Best of Oahu: 5 Day Itinerary for First Time Visitors to Hawaii
If it’s your first time visiting Hawaii, then Oahu is one of the best places to get to know the beautiful state. We’ll help you plan the perfect trip with our Oahu 5 day itinerary.
Oahu is the third largest of the Hawaiian islands and is home to state capital, Honolulu, where Jedd grew up. The island is an interesting combination of bustling city life and unmatched natural beauty.
We like to say that Oahu has a little bit of everything, from vibrant downtown streets lined with delicious restaurants, historic sites and galleries, mountains with panoramic views, scenic hiking trails, and of course some of the best beaches in the world.
Our 5 day Oahu itinerary includes popular must-visit places. But we also go beyond the tourist attractions to share some local insights and some fun underrated activities from our many years of visiting family on the island.
Our Suggested Oahu 5 Day Itinerary
With limited time to visit Oahu, we recommend picking a home base. This way you’ll spend less time moving around and more time enjoying yourself.
It would be easy to make a purely Honolulu itinerary for 5 days. However, you probably want to see the rest of the island, too. This five day Oahu itinerary aims to balance relaxation with sightseeing.
The best Oahu itinerary for 5 days: Overview
Here is a quick example 5 day Oahu itinerary.
Day 1 – Waikiki Beach
Day 2 – Hana’uma Bay, Diamond Head
Day 3 – Honolulu special interests
Day 4 – Island Road Trip & Polynesian Cultural Center
Day 5 – North Shore
Read on for more detailed recommendations and itinerary variations.
Find the perfect accommodations with our free Where to Stay on Oahu Guide
See how much you can save with the Go Oahu all-inclusive pass
Make packing easy with our free Hawaii packing checklist
Download our free Honolulu Trip Checklist
Disclosure: This Oahu guide contains affiliate links. That means if you make a booking or a purchase using the links, we may get a small commission at no extra cost to you. It’s how we cover the costs of running the blog!
Getting Around Oahu
Our Oahu itinerary does assume that you can self-drive. While we don’t love driving around Honolulu, it’s often the simplest way to get around.
If you don’t have a rental car, there are still ways to get around: ride share like Uber or Lyft, taxis, public bus, shuttles, package tours that include transportation, etc.
See more details on how to get around Oahu here.
Where to Stay on Oahu
If you’d like to base yourself in Honolulu, as we suggest for most of this itinerary, here are accommodation recommendations:
– Waikiki Central Hotel $$ – Great value, walk to Waikiki beach
Check price, photos & availability >
– Hawaiian Monarch Apt $$ -Condo for 2 within easy walking distance to Waikiki beach
Check price, photos & availability >
– Halekulani $$$$ – Ocean front hotel with spa and upscale restaurant
Check price, photos & availability >
We also have more detailed information about:
Best areas to stay in Honolulu outside of Waikiki
Where to stay elsewhere on Oahu
Oahu Itinerary: Day 1 – Waikiki Beach Day
Photo credit: PDXploration
After arriving from your long flight to Honolulu International Airport, one of the best things to do is to spend your first day by Waikiki Beach.
Get some light exercise while exploring points of interest along the beach by following one of our recommended walking routes in Waikiki.
At night, there are plenty of activities highlighting Hawaiian culture. On Tuesdays, Thursdays, and Saturdays, you can watch a hula show and torch lighting ceremony near the statue of Duke Kahanamokusuch. And on Fridays at 7:45pm, you can catch the weekly fireworks show above the Hilton Hawaiian Village.
Here are some places we recommend to eat:
- Goofy’s: Healthy and natural Hawaiian local dishes for brunch
- Katsumidori: Fresh, high-quality sushi for dinner
Day 2 – Hana’uma Bay & Diamond Head
Get an early start to your second day by hiking Diamond Head, a famous landmark recognized for its historic hiking trails. The trails are partially paved and are accessible for beginners, though it gets steeper towards the 99 stairs at the end.
You’ll be rewarded with amazing panoramic views from the lookout at the edge of the Diamond Head crater.
Entrance is $1 per pedestrian or $5 per vehicle. Since this is a popular hike, the parking lot does fill up quickly. We recommend going early in the morning to avoid crowds and the afternoon heat.
Then head to Hana’uma Bay, another of Honolulu’s most popular tourist attractions. This bay is a protected area where visitors can snorkel alongside the rich marine life or spend a relaxing afternoon by the shore. Try to get here as early as possible since parking also fills up quickly.
Keep in mind that reservations are needed and it’s closed every Monday and Tuesday so you may need to adjust your Oahu itinerary accordingly. Make sure to check for jellyfish warnings too! They usually take place a couple of days after each full moon.
If you have time, you can go visit any of the museums or historical sites from Day 3 or end the day by relaxing and going back to the beach!
Here are some places we recommend to eat in Hana’uma Bay:
- Moena Cafe: A sunny cafe serving breakfast and brunch with local ingredients
- Island Brew Coffee House: Our favorite coffee shop serving locally grown and roasted coffee
- Kona Brewing: Brewery with local beer and pub food
- Roy’s Hawaii Kai: High-end dinner restaurant specializing in Hawaiian fusion
Day 3 – Honolulu choose-your-own-adventure
Before heading out to the see the rest of the island on Day 4 and Day 5, wrap up your time in Honolulu with a day customized to your own interests.
Remember: Enjoy yourself on your vacation by doing what’s best for you. It’s impossible to do everything in 5 days, so don’t worry about missing out.
See our full list of Oahu activities here.
Beach, Pool, and Relaxation
If the whole point of your Oahu vacation is to rest, recharge, and relax, by all means: do that! Don’t worry about packing all the sights into your itinerary, just enjoy yourself.
Simply find the closest beach or pool. Bring a book, some sunscreen, a towel, and refreshments; and you’re set!
If you like to be at the heart of the action, head to Waikiki Beach. There are plenty of options from one end to the other: Kahanamoku Beach near the marina, in front of the many Waikiki hotels and resorts, or south by Kapiolani Park.
Honolulu History and Museums
The following museums are also good places to add to your Oahu itinerary if you have extra time during Day 2.
Pearl Harbor National Memorial. Learn about one of the most important moments in World War II. Sites to visit include the Visitors Center, USS Arizona Memorial, USS Bowfin submarine, USS Missouri battleship, and the Pearl Harbor Aviation Museum. The Visitors Center opens at 7am, other sites open at 7 or 8am.
Bishop’s Museum. Located in downtown Honolulu, this museum is dedicated to Hawaii’s natural history and living culture. Visit the permanent galleries and special exhibitions, or watch a show in the Planetarium. Open daily 9am – 5pm.
Iolani Palace. One of Hawaii’s National Historic Landmarks and the United States’ only royal palace. Used as a royal residence in the late 1800s, the palace has now been turned into a museum exploring the history of Hawaii’s royalty and the struggle between modernizing and maintaining autonomy. Open 9am – 4pm, closed Sundays.
Others worth visiting are the Hawaii State Art Museum to admire local contemporary art and the Shangri La Museum near Diamond Head, which showcases Islamic art and culture.
*Bishop Museum and Iolani Palace are included in the Go Oahu pass
Another way to dive into the history of Hawaii is through an downtown historical walking tour in Honolulu.
Hiking on Oahu
A great way to more of Oahu’s natural beauty is through hikes. There are many trails to choose from depending on your experience, and the difficulty level and location you prefer.
There’s everything from ridge hikes like the Wilhelmina Rise Ridge Trail, to hikes revolving around interesting structures like the Lankai Pillbox Hike or the Makapu’u Lighthouse Trail. There’s also several waterfall hikes like the Manoa Falls Hike.
All guarantee you a workout and scenic views!
For more detailed information, read our guide on the best hikes in Oahu.
Water sports or Other Adventures in Honolulu
With the Pacific Ocean at every turn, there are endless possibilities to enjoy water sports in Hawaii. The Go Oahu card provides access to many of these:
– surf lessons
– SUP (stand up paddle board) yoga class or turtle tour
– kayak rental
– catamaran sunset sail
– a snorkeling cruise
– shoreline fishing
Read our review of the GoOahu card to find out if the all-inclusive pass is worth it for your trip.
Day 4 – Island Road Trip & Polynesian Cultural Center
On your fourth day, prepare to make a road trip to Kailua, one of our favorite towns! The drive from Honolulu towards the east coast is best done before rush hour. You have two options, both of which are scenic drives.
You can drive via the H1/72 East to go around the coast where you’ll pass by Hana’uma Bay and Makapu’u Lighthouse. Or you can go over the majestic Ko’olau Mountains on the Pali Highway and stop by the Pali Lookout for coastal views.
Once you’re in town, you can make your way to Kailua Beach Park where you can choose from a variety of activities like swimming, kayaking, a Hawaiian Sailing Adventure, or boogie boarding. For more beautiful beaches head to Lanikai Beach, where you can also venture out to the famous Lanikai Pillbox Hike.
After your stop at Kailua, head to the Polynesian Cultural Center which is 45 minutes away from Kailua. It’s an interactive park made up of six simulated Polynesian villages.
Visitors can watch daily performances and participate in hands-on crafts and activities to learn about the history and culture of Hawaii in an immersive way. You can even experience a luau dinner and more performances at night.
If you opt for a self-guided tour, you can spend half a day in the Center. But if you more time, check out the all-access package which includes:
- 3-day pass for the villages
- IMAX show
- Canoe ride
- Luau dinner and reserved show seating
- Tram tour of BYU-Hawaii campus and Laie Temple Visitors Center and Gardens
- Optional add on: hotel pick up
After the luau dinner, head on to North Shore for an overnight stay.
*Polynesian Cultural Center entrance is included in the Go Oahu card
Day 5 – North Shore Oahu
After settling down for your last day, here are some things you can do in North Shore.
Watch surfers in Bonzai Pipeline (‘Ehukai Beach Park) or Sunset Beach. You’ll find some of the world’s biggest waves here being navigated by professional surfers. You can also spectate surf competitions happening at Haleʻiwa Aliʻi Beach Park.
See sea turtles at Laniakea Beach. Laniakea Beach, along Kamehameha Highway, is the best place to spot Hawaiian Green Sea Turtles. You can find them lounging on the sand or swimming in the shallow shore but please make sure to follow instructions and warning signs! They are an endangered species so it’s important to maintain a good distance away from the turtles.
Explore Hale’iwa Town. This is the main town on the North Shore. It’s pretty small but you’ll still find plenty to do from shopping at boutiques, eating at local restaurants, visiting galleries, and trying the famous Matsumoto Shave Ice.
Once you’re done, make your way back to Honolulu Airport. If you still have a bit of extra time, consider stopping by the Dole Plantation on the way. This historic pineapple plantation has fun activities like the Pineapple Express train tour and a giant maze. The best part is getting some delicious “Dole whip”, a soft serve sorbet with an intense, fresh pineapple flavor, for the drive back to Honolulu.
For first time visitors, traveling to Oahu first is a good idea to start your journey in Hawaii.
Our 5 day Oahu itinerary takes you to all the best spots and shows you everything the island has to offer. As you go on walks along the beach, try challenging hikes, take island road trips, and visit interesting historical sites, you’re guaranteed to have the best time in Oahu!
Staying longer? Check out our 7 day Oahu Itinerary and full activities list
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