A Stellar 5-Day Oahu Itinerary: Sunshine, Beaches, and Fun

If you’re visiting one of Hawaii’s most beautiful islands, Oahu, you might be feeling overwhelmed with what to do, where to stay, and how to get around. 

Oahu has so much to offer. It’s called “The Gathering Place” and lives up to this name thanks to diverse natural landscapes, cultures, and people. It’s home to iconic beaches such as Waikiki Beach, historical gems like Pearl Harbor, and a world-renowned capital city, Honolulu.    

With so much on your plate – where does one even begin?

With this practical 5-day Oahu itinerary, you no longer have to worry too much about these details. This insightful guide will take you to the top attractions and cover some tips and things to know before you go, such as what to pack and where to stay. 

If all that sounds good, waste no more time and get into this Oahu 5-day itinerary. Oh, and before you hop on your plane, check out the best things to do in Oahu. 

Disclosure: This post contains affiliate links. If you click one of them, I may receive a small commission (for which I am very grateful for) at no extra cost to you.

Map Of 5 Day Oahu Itinerary

I’ve embedded a Google map below with this itinerary! You can download and save it for offline use, but I recommend printing it out, too, so you’re covered if you find yourself without service on the trail.

An Epic 5-Day Itinerary for Oahu

If you don’t want to miss any of the highlights, consider this 5-day Oahu itinerary. 

Day 1: Pearl Harbor + Waikiki

Alrighty. Let’s kick things off with an exciting yet relaxing introduction to Oahu by seeing two of its most iconic attractions: Pearl Harbor and Waikiki.

Discover Pearl Harbour 

Any Oahu itinerary won’t be complete without visiting Pearl Harbor, Hawaii’s most notable historical site. That’s why day one should start with a morning visit to this famous attraction. Pearl Harbor is a U.S. naval base that was the scene of a disastrous surprise attack by Japanese forces in 1941. 

Today, the Pearl Harbor National Memorial is a war museum where you can learn more about this pivotal moment in World War II and U.S. history. It’s the resting place of over one thousand marines and sailors and home to the USS Arizona Memorial. People come here to commemorate and honor those who served and put their lives on the line for their country.

Explore Waikiki

After spending your morning at the historical Pearl Harbor, it’s time to enjoy what’s left of the sun on Waikiki Beach. This magical beach paradise is a haven for surfers, but Waikiki is also fantastic for exploring and sightseeing. High-rise hotels line its shores, with designer stores, fine dining establishments, and beach-side cocktail bars dotted all over. 

Head over to Kalakaua Avenue and nearby streets for sightseeing and shopping to collect souvenirs. Then, grab a cocktail at a nearby bar before experiencing a unique luau at Pa’ina Waikiki – a dinner party including traditional food, cultural stories, hula dancing and fire dancing. 

Day 2: Diamond Head Sunrise + Hanauma Bay Nature Preserve + Lānaʻi Lookout + Halona Blowhole Lookout/Cove + Makapuʻu Lookout 

Day two is all about embracing the natural beauty of Oahu and testing your fitness and endurance skills with some of the best trails. So, stretch your legs and get your camera ready — this day is all about hiking and unmissable views.  

Start Your Day With the Diamond Head Sunrise Hike 

• Mileage: 1.9 miles (out and back)
• Elevation Gain: 515 feet
• Difficulty: Moderate
• Trail Guide: Link

What better way to start your day than with a refreshing hike as you watch and capture the sunrise? This trail offers a breathtaking backdrop for photography as you meander through the Diamond Head volcanic crater. 

To catch the sunrise, ensure you start the hike early enough, which usually takes about 20 – 30 minutes. You’ll begin at the parking lot inside the Diamond Head volcanic crater and ascend to the southern edge of the rim, where unmissable vistas await.

The park gates open at 06:00 am, so if the sun rises before 06:20 am, you’ll want to be there when it opens and rush to the top to admire the sunrise. Otherwise, if the sunrise is around 07:00 am, you’ll have more time to reach the rim, so you can take it easy.

See the Hanauma Bay Nature Preserve

When in Oahu, you simply must pay a visit to Hanauma Bay Nature Preserve. Fair warning: as a tourist hotspot, this destination can get busy, but if you look past the crowds, you’ll understand why they’re there in the first place. Hanauma Bay may be the most beautiful sight in Oahu, thanks to its bright coral reefs and abundant marine life.

Remember to bring your snorkeling gear and swimsuit. Try arriving here as soon as you’re done with the Diamond Head hike if you plan on snorkeling, as it’s best done in the mornings. 

Hanauma Bay is open between 06:45 AM to 04:00 PM every day except on Mondays and Tuesdays. You’ll also pay a $25 entry fee upon arrival, or you can join a guided snorkeling tour. 

Enjoy the Views at Lānaʻi Lookout 

Going up to Lānaʻi Lookout viewpoint affords you stunning panoramic sweeps over the ocean, cliffs, and the crater. The popular lookout point is on the southeast coast of Oahu, right on Kalanianaole Highway. This scenic stretch of coastline features three main roadside lookout points, with Lānaʻi being a top choice for many. 

You can park in the small parking lot carved into the sea cliff. Try to visit the lookout on a clear day so that you can see more than just Lanai but Maui and Molokai, too. Also, remember your binoculars, as you might be able to spot some whales in the winter months (December to March).    

Go To the Halona Blowhole Lookout/Cove

The Halona Blowhole lookout and cove are some of the most awe-inspiring and scenic overlooks along Oahu’s East Coast. Halona Blowhole is a short four-minute drive (0.8 miles) east of Lānaʻi Lookout via HI-72. 

To reach the lookout/cove, go north of Hanauma Bay off the Kalanianaole Highway. You’ll find the lookout parking lot on the ocean-facing side of the highway.  

From here, you can see seawater shoot up to 30 feet into the air from a lava tube. The salty, misty sprays might make you a little damp, but that’s part of the experience, making it even more memorable. This geological wonder was formed by past volcanic activity thousands of years ago. 

End You Day at Makapuʻu Lookout 

• Mileage: 2.5 miles (out and back)
• Elevation Gain: 650 feet
• Difficulty: Moderate
• Trail Guide: Link

Oahu seems to have no shortage of scenic spots, and Makapuʻu Lookout contends for the top spot. This vista point is located within the 38-acre Makapuʻu Point State Wayside Park near Waimanalo Beach, with vistas over turquoise waters, a lighthouse, and a dramatic cliff. The quiet, serene area is also a hotspot for whale-watching from November through April. 

On a clear day, you can see the blowholes on Makapu’u Head’s rocky shore, Kaohikaipu Island, Rabbit Island, and Makapu’u Beach Park from the summit. While at the park, you can also pick up a moderate trail along the coast towards Makapuʻu Point Lighthouse if you have some time left over. This upward hike takes an average of one hour and 20 minutes to complete and has no shade.

Keep an eye out for whales while taking the hike and enjoy the relaxing atmosphere. Pack a light jacket since the wind can be pretty chilly here.    

Day 3: Hoʻomaluhia Botanical Garden + Pillbox Hike + Lanikai Beach

Day three is not too different, as the focus remains on Oahu’s unspoiled natural scenery. Only this time, you’ll have one hike, and the rest of the day involves relaxing on the beach and strolling peacefully through a botanical garden.  

Wander Through Hoʻomaluhia Botanical Garden

• Mileage: 1.9 miles (out and back)
• Elevation Gain: 505 feet
• Difficulty: Moderate
• Trail Guide: Link

Start your morning with a tranquil walk through the lush 400-acre Hoʻomaluhia Botanical Garden in Windward, Oahu. Thanks to its massive size, you can drive through the botanical garden in about 25 minutes, depending on how many times you stop. Strolling through it on foot is also an option, but it will take longer (roughly an hour) if you’re worried about time. 

The attraction is open daily from 09:00 AM to 4:00 PM and is free to enter. Wear sturdy boots if possible, as some parts of the garden can be muddy and slippery. This rainforest garden has majestic trees, a pleasant lake, and diverse plants, allowing visitors to bond with nature while bird-watching, fishing, and camping. 

Test Your Skills on the Pillbox Hike

• Mileage: 1.6 miles (out and back)
• Elevation Gain: 613 feet
• Difficulty: Hard
• Trail Guide: Link

The Pillbox Hike, or Ka’iwa Ridge Trail, provides gorgeous views over the Lanikai and Kailua Beaches. This beautiful hike along Ka’iwa Ridge is not for the faint-hearted, as it requires scrambling and has very steep sections. This does not stop some people from running the trail, but be careful of the rocky, uneven surface. 

You can bring your pup, but they must be on a leash. Also, don’t forget to pack in water to stay hydrated. You’ll be able to reach the summit of this hike in about 40 minutes, but the incredible views along the way might keep you there for longer. 

Unwind on Lanikai Beach

Located just south of Kailua Beach, it makes sense to venture down the road to Lanikai Beach after a brisk but strenuous hike. You can watch the sunset and cool off in the ocean — the perfect way to end day three.   

Lanikai Beach sits in the charming Kaʻōhao community in the town of Kailua. It’s widely regarded as one of the best in the world and boasts famous views of the Mokulua Islands. It’s a popular spot for windsurfing and kitesurfing — but if you just want to destress, simply take in the crystal-clear waters and sunbathe on the soft, white sand. 

Day 4: Koko Crater Trail + Kualoa Ranch

Day four is dedicated to exploration and discoveries. Think of geological wonders and learning all about Hawaii’s rich history and culture at a massive private ranch. 

Hike the Koko Crater Trail

• Mileage: 1.6 miles (out and back)
• Elevation Gain: 912 feet
• Difficulty: Hard
• Trail Guide: Link

Go on a steep hike up an abandoned railroad track on Koko Crater to see the most splendid panoramic ocean and cityscapes. Taking about one hour and 25 minutes to complete, this trail might not be for every fitness level as it is quite challenging. However, it is beyond beautiful once you reach the top after climbing a 1,000+ step track, so it’s worth pushing yourself if you’re a beginner. 

You can access this trail at Koko Head, but prepare for a “bridge” portion halfway up with no ground beneath, so use the bypassing trail if you’re scared of heights. The Koko Crater Botanical Garden is inside the crater if you want to veer off from your itinerary a little.  

Create Fun Memories at Kualoa Ranch

Kualoa Ranch brims with endless fun opportunities if you’re keen on some adventure in a 4,000-acre paradise. Peppered with lush tropical forests, balmy beaches, and verdant valleys, you’ll have much on your plate and a chance to immerse yourself in Hawaiian culture. 

What’s more, over 79 movies and TV shows have been filmed at this ranch, including Jurassic Park, Jurassic World, George of the Jungle, Godzilla, Kong: Skull Island, Jumanji, and 50 First Dates. See all these film locations with this Kualoa Ranch Hollywood tour. 

While here, you can also discover historical buildings, explore the grounds with a UTV raptor tour, or zoom through the skies on an exhilarating zipline adventure. 

Day 5: North Shore + Dole Plantation

Sadly, all good things have to come to an end. But to end things on a high note, the best was saved for last on this Oahu itinerary. 

Experience the Popular North Shore

Hawaii’s North Shore beaches are unmissable, and it would be a shame to miss it while you’re in Oahu. This renowned, laid-back stretch of coast is famous for its gigantic waves and surfing contests. This is where you let your hair down and throw all your cautions to the wind. 

While here, be sure to explore Haleiwa, a town known for its distinct charm and local Hawaiian artists filled with many free galleries. Then, take up horseback riding on the beach, golfing, or backcountry hiking to spice things up. 

Surprisingly, the North Shore is just as impressive and sought-after during the winter season, thanks to the massive surfing waves at Waimea Bay and Sunset Beach.  

Visit Dole Plantation

Now, heading back to central Oahu, the last activity on this banging itinerary involves pineapples. These are the one fruit that is always associated with Hawaiian culture, design, and aesthetics. Hawaii has such a large pineapple industry that it supplies over 80% of the world’s canned pineapples. 

Now that you understand the hype, it’s time to see one of the oldest plantations on the island that started as a fruit stand in 1950. Today, Dole Plantation attracts visitors for its harvests, open-air Pineapple Express Train, and a three-acre garden maze. It’s free to enter, and you can visit daily between 09:30 AM and 05:30 PM.  

How To Get to Oahu, Hawaii

Getting to Oahu is pretty straightforward. All you have to do is take a plane to the Daniel K. Inouye International Airport in Honolulu – also called Honolulu International Airport (HNL). From here, you can either use a rental car or public transport to reach your hotel. 

>>>Rent A Car Here<<<

Best Time to Go to Oahu

The best time to visit Oahu depends on your objectives. For example, most travelers visit the Hawaiian islands during summer, during peak season. This is when the weather is ideal for beach hopping and outdoor water activities. 

However, it also means the islands might get too crowded and tough on the pocket for some. So, if packed beaches and long lines are not your thing, it’s better to visit Ohau during its off-season between early April and May and then again from September to early October.    

The shoulder months are Oahu’s spring and fall seasons. Expect cooler temperatures, but remember that Oahu has excellent weather throughout the year. You will also experience cheaper accommodation prices as the demand lowers due to thinner crowds. 

Where To Stay in Oahu

Not sure where to stay during your trip to Oahu? Here are three fantastic options ranging from a budget-friendly hotel to an all-exclusive luxury resort. 

Budget | White Sands Hotel

Offering you luxury on a budget, opt for the stylish and elegant White Sands Hotel. This amazing place makes it a point not to skimp on amenities, services, and decor that make you feel like you’re at a 5-star hotel without breaking the bank. 

It’s a retro boutique hotel smack in the middle of the sought-after Waikiki, so the location is on point. You have Waikiki Beach and the Royal Hawaiian Shopping Center around the corner. Relax on the private balcony with pool or city views, or dip in the outdoor pool. 

Grab your morning cup of joe at the on-site cafe or sip on a sunset cocktail with Hawaiian flavors at the bamboo bar with swings as chairs. There’s also Heyday, a new restaurant inside the hotel, if you want to indulge in traditional Hawaiian cuisine with a modern twist. >>>Check Availability   

Mid-Range | OUTRIGGER Waikiki Beachcomber Hotel

Next is a mid-range accommodation option set within the bustling Honolulu that’ll knock your socks off. The OUTRIGGER Waikiki Beachcomber Hotel is an absolute stand-out in terms of its lavish appearance and stellar amenities worth four stars.  

Firstly, the views are breathtaking, with some rooms featuring balconies overlooking the ocean. Go to the stunning pool and lounge terrace for more sea views and city sweeps. There’s also a hot tub to unwind in after a long, busy day.  

The rooms are light and airy with dreamy ocean murals, plush beds, and soft, beachy design elements. Other amenities include a fitness area, a bar, a restaurant, and Wi-Fi. >>>Check Availability    

Luxury | Halekulani

While this may not be a hotel, there are so many excellent luxury resorts in Oahu that it makes sense to add it as a high-end option. Halekulani provides a romantic beachfront stay in the lap of luxury. The awe-inspiring scenery, palm-fringed pool area, and ocean views are postcard-worthy. 

This 5-star resort sits on the shores of Waikiki Beach overlooking Diamond Head. Here, you’ll be treated to three on-site restaurants, a live jazz lounge, and a tranquil day spa. Dine at the internationally awarded ocean-front La Mer restaurant, book yourself in for a massage and treatment, and simply savor life. 

Each contemporary room has a spacious lanai, with luxurious en-suites featuring marble vanities, plush bathrobes, premium toiletries, and deep bathtubs to soak in.  >>>Check Availability 

PSSST: Check out more places with this “Where to stay in Oahu” guide.  

Tips for an Oahu Itinerary

Below are some insider tips and insights to help you plan and prepare for the best Oahu itinerary. 

The Areas of Oahu

While Oahu has a handful of great regions, most travelers prefer to stay in downtown Waikiki due to the many accommodation options, including budget-friendly hotels and rentals. North Shore is more reminiscent of Maui, Kauai, and the Big Island if you want to have that type of experience.

Oahu is divided into five distinct areas: 

• Honolulu: The buzzing capital of Hawaii and gateway to the island chain. 
• North Shore: A laid-back stretch of coast that draws surfers and beachgoers with its big waves and iconic beaches. 
• Leeward Coast: The quiet western side of Oahu that’s home to white sand beaches and lavish resort complexes.  
• Central Oahu: A fertile valley in the heart of Oahu tucked between the Koolau Range on the east coast and the Waianae Mountains to the west. 
• Windward Coast: A slow-paced area famed for stunning natural scenery.     

Tours At Oahu

Safety Tips and Precautions When Visiting Oahu

Oahu and the rest of the Hawaii archipelago are among the safest destinations in the U.S., ranking in the lowest 25% for violent crime. It’s safe to say you won’t have to worry too much about your safety (pun intended). 

However, regardless of how safe a place may be, it’s always best to travel cautiously, as tourists are often a target for theft, fraud, and other crimes. With that said, here are a few tips to ensure your trip goes smoothly:

• Be aware of flash floods: Flash floods can be hazardous and even fatal, so never attempt to cross a flooded stream. Also, no matter how dry a streambed looks or how clear the skies may look above, a sudden rainstorm far away can cause a flash flood.

• Keep your valuables close: Don’t leave your valuables in your rented car where it’s visible or far out on the beach. While Hawaii is generally safe, it’s still a popular tourist destination, meaning some opportunists may take advantage of unsuspecting or ignorant travelers. 

• Watch out for box jellyfish and Portuguese Man-of-War: Stings from these jellyfish and bluebottles are common in Hawaiian waters. Just a quick touch can result in hours’ worth of burning stings.   

• Respect all “Kapu” or “No Trespassing” signs: Trespassing is a big deal in Hawaii, so they have strict laws to prevent private and government land not intended for public use. 

• Practice ocean safety: The Pacific Ocean is gorgeous and inviting but can be fickle and dangerous when least expected. That said, always go to beaches that have lifeguards present as they are more familiar with the currents and conditions.

• Respect beaches and surfing etiquette: When visiting beaches in Oahu and all over Hawaii, treat them courteously, as the locals have always deeply respected the ocean. Don’t litter, follow the signs and rules, and practice good surfing etiquette by waiting for your turn, as the surfer closest to the peak has the right of way. 

What To Pack for a 5-day Trip to Oahu

Having an idea of what to pack can give you the reassurance of not having to walk around in shopping malls while you could have been chilling on the beach. Here’s a few essentials to bring with you: 

• Reef-safe sunscreen: Yes, the sun protection you take to any Hawaiian island does matter. This is to protect the coral reef against any harmful chemicals, such as oxybenzone and octinoxate, that could be present in the product. Furthermore, mineral-based sunscreens that use ingredients like zinc oxide and titanium oxide are not associated with coral bleaching, making them less harmful. 
• Mosquito repellent: Bring insect repellent to stave off annoying and itchy mosquito bites. Citronella is an excellent natural repellent; you can buy it in an oil form at a drugstore.  
• Swimwear, beach bags, and towels: This one is a no-brainer. If you want to save money and time, bringing all your beach bum necessities with you is better.   
• Waterproof phone case: This is essential to take stunning underwater photos with bright coral reefs. It’s also a great way to keep your phone on you while swimming or doing other water activities.  
• Hiking shoes: If you plan to pick up a few trails, it would be best to wear proper hiking boots as the conditions are often muddy and rocky.
• Sandals: You can’t go to Oahu without sandals – it is a beach vacation destination, after all. These flip-flops are ideal as they dry quickly after getting wet. 
• Camera gear: Take some gorgeous snaps for the socials with good-quality camera gear.
• Lightweight clothing: You’ll experience warmer temperatures in Oahu, so it would be better to pack in lightweight layers such as tank tops, cotton t-shirts, shorts, and sarongs.   
• Snorkel gear: Don’t forget your snorkel gear if you plan on discovering marine life and vibrant coral reefs or Oahu’s ocean floor. 

Best Ways to Travel Around Oahu

If you’re based in Waikiki, you can rely on your feet to take you places as this area is walkable, and everything is close. Other areas like Honolulu are not very walkable, so a rental car will be far better. 

If you’re not too keen on renting a car, you can use public transport. TheBus is a public transportation service in Oahu that provides safe, air-conditioned, and dependable rides. 

Otherwise, you can also use rideshare services, including Holoholo, Lyft, and Uber. These are perfect for shorter trips around Honolulu, for example. Shuttles are more convenient for transporting from airports, for larger groups, and for day tours around the island. Aloha Airport Shuttle and Go Waikiki Shuttle and Tour are great shuttle options.    

Seasons and Weather  

Visitors flock to Hawaii’s warm, sunny beaches all year round. So, the weather is generally great no matter when you go, with average temperatures ranging from the mid-70s to low-80s Fahrenheit. And while Hawaii’s rainy season is from November through March, you can expect showers to fall anytime, especially on its wetter, windward (northeastern) side. 

For most of Hawaii, there are only two seasons, typical for tropical climates. “Summer” occurs from May through October, and “winter” falls between October and April. In Hawaii, the cooler, wetter season is called Ho’oilo, and the drier, warmer season is called Kau.

Oahu Trip Itinerary: FAQs

Here are the most frequently asked questions regarding an Oahu itinerary answered in case you need more clarity on a few things. 

How Many Days in Oahu Is Enough?

While an Oahu 3-day itinerary could work, this might not be enough time to get the most out of this gorgeous island. With so many beaches, snorkeling spots, and outdoor adventures, you’d need at least 5-7 days in Oahu. This allows you to cover all the basics, rest in between, and fit in a few spontaneous activities. 

Do You Need a Car in Oahu?

The simple answer is yes and no – you do not need a rental car in Oahu if you stay in Waikiki, as it’s very walkable. Also, this is due to all the major attractions, restaurants, shops, and beaches within walking distance of most hotels in Waikiki (where most travelers stay). 

However, you may want to rent a car if you’re staying in Honolulu and more remote, far-out areas. Getting around via bus is also an option, but it may take a while to travel from point A to B. 

Should I Go to Maui or Oahu? 

Again, this depends on what type of Hawaiian vacation you’re after, as these two islands have some notable differences. Oahu offers a more typical Hawaiian scene filled with historical memorials, modern culture, and Waikiki Beach. In contrast, Maui is more in tune with the outdoorsy, nature-loving type, with endless snorkeling and volcanic hikes.

Read Next: Check out this perfect 5-day Maui itinerary.  

Your Best Oahu Itinerary | Wrapped Up

Are you excited about this fun Oahu itinerary? You must be at the edge of your seat, and there’s a good reason for it: Ohau is simply that enticing. 

With fabulous beaches, fancy resorts, and fun activities to go around — it’s no surprise why this is a top holiday destination.  

Before You Go: Here’s how to plan a trip to Hawaii.   

Pin For Later: 5 Day Oahu Itinerary