4 Days In Oahu: First Time Visitor’s Guide To Hawaii

Last year, I spent 4 days on the Oahu islands in Hawaii and have ever since been yearning to revisit these heavenly islands!

I left my heart in Hawaii. I bet you will too.

Alohaaa! If you’ve never been to Hawaii before, planning a trip there can be completely overwhelming – which Hawaiian island to visit, the best time to visit Hawaii, how many days to spend on each Hawaiian island, and finally planning your Hawaii itinerary.

Hawaii offers so much to visitors that it may require a few lifetimes to experience it all. And, the majority of people get to visit these heavenly islands only once or twice in their entire life!

This ultimate 4 days in Oahu guide leverages my Hawaii travel experience (& research) to save you a lot of time and maximize your Hawaii experience!

Which Hawaiian Island To Visit?

There is no “best” Hawaiian Island to visit. All of the islands are very unique and appeal to travelers for different reasons. But depending on how you like to vacation, and what you expect to see in Hawaii, there may very well be a “best” island for you.

Let’s look at the four most popular islands.

Oahu

This is the most visited of the Hawaiian Islands and is home to the state capital of Honolulu as well as the world-famous Waikiki Beach.

You can relive the famous history at the museums and memorials of Pearl Harbor, soak up the sun and watch turtles at Waimea Bay, or dive into adventure at the North Shore.

Best For: Those who like a mix of action and relaxation. If you want to see the iconic Hawaii, it’s history, the Polynesian culture and relax at some of the best beaches, you’ll get the best bang for your buck on Oahu.

Maui

Known as the “honeymooner’s isle”, Maui draws many couples as well as celebrities looking for peaceful seclusion.

The island is famous for its beautiful beaches, winding Road to Hana, and gorgeous sunrises from the summit of Haleakala. It’s also the best island for whale spotting.

Best For: honeymooners, gorgeous beaches, big adventures, beautiful resort areas, scenic drives and local hideaways. The vibe is what most people expect of Hawaii.

Kauai

As you drive past mile after mile of lush foliage in every imaginable shade of green, it’s not hard to see how Kauai earned the nickname “The Garden Isle.”

It’s most famous sites are the Napali Coast and Waimea Canyon (also known as the Grand Canyon of the Pacific). Kauai feels very “country”, and less developed or spoiled than some of the other islands.

Best For: Nature lovers, beach bums, hikers, and travelers seeking adventure. While all of the islands offer this, Kauai by far has the best and most varied hiking while feeling like you’re truly off the grid.

Big Island

Put all the other Hawaiian islands together and they’re still only about half the size of the Big Island (officially known as the Island of Hawaii).

The Big Island’s sheer natural diversity encompasses 11 of the world’s 13 climatic zones – from molten lava rivers to snow-capped mountains to beautiful rainforests and black sand beaches.

This is also where you will find Hawaii Volcano National Park, the only active volcano in Hawaii.

Best For: The ultimate Hawaiian adventure and for travelers seeking a variety of climates and landscapes on their vacation. You’ll often find yourself driving or hiking and even paying for an excursion.

How Many Days In Hawaii?

You would need a minimum of 4-5 days to cover each of the above islands individually (excluding the roundtrip flight). If you really want to relax, I would recommend spending 7 – 10 days as these islands have plenty to offer!

When To Visit Hawaii?

The best weather in Hawaii is in April, May, September, and October. Hawaii has warm weather all year round, with average highs of 26-28ºC in the winter, and 29-31ºC in the summer.

The biggest variables for tourists are rain and surf conditions. November to March are the rainiest months, and June through November is hurricane season – though big storms are rare. Winter also brings the best waves for surfing, especially on north shore beaches. The quietest month for tourists is November.

What To Pack For Hawaii?

A visit to Hawaii mostly revolves around beaches and water-sports, scenic drives, nightlife (Oahu) and some easy to difficult hikes. This means packing proper beach gear (remember the sunscreen), comfy walking/hiking shoes, and your favourite summer attire. Also, don’t forget to carry water crates in the trunk of your car to stay hydrated!

Planning The Trip

Our group visited Hawaii in late May when the weather was just perfect! We decided to spend 4 days in Oahu for our first visit to Hawaii as we wanted to stay close to the action (culture, history) while getting some time to escape into nature.

Getting around Oahu

Honolulu is lined with sandy Hawaiian beaches and turquoise waters. But, make no mistake, the city is a buzzing urban metropolis! As the largest city in Hawaii and the state capital, Honolulu is a vibrant tropical city with everything from historical landmarks to fine dining to designer shopping.

While you can easily get around Honolulu in Uber/Lyft, there’s a lot more on this island to explore. So, I highly recommend renting a car.

We felt necessary to rent convertibles. After all, we were in Hawaii!

Tip: If you have a Costco membership, they offer some really good discounts. We rented out a Mustang for ~$50 per day. But, try to book in advance.

4 Days In Oahu Itinerary

Below is the itinerary to make the most out of a 4 days trip to Oahu. I have also included details for a 5th-day extension in case you can manage to take another day off (which I highly recommend).

This itinerary consists of an anticlockwise loop (refer image below) that was planned to optimize travel time. If you believe in creating your base at one location for the entire trip and not care much about travel time (and waking up early), you will still do fine! 😀

We started our trip from Waikiki beach (#1 on map) and then drove anticlockwise on Highway 72 to cover the Southern and Eastern points on the island.

Our second stay (#2 on map) was an Airbnb on the North Shore where we engaged in water sports, some crazy adventures, and experience the Polynesian culture.

The final stay was near the Honolulu Airport area (#3 on map) where we could easily visit the memorials of Pearl Harbor and get on a helicopter tour of the island (nothing beats the bird eye view!).

Ready? Let’s get exploring! 😀

Day 1: Take it easy at Waikiki Beach In Honolulu!

Waikiki, one of the most famous beaches in the world, is a busy tourist mecca where you’ll find the majority of Oahu’s resorts. Waikiki is to Hawaii as The Strip is to Las Vegas. It’s loud, busy, and very touristy. If you’re looking for large luxury resorts, restaurants galore, shopping, and nightlife, Waikiki has it all.

We arrived at Honolulu around 2 pm on Saturday and stayed for a day at the Hilton Waikiki Beach Hotel. It’s cheaper than you’d think if you book early. The ocean-facing view from the balcony of our room on the 18th floor was absolutely spectacular and worth every penny.

We quickly freshened up and reached the Waikiki Beach which is just a 5-minute walk from the hotel. The vibe here is so touristy!

We soaked up some sun and relaxed on the beach for some time. Soon, we boarded a sailboat where we spent a relaxing two hours cruising away from Waikiki, watching the sunset from the deck and see Waikiki as it begins to light up for the evening.

The sailboat was really fun and its low height made us notoriously wet. We went back to change at the hotel and then came out to explore the night streets of Waikiki.

The first thing we did was to grab a Lei (garland) to get into that Hawaiian mood. We dined at a local Hawaiian place and ended the night at the Sky Waikiki, which has a rooftop bar, lounge and restaurant.

Day 2: Hike To Diamond Head Crater, Snorkel At Hanauma Bay, Scenic Drive And Sunset At Lanikai Beach

After a relaxing evening at Waikiki Beach, we woke up the next morning and hiked to the top of Diamond Head Crater. This 1.8 mile round trip hike gains 452 feet and has various lookout points offering sublime 360-degree views of Honolulu and the East Side.

However, it is the view from the summit that is the most rewarding – a nearly unobstructed view of the Waikiki Beach coastline and its endless collection of high rises.

Our hike was later rewarded with thirst-quenching local refreshments at the trailhead – coconut water, pineapple, and acai served on a pineapple base (so Hawaiian). Make sure you save some room for shave ice.

Hawaii boasts some of the best snorkeling spots in the world. We spent the afternoon at the gorgeous Hanauma Bay that is famous for being the best snorkeling spot on the Oahu island thanks to an ancient coral reef that is almost completely sheltered from the violent forces of the Pacific Ocean by tall cliffs.

You can carry your own snorkeling gear or rent it from the small hut near the restrooms (costs approx $20 for the day).

Even if snorkeling isn’t your thing, I highly recommend visiting just to enjoy the views from the top before continuing your road trip along the coast.

We picked up Highway 72 and drove along the southeast coast. You can choose to stop at the Lanai Lookout which is slightly reminiscent of Bixby Bridge on California’s Pacific Coast Highway.

Drive through Lanai Lookout to the beautiful Halona Beach Cove, which has been the backdrop for Pirates of the Caribbean, 50 First Dates, an Elvis music video, and more recently Nicki Minaj’s “Starships”. Also, there’s a blowhole that you can view from the parking area.

There are a few more really good spots on this drive which we couldn’t cover because we were short on time (refer Day 5 extension below for details). So, we headed straight to soak in the sunset and dine at the beautiful Lanikai Beach. We ended the day chilling out at our North Shore Airbnb.

Day 3: North Shore Adventures and Cultural Escape

The towering, glassy winter waves of the legendary surf mecca at North Shore draws the best surfers in the world, while smaller and gentler summer waves are better for beginners. You can also get a surf lesson here.

Our group had a slightly different idea of adventure. Shark cage diving at North Shore is simply the most adventurous activity to add to your next Hawaiian vacation. Imagine diving into a glass cage surrounded by a bunch of 10 foot long Galapagos and Sandbar sharks. Does that give you an adrenaline rush? 

It definitely was one of the top highlights of our vacation, and I sure had flashbacks from movies Deep Blue Sea and Jaws. There is absolutely no diving experience required as you are basically snorkeling to watch the sharks through the large polyglass windows of the cage.

We were super hungry by the time we returned to the shore. We quickly changed and drove to Kono’s (the breakfast bombers are so appetizing) which is located in the small laid-back surfer town of Haleiwa. This town offers beautiful beaches, tasty local restaurants, food trucks, cool local shops, and plenty of shave ice.

Considered the best shave ice in Oahu, the wait time at Matsumoto Shave Ice can be over 20 minutes long. Alternatively, you can get one from the Aloha General Store and it will not disappoint.

We then spent some time at Laniakea Beach, where you can spot a sea turtle on the beach if you’re lucky (we were not)!

The rest of our day was spent exploring the rich culture on this island. We arrived at Waimea Valley where we were greeted with the quiet of nature, beautiful flowers, rare plants, cultural sites, and a beautiful waterfall for swimming.

The Waimea Valley Trail is a very relaxed walk leading to the waterfall, suitable for all ages. We even spotted this beautiful peacock spreading its tail and had our Morni (peacock) moment.

Our last destination for the rest of the evening was Polynesian Cultural Center which features 6 authentic villages representing the island cultures of Hawaii, Fiji, Aotearoa (New Zealand), Samoa, Tahiti, and Tonga. The royal feast at Ali’i Luau blends a delicious array of island and mainland dishes with the excitement of authentic island entertainment from across Polynesia.

We ended the evening with the power of Ha: Breath of Life, an action-packed story of a passion ignited by fire, song, and dance. I would recommend this to any first-time visitor interested in diving into Polynesian culture. Do buy tickets in advance!

Day 4: Pearl Harbor and Helicopter Tour

On our final day, we were ready to dive into one of the most pivotal moments in US history that dragged the United States into World War II.  The Pearl Harbor National Memorial commemorates the events of the Japanese attack on Pearl Harbor, which killed over 2,400 Americans and sank twelve ships.

I strongly recommend making reservations in advance or you can find yourself struggling in a long queue on a busy weekend. Depending on your interest, you can spend 1-3 hours exploring the memorials and museums.

Now that we have visited most of the popular points on the island, it was time for the most awaited Helicopter Tour to view the picturesque bird eye view of this beautiful island. We found amazing deals on Groupon from Novictor Aviation. Keep an eye for them as they appear to be sold out at the time of writing!

As we stepped out of the chopper, the thought that it’s time to leave Hawaii was already starting to sink in!

We went back to soak in the Hawaiian sunset for one last time at Waikiki Beach, sipping in our drinks at Duke’s which has a barefoot bar and beautiful outdoor seating overlooking the beach.

After a couple of hours, we found ourselves in the boarding area crying – it was time to leave Hawaii! 🙁

Day 5: Have an extra day?

There’s so much to do on Hawaiian islands that makes tourists visit them over and over again, year after year. We really wanted to cover some more points on Day 2 but had to skip due to shortage of time. If your schedule allows an extra day, you should definitely try to tick these off.

Note: As per the itinerary stated above, you can do this on Day 3 instead, staying at South or East Oahu, and move over the subsequent days as is such that you still end the trip (Day 5) in the vicinity of Honolulu airport. This will keep you moving in that 1->2->3 anticlockwise loop that was planned to optimize travel time.

Start the morning with a beautiful sunrise at the top of Koko Head Crater. The hike to the summit is a steep climb with 1048 railroad ties (stairs), but the pain is totally worth the spectacular view from the top. Don’t forget to carry ample water as there is no shade on this trail.

This hike is the closest experience to the Haiku Stairs (Stairway Of Heaven) which is now forbidden and illegal to access.

After the hike, reward yourself with breakfast and coffee at Island Brew Coffeehouse and then continue up on the Highway 72 to the Makapu’u Lookout to catch panoramic views of the dramatic coastline in front of you.

You can either just soak up the views from the parking area or you can spend a little bit more time to hike to the lighthouse lookout, which is just a mile in each direction with very little elevation. This is a nice place to sit and enjoy your lunch if you can manage to pack it before.

Next drive up to the 1200 ft Nu’uanu Pali Lookout where you are treated to a panoramic view of Oahu’s windward coast and sweeping views of Kaneohe, Kaneohe Bay and Kailua.

If you have time left, visit Kualoa Ranch which is also known as Hawaii’s “Jurassic Valley“. You can do Jurassic Valley Zipline, Electric Bike Tours, ATV Tours, Horseback Tours, Jurassic Jungle Expeditions, Ocean Voyage Tours and so much more here!

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Itinerary on Google Map

I know there’s a lot to track! As always, I have added all the points of interest on Google Maps as per the itinerary above (color-coded by day). You can easily refer to it during your trip – simply copy the link or favorite it.

I would also suggest you to download offline maps beforehand as some areas on the island can have connectivity issues.

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I hope the above itinerary helps you plan your trip to Oahu! All information shared is from my first-hand travel experience and research. Feel free to leave any questions or feedback that you might have.

Looking for more travel inspirations? You’ll like some of my other travel guides!

3 days in Yellowstone and Grand Tetons National Park

Bryce, Zion & Antelope – 4 days Utah & Arizona Roadtrip From Las Vegas

One Day Itinerary For Death Valley National Park

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