Get ready for Oahu itinerary with 5 days of non-stop adventure and unforgettable experiences!
This tropical paradise has everything from stunning beaches to lush hiking trails.
In this blog post, we’ll start off with some need-to-know basics like where it is on the map and the best time to visit.
We’ll then guide you through an epic 5 days in Oahu to ensure that you make the most of your time on the island.
Whether you’re a first-time traveller or a seasoned explorer, these activities will leave you in awe.
Todays guide is written by Bridget, who has been living in Hawaii for quite some time and runs Bridget Gutierrez Travels.
Where is Oahu
Oahu is an island in Hawaii and is one of the most popular tourist destinations in the world.
It’s one of the eight Hawaiian Islands in the middle of the Pacific Ocean, about 2,472 miles away from California, and holds the title of the third largest island in Hawaii.
Below is an interactive map so that you can see the exact location.
Best time to visit Oahu
The best time to visit Oahu will be during the low season for the best prices, less crowds, and availability of activities.
I personally think that the best months to visit are May, September, October, and November before Thanksgiving.
However, here is what you can expect by the season in more detail:
Winter (December to February)
Winter is the peak season on Oahu, attracting visitors seeking warmth and escape from colder climates – and what better place than here!
The North Shore’s impressive surf draws enthusiasts and competitions and the weather is generally pretty good, ranging from the mid-60s to mid-80s Fahrenheit (18-29°C).
The downside is that crowds can be heavy, so you’ll need to book accommodation and activities ahead of time.
Whale watching is also a major draw during winter, with humpback whales visible from December to April.
Spring (March to May)
Spring is a great time to experience Oahu with fewer crowds and pleasant weather in the mid-60s to mid-80s Fahrenheit (18-29°C).
Plus, the Cherry blossoms bloom in March at Wahiawa Botanical Garden which is an absolutely stunning sight.
Outdoor lovers will also enjoy the uncrowded trails and favourable conditions for hiking.
The Honolulu Festival in March showcases the island’s cultural diversity through events and exhibitions.
Summer (June to August)
Summer brings lovely warm temperatures to Oahu – from mid-70s to mid-80s Fahrenheit or 24-29°C – and a bustling atmosphere.
You can expect to see more visitors, especially families due to the school holiday season.
For those into surfing, you’ll get some smaller waves, but the waters are great for swimming and snorkelling.
Fall (September to November)
Heading to the island in the Fall will be pleasant as there will be fewer crowds, but temperatures still range from the mid-70s to mid-80s Fahrenheit (24-29°C).
This is considered the shoulder season, making it ideal for outdoor activities, including uncrowded beach visits and hikes on serene trails.
The Aloha Festivals and surf competitions add cultural and exciting elements to this relaxed period, making it a great time to explore the island’s traditions and natural beauty while enjoying more affordable accommodations.
Oahu itinerary: 5 days
Day 1: Discovering beaches, local spots and sunset cruising in Waikiki
Explore Waikiki Beach
After a long flight to the Oahu, it is best to take it easy and adjust to the time difference.
Most likely, you booked your accommodation in Waikiki, where most hotels are located.
After checking in, grab your swimsuit and a towel and kick off your 5 days in Oahu by heading to Waikiki Beach, one of the most famous beaches in the world.
It’s perfect for relaxing, laying out, watching, swimming, and even, if you’re lucky, spot a Hawaiian sea turtle.
If you still have energy and want to make the most of the day, you can go on a catamaran, canoe ride, take surf lessons, or snorkel.
Check tour prices: Turtle Canyon Catamaran Snorkel Cruise from Waikiki
Try Hawaiian Shave Ice
After laying in the hot sun, you’re bound to need something to cool you down.
And, Hawaiian shave ice (not shaved ice) – a sweet treat that is made up of primarily ice and syrup – is the perfect thing for for it.
There are many spots on the island where you can get shave ice, but just a few steps from Waikiki Beach is Island Vintage Shave Ice kiosk.
You can pick standard flavours and toppings or create a custom one with your desired tastes.
Stay calm if you see a long line; it goes by quickly and will be worth waiting for.
This shave ice differs from many places because this one comes with ice cream on the bottom and delicious mochi toppings.
Check out Dukes Marketplace
To help you digest that delicious shave ice, head to Duke’s Marketplace, just a few steps away.
This outdoor marketplace is where you can find great souvenirs to take home, like keychains, ukuleles, t-shirts, handmade art pieces, necklaces, and everything in between.
Dinner at Dukes Waikiki
For dinner, head to the famous Duke’s restaurant at the Outrigger.
Duke’s is a super popular spot with many interiors designed with wood surfing and all things Hawaiian.
Going to Duke’s is an excellent choice because they have delicious items on their menu to suit every type of foodie.
And, what makes this place even better is that it’s right on the beach.
Make reservations a few days prior, especially during the High season.
Waiting for a table during the high season can be a 3-hour wait time.
Walk along the infamous Kalakaua Ave
After dinner, a great way to wind down is to walk on the main street of Kalakaua Ave.
At night, it becomes lively with singers, street performers, cartoon artists, and even a parrot with which you can take pictures.
You can also do a little shopping in the boutiques that are on this street.
Day 2 Famous hikes, viewpoints and sites + beautiful beaches
On the first official day in Oahu, make the most out of it to set the tone for the rest of our trip.
It’s best to start your day early by heading to breakfast at Hula Grill for a sit-down meal, or if you want something quick and fast, head to Liliha Bakery and try out their Mochi Donuts which are taro-based (purple potato).
Drive to Nuʻuanu Pali Lookout
Once you’re filled up and have the energy, you’ll need to drive from Waikiki to the island’s east side via the Pali highway.
The first stop is going to be the Nuʻuanu Pali Lookout – a historical site where King Kamehameha won the struggle that finally united Oahu under his rule in 1759.
This beautiful lookout is on the mountains with a beautiful view of the island’s east side.
Most of the time here is cloudy and super windy, but it still gives you a great view.
Hike Pu’u Ma’eli’eli Trail
No Oahu itinerary is complete without conquering the beautiful Pu’u Ma’eli’eli trail.
I’m sure you’ve heard of the Diamond Head and Lanikai Pillbox hike – which are excellent – but this hike is a hidden gem.
This hike is easy to moderate, but the beginning is the most difficult because of the muddy, steep hill.
But don’t worry – there is a rope that you can hold on to to help you get up.
Other than that, the whole way is shaded.
You’ll be immersed in nature and only be able to hear the birds sing.
And for the most part, you can expect to have the path to yourself.
The endpoint has impressive and unique views of Kaneohe and Kualoa Valley.
This hike is 2.3 miles and takes less than 2 hours to complete.
Just make sure that you wear sunscreen and bring plenty of water.
Route map: Pu’u Ma’eli’eli Trail
Visit Byodo-In Temple
Just a few minutes’ drive from the amazing hike is Byodo-In Temple.
It’s nestled in the lush Ko’olau Mountains of Oahu and is a mesmerizing place of tranquillity and beauty.
As you enter the temple grounds, you’ll be greeted by the majestic sight of the stunning architecture, intricate detailing, and tranquil surroundings.
Modeled after the 900-year-old Byodo-In Temple in Uji, Japan, this stunning replica must be added to your 5 day Oahu itinerary.
Drive through Hoʻomaluhia Botanical Garden
Next up is a drive through the iconic Hoʻomaluhia Botanical Garden.
This breathtaking stop is filled with heaps of flora and fauna – and with the mountains in the background, it is such a special place that it almost looks unreal.
If you don’t have much time, you can quickly drive through this Botanical Garden, get out, and take a few pictures.
However, remember not to take any images on the road because this is not allowed anymore.
You need so make sure you’re in the designated area to take photographs.
If you have time, it’s a great place to enjoy a picnic by the lake and the scenery.
Beach day at Kailua
To wrap up day 2, enjoy the beautiful clear blue water of Kailua Beach and its soft sand.
This beach is super long, making it perfect to go on a long walk.
Alternatively, you can take this opportunity to go for a little swim without worrying about any big waves, since this beach doesn’t have any.
If you are feeling adventurous, you can hire a kayak near the islands in front of Kailua Beach.
When you get hungry, wander across the street and grab something to eat from Buzz’s Original Steak House.
Everything on the menu is delicious!
Day 3: Enjoy stunning views and epic watersports
In everybody’s Oahu 5 day itinerary, a day for sightseeing is a must.
Diamond Head Lookout
A few minutes’ drive from Waikiki is Diamond Head Lookout, where you can watch surfers take on amazing waves.
Honestly, this is a great first stop and it’s just mesmerizing to watch these talented humans!
Hawai’i Kai Lookout
In Hawaii, Kai Lookout is an excellent spot to see Koko Head, a popular hiking spot.
During the winter, the Koko Head is typically green and during the dry season, you will see a brown.
It also gives you a great view of the area of Hawaii Kai City.
Lanai Lookout is a scenic point great for photos and to see the layers of lava and how they have transformed or eroded throughout the years.
You can also enjoy panoramic views of the ocean here.
Local tip: this is a great spot to visit during the winter to see humpback whales migrate with their new baby.
Hike up Makapuʻu
This hike overlooks the water and has excellent views and ocean breezes.
It’s an easy hike for all the family members because the trail is paved to the top.
And let’s not forget about the majestic Makapuʻu Lighthouse that stands proudly at the top, providing the perfect backdrop for those photos.
There is no shade throughout this trail, so bring some protection and plenty of water.
If you’re not in the mood for hiking, you can head to the Makapool Lookout and see a great view.
Go swimming at Waimanalo
Let’s cool off at a hidden gem by heading to Waimanalo Beach Park.
This beach is more of a local beach, and because it’s so vast, you will have so much space.
You can almost have this beach to yourself on a weekday.
And, because this beach is so near the mountains, you will have beautiful views of the mountains right on the beach.
Tip: sadly, there is a lot of homeless people who stay in front of the beach park and the parking lot. Although they don’t usually cause any trouble, but I always recommend further down the road to avoid any mishaps.
Day 4: Exploring historical sites, hidden gems and watersports on the North Shore
Visit Pearl Harbor
Visiting the Pearl Harbor Memorial is free, and learning all about the events that occurred on that fateful day in 1941 is something not to be missed.
You can even take a boat ride out to the memorial and see the remnants of the sunken battleship up close.
If you’re into Aviation and the Military, then you can also take advantage of other tours like the Battleship Missouri Memorial, Aviation Museum, and Pacific Fleet Submarine Museum.
With its stunning views and rich history, Pearl Harbor is an unforgettable experience that will leave you feeling inspired and grateful for those who have fought for our freedom.
Check tour prices:
- Pearl Harbor USS Arizona Memorial
- Pearl Harbor: USS Arizona Memorial & USS Missouri Battleship
- Pearl Harbor, Arizona Memorial & Polynesian Cultural Center
Exploring Haleiwa must be included in everyone’s Oahu 5 day trip for a taste of authentic island charm.
Located on the island’s North Shore, Haleiwa is a vibrant, laid-back town known for its surf culture, natural beauty, and delicious food.
You can stroll through the historic district and admire the plantation-style buildings that house local boutiques, art galleries, and restaurants where you can indulge in local cuisine and pick up unique souvenirs.
Visit Waimea Valley
This stunning botanical garden is filled with rare and exotic plants is a paradise waiting to be discovered.
As you explore the valley, you’ll have the opportunity to walk along the scenic trail with many plants and plantation houses.
The highlight of your visit will undoubtedly be Waimea Falls, a majestic waterfall that cascades into a serene pool below.
To swim in the falls, you must pay a $25 fee and wear a life vest for safety.
With its rich cultural heritage and commitment to conservation, Waimea Valley offers a unique experience for all who visit.
If you’re visiting Oahu during the summer months (April through October), then I highly recommend you go snorkelling on the North Shore.
The most popular spots inlcude Shorts Cove and Three Tables, which are great North Shore beaches to spend the day at.
The water is usually calm, not too many waves, and most importantly, quite warm.
Unfortunately, if you’re travelling during the winter months, it’s unsafe to snorkel or even swim on the North Shore due to the large swells and currents in winter.
Watch pro surfers
Alternatively, If you are visiting in the winter, it is a perfect time to head to North Shore Beaches to see pro surfers take on the most dangerous waves in the world.
If you didn’t know, surfing was born in Hawaii, so the surf culture here is vital.
Waves can reach from 10 to 30 ft high, which is crazy.
But it’s so amusing to watch these pro women and men taking on these massive, dangerous waves, and it’s a once-in-a-lifetime experience.
Day 5 Craters, surfing, shopping and food in Honolulu
Squeeze in your last workout for this trip by heading to Diamond Head and hiking for 30 minutes to reach the top.
Diamond Head Crater offers a fantastic view of the city, the mountains, and the ocean.
This hike is so worth it for those impressive views.
You’ll need to make sure you make a reservation to visit here, and they can be reserved up to two weeks in advance from the day you want to go, so make sure to select the correct time you plan to arrive at the park.
It goes without saying, but you’ll need to take PLENTY of water and bring sun protection like sunscreen and rash guard on this hike, as there’s no shade during this trail, and it gets hot very quickly.
Sign up for a Surf Session
If you’ve ever fancied surfing, then now is your chance to give it a go.
You’re at one of the best locations in the world for this sport, so why not take your chance and get surf lessons at Waikiki Beach.
Waikiki Beach has the best surfing conditions for beginners all year round.
There is no need to be afraid or intimidated because many beginners take lessons and even more advanced surfers are constantly trying to learn and practice their skills.
With the shallow waters of Waikiki and the best wave conditions, you are almost guaranteed to stand up and surf away here.
Remember to book a lesson that includes photos as part of the package – it’s so worth it!
Shop at Ala Moana Center
Before heading out, be sure to check out the Ala Moana Center.
It is the world’s largest outdoor mall, with 350 shops and restaurants.
It quite literally has all the stores you can think of – from Hawaiian brands to more affordable brands like Target, J Maxx, and Old Navy, as well as high-end designer brands like Gucci and Prada.
Pro tip: if you are in the market for designer products, Hawaii has Hawaii prices, which means you can get anywhere from 5 to 15% discount compared to the places like Los Angeles or New York.
Dinner at The Signature Prime Steak & Seafood
A great way to end such a fantastic 5 day trip to Oahu is to head to The Signature Prime Steak & Seafood, a restaurant on the top floor of the Ala Moana Honolulu Hotel.
The best time to go is during sunset because you can see the beautiful sunset over the water.
But if you’re unable to be here during this time, then the view is also epic at night, since you can see the city skyline that reflects in the water.
To make this dinner even more unique, they have live music or sometimes a piano playing during your meal.
What to do if you have more than 5 days in Oahu?
If you find yourself with more than five days in Oahu, here are a few unforgettable experiences to enjoy:
- Go on a food tour: start your journey with a mouthwatering food tour, where you can indulge in the island’s diverse culinary scene.
- ATV Tour at Kualoa Ranch: embark on an ATV tour through the scenic landscapes of Kualoa Valley, where many movies like “Jumanji” and “Jurassic Park” were filmed.
- A Day at Kaneohe Sandbar: for aquatic adventures, joing an afternoon tour and spend some time at the Kaneohe Sandbar and enjoy activities like stand-up paddleboarding, volleyball, snorkeling, and even go on a banana boat ride.
- Swimming with Sharks in North Shore: face your fears and swim cage-free with a swimming with sharks tour and experience one of the most incredible moments of your entire life.
These activities will surely make your time in Oahu unforgettable!
Where to stay for your five days on Oahu
When staying in Oahu, there are three areas where you can visit:
- North Shore
- Ko Olina
Each location is different.
Waikiki is right on the beach, with many boutique hotels and resorts.
It’s where you will find restaurants, shopping, and activities.
On the North Shore, there are only two hotels to choose from, and it’s quieter, more residential, and has a surf vibe.
Ko Olina offers a few resorts and condos in a resort-style manicured area with only hotel restaurants available and not much shopping or activities unless organized through the hotel.
So basically, Waikiki is the best place to stay.
Below are some places I’d recommend checking.
- Budget: Polynesian Hostel Beach Club- Waikiki Hostel
- Mid-range: White Sands Hotel – Waikiki
- Mid-range: Kaimana Beach Hotel -Waikiki $$
- Luxury: Turtle Bay Resort- North Shore $$$
Is 5 days enough in Oahu?
Yes, 5 days is enough to visit Oahu.
It allows you to relax, explore, and experience the Hawaiian culture.
You will fit some great highlights and enjoy your Oahu trip, but there is always more to do if you’re here for longer.
Is Oahu an expensive vacation?
Yes, a trip to Oahu is expensive compared to other major cities because you are in the middle of the Pacific Ocean.
There are great ways to save on your Oahu vacation, like enjoying free things to do in Oahu, buying food at the grocery store to have picnics, and avoiding eating out.
Should I spend more time in Oahu or Maui?
Depending on the type of travel you prefer, it will determine which island you want to spend more time on.
If you like rural, up-country hikes, waterfalls, and a quieter, less crowded atmosphere, spend more time in Maui.
If you want to do many activities, have accessibility to different restaurants and activities, and don’t mind the city and crowds, then definitely spend more time in Oahu.
Explore beyond your 5 day itinerary for Oahu
And thats a wrap for our Oahu itinerary with 5 days of epic sites and activities!
Exploring the beautiful island of Oahu is an adventure you will want to take advantage of, but if you’re considering other destinations in the USA, then why not check out our 10 day Florida itinerary – or more specifically, a weekend in Tampa.
Stay Wild Travels.
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About our author: Bridget is a travel writer and owner of Bridget Gutierrez Travels, where she helps you plan memorable vacations to Oahu. She specializes in authentic and hidden gems of Oahu, Hawaii, as a Hawaii local.
You can follow her on Instagram, TikTok, and Pinterest for Oahu content and travel tips.