If you’re planning your first trip to Oahu, I’ve put together the perfect 5 day itinerary that hits every highlight.

This itinerary assumes you’re staying in Waikiki and you want to get out and explore the whole island…not just sit around at your hotel ; )

5 Day Oahu Itinerary for First Timers

Day 1: Waikiki Beach

Spend day 1 getting rested up from your big travel day and getting to know the most famous part of Oahu…Waikiki Beach!

Start the morning bright and early with Kona coffee at Kona Coffee Purveyors on the ground floor of the International Marketplace. Since you’ll be up early due to the time change, get there when they open so you avoid the long lines that form later.

For a proper breakfast, I love Aloha Kitchen. Their famous for their souffle pancakes (and they are DECADENT), but their kalua pork eggs benedict is my favorite.

Spend the day at Waikiki Beach. Yes, it gets crowded, but it really is one of the most beautiful beaches in Hawaii.

If you need an “activity,” book a spot on one of the snorkel catamarans that leaves right from the beach.

Spend your first night in Hawaii at House without a Key.

If I only have one night in Waikiki, this is where I’m coming. Hidden away in the luxurious Halekulani Hotel at the quiet, older end of Waikiki, this place feels like old Hawaii.

It’s sophisticated, the views are as good as they come, and there’s nightly live music and hula dancing.

I don’t know about you, but sipping a mai tai on the lawn while watching a hula dancer silhouette at sunset is as “Hawaii” as it comes.

Make reservations in advance if you want a table and full menu. Otherwise, the smaller tables up around the stage are first come first serve. They serve a drink menu and smaller selection of food (however I’ve always been able to order anything off the main menu).

Their mai tais are legendary. I’m always pleasantly surprised by their pizzas. And they’re famous for their coconut cake.

Live music is from 5 PM – 8 PM with a hula dancer from 6 PM – 8 PM.

Day 2: North Shore

The north shore is my favorite part of Oahu. You could spend a whole trip here, but these are some of my don’t miss spots.

Also, a lot of this will depend on the time of year you’re there. In the winter, the surf is big and you can’t swim or snorkel much, but you’ll be able to watch the surfers.

Haleiwa

Haleiwa is probably one of the cutest towns in Hawaii. It’s picturesque, walkable, and full of cute shops and restaurants. I especially love Guava Shop.

For food, I love Haleiwa Bowls, Surf & Salsa, and Kono’s.

Getting shave ice from Matsumoto is classic. Lines get long in the afternoons, but they move quickly. And it’s worth it to try this tasty treat with local toppings like ice cream, azuki beans, condensed milk, and mochi balls in addition to the ice and syrups.

And don’t miss the cute signs on the way into and out of town!

See Turtles at Laniakea Beach

A few miles from Haleiwa, Laniakea Beach is a great spot to see honu (green Hawaiian sea turtles).

There’s a bit of parking across the street, but this place gets really popular midafternoon (when you have the best chance of seeing turtles) so you’ll probably have to park along the road.

Plan to spend 20-30 minutes here admiring the turtles (but don’t get too close!).

Also, last time I was here, there were a ton of chickens!

Cliff Jump at Waimea Bay

Waimea Bay is one of the most famous beaches in Hawaii. It’s a gorgeous swimming and snorkeling (and rock jumping) spot in the summer, but it’s one of the biggest surfable waves in Hawaii in the winter.

It’s still a beautiful beach in the winter, but it’s not always swimmable. Be sure to listen to the lifeguards about when it’s safe to get in the water here.

There’s not much parking here, so if it’s summer and you’re planning to spend time here, definitely get here early.

Snorkeling at Sharks Cove

At Pupukea Beach Park, this protected cove is an excellent snorkeling spot in the summer.

The rocks make it protected from the open ocean, which means not only excellent swimming conditions but a natural “nursery” for some of the ocean’s smaller critters.

This is mostly a summer snorkeling spot (you definitely want to make sure conditions are safe before you get in!), but sometimes when there’s not much swell, it’s good in the winter too.

There are several food trucks across the street as well as snorkel rentals and lockers so this is a pretty accessible spot.

There’s limited parking so I suggest arriving early if you’re planning to snorkel.

Get Acai Bowls at the Sunrise Shack

If you’re looking for the most “instagram famous” spot on Oahu’s North Shore, it’s the Sunrise Shack.

Famous for their acai bowls and charming, tropical aesthetic, this place is just a day dream.

The original shack across from Sunset Beach closed earlier this year, but the one across from Sharks Cove is my go to anyways. There’s more parking, and they have more space so there are places to sit plus they have a slightly bigger menu.

I always get a bowl (they have a variety besides just acai), but their avocado toast is phenomenal as well.

Kawela Bay & Turtle Bay Trails

Forget just the north shore, this is probably my favorite beach on ALL of Oahu. There’s parking across the road (or you can park at Turtle Bay and walk through the forest or along the coast) and most of the time there’s only a handful of people here.

The sand is so white, the water is so blue, and trees hug the beach so there’s always shade.

They’ve filmed a lot of movies here like Hunger Games: Catching Fire, Pirates of the Caribbean: Stranger Tides, and Forgetting Sarah Marshall.

Whether or not you’re staying at Turtle Bay (it’s my favorite place to stay on Oahu!), the beaches, stables, and hiking trails around the property are one of my favorite spots to explore.

Book a horseback riding tour with the Stables at Turtle Bay. They’ll take you along the beach and through all the trails around Turtle Bay.

Even if you’re not interested in riding the horses, this is still such a great spot to visit. There are miles of hiking trails along the beach and through the forest leading to the hidden Kawela Bay (a great spot to find turtles in the afternoons).

If you’re staying at the resort, follow the signs towards the Stables and from there you can pick your trail along the beach or through the forest. There’s a pillbox on the point you can explore too.

If you’re not staying at the resort, there’s plenty of parking around the stables.

Try the Shrimp Trucks

Oahu’s North Shore is famous for their shrimp trucks. Giovanni’s (with locations in Kahuku and Haleiwa) is the original and most popular.

But my personal favorite is Famous Kahuku Shrimp Truck in…Kahuku!

Soooo many places do a variety of the local garlic shrimp or “shrimp scampi” special and many have other options like spicy shrimp, coconut shrimp, etc.

Some other places known for their shrimp: Romys, Tanaka (formerly Fumi’s), Honos, and Jenny’s

Sunset Drinks at Turtle Bay

I saved my favorite thing for last! The newly renovated (and rebranded) Ritz Carlton Turtle Bay is STUNNING and the best part is how they’ve polished up the lobby area to be the coziest hang out spot with views everywhere you look.

The Off the Lip bar is spectacular and not to be missed. Plan to arrive well before sunset to snag one of the little tables or a spot at the bar and prepare to be dazzled.

The mai tais are stout (and well flavored). And all of the small bites are yummy, but be sure to save room for the turtle cheesecake.

Day 3: Diamond Head & Pearl Harbor

Waikiki is one of the most famous beaches in the world and the image of Diamond Head in the background is so iconic.

The top of the now extinct volcanic crater offers amazing views of Waikiki and Honolulu so it’s no wonder it’s one of the most popular hikes on the island.

If you’re not an avid hiker, this is one I still think you should do. And it’s fairly accessible to all ages and fitness levels. Most folks should be able to make it to the top in 40 minutes or so even if you’re in the greatest shape.

And it’s definitely worth the push. The trail (while a steady incline) is fairly mild and well traveled and for a relatively short hike, it has a big payoff.

Increasing popularity has triggered a new reservation system, so you’ll need to plan this one in advance.

Reservations can be made 30 days in advance here for either just entry or parking and entry. If you’re booking the entry and parking options (what I would recommend if you have a car), reservations are made in 2 hour increments starting at 6AM (6AM-8AM, 8AM-10AM, 10AM-12PM, etc.) and you’re asked to arrive within the first 30 minutes of your time slot. If you’re just booking entry, reservations are made in hour increments starting at 6AM.

Entry is $5/person (whether you park, Uber, or hike in) plus $10/car for parking.

I highly recommend booking an early time slot as there is NO SHADE on this hike. And if you plan this for the first morning of your trip, that early time frame won’t seem shocking at all since you won’t be adjusted to the time change yet.

After you finish hiking Diamond Head, head to Hau Tree for breakfast.

Hau Tree in the Kaimana Beach Hotel (at the far less hectic end of Waikiki) is one of my new favorite spots on the island.

It’s about a 15 minute walk from the heart of Waikiki and totally worth it!

The Kaimana Beach Hotel has just been totally renovated in a really chic way and the restaurant is about as close as you can get to toes in the sand dining.

You’ll get those coveted Waikiki views, but without the crowds and masses tooling around.

Spend the rest of your day at the beach OR head out to Pearl Harbor to tour the USS Arizona.

For everything you need to know about visiting Pearl Harbor, read this post.

Wrap up the day with mai tais at the Monkeypod.

I’ve been a Monkeypod stan for well over a decade now, and I never feel like I’m in Hawaii until I have one of their famous mai tais with the lilikoi foam.

So I was over the moon when they finally opened a location in Waikiki. Situated beachfront in the Outrigger REEF Waikiki (there’s more than one Outrigger hotel in Waikiki), this is your typical Monkeypod experience (lively atmosphere…their motto is “a party every night”) but with even extra Waikiki energy.

Like I said, they’re famous for their mai tais which have a lilikoi foam on top, but they’re REALLY famous for their happy hour. Double check the hours seasonally (and by location) but it’s usually 3:30 PM to 5 PM and covers half priced appetizers (no seafood options though), $14 pizzas, and $4 off craft cocktails.

Side Note: If you’re looking for a rental car for your trip, I LOVE Discount Hawaii Car Rentals. They’re seriously the only company I ever use. They’ll give you the very best prices, you don’t have to reserve with a credit card or pay until you show up, you can cancel and re-book anytime if you find a better rate, and they usually have a special that adds additional drivers for no fee. It’s a no brainer. Click here to check rates for your trip.

Day 4: Hanauma Bay

Before you head to Hanauma Bay for snorkeling, squeeze in a morning hike.

If you’re looking for a trail with stunning coastal views that will get your lungs burning a bit, but that’s still really accessible, the Makapu’u Lighthouse Trail on Oahu is a must do.

This popular hike on Oahu’s southeastern coastline is not only accessible to hikers of all skill levels but also offers breathtaking panoramas and a chance to spot SO MANY WHALES in the winter.

Here’s what you need to know:

The Makapu’u Lighthouse Trail is a 2-mile out-and-back hike. This is just the kind of hike I like. It’s short and sweet with a big payoff of great views at the top.

From the top, you’ll see Makapu’u Lighthouse down below and spectacular views of the Waimanolo coastline and offshore islands.

Yes, it’s only a mile to the top and it’s completely paved, but it is fairly steep so I recommend wearing sneakers or strap on sandals.

Also, there is NO SHADE on this hike so go early in the day and take plenty of water and wear sunscreen.

Located on the southeastern side of the island, you’ll find the trailhead on the right (ocean) side of the road after you pass Sandy Beach Park and come around the point. The road you turn off on is usually lined with cars and there’s a small parking lot at the bottom. If you come to the Sea Life Park you’ve gone too far.

Last time I did this hike in January, I saw soooo many spouts and whales breaching in the ocean below so be sure to keep an eye out.

There are plenty of places along the path to stop and take in the view so don’t be in too big of a hurry to make it to the top.

And once you do make it to the top, be sure to go to all of the viewing platforms because they all have different angles.

The one at the very top is where you’ll look down and see the lighthouse.

If you get an early start, and you make your Hanauma Bay reservations for about 10AM or 10:30AM (more on that below), you should have time for breakfast first.

There are several spots in the Koko Marina (Heavenly Island Lifestyle, Moena Cafe, and Island Brew Coffeehouse) or grab malasadas from Leonard’s Mobile Truck.

Snorkel Hanauma Bay

Hanauma Bay has been Oahu’s most popular snorkeling spot for decades…and for good reason!

It’s largely protected from the ocean and the large reef is home to a huge range of species, some that are only found in Hanauma Bay. It’s also a perfectly idyllic beach to wile away the day.

And that’s a recipe for popularity. After years of abuse and overuse, the state has taken measures to better preserve the bay and reduce the impacts of visitors.

Hanauma Bay was declared a protected marine life conservation area and underwater park in 1967. And since the 1990s, they’ve taken steps to educate visitors with a marine education center and a requirement that all visitors watch a 9 minute video about the preservation and safety rules for the park before entering.

But the biggest changes have happened since reopening after COVID. The bay is now limited to 1400 visitors per day (which is a fraction of the crowds it used to see) dispersed through a reservation system. It also has reduced hours and is closed two days a week.

Yes, a bit of a logistics headache for vacationers, but after the rest during the COVID closure and the new protocols, the bay is FLOURISHING.

I jumped through the hoops to get a reservation on my last trip to Oahu (I hadn’t been in almost 10 years), and I was BLOWN AWAY by how good the snorkeling was.

Seriously. I’ve snorkeled at all of the “best” spots in Hawaii…done all the big snorkel tours…and this was by far the best snorkeling experience I’ve ever had in Hawaii.

I saw types of fish I’d never seen before, and in such concentrated numbers.

So yeah…you have to make an effort to snorkel Hanauma Bay (and pay the fee…more on that in a bit), but it is 100% worth it and I think it should be on EVERYONE’S Oahu itinerary.

Hanauma Bay Logistics

Like I said, parking and entry is limited and fairly, er, complicated, so you’re going to have to plan ahead if you want to visit Hanauma Bay.

Currently, here are the details:

Hanauma Bay is CLOSED on Monday and Tuesday to give the reef a chance to rest.

Closed Christmas Day (Dec 25th) and New Years Day (Jan 1st).

Daily hours are 6:45AM to 4PM (last entry at 1:30PM, they start to clear the beach at 3 PM, and the gates at the parking lot are closed at 4PM).

The entrance fee is $25/person (12 and under, active military, and local residents with Hawaii state idea are FREE).

Parking is $3/vehicle, cash only. But there are only about 300 spots and they’re first come, first serve.

RESERVATIONS ARE REQUIRED for entry, and they book quickly.

They can be booked online here at 7AM HST two days in advance. They’re limited and are usually gone within 5-15 minutes of the release time.

Only 1400 people are allowed into Hanauma Bay each day (40 people every 10 minutes). Reservations are spaced in 10 minute increments throughout the day.

When you make your reservation, you’ll select a specific entry time and then line up 15 minutes prior. So they recommend you arrive about 30 minutes before your reservation so you can find a parking spot and get sorted.

This is a well oiled machine. They won’t even let you down into the parking area if you don’t have a reservation (unless you’re local or you’re arriving first thing in the morning as a walk in).

There are a limited number of walk in tickets available each day if you show up in person when the park opens. If you’re not able to get reservations online in advance, this is your only option. But you’ll have to show up early.

Locals (with valid Hawaii state ID) can enter for free without reservations between 6:45AM and 1PM daily.

A few more details:

Snorkeling equipment, life vests, and chairs are available to rent. You can also bring your own.

The snack bar on the main level (near the parking lot) is now open (including a small gift shop with beach essentials), but you’re also welcome to bring small coolers.

Lockers are available to rent down at the beach level.

A shuttle down to the beach and back is included. It’s a pretty steep walk.

Things you should bring with you (if you want them): towels, swimsuits, chairs and umbrellas, life vests, waterproof phone cases or cameras, reef safe sunscreen.

Day 5: Windward Coast

Spend the day on (what I think is) the most beautiful part of the island.

Lanikai Pillbox Hike & Lanikai Beach

Lanikai Beach is arguably the most beautiful beach in Hawaii, and while it’s getting increasingly harder to access, I think it’s 100% worth the effort.

Here’s what I do when I go to Lanikai:

Park at the Kailua Boat Ramp and walk over into Lanikai (it’s not far!). First I head up and do the Lanikai Pillbox Trail.

If I was only going to do one hike on my trip to Oahu, I think this would be it.

The trailhead is located in a residential neighborhood in Lanikai (off Ka’elepulu Drive) and there’s no parking here, but it’s easy to find. It’s a pretty steep initial climb along a fenceline before you’ll find the ridge.

The trail is only about a mile round trip to the first pillbox and back, but you can walk further along the ridge to a second pillbox (about 1.5 miles round trip).

This hike only takes me about an hour up and back, but you really have to scramble in some places. The first part is by far the steepest. Most people stop when they reach the first pillbox, but definitely keep going to the second one for even better views.

Since the trail is relatively short, I wouldn’t necessarily call it a “hard” hike, but the trail is a lot less defined and cleared than Diamond Head so you have to do a bit of negotiating.

Because the view faces east, some people like to go for sunrise, but there’s no way I would do this in the dark.

If you’re trying to beat the heat, go first thing in the morning. But if you’re wanting to photograph the most vivid colors, you’ll get better lighting in the afternoon.

I like to pack a pair of flip flops and a towel in my backpack so I can stop at Lanikai Beach after the hike.

Drive Windward Coast

Spend the afternoon driving the Windward Coast past Kualoa Ranch up as far as Ka’a’awa. This is the prettiest drive on Oahu.

Byodo-In Temple

Dedicated in 1968, this replica of the Byodo-In Temple in Japan commemorates the 100th anniversary of the arrival of Hawaii’s first Japanese immigrants.

Nestled in Valley of the Temples Memorial Park in the beautiful Ko’olau Mountains, the Byodo-In Temple is a sight to see. It’s incredibly peaceful, and definitely worth a stop when you’re exploring the Windward side of the island.

Admission is $7 per person ($4 per child).

Lunch & Drinks at Crouching Lion

I love a good destination restaurant, and this is one of my favorites on Oahu. Take a break from your drive up the coast and pop into the Crouching Lion for their take on modern Hawaiian cuisine and craft cocktails.

The view from the restaurant (and looking up at the restaurant from the street) is incredible.

Hoʻomaluhia Botanical Gardens

Once you’ve driven as far north as you’re going, reverse course and head back south.

Just north of Kailua in Kaneohe you’ll find the Hoʻomaluhia Botanical Garden. Admission is free and the gardens are lovely, but the real star is the drive back to the gardens. The mountains are beautiful and seem to rise up right in front of your vehicle. It closes at 4PM, but you don’t really need much time here so you could pop in for a bit before they close on your way to dinner.

Haleiwa Joe’s

I think this is the best spot for a nice dinner on Oahu and the place that’s probably most comparable to Mama’s Fish House on Maui (although still not in the same league). The location in Kaneohe (Haiku Gardens-not to be confused with the one that’s actually in Haleiwa) is one of the loveliest spots on Oahu, the food is delicious, and the atmosphere feels special but not pretentious. It’s a favorite spot with locals to celebrate special occasions.

They don’t take reservations, so be there when they open at 4:30 or be prepared to wait. If you just want drinks and pupus (appetizers), the bar area is first come first serve and has quite a few tables.

P.S. One of the reasons I’m able to travel to Hawaii so often is because I get free flights with my Southwest credit card AND I can fly someone with me for free with my Companion Pass.

I have this Southwest Premier Rapid Rewards Visa card through Chase. The current sign up offer is 50,000 points. Depending on where you live and fly from, that’s at least one completely FREE ticket to Hawaii and it could be two depending on the time of year (or more if you catch a crazy sale).

But the real pro travel hack is getting the Southwest Companion Pass.

If you acquire a certain amount of annual points with Southwest (either through flying or credit card spend), you get a companion pass where you can bring someone with you on every flight you take FOR FREE for the entire year. I can’t tell you how many thousands of dollars I save using this every year.

What makes this doable is that the sign up bonuses from Southwest credit cards goes towards the point requirement.

By far the quickest way to qualify for the companion pass is by signing up for a personal AND business card through Southwest.

**Besides being a business owner, if you’re self-employed, a freelancer or contractor, a gig economy worker, if you own rental properties, etc…you qualify for a business card.

And you’ll be most of the way towards qualifying for a Companion Pass PLUS you’ll have 110K points to book flights to Hawaii. That’s enough points to book 3-4 flights to Hawaii! AND you can take someone with you for FREE.

P.P.S. Here’s one more really important thing you need to know before your Hawaii trip…

You’ve got your airfare, hotel, rental car and your big activities booked, so you should be good to go, right? Wrong!

Travel is BOOMING in Hawaii and a lot of state and national parks have instituted reservation systems at some of the island’s most popular spots to help manage the crowds and make things a little more sustainable.

That means that there are now over half a dozen sites (beaches, trailheads, etc.) that require advance reservations. And some sell out well before you arrive on the island so you really need to have some sort of a plan.

I recently saw somebody in a Hawaii travel group post in a panic that they didn’t know they had to make reservations for things in advance…they thought they could just show up and “go with the flow.” I was tempted to say, well, “as long as the flow doesn’t take you somewhere that requires reservations, you can!” ; )

But I don’t want YOU to be that person, so I’ve pulled together a list of all the places you need to reserve entry in advance (plus all the details on booking windows, price, links, etc.) and a handful of popular tourist hotspots that book out really far in advance too.
Get that info >> HERE