Ultimate 5 Day Oahu Itinerary (updated 2023)
Aloha! Oahu is an incredible Hawaiian island and has so much to offer for your 5 day Oahu itinerary! Aqua water and white sugar sand. Juicy pineapple and fragrant hibiscus flowers. Stunning hikes and cascading waterfalls. And don’t even get me started on the sunrises!
Oahu is an island that we keep returning to over and over again. Its beauty is unmatched and there is so much to do that we can never seem to see enough of it.
So many travelers stick to the Waikiki Beach area and never venture out – what a shame! We are so glad you are here so that we can fill you in on all the hidden gems for your 5 days in Oahu itinerary.
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Heading to Oahu soon? Don’t forget advance reservations!
Planning for your 5 Days in Oahu
Hawaii is a popular spot – for good reason, of course! So be prepared to book accommodations, flights, and rental car as soon as you spot a good deal. Time and time again, I hear about a family snagging a great fight deal and then breaking their budget with their rental car.
Below please find our best tips for booking an affordable trip so that you can splurge on the things most important to you! Shave ice everyday? Romantic beachside dinners? Catamaran sunset sail? You got it!
Oahu Trip Planning Tools
Oahu 5 Day Itinerary
I’m going to be honest – Oahu has SO much to offer that it was really hard to write an itinerary for five days! Everything listed is possible to experience in 5 days on Oahu, but count on early mornings to take advantage of easy parking and less crowds. We have personally experienced every activity on this list and promise that they are all worth your valuable time!
If you can squeeze in two more vacation days, check out our 7 day itinerary here for a bit more time to add in some other great spots.
Arrival Day & Check-In
Depending where you are coming from you are likely to land on Oahu in the early to mid-afternoon. If your arrival day is 1 of your 5 days on Oahu, pick one of the daily itineraries below to fill your afternoon and evening. Waikiki or some time in Kailua would both be great choices.
We recommend hustling over to the rental car counter as quickly as you can. An hour long wait is not uncommon and it feels like forever when the beach and palm trees are calling your name. When possible, one member of our party runs to the rental car line while another grabs any checked bags or car seats.
If you were able to pack carry-on only, good for you! We always recommend packing light when traveling to Oahu as you never need as much as you think you do! Check out our Hawaii Packing List for a full list of our must-have items.
On the way to your accommodations, you’ll want to stop for a few things. I personally hate running errands on vacation, but a few quick stops will save you oodles of time later – I promise!
- Costco / Foodland / Safeway
- Snacks – we like protein like jerky and nuts, fresh fruit (definitely pineapple!), tropical cookies + chocolate covered macadamia nuts
- 2-3 easy dinners for evenings in if you have a vacation rental
- Picnic supplies for lunch on the beach
- Beach Umbrella from Costco (its cheaper to buy it than rent it for a few days)
- Flip-flops (If you happen to forgot them like my husband…giggle…I can tease because I forgot my tennis shoes on a camping trip in the Redwoods. Oops!)
- Snorkel Gear
- We rent our snorkel gear from Snorkel Bob’s for the week or pack our own
After dropping off your bags, head to the beach as soon as possible. Unpack later! Soak up the tropical breeze, grab a cocktail or shave ice, and get those toes in the sand. Duke’s or Cheeseburger in Paradise re both fun places for dinner your first night on the island. Watch the sunset and don’t be afraid to crash early – tomorrow starts early!
Day 1: Itinerary Oahu 5 Days: Windward Side – Kailua + Lanikai
Lanikai Beach Sunrise
I hope you let your jet lag win and turned in early last night. Waking up early on the first day of your vacation is the best way to start your 5 day itinerary on Oahu!
Lanikai Beach is perhaps the most beautiful beach in the entire world and it is definitely the best place on Oahu to watch the sunrise. You’ll want to arrive about 20 minutes before the sun rises in order to get the full experience.
Check sunrise times here and map it, leaving plenty of time to park. It should be pretty easy in the morning. You can access the beach from Mokumanu Drive. Carefully read the signs on the road and park respectfully in front of the houses without blocking driveways or waking the residents.
Spend sunrise soaking up the vibe of Oahu and preparing to start another amazing day. Consider packing a breakfast picnic or just walking along the sand. The view of the sunrise with the islands in the backdrop are STUNNING.
Lanikai Pillbox Hike
Oahu offers several easy hikes, and the Lanikai Pillbox Hike is one of the best. The hike is short but steep, so just be prepared with some footwear other than flip-flops.
Some prefer to hike to the pillboxes in the dark and watch the sunset from the top, but we recommend soaking up the stillness of the beach first and then making your way up.
The trailhead is right across from the Mid-Pacific Country Club off of Ka’elepupu Drive. Parking is easy in the morning but not so much as it gets later in the day.
Lanikai Pillbox is 1.6 miles round trip. It took our family of five about an hour to complete it. Expect to get hot even in the early morning and don’t forget to pack water.
The first 100 feet are the steepest, so don’t let that deter you. The dirt is slippery, so take advantage of the tree roots and installed ropes to keep your balance on the way up and down.
The views at the top are incredible! Hop on the pillboxes and take in the birds eye view of the aqua colored water and beach below. Don’t forget your camera! This view is one of the best on the island.
Breakfast in Kailua
Whether you skipped the Lanikai Pillbox hike in return for more time on the quiet beach, you’ll be ready for some breakfast by now. Here are a few of our favorites in the area:
- Kono’s – highly recommend the Waimea Bomber (like a breakfast burrito – only better!)
- Cinnamon’s – popular spot for Guava Chiffon pancakes – yum!
- ChadLou’s Coffee Roasters – coffee lovers are sure to love it!
Ho’omaluhia Botanical Gardens
As you drive deeper into the mountains from downtown Kailua, the landscape grows greener and more lush. Head to Ho’omaluhia Botanical Gardens for a gorgeous morning in the gardens.
The entry road into the garden has made its beauty known on social media due to the picturesque surrounding Ko’olau Mountains. De to safety reasons, photography is no longer allowed near the main gate.
However, you need not worry! This ENTIRE place is beautiful and there are gorgeous spots to take portraits and photograph the landscape around every turn.
The Visitor’s Center is located about a mile into the gardens and you can pick up a trail map here. Miles of paths wind their way through Ho’omaluhia with signs educating visitors about the plants and many spots to take in the view.
You’ll want to bring a water bottle, camera, and bug spray with you here. We didn’t need bug spray despite the humidity when we visited, but I imagine it is often needed.
There are numerous places to park along the road throughout the park. Visitors can drive through or park and walk along the road or adjacent trails. A fishing pond is also available with periodic free fishing days.
Don’t miss the Kilonani Mauka Overlook – it was our favorite spot! Visitors should also make sure that they have time to drive to the end of the park as the mountains really rise up out of the ground here and make for an incredible backdrop.
Gates close at 4pm sharp so make sure you have exited by this time to avoid having your car locked inside the gate all night.
Sigh…Kailua beach. Seriously, my personal favorite beach on the planet.
No trip to Oahu is complete without a day at Kailua Beach. Plan to relax in the sand, splash in the waves, and hear the wind in the palm trees. The water here is an incredible shade of blue. The sand is sugar white and the whole beach is just pure paradise.
If you walk far enough, Kailua Beach connects to Lanikai Beach. Kailua has the added benefit of a large parking lot as well as restrooms, but Lanikai is undoubtedly quieter and more relaxed if that is more your jam.
Many shade trees at Kailua Beach make for a great spot to hang out all afternoon. If you picked up an umbrella at Costco, you are set either way! Our kids were in love with riding the gentle waves and digging in the sand with their collapsible buckets.
If you are lucky, you might catch a rainbow! Nothing makes Kailua Beach more magical than that, Don’t miss this stop on your Oahu 5 day itinerary – its one of the best!
>> For some added adventure, check out this trip out to the Kaneohe Sandbar (ridiculously beautiful!) or kayak out to the Mokolua Islands (bucket list item!).
Head to Island Snow when you are done at the beach (are you ever really done?) for shave ice before leaving Kailua. They close at 5pm on weekdays and 6pm on weekends.
Favorite Nearby Lunch or Dinner Spots:
- Bob’s Pizzeria (whole pie or by the slice)
- Kalapawai Market (sandwiches and salads to go)
Pro Tip: Book a Photo Shoot!
Have you ever considered booking a photo shoot on vacation?! We HIGHLY RECOMMEND it!
Everyone is happy, looking their best, and often celebrating a special moment. We used Tara with Flytographer on Kailua Beach and it was incredible! Photos of our trip now adorn our walls at home – best souvenir ever! Check them out and get $25 off!
Day 2 of Oahu 5 Day Itinerary: Hanauma Bay + Eternity Beach
Hanauma Bay is one of the most popular things to do on Oahu and for good reason! However, some prior planning will take your visit from average to fantastic.
The entry requirements to Hanauma Bay have changed considerably in the last year. Please see these important updates for 2023.
- RESERVATIONS ARE REQUIRED (check here)
- $25 admission fee for visitors ages 12+ (cash or credit card (MC or VIsa)
- $3 parking fee per vehicle (CASH ONLY)
- Open Hours: 6:45am-4pm; no entry after 1:30pm
- CLOSED on Mondays + Tuesdays
Two days before visiting Hanauma Bay, reservations can be made online at 7am local Hawaiian time. If you miss this window or find them sold out, try to get a walk-in ticket at 6:45am on the morning of your visit.
We are big fans of self-exploring Oahu in our own rental car, however, there are a few instances when this Hanauma Bay Tour is highly recommended. If you do not have a rental car the day you want to go OR if you weren’t able to get a reservation OR you just really hate fighting for a parking spot. This tour will take care of all of those issues for you AND it is also comes with snorkel gear included.
I can’t emphasize this enough – GET THERE EARLY.
We arrived at 6:45am and took our time making our way down the hill and eating a breakfast picnic in the sand. We started snorkeling and swimming at about 7:45am and the water was clear and filled with hundreds of beautiful fish.
Within about two hours, the beach was very full and many people were in the water. Due to the crowds the fish began to disperse and the the water had so much stirred up sand that the visibility was poor. Only about 25% of the fish remained visible by mid-morning.
Visiting Hanauma Bay in the early morning is hands-down the best way to experience it!
Entry is allowed until 1:30pm with a reservation, however, this would not be the optimal time to visit. Also, they will start clearing the beach at 3:15pm for a 4:00 sharp closing time.
The water at Hanauma Bay is calm and perfect for beginner snorkelers to try out their masks and fins with great rewards. One of our children learned to snorkel here and it was magical! The water is shallow and it is easy to stand when needed. We pack a whole suitcase of life jackets to ensure safety in the water for our kiddos. They can be rented at Snorkel Bob’s as well.
Please be VERY careful not to stand on the coral though! Destroying the habitat leads to a lack of fish to explore and a complete destruction of the underwater eco-system.
- Rent your snorkel gear before arriving to save $$$
- Rent a locker for $10 for valuables or bring this waterproof bag (it works great!)
- Bring cash for parking and if you’d like to ride the tram up the hill when departing
- Don’t step on the coral!
- ARRIVE EARLY!
- Hanauma Bay is closed on Mondays and Tuesdays, so adjust your itinerary accordingly
Halona Blowhole is a great quick stop just a few minutes from Hanauma Bay. The parking lot is usually full, but not too worry as most people move along pretty quickly and we have always gotten a spot within a few minutes.
This powerful blowhole puts on quite a show! Stay for a bit and watch the water as it shoots up through the blowhole. Unlike some blowholes, it doesn’t take much patience as the water displays are pretty frequent.
This parking lot also serves as a great vantage point for a couple beaches. To the left is Sandy Beach Park and to the right is Eternity Beach (more on that below). You can capture some great photos of the beaches from here.
From the blowhole parking lot, you can also access Eternity Beach via a small path on the right side of the parking lot. The trail is steep but short and a sign advises visitors not go past the sign. Many, many people ignore this sign and spend all day on the beach, but please be advised of the risk.
The water at this beach is pretty rough and the large rocks surrounding the cove could be brutal. Many people were swimming but we opted not too. We did enjoy the gorgeous beach though and enjoyed exploring the lava cave on the back side of the beach. Don’t forget a flashlight if you wish to explore the cave! It runs under the highway and is VERY dark.
There is something unique about Eternity Beach and we highly recommend taking the time to explore it, even if just from above!
Koko Crater Botanical Garden
Koko Crater is a quick stop but worth your time if you love flowers! By the time it came for us to visit, we were pretty hot and tired, but still glad that we stopped.
Admission to this garden is free. You can pull right up to the plumeria grove and walk right in. There are many trails here, but they are of the rocky desert variety, so we opted to skip them. we headed straight to the trees filled with flowers, led by their beautiful fragrance.
There are many rows of plumeria trees and flowers were sprinkled all over the ground. We snapped some photos, explored the trees, and found some flowers on the ground for our hair. Koko Crater is definitely a hidden gem on your Oahu 5 day itinerary!
The flowers aren’t really in bloom in winter, so you might want to skip this stop if you are traveling then.
Additional Option: Makapu’u Lighthouse Trail + Baby Makapu’u Beach
Baby Makapu’u is a sweet beach that is perfect for young children. It is perfect for exploring the tidepools and a shallow swimming beach. You can pass the entrance to the main Makapu’u Beach and the Oceanic Institute, and park in the second parking lot. Head to the left toward the tidepools. The lighthouse trail is also here and is a great choice for an easy sunset hike.
5 Days on Oahu, Day 3: North Shore Snorkeling + Gardens
Too many people spend 5 days on Oahu (or more!) and never make it to the North Shore. Don’t let that be you! The chill towns on Oahu’s north shore are beautiful, offer many fun things to do and see, and should not be missed!
The North Shore has the calmest water in the summer. The beaches are pretty smooth and have wonderful swimming spots. In the winter, however, the water is very rough from November to April. Plan to catch some surf competitions if you visit during these months, but stay out of the water. It can be extremely dangerous.
Exploring the North Shore can be a long day, so if you’d rather not drive yourself, there are some incredible guided tours available.
Oahu Circle Island Tour
If you prefer not to drive yourselves so that you can relax and enjoy the extra history and culture that a guided tour provides, here is our top pick!
Includes: Dole Plantation, Snorkeling with turtles, Shrimp Truck lunch, Halona Blowhole, Macadamia Nut Farm + more!
Arriving at Three Tables before 9am will make it MUCH easier to snatch a parking spot in the adjacent Sharks Cove parking lot. Sharks Cove is also an excellent snorkeling spot, but we preferred Three Tables where it was like snorkeling in an aquarium!
Check the surf report before arriving, especially if you are traveling during a shoulder month. If the wave height is under 2 feet, the water should be calm enough to snorkel.
The blue water at Three Tables looks like it is out of a movie. It is stunningly gorgeous and I could stare at it all day. Underwater was even more incredible and my children could snorkel with ease. My daughter counted more than 200 fish is about 15 minutes when she first entered the water. This was our favorite snorkeling spot during our 5 days on Oahu.
Plenty of shade trees lined the sand making this beach the perfect spot to set up a home base for a couple hours. The sand was super hot, so plan on water shoes when traveling back and forth from your towel to the sand.
Due to the small parking lot, it is difficult for this beach to become very crowded. Plan on spending at least a few hours here; I could have stayed from sunrise to sunset. It was perfection.
Hale’iwa: Shrimp Trucks + Shave Ice
Shrimp Trucks in Haleiwa are the popular spot to grab lunch, and we highly recommend the garlic shrimp plates. Giovanni’s is perhaps the most popular and also the most crowded. When we checked yelp reviews, the other trucks had similar positive reviews.
If you are craving cheeseburgers instead, Kua Aina is a solid choice. The air conditioning was also a lovely treat over eating outdoors during a long day in the sun.
Matsumoto’s is the hot spot in Haleiwa for shave ice, but expect crazy long lines. If you want a real Hawaiian shave ice, don’t skip the azuki beans and cream!
Laniakea Beach has a difficult parking situation with spots just lining the street, but if you can snag one, stop and see if any turtles are lounging around on the sand. This is known as Turtle Beach and it is common for the sea turtles to some ashore here and lay in the sun. Between 11:00am and 1:00pm is the most likely time to find them there. If you are lucky enough to experience them, please remember to give them their space as they are a protected species.
However, one of the best ways to see turtles on Oahu is to snorkel with them!
Waimea Valley Botanical Gardens are great spot to explore the gardens and see the cascading waterfall. There is an entrance fee, but most visitors find it worth the price. We enjoyed these gardens, but if you don’t have time for everything, we suggest skipping these and doing Ho’omaluhia instead.
The shaded paved path makes this garden an easy walk for all skill levels. Our children loved exploring the Living History dwellings here. Periodically, children’s activities are offered as well as a Thursday Farmer’s Market.
A map and placards will help you identify the various plant species and unique floral varieties. A tram is available and wagons are also handy for carting children along the paths.
Many visitors head straight to the waterfall at the end of the garden trail. It is .8 miles from the entrance and the easiest waterfall on Oahu to access. There are free life jackets available to rent for swimmers to try swimming at the base of the waterfall.
Please note, the waterfall signage warns of leptospirosis risk which can cause sever illness when the bacteria enters open cuts or wounds. Visitors should proceed with caution.
There is a gorgeous beach across the highway from Waimea Valley Gardens called Waimea Bay. This crescent shaped beach is filled with golden sand and is a great summer swimming spot. A large black rock is commonly used for cliff jumping. It looks insanely fun, but please only jump at your own risk. When we were there, we did witness an injury.
Parking at Waimea Bay can be tricky as the large parking lot does fill up. is it possible to leave your car at the gardens and dash across the highway, but this is fairly dangerous. Restrooms facilities are available at this beach.
Sunset is perhaps the most beautiful time of day at Waimea Bay, but you’ll likely need to leave before then if the Dole Plantation is on your to-do list.
The Dole Plantation closes at 5:30pm, so can be tricky to make at the end of a North Shore Day. However, if you head there in the morning before heading to the North Shore, parking will be a beast and you will not be able to snorkel at Three Tables. I wouldn’t advise making that trade!
The Dole Whip with fresh pineapple is definitely worth your cash. So creamy and refreshing. Take some moments to tour the pineapple garden and take advantage of the photo opportunities. The gift shop offers some incredibly cute pineapple souvenirs.
I would not advise creating a whole day around the Dole Plantation’s activities. There is so much more to see and this is best as a quick stop.
Optional Idea: Sunset Beach
If you’d rather watch the sunset on the beach, Sunset Beach is another great place to do so. It might even be the best spot on north shore due to its west facing view.
Fun challenge: Watch the sunrise on Lanikai on the east side of the island and watch the sunset here on the west shore on the same day! Bucket list: check!
5 Day Oahu Itinerary: Day 4- Diamond Head + Kualoa Ranch
Diamond Head Hike
Diamond Head is a very popular hike in Waikiki. The views are incredible but the hike contains many stairs and is very hot. Early morning is the very best time to make this climb. The gates open at 6am and so the earlier the better! I would suggest sunset too, but it closes before then!
Reservations are required hike Diamond Head and may be made up to 30 days in advance. Admission is $5 per person and parking is $10 per vehicle.
This hike is about 1.6 miles round trip and will likely take an hour to the top and half that to climb back down. Plan on two hours in order to capture some great images at the top!
Kualoa Ranch Movie Tour
Kualoa Ranch is one of the most popular excursions on the island and a highly recommended activity on your 5 day Oahu itinerary. Located in the valley of the lush, majestic Ko’olau Mountains, the ranch offers many activities such as ziplining, catamaran tours, ATVs, horseback riding, and their famous tours of Jurassic Park Movie Filming locations throughout the ranch.
Their tours are really just icing on the cake, The gorgeous views everywhere you look are the real stars of the show! Check out all their tour options and choose which one(s) best suit your family’s interests. You will be so glad that you did!
We have personally experienced the Secret Island Tour, Jurassic Movie Tour, and Ocean Voyage Catamaran Tour so far and we loved them all!
Oahu Itinerary Day 5: Pearl Harbor + Waikiki Beach
Beach Front Breakfast
On every trip to Oahu, we always plan an early morning breakfast at Duke’s Canoe Club. Their buffet includes made-to-order omelets, eggs benedict, tropical fruits and juices, sausages, pancakes, cinnamon French toast, bacon, steamed and fried rice, and fried potatoes.
Make a reservation online for 7am and request a table on the rail in order to soak up the best oceanfront view. The beaches will be almost empty which is a rarity in Waikiki!
When visiting Pearl Harbor, there are many options to consider. Options include the Visitor’s Center, Arizona Memorial, and additional tours of the Battleship Missouri Memorial, USS Bowfin Submarine, and Pacific Aviation Museum.
Admission to Pearl Harbor is free. You may tour the Visitor Center, museums, and outside statues and memorials on your own schedule. Visiting the Arizona Memorial is also free, however it does require a reservation.
Tickets can be reserved up to 8 weeks in advance at 3pm HST for a small convenience fee of $1.00 each. Be ready to book right when they go live, as they don’t last long. You can also try to reserve tickets the day before your visiting day at 3pm HST if you missed out 8 weeks prior. Walk-in tickets are not available.
If you need transportation or don’t manage to snag a reservation, we love this Pearl Harbor City Tour. This option is great for those that would love to learn more about Oahu’s history as the guide will take you not only to Pearl Harbor, but also around historic downtown.
Tours of the Bowfin, Missouri, and Aviation Museum all require an additional fee. Advance reservations are not required.
My husband and I had toured the whole property previously, and for this particular visit, we chose to only visit the Pearl Harbor Visitor’s Center and free Museum area as we had our children with us. Our children were 6 and 9 years old. My daughter had specifically requested the visit, but ended up being affected more than she expected and wanted to leave quickly.
Note: Traditional bags are not allowed at Pearl Harbor. Only clear bags like this one, very small fanny packs or clutches, and strollers without a removable bag are allowed. Lockers are available for storing other bags if you get stuck. It is not advised to leave bags in your car.
Explore Waikiki’s Culture + Shopping
Waikiki has so much to offer – tasty restaurants, cultural activities (often free!), shopping, and all with a gorgeous view and lively atmosphere.
Check out some cultural activities, like hula lessons and lei making at the Royal Hawaiian Center and Hyatt Regency. Schedules vary and they are so much fun!
Walk through International Marketplace, Waikiki Beach Walk, or Ala Moana Center and window shop or pick up souvenirs to take home with you. Our favorite take home items are cookies from Honolulu Cookie Company and Christmas ornaments from Waikiki Christmas Store. Children will enjoy the tree house and splash pad here.
If you start to get toasty, stop by Island Vintage Shave Ice for shave ice.
You’ll find an ABC Store on every corner. They are great for picking up forgotten sunscreen, picnic lunches, and fun treats.
With all there is to see and do, don’t forget to spend plenty of time on the sand and in the water! Stretch out a towel in the sand or rent a towel and umbrella and enjoy the atmosphere of Waikiki Beach.
Choose from these popular activities for your time on the beach:
- Sunset Catamaran Sail from Waikiki *our top pick*
- Outrigger Canoe Ride
- Surfing Lessons
- Rent an Fun Island Float from Koa Beach Service down by the Hale Koa
- Rent Snorkel Gear and head to the Waikiki Marine Conservation District
We hope you now have a solid plan for your Oahu Itinerary for 5 days!
Check out the graphic below to see our suggested activities in a nutshell. They were carefully chosen for you based on geographical location and best time of day for each activity.
Oahu 5 Day Trip Itinerary
- Sunrise at Lanikai Beach
- Lanikai Pillbox Hike
- Breakfast in Kailua
- Ho’omaluhia Gardens
- Kailua Beach
- Hanauma Bay
- Halona Blowhole
- Eternity Beach
- Koko Crater Botanical Gardens
- Head to the North Shore
- Snorkel at Three Tables
- Food trucks for lunch
- Hale’iwa for Shave Ice
- Waimea Bay + Botanical Gardens
- Dole Plantation
- Hike Diamond Head
- Kualoa Ranch
- Breakfast at Duke’s
- Visit Pearl Harbor
- Souvenir shopping in Waikiki
- Outrigger Canoe Ride on Waikiki Beach
- Acai Bowls + Honolulu Cookie Company
- International Marketplace