The Ultimate 5 Day Oahu Itinerary

The Ultimate 5 Day Oahu Itinerary

Oahu – where I'm from! – has something for everyone. To get the most out of your trip, here's what I recommend for your 5 day Oahu itinerary.

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Rachel Off Duty: A 5-Day Guide to Oahu

Oahu, also known as ‘the Gathering Place,’ is where I grew up. With equal parts city life and endless beaches, Oahu is always my go-to recommendation whenever anyone asks me which island to visit first! 

From the world-famous beaches of the North Shore to the ever-evolving urban scene in Honolulu, Hawaii’s ‘main’ island Oahu is ripe with activities and things to do

Keep reading for all my local recommendations for a perfect 5 day Oahu itinerary. And, be sure to scroll down to the bottom to find out where to stay, where to eat and drink, and other need-to-know tips for visiting the Aloha state!

P.S. Already have your Oahu itinerary, and just looking for some more things to do? Don’t miss my guide to Things to Do on Oahu!

RELATED: How to Plan a Trip to Hawaii – Everything You Need to Know

The Ultimate 5 Day Oahu Itinerary

DAY ONE: Waikiki and Diamond Head

Rachel Off Duty: How to Spend 5 Days on Oahu - Waikiki

Odds are, if you’re coming to Oahu, you’ll be flying into the Daniel K. Inouye International Airport in Oahu (HNL), and most likely staying nearby Waikiki for at least some of your trip. 

Because of the long flight, I recommend spending your first day wandering the streets and beaches of Waikiki. At sunset, kick off the start of your amazing 5 day Oahu itinerary with a quick hike up Diamond Head, or a sunset catamaran ride, and take in the beautiful views of Waikiki.

Waikiki

Rachel Off Duty: How to Spend 5 Days on Oahu - Waikiki
Rachel Off Duty: How to Spend 5 Days on Oahu - Waikiki

Some people will tell you Waikiki is overrated and not a true representation of Hawaii. But, I would be remiss not to encourage you to spend your first day getting to know the area around your hotel! In fact, I find Waikiki pretty fun (in small doses), and I think you will too. 

Waikiki is famous for its long stretch of beach, generally calm water conditions, and postcard-worthy view of Diamond Head. You could easily spend a full afternoon strolling down Kalakaua Avenue’s shops and restaurants, visiting the Royal Hawaiian Center, taking a tour of the Moana Surfrider – Waikiki’s oldest hotel (built in 1901), or lounging around at the beach. 

If you don’t know where to stay on Oahu, there are some really fun new Waikiki hotels in the area, like The Surfjack and The Laylow. At the bottom of this post, you’ll find all of my recommendations for Oahu hotels.

Diamond Head

Diamond Head is one of the island’s most iconic landmarks. Formed more than 300,000 years ago by a volcanic explosion, Diamond Head is believed to have once been a residence for the Hawaiian goddess of fire, Pele. 

Today, the perfectly shaped volcanic cone is a US National Natural Monument and one of the most popular hikes in the entire state. Diamond Head is just 15 minutes from Waikiki by car and because of that, it can get pretty crowded. Go early if you can – sunrise offers some of the most spectacular views of Waikiki, Honolulu, and the ocean. 

Sunset Catamaran Ride

As the late afternoon begins to roll in, Waikiki transforms into a happy hour and nightlife hotspot for travelers, and you usually won’t have any difficulty finding live entertainment any day of the week. But, I recommend spending your first day on Oahu on a sunset catamaran ride! There’s something pretty magical about getting to see the sun set on Waikiki and Diamond Head while out at sea that makes you feel like you’ve really arrived. 

If you’re feeling lively, you can even take a sunset catamaran ride complete with an open bar. Not a bad way to start the evening before heading out to dinner!

Rachel Off Duty: Sunset Catamaran Rides in Oahu

DAY TWO: Oahu’s Windward Side

Rachel Off Duty: How to Spend 5 Days on Oahu - Windward Side

Now that you’ve explored Waikiki, day two of your 5 day Oahu itinerary includes checking out another one of the famous Oahu beaches, Kailua. 

Driving over to the Windward side of Oahu, you’ll instantly be blown away by the difference in scenery. The Ko’olau Mountains perfectly divide Oahu’s dry and wet sides. While Waikiki is generally dry most of the year, the Windward side boasts tropical, emerald greens.

On your way to Kailua, you’ll most likely take the Pali Highway (HI-61). If you do, make a pitstop at the Nu’uanu Pali Lookout for panoramic (and historic) views of Oahu’s greener side. 

Kailua Beach

Frequently ranked one of the most beautiful beaches in the country, Kailua Beach is no doubt a stunner. Perfect sand and gorgeous reef spread not far from shore gives way to the infamous “Mokes” (the Mokulua Islands) and Flat Island (also known as Popoia). Here, kitesurfers, parasailers, kayakers, paddleboarders, tourists, and locals alike are always frequenting Kailua Beach for its calm conditions and spectacular views. 

Because of its popularity, it’s important to know that Kailua Beach is unfortunately often overcrowded and parking can be scarce, especially on weekends. Please don’t park illegally or idle around just because you don’t see an open spot – it’s a huge pain for locals trying to get in and out of town. 

I recommend going to Kailua Beach during off-peak times, like weekdays, early mornings, or late afternoons to help reduce the strain on the destination. Or, as an alternative, check out nearby Waimanalo Beach which is just as stunning and incredibly underrated! 

Rachel Off Duty: How to Spend 5 Days on Oahu - Kailua Beach
Rachel Off Duty: How to Spend 5 Days on Oahu - Kailua Beach

Kayak and Paddleboard Rentals

Kailua Beach is a popular spot for kayaking and paddleboarding. If you’re feeling adventurous, spend your afternoon paddling out to Flat Island or the Mokes! Kailua Beach Adventures is the go-to spot for rentals here.

Lanikai Pillbox Hike

Rachel Off Duty: How to Spend 5 Days on Oahu - Lanikai Pillboxes
Rachel Off Duty: How to Spend 5 Days on Oahu - Lanikai Pillboxes
Rachel Off Duty: How to Spend 5 Days on Oahu - Lanikai Pillboxes

If kayaking and paddleboarding aren’t your thing, consider doing the quick Lanikai Pillboxes hike, not far from Kailua Beach.

DAY THREE: Honolulu and Hawaii History

Rachel Off Duty: Iolani Palace OahuImage Credit: Go Hawaii

Here, in Hawaii’s bustling capital city, you’ll find some fascinating opportunities to learn a bit more about Hawaii’s history, while also exploring Hawaii’s best food and shopping scenes along the way. Here are some suggestions for spending a day off the beach, or as locals will say, ‘in town.’ 

Pearl Harbor

Pearl Harbor is still an active military base to this day, but it’s also home to five historic sites that you can visit – the USS Arizona Memorial, the Battleship Missouri Memorial, the USS Bowfin, the Pearl Harbor Aviation Museum, and the USS Oklahoma Memorial. It’s one of the most-visited sites on Oahu.

Honolulu Chinatown

Downtown Honolulu is the urban jungle of Oahu, and a place I never really paid much attention to as a kid. But as I’ve gotten older and developed a bit of a foodie palate, I now see that downtown Honolulu is not to be missed if you’re curious about Hawaii’s culinary scene! 

One place that’s currently undergoing a massive renaissance is Chinatown. Chinatown, though no doubt in need of some TLC, has become the destination for new restaurants, bars, art galleries, and nightlife. 

At the bottom of this post, I share a long list of my favorite places to eat and drink in Oahu, but when it comes to Chinatown specifically, The Pig and the Lady, Manifest, Skull & Crown Trading Co, and Jolene’s are some of my favorite spots to return to over and over again!

Rachel Off Duty: Jolene's Chinatown Oahu

Iolani Palace

Located in the middle of downtown Honolulu, Iolani Palace (pictured above) was the official residence of one of Hawaii’s last reigning monarchs, King Kalakaua and his sister who succeeded him, Queen Liliuokalani. She was later tried, convicted, and imprisoned in this very same Palace when the monarchy was overthrown, in 1983. I highly recommend that anyone coming to Oahu for the first time visit this place, to gain a deeper understanding of Hawaii’s monarchy and history.

Iolani Palace was designated a National Historic Landmark and is open to the public for audio and docent-led tours. 

Shopping in Honolulu

If you’re in the mood to shop and need a break from Waikiki, check out these Honolulu shopping venues: 

  • Ward Village: A massive five-mall complex of small boutiques, shops, restaurants, and a movie theater.
  • SALT at Kaka’ako: A newer outdoor shopping center with local boutiques, cute bars and restaurants, and lots of outdoor seating with public wifi. This is where I like to meet friends for drinks or coffee, and where I like to work remotely from when I need a change of pace from my childhood bedroom. 
  • Ala Moana: The largest open-air shopping center in the world, Ala Moana is where I’d go whenever I need, well, anything. From convenience stores to high-end luxury brands, chain restaurants to Pan-Asian food courts, Ala Moana has a little bit of everything and is fun to wander around in, even if you’re not shopping for anything special.

DAY FOUR: Kualoa Ranch and North Shore

Rachel Off Duty: 5 Day Oahu Itinerary – Kualoa Ranch

Plan to wake up early on day four of your 5 day Oahu itinerary. The north shore is one of the absolute best things to do in Oahu. Because of this, you’ll want to savor every second! 

Kualoa Ranch

Rachel Off Duty: 5 Day Oahu Itinerary – Kualoa Ranch
Rachel Off Duty: 5 Day Oahu Itinerary – Kualoa Ranch

You can head straight to Oahu’s North Shore, but if you have the time and want to see Oahu’s famous Ka’a’awa Valley (also known as Jurassic Valley, where Jurassic Park and a ton of other shows and movies were filmed), plan to stop at Kualoa Ranch. 

RELATED: The Ultimate Local Guide to North Shore Oahu

Rachel Off Duty: 5 Day Oahu Itinerary – Kualoa Ranch

Spanning 4,000 acres, Kualoa Ranch is a stunning property of steep mountainside, dense tropical rainforest, and picturesque ocean. The ranch offers tons of activities and tours, but I personally recommend the ATV Raptor tour or the horseback tour!

North Shore Oahu

Rachel Off Duty: Oahu North Shore - 5 Day Itinerary Oahu

From Kualoa Ranch, as you continue up Kamehameha Highway, you’ll find yourself on one of my absolute favorite driving routes on Oahu, as the highway hugs the ocean and winds through the island’s slower-paced countryside. My favorite way to enjoy the North Shore is by beach-hopping. But, you’ll also find tons of food trucks and restaurants, water sports, and boutique shops to keep you busy too. 

Find a full rundown of my favorite part of the island here: Ultimate Local Guide to Oahu’s North Shore.

DAY FIVE: South Shore

Rachel Off Duty: 5 Day Oahu Itinerary – South Shore Beaches

On your last day on Oahu, spend it a bit closer to your hotel and explore Oahu’s dramatic South Shore. Here, I love doing an intense hike in the morning and spending the rest of my day relaxing on the beach. Of course, you can also skip the hike and head straight to the relaxation – it’s your vacation, after all! 

Koko Head and Makapu’u Lighthouse Hikes

Rachel Off Duty: Koko Head Stairs
Rachel Off Duty: Makapu'u Lighthouse

If you feel like doing a quick but effective hike that’ll get your heart rate up in no time, Koko Head is my go-to! Koko Crater Trail, known locally as Koko Head or nature’s StairMaster, is an old railroad track trail consisting of 1,048 steps and a 1,200 foot elevation gain. Most people will reach the summit in 45 minutes to an hour (30 minutes if you’re quick!). However, it’s important to pace yourself and go early before the sun is overhead.

For an alternative hike that’s more leisurely, check out Makapu’u Lighthouse (pictured above right), which is paved the entire way.

South Shore Beaches

Rachel Off Duty: Hanauma Bay Oahu

After your morning hike, head to Hanauma Bay or Sandy’s for one more afternoon at the beach! 

I recommend Hanauma Bay if you want to snorkel in one of the most spectacular marine life preserves in the country. But (and it’s a pretty big but), because of its booming popularity and its commitment to keep the marine ecosystem protected at all costs, visiting has become a bit more complicated. You’ll need to make a $25 reservation online ahead of time, and you will need to enter the park before 1:30 pm. Reservations only open two days in advance and can be found using this online reservation system (spots are released for the next two days by 7 am HST each morning). 

On the flip side, if you want to just relax on the sand and soak up Oahu’s beautiful scenery, head to Sandy’s. Depending on the time of year, you’ll be able to witness Sandy’s incredible (and dangerous!) shore break. I don’t recommend swimming here unless you’re very experienced or if ocean conditions are calm.

Whether or not you get in the water, anyone can appreciate this beach’s beautiful isolation, soft sand, and powerful waves.

Other Things to Do if You Have More Time

Rachel Off Duty: What to Do on Oahu - Waterfalls

While these next suggestions might not fit in a 5 day Oahu itinerary, consider looking into some of these if you have more time to spare!

  • Go to the Polynesian Cultural Center: The ultra-popular Polynesian Cultural Center allows visitors to learn more about Polynesia. Through interactive performances, exhibits, and activities, you can explore Hawaii, Tonga, Fiji, Autearoa, Samoa, and Tahiti all in one place. I suggest dedicating a full day to this, which is why I didn’t include it in my core 5 day Oahu itinerary above.
  • Take a Helicopter Tour: One of the best perspectives of any Hawaiian island is from up high. While helicopter tours in Oahu are pretty pricey, they’re well worth the experience if you can swing it. I recommend Mauna Loa Helicopters.
  • Visit a Botanical Garden: More than just pretty beaches, Oahu is also known for some insane flora. Visiting a botanical garden, like Waimea Valley or Ho’omaluhia Botanical Garden, is one of the greatest ways to experience Hawaii’s unique landscapes and plants up close.
  • Swim With Sea Turtles: While you’ll need to keep a respectful distance from Hawaii’s protected sea turtles (honu), swimming with them is no doubt one of the most awe-inspiring encounters you can have in Oahu. Wild Side Specialty Tours and Holokai Catamaran offer snorkeling tours to witness these gentle creatures in their natural habitat.
  • Hike to a Waterfall: Some of the easiest waterfalls to see in Oahu include Waimea Falls (in the Waimea Valley botanical garden) and Manoa Falls. However, if you’re willing to get a little dirty, Maunawili Falls, Lulumahu Falls, and Waimano Falls are also incredible.
  • Try a Surfing Class: Waikiki is one of the easiest places to learn to surf in all of the Hawaiian islands because of its long, rolling wave break. There are countless surf schools in Waikiki, but I’ve heard great things about Moniz Family Surf, a family-owned operation on Oahu.
  • Volunteer and Give Back to Oahu: Spending the morning volunteering on Oahu is a great way to give back to your favorite vacation destination. Some of my suggestions to malama (‘care for’) Oahu include planting native trees in Oahu’s Legacy Forest, cleaning beaches with Sustainable Coastlines Hawaii, and learning about native Hawaiian farming practices and endemic plant species at Kualoa Ranch.

RELATED: 20+ of the Very Best Things to Do in Oahu

Where to Stay on Oahu

Rachel Off Duty: Where to Stay on Oahu
  • The Surfjack: Hip, affordable, and pet-friendly, this boutique hotel will transport you back in time to Waikiki’s mid-century heyday. Be sure to check out their Society6 suite!
  • The Laylow: Another chic, retro-inspired boutique hotel, The Laylow is part of Marriott’s Autograph Collection and features Instagrammable rooms, a cool pool area, and delicious food and drinks at The Hideout.
  • Royal Hawaiian Resort: At nearly 100 years old, this pink hotel is a Waikiki icon. Part of Marriott’s Luxury Collection, a stay at the Royal Hawaiian Resort is bound to be endlessly memorable (and photographable).
  • Hilton Hawaiian Village: I have fond memories of staying in the Hilton Hawaiian Village as a kid (I always wanted to stay in the Rainbow Tower!). The Hilton is adjacent to Duke Kahanamoku Beach, and hosts weekly firework shows on Friday nights.
  • Turtle Bay Resort: Turtle Bay is the only resort you’ll find on Oahu’s North Shore. This property is where Forgetting Sarah Marshall was filmed, and also where my parents got married!
  • Four Seasons Resort: Oahu’s Four Seasons Resort, also located at Ko Olina, has a beautiful pool, private lagoon, and impressive spa that will transport you to Bali.
  • Other Hotel Options in Oahu (Click Here)
  • Oahu Airbnbs (Click Here)

PRO TIP: Some Oahu hotels will give you a discount or a free night’s stay just for volunteering! It’s part of Hawaii’s Malama Hawaii initiative, which you can get involved with during your trip. See all volunteering options and participating hotels here.

Where to Eat and Drink on Oahu

Rachel Off Duty: Where to Eat and Drink on Oahu

This 5 day Oahu itinerary wouldn’t be complete without food recommendations. My list is endless (and growing), but here are some culinary highlights that are either crowd-pleasers or personal favorites.

Other Tips to Know Before You Go

Rachel Off Duty: Oahu Travel Tips
  • Currency: The Hawaiian islands use the US Dollar (USD). Credit cards are widely accepted, but carry spare cash for food trucks, tipping at hotels, etc.
  • Language: Hawaii is the only state with two official languages: English and Hawaiian. However, English is the language you’ll use to chat, get around, and read on street signs. You’ll also hear a third ‘language,’ called Pidgin, which is a sort of English creole formed over the past two centuries as various generations of immigrants began coexisting here. Today, it all blends together into a unique version of colloquial English you won’t hear anywhere else 🙂
  • Transportation: If you’re staying in Waikiki and only plan on venturing out one or two days in your 5 day Oahu itinerary, you might be able to get by with public transportation, ride-share, or pre-arranged transport (like a shuttle service). However, renting a car is going to be the best way to see Oahu and successfully do this itinerary.
    • Renting a Car on Oahu: Use Kayak to compare rental car rates, Turo to find peer-to-peer car rentals, or Hui to find peer-to-peer car rentals from a locally owned company.
    • Renting a Camper or RV: Used RVshare to look up Hawaii RVs, camper vans, and the occassional rooftop tent.
    • Rideshare on Oahu: Uber and Lyft are both easily accessible on Oahu. Another contender is locally-owned Holoholo, which functions the same way as the other rideshare apps you’re already used to.
    • Public Transportation on Oahu: The public bus system, called TheBus, on Oahu is a generally reliable and inexpensive way to explore the island.
    • Waikiki Trolley: The hop-on, hop-off Waikiki Trolley is a reliable way to get around Waikiki, Honolulu, and East Oahu.
    • Bike: I don’t recommend biking as a main method of transportation, but for bike rentals you can check out Biki on Oahu.
  • What is the Best Time to Visit Oahu? Because of Oahu’s ideal climate, there is no true “bad” time to visit Oahu. That said, there are some things to consider – whether you want to avoid the crowds (shoulder seasons), what kind of surf conditions you’re looking for (winter brings North Shore swells), whether you want to go whale watching (Dec – Feb), etc. – that will help you determine the best time for you to go. In general, peak season for Oahu travel is May – August and December – June.
  • Etiquette for First-Time Visitors: To avoid any unfortunate travel bloops, be sure to check out my Hawaii trip planning guide next. This breaks down everything you’ll want to know before you go to Hawaii! Safe travels!

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A 5-Day Guide to Oahu - Rachel Off Duty
A 5-Day Guide to Oahu - Rachel Off Duty

Hey there! I’m Rachel, a travel writer and a full-time advertising / marketing expert. In 2019, I traveled more than 25 times while working 9 to 5, and since then I’ve committed myself to living a more adventurous life, even if it means bringing my laptop along for the ride.

Are you hungry to travel more, but overwhelmed with how to juggle work and play? You’ve come to the right place!

Recent Adventures:
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