The Perfect Oahu Itinerary – A Must See & Beyond Trip Planner

Oahu being the capital of Hawaii is somewhat more commercial compared to the other Hawaiian islands with certain areas being more crowded and touristy. This put Oahu on the bottom of our list of islands to visit for a long time. But we were wrong and how! This place has something for everybody – remote waterfall hikes, pristine white sand beaches, lush rainforests, bustling city life of Waikiki and is a world-class surfers’ paradise. It offers a perfect blend of urban and outdoor experience. 

We spent 10 days on the island filled with a fun mix of adventure activities, relaxed beach time, nightlife at Waikiki, museum time, and the only thing common to all 10 days was catching sunset from wherever we were on the island.

Where to stay in Oahu

Waikiki is the hub of Oahu tourism. It is more commercial than the rest of the island with plenty of hotels & resorts. Most places on the island are within an hour’s drive from Waikiki. There is lot to do in this area. Activities, Shopping, Restaurants, Night life, Beaches etc. Since this is a popular place to stay, it is crowded and expensive. Parking is hard to find & costs a lot too – there is no such thing as free parking. With these factors in mind, we would recommend staying in and around Waikiki for most tourists mainly because of the proximity to other places and range of things to do.

Leeward Coast with its dry and sunny weather is home to luxury resorts. If you plan on staying in a resort & enjoy a relaxed vacation, this might be the place to stay.

North Shore is a laidback surf town far from the hustle and bustle of Waikiki with not much to do after dark. If you are looking for a quiet, less crowded place to slow things down, you can consider staying in this region.

Things to do in Oahu

In the following sections we have broken down things to do on the island region-wise.

South Oahu – Waikiki/Honolulu

This is perhaps the most touristy region of the island and rightly so as it has plenty of food and accommodation options for all budgets ranging from luxury resorts to functional airbnbs and modest hotels.

Things to do in Waikiki

Waikiki – The vibrant town of Waikiki is lined with high-end shops, boutiques, world-class restaurants, high-rises and beach side resorts. It is the hub of the island bustling with tourist activity any time of day. Take an evening walk along Kalakau Avenue to get a feel of all the glam and glitz this town has to offer.

Waikiki beach – One of THE MOST popular beaches on the island, boasting gorgeous sunset views. But expect big crowds. Also popular for beginner surfing, paddle boarding and canoeing. There are a few places close to the beach that rent surfboards and paddle boards.

Pearl Harbor National Memorial – Learn about the history of Japan’s attack on Pearl Harbor and the entry of US into World War II. The visitor center and the museum are free for all visitors. Additionally, paid guided tours are available for those interested. Find out more information about reservations to visit USS Arizona Memorial program here.

Lolani Palace – This is a historic landmark that belonged to the rulers of Hawaii. Tour the insides of the palace and the gallery exhibits. Click here for more information on reservations and tour timings.

Tantalus Lookout – One of the best spots on the island for sunset views. Conveniently accessible as it does not involve any hiking, you can drive up all the way to the lookout. This spot offers great views of the diamond head crater – you can almost see into the crater, the whole of Waikiki and downtown Honolulu extending into the Ocean – all awash in golden light during sunset.

Nuuanu Pali lookout – Another drive-able lookout that offers panoramic views of sheer cliffs and lush greenery. As you drive towards this lookout, you will see concrete jungle disappearing and making way for a natural jungle. Because this is on the windward side of Oahu facing trade winds, the winds can get incredibly strong, sometimes enough to blow a small person off their feet! Expect random bursts of downpour when in this area.

Best hikes around Waikiki

Manoa Falls Hike

This is one of the most rewarding hikes for the effort. The short trail is surrounded with lush tropical rainforest and ends at the base of Manoa Falls. The trail could get muddy, so make sure to wear shoes or enclosed footwear. The trail officially ends at the viewing area but if you are seeking thrill, go ahead and jump into the pool at the base of the waterfall! Note: There is a $5 parking fee at the entrance.

Wiliwilinui Ridge Trail

The trailhead is in a gated residential community and so a limited number of visitor vehicles are allowed to enter and park at the trailhead. Drive up to the security checkpost which is hard to miss as it sits in the middle of the road at the entrance of the community and obtain a parking permit here. Best chances of getting a permit immediately are if you arrive early in the morning.

If you don’t get a permit immediately, you could either wait for hikers to return (which could take a while). Or find a safe curbside parking for your car and make the additional 0.6 mile hike uphill from here. We chose to do the latter as we arrived at the checkpost around 11.30am and did not get a permit.

The hike itself is super scenic with panoramic views of surrounding ridges and valleys. As the trail gains elevation, views of the Pacific start opening up. The hike up the ridges will surely leave you gasping for breath, and that is a good reason to slow down, enjoy the gentle breeze and watch the movement of low hanging clouds across surrounding mountain peaks. The wind does get stronger at the very top depending on the time of day. Chances of shower increases towards mid-afternoon so carrying a light rain jacket is highly recommended.

The trail is very muddy and slippery so make sure to wear shoes with good grip. Some parts of the trail get very steep and the wet, slimy mud makes the climb up a little nasty. But there are ropes at several places to help with dragging yourself up.

Overall, this hike is completely worth the views and experience. However, definitely keep in mind that the trail gets very muddy, slippery and steep at some places.

Lulumahu Falls Hike

This trail is an adventure in itself. It involves walking through a lot of sludge and mud on a narrow path. Involves stream crossing at a few places, and chances of going off trail are high since most of the trail is not well defined. There are red ribbons tied to some trees that help in staying on track but could easily go unnoticed as you watch for those muddy puddles.

The reward are two waterfalls within .25 miles of each other. First one is a small waterfall followed by a really tall one. The second waterfall has a small, shallow pool that allows for wading and maybe a refreshing shower under the falls.

Less crowded when compared to Manoa Falls, and adds a lot more adventure as the trail is not maintained.

South East Oahu

This 10-mile stretch of the south eastern shoreline covering China Walls, Spitting Caves, Halona Blowhole, Halona Beach Cove, Sandy’s Beach and Makapuʻu Point Lighthouse Trail can be done in 4-5 hours since all of them are quick stops except the lighthouse trail. Read on to know more on each of these places.

Things to do in South East Oahu

Makapuʻu Point Lighthouse Trail – This is an easy 2.5-mile trail on a paved road offering beautiful views of the South-Eastern coastline. There is no shade on this trail so it is best to do it either early in the morning or late afternoon to beat the heat. The trail ends at a lookout with views of the lighthouse against the deep blue of the ocean.

Hanauma Bay – This is THE place to be on the island for snorkeling enthusiasts. Since this is a state park, there is a $25 entry fee and a $3 parking fee. The water here is calm and shallow with abundant marine life making it a great choice for beginner and experienced snorkelers alike. Make sure to get here early in the morning to find a parking spot as the park gets crowded by 9am. Find out details about the park’s timings, reservations, pricing etc. here

Spitting Cave – The rocks at this place have a distinct layered pattern to them. The rocks have caved in at some places where the waves come crashing in and are spat out with great force. This is a good place to sit on the rocks and enjoy a peaceful sunset. Adventure seekers come here for cliff jumping, although it is dangerous and could get fatal since there are rocks just below the surface of water but not visible due to dense froth created by the spitting caves.

China Walls – A few blocks away from Spitting Cave with similar wavy rock patterns, China Walls is another good place for sunset. Rock jumping from here is considerably safer.

Halona Blowhole lookout – This is a quick stop to watch some of the most violent waves crash against the rocks making a whirlpool. Spend some time here before taking a quick walk down to the Halona Beach Cove.

Halona Beach Cove – Turn around from the Halona Blowhole lookout and make your way down to the beach cove for a closer look at the crashing waves. If you are feeling adventurous, climb up the layered wall of rock. There is a lava tube here that looks like a tunnel ending into the beach. This is another great place for sunset!

Sandy’s beach – The best place on the island for body surfing. Watch body surfers ride those tube waves which are more common here than anywhere else.

East Oahu – Kailua

The drive up North via the Eastern coastline is scenic with views of rugged cliffs and the ocean throughout. This section of the island is also comparatively less crowded.

Things to do in East Oahu

Lanikai and Kailua beaches – Both these sprawling white sand beaches are a mile away from each other and very popular. Lanikai beach offers unobstructed views of the twin Mokulua islands. It is is possible to kayak to one of these islands from Kailua Beach Park and also do a short hike there. Kayak & SUP rentals can be found here. Lanikai beach offers great sunrise views.

The Byodo-In Temple – This Buddhist temple located in a valley surrounded by soaring mountains on three sides truly feels like a slice of paradise. Being on the windward side of the island, the mountain peaks are almost always covered in low hanging, drifting clouds. There is lush greenery all around. We had initially planned to make this a quick stop but ended up spending 2 hours here soaking in the breathtaking views.

Ka’a’awa Beach – This a quiet little beach, not so crowded and makes for a good picnic spot.

Best hikes in East Oahu

Lanikai Pillbox – Kaiwa Ridge Trail

The is one of the more popular hikes on the island. It is short but steep so expect to get a good cardio workout by maintaining a reasonable pace. Throughout the hike you get to enjoy sweeping views of the residential suburb of Kailua extending into the turquoise Pacific ocean. Also enjoy views of the twin Mokulua islands just off the coast of Oahu, and Lanikai beach.

The first section of the trail is steep and slippery but there are ropes to help you climb up if needed. There are two concrete military bunkers popularly known as “Pillboxes” along the trail. The first stretch of the Hike ends at the second Pillbox. If interested, you can proceed further along the Kaiwa Ridge trail beyond the Pillboxes for close up views of the ridges against the beautiful backdrop of the ocean. There is not much incline on this stretch and will add not more than 40-45 minutes to the total hike time.

North Oahu – Waialua

North Shore Oahu is the epicenter of surfing on the island and draws the best surfers in the world for competitions held here. If you are a surfer yourself, you will probably end up spending most of your time on this part of the island. Even if not, it is worth spending a day or two here watching skilled surfers navigate big waves while enjoying shaved ice yourself.

If you are staying in the Honolulu-Waikiki region and planning to visit the North Shore, we recommend taking the eastern coastal route up and coming back to Waikiki the central route down as in the map below. The drive up the east coast is scenic with numerous calm and peaceful beaches that are not as crowded but equally good.

Things do in the North Oahu

1. Dole Plantation – This place is technically not in the North but in the Central region and can be covered as a stopover when driving from South to North or vice versa. It boasts the world’s largest Pineapple maze garden and is a fun place for families with kids as it has a train ride and a store with everything pineapple – soft serves, goodies, fresh pineapples. Visiting this place is optional. Skip it if learning about the history of pineapple farming and the train ride does not interest you.
2. Haleiwa Town – This neat little beach town is small enough to walk the entire length with quite a few options for food, shopping and of course shaved ice! Definitely binge on the Acai and Pitaya bowls along with Shaved ice. Check out our recommendations for food in Oahu.
3. Banzai Pipeline at Ehukai beach – This is the place to be to watch pro surfers navigate enormous tunnel waves with ease.
4. Shark’s Cove at Pupukea beach – A good place for snorkeling and scuba diving with its diverse marine life. Remember to wear reef shoes to avoid scratches and pricks from the sharp corral reef.
5. Sunset beach – A good place to be at to watch the sunset. Walk a few meters away from the entrance to avoid crowd and enjoy a peaceful sunset.
6. Laniakea (Turtle) beach – Want to watch turtles at their natural best in their natural habitat? This is the place.

Best hikes in North Oahu

Waimea Valley Trail

This trail is paved and well maintained and ends at a waterfall with a swimmable pool. Waimea Valley requires an admission fee of $20 and has several points of interest including botanical gardens and the Waimea Valley trail. The setup is more commercial than natural, but is probably the safest place for waterfall swimming as they provide life vests which is included in the admission fee.

Kaena Point Trail

Views of the beautiful, rugged coastline throughout. Can get very hot around mid-day so bring plenty of water. There are numerous little blowholes spouting water on the rocks. Don’t miss this hike if you are on the North Shore with some time in hand.

West Oahu

This is the leeward side of the island with sunny and dry weather. Home to luxury resorts along with off-the-beaten-path beaches and rugged landscape. Unfortunately, it was time for us to leave before we could visit this coast. But here’s what will top our list the next time we find ourselves on this island.

Things do in the West Oahu

• Kaneana Cave (Makua Cave) hike for sunset
• Makaha Beach
• Yokohama Beach
• Ko Olina Lagoon

Where to eat/drink in Oahu

If you are looking for a variety in cuisines to flatter the tastebuds, look no further than Waikiki. But if you are simply looking to beat the heat with something light and chilled, North Shore has quite a few places with mouthwatering acai and pitaya bowls. And of course you will find shaved ice everywhere on the island! Read on to know our personal favorites.

Waikiki/Honolulu

• Istanbul – Meze platter & Chicken shish are to die for. Try the punishment spicy sauce
• Hiking Hawaii Cafe – Nice cafe with great paninis, fresh fruit juices & acai bowls
• Ramen Nakamura – Great vegetarian ramen option
• Hula Grill
• Roy’s – We decided to skip this one as it was very busy but this place is a must if you are in for a $$$ special occasion dinner and Lillikoi Cheesecake
• Dukes Waikiki – Fish Tacos
• Marukame Udon
• Noi Thai – Expensive but delicious thai food
• Arvo Cafe for Brunch/Lunch – Loaded avocado toast & Lavender tea
• Aloha kitchen – Omelette, French Toast & Mimosa
• Island Brew Coffeehouse – High quality Hawaiian coffee
• Leonard’s bakery – Malasadas are worth the wait. Do not be discouraged by the line.
• Island Vintage Shave Ice
• Maui Brewing – Loved the Pineapple beer
• Waikiki brewing – Jalapeno beer here is our personal favorite.
• Deck at the Queen Kapi‘olani Hotel – Rooftop sunset view with mai Tai
• The Royal Hawaiian – Mai Tai on Waikiki beach

East Oahu – Kailua

• Maui Brewing Company
• Himalayan Kitchen – Not the best Indian food, but this place can help ease the craving for Indian spices
• Yamas Mediterranean Cuisine

North Oahu – Waialua

• Uncle Bo’s Haleiwa
• Ted’s Bakery – Chocolate Haupia Pie
• Haleiwa Bowls – Acai & Pitaya bowls
• The Sunrise Shack – Avocado toast & the fruit bowls with lush green farm on one side & a beach across the road.