The Perfect 5 day Oahu Itinerary + Practical Info and Tips

Looking for the best 5 day Oahu Itinerary? You’re in the right place!

If you only have a little time to explore this tropical paradise, I’ve got you covered.

I’ve lived in Maui for 5 years but love visiting Oahu. It’s a small island that packs a big punch! 

You have delicious food, incredible hikes, gorgeous emerald water, and the bustling downtown area of Honolulu. It’s 600 square miles jam-packed with things to do. 

Of course, you can’t forget to nap on the beach! 

At the bottom of this article, you’ll find my top tips for visiting Oahu and recommendations on the best places to stay. 

Best 5 day Oahu Itinerary

This 5-day itinerary is perfect for an adventurous trip to Oahu. Feel free to adjust it as needed— you can easily focus your time on your interests.  

☀️ 5 day Oahu Itinerary – Day 1: Oahu Arrival (Waikiki)

The first time I ever flew into Oahu, my heart literally skipped a beat when I saw the gorgeous blue water and the Honolulu skyline from the plane window.

I’d lived in Maui for nearly a year at that time and wasn’t expecting the two islands to feel so different. I was definitely wrong! 

Part of the beauty of the Hawaiian islands is the unique nature of each island— and Oahu is a vibrant island with bustling charm.  

When you arrive, you’ll be flying into the south shore of Honolulu. The world-renowned Waikiki is located in the central hotel and resort area.

 This itinerary is based on the assumption that you’re staying in Honolulu. You’ll want to switch around the first day’s activities if you’re not!

✔️ Hotel Check-in

Depending on your hotel check-in time (typically 3 in the afternoon), you might not be able to check in to your room right away.

However, most hotels allow you to drop off your bags and store them while you go off and explore. 

I recommend changing into a swimsuit and comfortable clothes, dropping your things off, and heading out to explore the area!

✔️ Waikiki Beach Time

Waikiki is famous for its beaches. Walking around your hotel, you’ll see surfers walking by with boards and families heading to the ocean. All within a typical city street! 

Most hotels in Hawaii are just two or three blocks from the beach (if not right on the beach itself). Head over to the sandy area and find a place to camp.

Duke Kahanamoku Beach is the widest in Waikiki and is located on the western end.

Waikiki Beach is located just behind the Waikiki Police Substation. It’s a great spot to take a surf lesson, rent beach gear, or sit and watch the waves.

Regardless of what stretch of sand you end up at, you will want to take sunscreen. Hawaii has a high UV index all year long.

✔️ Lunch at a Local Cafe

After you’ve worked up an appetite at the beach, head to a nearby local cafe for lunch. Honolulu has impressive food options, and many spots are close to Waikiki. 

Barefoot Beach Cafe is a unique beachfront cafe towards the south end of Waikiki.

You’ll find delicious local-style food (and some American favorites) for reasonable prices. The location is an added bonus. Listen to the waves while you munch.

Marukame Udon is another good option. This is a well-known Japanese restaurant that serves homemade udon. 

This cafe almost always has a long line, but it’s worth the wait. Enjoy large portions without breaking the bank.

 Plenty of Japanese and locals enjoy the food (always a good sign!).

✔️ Evening Stroll at Kalakaua Avenue

The main shopping street in downtown Waikiki is Kalakaua Avenue. A large international shopping center, high-end shops, and famous surf brands are along the road.

Walking along and window shopping is still fun, even if you’re not interested in making purchases. 

Plus, plenty of buskers and street artists are performing in the evening.

✔️ Sunset Dinner Cruise

Head out on a sunset dinner cruise to finish your first day strong! The menu and specific entertainment options vary depending on which one you book. 

Typically, you’ll cruise along the Waikiki shoreline to Diamond Head. Once the sun sets, you’ll see the iconic Honolulu skyline glittering from the water. 

If you go out on a Friday night, you’ll also see a free fireworks display! Every week, the Hilton Hawaiian village sets off a ten-minute show that you can enjoy from the water (or along the Waikiki beach). 

☀️ 5 day Oahu Itinerary – day 2: Pearl Harbor and Downtown Honolulu

Day two is full! Start with the Pearl Harbor memorial, then head to some of the cultural and historic districts afterward.

It’s a lot of walking around, so I’d recommend wearing comfortable shoes. 

✔️ Pearl Harbor & USS Arizona Memorial

For any history buff, Pearl Harbor and the USS Arizona Memorial should be high on your list. 

You can easily spend your entire day here— a few hours at each of the 4 sites. 

However, if the USS Arizona Memorial is your priority (which it would be for me), plan on 2 or 3 hours. 

The USS Arizona Memorial marks the resting place of 1,102 sailors and Marines killed during the Pearl Harbor attack. 

The infamous attack led to the United State’s involvement in World War II. 

The memorial is only accessible by boat and straddles the battleship’s sunken hull. It’s a neat way to see history “come alive” in front of your eyes. 

✔️ Lunch at a Hawaiian Restaurant

There aren’t as many good food options near Pearl Harbor— but Kehau’s Kitchen is a real gem.

You get delicious (or “Ono”) Hawaiian food. Crowd favorites are Lau Lau and Pulehu Ribs. 

Another good choice is the Forty Nine Restaurant. It’s a casual restaurant with some of the best burgers and pancakes.

That’s not all they make— the garlic chicken and saimin are highly recommended. 

✔️ Iolani Palace 

Keep the learning going by visiting the Iolani Palace in the afternoon! It’s recognized as the spiritual and physical multicultural epicenter of Hawaii. 

The palace was built in 1882 by King Kalakaua and was the home of Hawaii’s last reigning monarchs.

No one ever regrets exploring the grandeur and opulence of Iolani Palace. 

Please note that you need a reservation— ticket sales are online and must be purchased 24 hours in advance. 

There’s also a strict dress code. The palace is sacred, and beach attire is not permitted. This won’t be an issue since you’ll be coming from Pearl Harbor!

✔️ Explore the Historic Downtown or Visit Kapena Falls

Downtown Honolulu is full of historic buildings and things to see. If you have the energy to spare, head to the historic district and check some of it out!

The King Kamehameha Statue is impressive. Take in his striking pre-scene in front of the Ali’iolani Hale (the State Judicial building of the Hawaii Supreme Court). 

The Hawaii State Art Museum is another excellent stop. It’s located in a hacienda-style building. 

Check out works by Hawaiian artists and an outdoor garden area with sculptures. Local artists from each island are featured. 

Another great place to stop is the Aloha Tower. It’s right on the waterfront and used to be the official greeting place for passengers arriving by ship.

The complex has various shops and restaurants, and you can climb up to some neat observation areas. 

As an alternative, if you’d rather spend some time in nature, the nearby Kapena Falls is a 20-foot-high waterfall in the middle of Honolulu.

✔️ Dinner and Nightlife in Chinatown 

One of the largest Chinatowns is in the downtown area. It’s full of charm, busy shops, an outdoor mall complex, and (of course) excellent restaurants.

Find exotic fruits, traditional herbs, or just people-watch at Maunakea Marketplace.

Feeling peckish? Lucky Belly has amazing ramen. Want Vietnamese food instead? Head over to The Pig and The Lady. 

☀️ 5 day Oahu Itinerary – day 3: South Oahu

Now that you’ve seen the best of the best in Honolulu, it’s time to venture further afield! The south side of Oahu has plenty of gorgeous beaches and hikes to keep you busy for days. 

Since you will only have 5 days, here are my top recommendations. 

✔️ Diamond Head Crater Hike

Diamond Head (Lē’ahi) is an iconic landmark near the eastern edge of Waikiki.

The crater was formed 300,000 years ago, but the trail to the summit was built in 1908 as part of the island’s coastal defense system. 

Clocking in at 0.8 miles one way is a steep and strenuous hike. It’s worth the effort! You’ll be rewarded with stunning views all around you. 

There are a lot of stairs on this hike, so come emotionally prepared for that (175 of them). Beat the heat and the crowds by doing this hike early in the day.

Reservations are required! So plan ahead for this excursion. 

✔️ Breakfast at Sweet E’s Cafe

Whether you hike before or after breakfast, Sweet E’s Cafe should be on your Oahu trip itinerary.

Described as “casual-chic,” this affordable eatery has delicious local foods. I’d highly recommend the eggs Benedict (my mouth is watering thinking about the Kalua pork). 

✔️ Snorkeling at Hanauma Bay

Hanauma Bay is a gorgeous marine ecosystem formed within a volcanic cone. It was voted the best beach in the United States in 2016.

The crater walls help calm and tranquil the water, making it ideal to observe the underwater world. 

There’s a $25 fee to enter the park, but it’s worth every penny. You can expect to see hundreds of fish, coral, and other aquatic creatures. 

Please note: the bay is closed on Mondays and Tuesdays! 

✔️ Halona Beach Cove

Halona Beach Cove is a beautiful and secluded beach often overlooked by visitors to Oahu.

Stop and check out the Halona Blowhole, then head down the steep (but short) path to the beach.

The undertow at this beach can be intense, so you might not want to snorkel. It’s perfect for sunbathing and swimming.

Make sure to bring a water bottle and some snacks with you! There are no facilities at this beach.  

✔️ Lunch with a View in Koko Head Cafe

Since you’ll be in the area, Koko Head Cafe is the perfect lunch spot. Don’t be surprised to see a line out the door — this cafe is a local favorite.

The Loco Moco is absolutely fantastic, and the ambiance is unmatched. You can sit outside and enjoy the tropics while eating award-winning food. 

Please note that the Koko Head Cafe is also closed on Tuesdays.

✔️ Makapu’u Point Lighthouse Trail

For unmatched sunset views and some exercise to round out your day, head over to the Makapu’u Point Lighthouse Trail. 

You’ll want to budget 1.5-2 hours for this excursion. It’s a paved, 2-mile out-and-back trail with some elevation gain leading up to a lookout point.

Bring a camera to snap pics of the outstanding views. You can see the island’s southeastern coastline, the offshore islets, and the historic red-roofed Makapu’u Lighthouse.

If you’re visiting during winter, you may even get to see a humpback whale or two!

✔️ Dinner

Reward yourself with dinner at the iconic Duke’s Waikiki. Right by Waikiki Beach, this casual (but pleasant) restaurant has a fun vibe. 

Dine under tiki lights and enjoy live music in the evening. Craving something sweet? 

Try the Hula Pie—macadamia nut ice cream with a chocolate cookie crust and delicious fudge sauce.

☀️ 5 day Oahu Itinerary- day 4: East Oahu (Winward)

Winward Oahu (the eastern shore) is 30 minutes from Waikiki. It’s scenic and worthy of a drive. You’ll see cute coastal towns bordered by the Ko’olau Range.  

This side of the island is perfect for adventurers looking to swim, hike, kayak, or snorkel. 

✔️ Sunrise at Lanikai Beach 

Lanikai Beach is absolutely stunning. It’s appropriately named “heavenly ocean.” It’s known for its gorgeous scenery and incredible views.

It’s the perfect spot to watch the sunrise on your fourth vacation day on this 5 day Oahu itinerary. You’ll get to see the offshore islands (known as “the mokes”).

With calm waters and a nice (albeit small) stretch of sand, it’s the perfect spot to take an early morning dip— or even a pleasant stroll. Early mornings are great for snorkeling!

This is a trendy spot for locals, and it’s family-friendly.

✔️ Lanikai Pillbox Hike 

Add the Lanikai Pillbox hike to your morning itinerary for more stunning views. 

This out-and-back hike spans 1.6 miles long and has an elevation gain of 613 feet. 

You’ll hike along the Ka’iwa ridge. Please note that some spots are steep, and no guardrails exist. You’ll definitely want shoes with good tread!

It’s a busy trail, but it’s got amazing views of both Lanikai and Kailua. 

If you head up there in the morning, you’ll beat the crowds. 

✔️ Breakfast at Kailua

Have you worked up an appetite yet? 

I highly recommend eating at Moke’s Bed and Breakfast. It is a fabulous breakfast and sandwich spot in Kailua.

It’s got a fun, beachy vibe and delicious food. Honey butter biscuits? Sign me up!

Over Easy is another great option close to Lanikai, with short waits and a quick and hearty breakfast. Many menu items feature pork, so it’s a good option for meat lovers.

The pancakes are made with cream cheese, giving them a crispy edge.

There are tons of good eats in Kailua, so you’ll find something you’ll enjoy. 

✔️ Ho’omaluhia Botanical Gardens

If you’re tired of walking around, this next activity can be done entirely in your car! (If you’re not, you can definitely get out and walk around.)

The Ho’omaluhia Botanical Gardens are open daily, without fee, and span 400 acres. There are 8 tropical gardens, each featuring plant species from different regions.

Serious trekkers can easily spend half a day here, but you can also drive through the gardens in half an hour. 

It’s a beautiful place to come and take in the fresh air. The gardens are open from 9 am to 4 pm. 

✔️ Relax at Kailua Beach

Kailua Beach Park is a lovely, large beach park on Oahu’s windward side. It’s the perfect spot to take a nap after your eventful morning!

There is plenty of shade, a great swimming area, and soft white sand. It’s also an excellent spot for kayaking or paddle boarding. 

If you visit during July, there’s a large annual fireworks display to enjoy.

Make sure to use reef-safe sunscreen while in the Hawaiian ocean. 

✔️ Luau Dinner

What better way to spend your last night on Oahu than a Luau dinner? 

It’s a fun way to try traditional Hawaiian foods, watch traditional hula dances, and learn about the unique cultures that have contributed to and are present on the islands.

There are tons of great Luau’s to choose from— but I’ve found my top two recommendations and included them below.

🏝 Paradise Cove Luau

4.5 ⭐️ 3,558 Reviews

This Luau is uniquely situated in Paradise Cove. You’ll be greeted with a welcome Mai Tai, a traditional lei, and get to watch the sunset.

Meander through the Hawaiian village to see traditional crafts, games, and art. 

You can also participate in the Hukilau on the beach and learn all about traditional net fishing techniques. 

Then, watch the Royal Court Procession and Imu (earth oven) ceremony before loading up your plates with a Hawaiian feast.

After you eat, you’ll see live music, songs and dancing. 

The best experience in Hawaii. “Mahalo” to the people working there–everybody from the driver to the dancers.

⭐️⭐️⭐️⭐️⭐️ manny_b,october 2023

🏝 Paina Waikiki Luau at the Waikiki Beach Marriott

5.0 ⭐️ 82 Reviews

If you don’t want to leave Waikiki, the Paina Waikiki Luau is highly rated.

It’s a 3-hour Luau where you can see the history of Waikiki live on the stage. Listen to the nā mele (songs) and watch the hula. 

For a finale, watch a jaw-dropping, heart-stopping, fire knife dance.

This Luau has delicious food; you’ll learn about Hawaiian history and culture. Plus, if you’re staying in Waikiki, it’ll be within walking distance of your hotel.

AKA, the perfect excuse to have more than one Mai Tai! 

Paina Waikiki Luau was awesome! I went with my husband and it was great small and intimate.

⭐️⭐️⭐️⭐️⭐️ Morgan_P, Sep 2023

☀️ 5 day Oahu Itinerary- day 5: North Shore 

Only a 45-minute drive from Honolulu, the North Shore of Oahu is well-known for its fantastic beaches, big wave surfing, and gorgeous views. 

I love the North Shore— even just driving around is lovely.   I’ve gone to Oahu on a couple of day trips just to do the North Shore loop. 

✔️ Breakfast at Haleiwa Bowls

Haleiwa is a cute surf town on the north shore about an hour from Waikiki. 

You’ll find a fun, vibrant town with cool surf shops and boutiques, charming art galleries, and plantation-style buildings.

Haleiwa Bowls is located in the middle of town and is the perfect way to start your morning. Acai bowls and smoothies are delicious. 

✔️ Shark’s Cove

After your healthy breakfast, head to Shark’s Cove. It’s famous for snorkeling and scuba diving. Don’t worry, there’s no sharks to be found!

It’s a fantastic spot to snorkel— there’s protected water, and you’ll see many different multicolored fish. 

You should definitely wear either fins or water shoes. With so much reef around, you don’t want to risk accidentally stepping on and killing coral.

There are restrooms and parking, but no lifeguard. 

✔️ Waimea Valley or Sunset Beach

Depending on what you feel like doing, spend the rest of your morning at either Waimea Valley or Sunset Beach.

Waimea Valley is a lush region with various historical structures and a 45-foot-tall waterfall.

Give yourself plenty of time to explore. There are gorgeous lush areas and lots of information. Take a hike to the waterfall and swim in the pool underneath. 

Sunset Beach is another excellent choice— it’s located right past the Banzai Pipeline. It has a 2-mile stretch of gorgeous sand. 

You can drive right next to the beach on the Kamehameha Highway. It’s an excellent spot for relaxing, snorkeling, and walking on the beach during the summer.

During the wintertime, you can watch big-wave surfers.

✔️ Lunch at North Shore Food Trucks

There are tons of great food trucks on the North Shore. 

Ali Limo Truck is a cute food truck with a pleasant outdoor picnic area. It’s a great spot for fresh food and seafood. The poke is the most popular thing to get. 

Are you more interested in some cheesy goodness? Check out North Shore Pizzas! They have super thin-crust pizzas. 

Try everything from the classic margarita to their Pipeline Special.

For dessert, hit up Matsumoto shave ice! Get ice cream centers, tropical flavors, and fun toppings at this family-owned shop in Haleiwa.

Shave ice is an iconic Hawaiian treat; no trip to paradise is complete without it. 

5 day Oahu Itinerary- How to Get Around Oahu, Hawaii

You can have a full trip on Oahu without a car, but you’ll be limited in where you can go. 

If you want to explore more of the island than just Waikiki, you have two main options in terms of transportation: renting a car or using public transportation. 

🚘 Renting a Car

This 5 day Oahu Itinerary is best done by renting a car. You’ll have complete control of your schedule and can explore as much (or as little) as you want.

You can rent a car from a variety of different companies. There are 8 nationally recognized Honolulu car rental agencies. I always recommend checking on Discover cars because the platform allows you to compare different rental companies and choose the best deal.

You will want to reserve a car as early as possible. Cancellation policies are generally really lenient. 

If you wait until you arrive, you might get charged higher fees. Plus, during the busy seasons, rental companies sometimes run out of cars.  

If you only drive around for a day or two, you can also use Hui, a car rental app. It works similarly to ride-sharing. 

Just get approved and then rent a car when you need it. You’ll use the app to unlock it and then return it to the spot you picked it up. 

🚍 Public Transportation

You can use the Oahu bus if you don’t want to rent a car. It’s reliable and cheap. 

Most Oahu buses arrive at the bus stops every 10 to 30 minutes, but you will want to check the schedule.

Pay with exact change in cash upon boarding or purchase your bus fare online with a Holo Card.

Oahu – Where to Stay

While the itinerary above assumes you’re staying in Waikiki, you can always choose to spend your nights on a different part of the island. 

Each area has something unique to offer. Check out my top recommendations for where to stay in Oahu here.

🌊 Waikiki

Waikiki, right in the middle of the hustle and bustle of the city, is terrific if you’re interested in sparkling city lights, shopping, and possibly even ocean views from your room.  

🛏 Recommended Stay: Halekulani

The Halekulani is right on Waikiki Beach and overlooks Diamond Head. You’ve got 3 on-site restaurants to choose from, a live jazz lounge, and a day spa.

Be welcomed into your room with a fresh fruit bowl and chocolates, and enjoy the luxurious accommodations wrapped in cozy bathrobes.

There’s even a heated swimming pool with views of Waikiki Beach. Talk about dreamy!

Everything!!! What’s there not to like? The cleanliness, the food, hospitality, the AMAZING staff!!! Everything was at 110%

⭐️⭐️⭐️⭐️⭐️ Daniel, AUGUST 2023

🌊 Downtown Honolulu (Ala Moana)

Downtown Honolulu has a rich history, a vibrant local scene, and all the benefits of big-city living.

 If you want to be close to Waikiki but not right in the middle of the city buzz, downtown Honolulu is the place to be. 

🛏 Recommended Stay: Aston at the Executive Centre Hotel

The Aston at the Executive Centre Hotel is only a 5-minute walk away from some of the best historical attractions. Think of a quick walk to the Hawaii State Art Museum.

Each room has floor-to-ceiling windows with either city, ocean, or mountain views.

Some units even come with fully equipped kitchens to cook your own meals.

There’s a heated swimming pool and a hot tub to relax and unwind in. 

Very friendly, organized reception with good instructions. Places to eat are close to the hotel. Very good beds.

⭐️⭐️⭐️⭐️⭐️ lucas, october 2023

🌊 East Side (Windward)

The Windward side of Oahu is lush and beautiful. Wake up and see the dramatic Ko’olau mountains and vibrant tropical plants. 

You might get some rain if you stay on this side of the island, but they’ll add to the paradisiacal charm. 

🛏 Recommended Stay: Mango Retreat

If you want to stay on this side, you can’t do much better than the Mango Retreat. 

You get air-conditioned accommodations in this holiday home, a dining area, a fully-equipped kitchen, and garden views from the cute terrace.

Enjoy the barbecue, or make use of its excellent location and head out on a hike!

The place was so pretty… It’s located in a quiet and nice neighborhood. The room was so comfortable… I loved the back patio with all the trees around it. So peaceful!

⭐️⭐️⭐️⭐️⭐️ GLORIA, SEPTEMBER 2023

🌊 West Side (Ko Olina)

The oldest and driest side of Oahu, Ko Olina, has lots of beach lagoons. If you want to spend a lot of time swimming and snorkeling, you should stay on the West Side.

 

🛏 Recommended Stay: Marriott’s Ko Olina Beach Club

The Marriott’s Ko Olina Beach Club has gorgeous and comfortable rooms. Enjoy a fully equipped kitchen, washer, and dryer, and use the on-site spa by the sea.

After a busy day exploring the island, a full-body massage sounds dreamy to me.

There’s an on-site restaurant, and you can even watch the Fia Fia Polynesian Dinner Show on Tuesday evenings. 

Enjoy live Polynesian entertainment and local dishes all steps away from where you are staying.

This is an amazing property and we enjoyed our stay very much! We’d return!

⭐️⭐️⭐️⭐️⭐️ CAROLYN, JUNE 2022

🌊 North Shore day

The North Shore is quiet and laid back. It’s the perfect place to go if you want to explore the island and escape the busyness of the city. Plus, it’s gorgeous. 

🛏 Recommended Stay: Turtle Bay Resort

Turtle Bay Resort is one of the top places to stay on the North Shore. There are 12 miles of biking and hiking trails and 5 miles of shoreline nearby.

Plus, it’s in a fabulous location. Haleiwa and Waimea Bay are both just a few minutes away.

All 408 rooms in the main building offer ocean views and are just steps away from the beach.

There are also 6 different restaurants and bars. You’re within walking distance of 7 beaches and close to helicopter tours, horseback rides, golding, a spa, and more.

It’s a beautiful location and a charming property. You won’t be disappointed if you stay here.

All in all, we had a wonderful 3-day stay. Will definitely recommend to other family members and friends.

⭐️⭐️⭐️⭐️⭐️ GEORGE, APRIL 2023

When is the Best Time to Visit Oahu?

Hawaii is gorgeous all year, but the best time to visit Oahu is from mid-April to mid-June or between September and the beginning of December.

These are considered “shoulder seasons,” you’ll see fewer crowds and room rates will be at their lowest. 

What to Pack for an Oahu Hawaii Trip

What you want to pack for an Oahu trip will depend on several factors. The main element to consider is what activities you’re planning on doing.

📌 Bring a good book, lightweight clothes, and beachwear if you want to spend most of your time by the beach. 

📌 You should also pack sunglasses, sandals that are easy to slip on and off, rash guards, and one nice pair of clothes (for any luau’s or fancy dinners). 

📌 If you want to hike, sneakers and comfy, lightweight clothing are necessary. 

 📌 Bring a light jacket if you’re staying at a higher elevation. Despite being in the tropics, it can get chilly in Hawaii— on some islands, it can even snow. 

📌 Despite the weather, I wouldn’t bother bringing a rain jacket. I live in Maui and have only worn mine twice in the last five years.  

📌 Your hotel will provide you with beach and bath towels, so save the space and leave those at home.

📌 Don’t forget your camera! You’ll want that for sure. 

If you forget anything, don’t worry. You can always buy it when you arrive. 

Frequently Asked Questions

Wrapping Up: Oahu 5 day itinerary

Oahu is a great place to go for a fantastic tropical vacation. The only island to offer city nightlife, you’ll find plenty to fill your time. This Oahu itinerary: 5 days of the ultimate adventure will get you to every side of the island. 

There are soft white beaches, fantastic hiking trails, and historical sites. Soak in the hot sun, check out the emerald green waters on the beach, and see the underwater world. 

Feel free to edit your schedule as needed. You can always nap at the beach instead of the next adventure on the list. 

What are you most looking forward to seeing?