First Time in Oahu: 5-Day Itinerary
Oahu and Honolulu
Since Los Angeles (LA) is only a 5-6 hour flight, we had the opportunity to take advantage of a great flight deal to Hawaii! We spent months learning about all things Hawaii! The big question was which island to start with for a first timer?? Our consensus was Oahu (where Honolulu is)!! Since then we have been to Hawaii a few times, and still agree that Oahu is a great choice for the first time.
Oahu offers a nice tropical flavor including hikes, beaches (combo of secluded and touristy), luaus, snorkeling, island food and coffee, and an introduction to Polynesian Culture.
We know for most people a trip to Hawaii is kind of far and so you want to plan your best trip that works for you! Here are our recommendations for a 5-day itinerary for Oahu filled with snapshots we took to inspire your travels!
A quick preview before we go for it:
Day 1: Flight, Waikiki Beach Day, and Dinner
Day 2: Hike, Brunch, and Luau Day
Day 3: Southeast and Windward Coast- Hanauma Bay + Beaches
Day 4: Northshore, Pearl Harbor, Kualoa Ranch
Day 1: Flight, Waikiki Beach Day, and Dinner
Flight getting in the afternoon/evening
Time Zone
Time zones are a thing! Hawaii has its own time zone known as Hawaii-Aleutian Standard Time. For reference, it is three hours behind Western time zones and six hours back from Eastern time. So we suggest enjoying strolling the beaches and catching a wave on your first day.
Head to Waikiki Beach
While we did a beach crawl around Oahu, this is definitely the one we would recommend to start with! It is a great welcome beach located centrally with so much to do. There is also a good chance that your accommodations may be around here too. It is a good spot to be located in!
In Hawaiian, Waikiki means “sprouting fresh water.” In the 1800s, the area was a place for Hawaiian royalty who also enjoyed surfing there. The surf tradition is very much alive today!
Day 2: Hike, Brunch, and Luau Day
Diamond Head Crater Hike
Diamond Head Crater is known as the summit of Leʻahi in Hawaiian. The scenic hike is full of history and views. It once was a site of a volcano eruption >300,000 years ago! Also, the area was used for defense operations in the ~1900s. Be sure to spot old military bunkers on your way up! You will even walk through a 225-foot tunnel.
Once we finished the hike, we were met with pineapple ice cream and a fruit stand in the parking lot making for great post-hike treats!
Insider Tips:
This is an easy-to-moderate 1.6-mile round-trip hike that can take about 2-2.5 hours total.
There is a paved pathway in the parking lot with signs leading you to the start.
Make sure you have good footwear, as the hike goes up steep climbs and stairs. Take your time and take as many breaks as you need.
Come early in the morning and plan to be done by noon to avoid the heat and crowds.
As always check online for updated hours, times, and reservations if needed. When we went they were requiring reservations ahead of time.
It will be worth it once you get to the top for the famous postcard view of the shoreline and Honolulu.
Brunch/Lunch
Enjoy one of the island’s delicious brunch/lunch spots. You might even consider calling ahead as some of the spots can be pretty busy.
Polynesian Cultural Center
This is an interactive 42-acre center that has six villages offering hands-on cultural activities and shows. Enjoy the day immersing yourself in the heritage of the Polynesian culture and Pacific Islands. The villages include Tahiti, Tonga, Fiji, Hawaii, Aotearoa, and Samoa. Good for all ages!
Tip: You can consider adding on the evening show or even choose to celebrate the Luau there!
Attend a Luau
Luau is a vibrant and lively Hawaiian feast that often includes traditional Polynesian and Hawaiian feature foods along with entertainment in the form of music and dance. This is a definite experience to take part in at least once on a first-time visit to Hawaii.
Choose the right package for you based on your interests. Locations are all across the island. We opted for the Ali Luau Polynesian Cultural Center and show and it was a great experience.
Tip: Look at the menus to make sure your dietary needs are accommodated. While most things may appear meaty, there are several varieties offered.
Day 3: Southeast and Windward Coast- Hanauma Bay + Beaches
For your orientation, all Hawaiian Islands have a windward side (usually facing North or east, wet side-more luscious and green) and a leeward side (usually faces South or West and is typically more sunny and dry with lots of beaches).
Hanauma Bay
Enjoy a unique snorkeling experience for all levels. We recommend giving it a try! It was our first time snorkeling but it’s such a great place to learn with so much to see so close to shore.
It did take some time and swallowing lots of ocean water to figure it out, but once we did, it was magic!! Be sure to enjoy the beautiful bay and relax on the beach as well!
The bay was formed by a volcanic cone. In Hawaiian, “Hana” is the word for bay, and “uma” refers to the curves of canoes. In the past, this area was used by Hawaiian Royalty for recreation. It is easy to see why!
Insider Tips:
While rental equipment might be available at the bay we recommend being prepared beforehand either from your hotel or local shops.
Be sure to pack reef-safe sunscreen and your beach gear including beach towels.
Reservations?: We did have to make a reservation weeks in advance, so be sure to check their website for updated procedures, hours, and costs. Plan ahead as this is very popular!
Beach Drive and Crawl
Check out the other beaches along the coast. Pick one or check them all out!
Halona Beach Cove
Sandy Beach
Makapuu Beach Park (see our photo next to this)
Waimanalo Beach
Kailua Beach
We took this picture at Makapuu Beach Park.
Consider adding on a hike if you desire
The Lanikai Pillbox Hike is a popular scenic hike that is a little over 1 mile in length each way and takes around 20-30 minutes each way
Trailhead can be found at 265 Kaelepulu Drive
Day 4: Northshore, Pearl Harbor, Kualoa Ranch
Nu‘uanu Pali Lookout
As you drive up 1200 feet, you will see the city slowly disappear. Pali means cliff in Hawaiian. As you walk, you will feel the strong winds sway you and also hear the wind whistle in the mountains while you take in the scenic panoramic view of the Koolau Cliffs and the Windward Coast. It is absolutely breathtaking!
This actually is also an important historical site where the Battle of Nuuanu -where in 1975 Oahu was united under the King’s rule.
location: Nuuanu Pali Dr, Kaneohe, HI 96744
Pearl Harbor
This area of remembrance comprised of an open-air Pearl Harbor Visitor Center, multiple museums, and memorials - including the USS Arizona, USS Utah, and USS Oklahoma. It is the gateway to WWII history and a place to reflect on the events surrounding 12/7/1941. Check online for updated hours and events.
Dole Plantation
Just a half-hour drive away, you will find the Dole Plantation which started as a fruit stand in 1950s. Now it is THE PLACE to have a pineapple experience in Oahu (including mazes, train tours, gift shops, and food). Don’t forget to try the Dole soft serve!
Explore a Surf Town - Haleiwa and Food Trucks
A short 10-minute drive away is our next experience!
Here you will find a variety of food trucks! We recommend checking out the popular Giovanni's Shrimp Truck! The line can be 45 minutes to an hour long, but it’s worth it! There is another parking lot just a few minutes down that usually has more food stalls and options (especially if vegetarian!) Enjoy some time shopping as well.
Details: Shrimp truck address: 66-472 Kamehameha Hwy, Haleiwa, HI 96712; more food: 66521 Kamehameha Hwy, Haleiwa, HI 96712
Visit Turtles at Laniakea Beach
After lunch, a short 5-minute drive to our next scenic destination!
Honu is the Hawaiian word for turtles. You will see the native and one of the largest green sea turtles weighing over 300 pounds! They are considered sacred and are considered good luck.
Insider Tip: Make sure you go to this beach and not turtle beach (misleading) to get the best views of the turtles.
Check out more beaches/bays:
Waimea Bay
Sunset Beach Park
Kualoa Ranch
Established in 1850, this is a beautiful 4000-acre private nature reserve that has been now managed by the eighth-generation descendants of Dr. Kualoa.
It is actually a working cattle ranch and the mission is to protect the sacred land while developing sustainable activities and enterprise. The ranch offers a variety of fun activities and tours. We took a basic tour and then took some time just taking in the beautiful views from the ranch. Also, it is a popular home to filming locations in Hawaii, including Jurassic Park! Check online for updates, hours, and costs.
Day 5: Gardens and Shop
Choose one: Hike or beach
After breakfast, start the day with your favorite beach or a hike.
Hike Suggestion: Manoa Falls, Honolulu, HI 96822. The total is about 1.6 miles ( 1-2 hours).
Tantalus Lookout
Close to downtown Honolulu, provides a beautiful view of Southern Oahu including Pearl Harbour, Diamond Head, Honolulu, and the Manoa Valley. Stunning tropical views of nature mixed with civilization! A great place for sunset, a picnic, or a simple pit stop.
Ho’omaluhia Botanical Gardens
This is a beautiful 400-acre garden filled with nature, hikes, and driving trails. Also, entry is free! Check online for any updated hours.
Did you know that Ho’omaluhia in Hawaiiana means “to make a place of peace and tranquility?!”
Aloha Swap Meet and Marketplace
Located in Aloha Stadium, this site hosts the state’s largest open-air flea market with over 400 stalls! There is a small admission fee and limited hours/days, so be sure to check online. This makes for great local souvenir shopping and also the market offers some bites for purchase.
Modifications/must do:
These five days in Oahu provide a perfect blend of relaxation, exploration, and cultural immersion, creating lasting memories of your time here.
Consider adding another island- check out our post on Big Island!
If you have a limited amount of time: our top 5 things to do in no particular order include: Diamond Head Hike, Kualoa Ranch, Hanauma Bay, Waikiki Beach, and Nu‘uanu Pali Lookout.
If you are looking for more things to do then consider Koko Head Crater Hike (a hard hike but amazing views!), Tropical Farms Macadamia Nuts, Byodo-In Temple, Ka'ena Point State Park- which has a lava shoreline of 3.1 miles!
Make sure to add your favorite places to eat to take time out for breakfast, lunch, dinner, and snacks:) Check out our foods to try post!
Please comment below on what you are most looking forward to on your trip to Hawaii or any Oahu favorites. We can’t wait to hear from you!
Mahalo (Thank you) for reading!
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