens at 7:00 AM, and getting there early can help you avoid the crowds. This also increases your chances of getting same-day tickets if you haven’t booked in advance.

➦ Plan for Security Restrictions: Security at Pearl Harbor is strict. No bags of any size are allowed at the memorial or on the boat to the USS Arizona, including purses, camera bags, and backpacks.

Small cameras and wallets are allowed. Storage lockers are available for a fee near the entrance, so plan to store your things or leave them in your car.

➦ Wear Comfortable Footwear and Sunscreen: You’ll be doing a lot of walking, often outdoors, so wear comfortable shoes. The Hawaiian sun can be intense, even on cloudy days, so wear sunscreen, a hat, and sunglasses.

➦ Respect the Site: Pearl Harbor is a national memorial and a site of huge historical significance. Be respectful of the area and those who come to pay their respects. This is not just a tourist attraction but also a sacred site where many lives were lost.

➦ Check the Calendar: Look for special events, like ceremonies on December 7th, the anniversary of the Pearl Harbor attack. These can add additional historical context to your visit but may also affect crowd size and availability.

➦ Take a Guided Tour: Consider booking a full-day guided tour for more in-depth historical insights. Guides can provide background and stories that enrich your understanding of the events and sites. They pick up from Waikiki hotels only, though.

➦ Snacks: There are limited food services within Pearl Harbor, but there is a snack shop and vending machines.

Day 5: Byodo-In Temple and Polynesian Cultural Center and Luau

Breakfast

Stop to eat at Moke’s Bread and Breakfast on Hoolai Street. They’re known for their traditional Hawaiian breakfasts and particularly for the fluffy pancakes and local-style plates.

Moke’s has a laid-back, homey feel that makes it a perfect stop for a relaxed breakfast.

🍍 Fun Fact: A traditional Hawaiian breakfast often includes Portuguese sausage, rice (instead of potatoes, like hash browns), Spam, eggs, and fresh tropical fruit.

Morning: The Byodo-In Temple

The Byodo-In Temple is a tranquil and scenic site at the foot of the Ko’olau Mountains in Kaneohe. It’s in the Valley of the Temples Memorial Park, and is a non-practicing Buddhist temple. It’s a smaller-scale replica of the over 950-year-old Byodo-in Temple in Uji, Japan.

It was built in 1968 to commemorate the 100th anniversary of the first Japanese immigrants to Hawaii.

The architecture of the Byodo-In Temple itself is stunning, featuring intricate woodwork and a large Amida Buddha statue inside the main hall. The temple is surrounded by gardens, koi ponds, and small waterfalls.

The grounds around the temple are home to wild peacocks and hundreds of Japanese koi carp in the ponds. There are also small meditation niches and large, ringing bells (Bon-sho or Sacred Bell) that you can ring for happiness and longevity.

The temple also has a tea house, but it’s only there to add to the overall aesthetic and cultural authenticity of the temple grounds. There’s no tea or refreshments available.

The best time to visit the Byodo-In Temple is in the morning during the week, when it’s at its quietest.

Open daily from 8:30am to 5:00pm.

Lunch

Waiahole Poi Factory is the place to go for real local ono grinds (“delicious food” in Hawaiian). It’s about 10 minutes north on the HI-83, Kam Hwy.

Left out of the temple parking lot. It doesn’t look like much on the outside, but the food is worth it.

It’s take-out only, so you can eat in your car, or hang onto your food for the 10 minute drive to Kualoa Park, next to the Kualoa Ranch. Just keep going north on Kam, and you’ll see the signs.

Grab a picnic table or patch of grass, and gaze at Chinaman’s Hat while you eat.

🌴Fun Fact: During a low low tide, you can walk across to Chinaman’s Hat and climb to the top.

Afternoon: The Polynesian Cultural Center and Luau

You’ll have passed The Polynesian Cultural Center (PCC) in Laie, Oahu, on day 3, on the way to Shark’s Cove. It’s a unique cultural park where you can experience the different cultures of Polynesia.

It has six Polynesian villages representing Hawaii, Samoa, Aotearoa (New Zealand), Fiji, Tahiti, and Tonga. You can take part in interactive experiences, like Samoan cooking demonstrations, Hawaiian games, Tahitian dance lessons, and Maori tattooing exhibits.

The Center also has an award-winning luau known as the Ali’i Luau. You can enjoy a traditional Hawaiian feast that includes dishes like kalua pork (yes, cooked in an underground pit), lomi lomi salmon, and poi.

There’s live music and hula dancing, as well. It’s definitely a tourist experience, but it’s a lot of fun, and the food is amazing. It’s complete with a lei greeting and the unearthing of the imu (underground oven) where the pork is cooked.

You can even watch the “HA: Breath of Life” show, a really stunning evening performance with over 100 Polynesian natives in a story told through song and dance.

The narrative follows the life journey of a Polynesian warrior, incorporating traditional Polynesian dance, fire knives, and impressive digital effects. This show is a highlight for a lot of people.

There are shops and spots to eat, too. You could actually spend hours just wandering around.

Dinner

There are snack bars throughout the PCC, or sit down at Pounders for gourmet pizza or seafood. The buffet at Gateway Restaurant is good, too.