5 Days on Oahu Itinerary

Heading to Oahu? We’re sharing a detailed 5 days on Oahu itinerary and guide filled with the best beaches, things to do, food and coffee, hikes, and so much more!

It’s no secret that we LOVE Hawaii. We have now been to the islands 6 times together and every time we have to force ourselves to leave, spend weeks (or months) sad that we left, and instantly begin planning another trip back.

During our second trip to Oahu (you can watch all of our Oahu vlogs here) we had the most incredible 5 days beach hopping, eating shave ice and acai bowls, going on sunrise and sunset adventures, soaking up tons of sunshine (it was our first ever Hawaii trip without an ounce of rain!), and so much more!

To hopefully make planning a trip to Oahu a bit easier for others, we’ve created a 5 days on Oahu guide filled with tips on where to stay and an itinerary for 5 days that will give you a good taste of what the island has to offer, especially if you’re limited on time (like us) or it’s your first time to Oahu. You could easily spend more than 5 days on Oahu, so we included a bunch of extra ideas if you have more time or just want more options!

A few disclaimers before we dive on in:

  • We craft our travel guides based on our experiences and a lot of research. With that said, we haven’t spent a ton of time on the Leeward Coast (West side) or Northeastern portion of the island, so there aren’t many spots in those areas included on our guide. However, we do have some suggestions in our “if you have extra time” section based on our research.
  • We absolutely love the North Shore and East Side of the island, so we are dedicating a lot of the guide to those regions.
  • We are not lay out at the beach all day type people. We like to spend our days doing a mix of beaches, hiking, eating, and exploring towns, so our guide definitely caters more to our busier travel style, but it still will give you tons of ideas even if you prefer to travel differently!
  • We have gotten some questions about leaving your items on the beach while you’re swimming. We aren’t the biggest ocean swimmers, so we tend to be on the beach most of the time, but we have had no issues leaving our belongings (and hiding valuables very well) when in the water and keeping an eye on it the whole time. Aloha Lockers is a great option at Waikiki to store your stuff for more peace of mind!

We hope you have a relaxing, magical, and adventurous trip to Oahu! If you have any questions about the island or our guide, please shoot us an email or send us a message on Instagram!

More Oahu guides:

Heading to the Big Island, Maui, or Kauai? Check out our other Hawaii guides:

Before embarking on your adventure, please review the Leave No Trace principles to ensure you leave every place better than you found it, so that others can enjoy these beautiful places for many years to come!

These seven principles include planning ahead and preparing, hiking and camping on durable surfaces, disposing of waste properly (pack out what you pack in!), understanding campfire rules and always fully extinguishing your fires, respecting wildlife, and being considerate of other visitors. 

Note: this blog contains affiliate links. Full disclosure– if you click on these links and make a purchase, we get a small commission at no extra cost to you. We will only ever recommend products we truly love, actually use during our adventures, and think you can benefit from too!

When to visit Oahu

While there is truly no bad time to visit Oahu, there are a few important things to know about both weather and crowds to help you decide when is the best time for you to visit!

Oahu weather

As you can see in the image above, the weather on Oahu is pretty dang perfect year round. We have visited Oahu in both November and June and the weather was incredible both times.

As it gets closer to your trip, you may notice the weather forecast says it’ll rain on Oahu…don’t panic! During almost every trip we have taken to the Hawaiian islands, typical weather websites would call for rain, but we ended up not having much (or any at all!) during all of our trips. And even if it does rain, it is usually just for a little bit and then it’s sunny again. 🙂

We found that the best weather website for Hawaii is Hawaii Weather Today. It will tell you the weather for different regions of the island, which is very important because the island is full of different ecosystems.

The Leeward side (West side) is the “dry” side of the island, whereas the Windward side (East side) is wetter and more lush. So just because it’s raining on one area doesn’t mean it’s raining in the other!

Oahu visitation
Photo Credit: Hawaii-Guide.com

One important thing to know about Oahu is that it is the busiest and most visited of the four main Hawaiian islands, so it will feel more crowded than the Maui, the Big Island, and Kauai. If you want to avoid some of the crowds, we’d suggest avoiding the summer and holidays. The island is much busier during these times of the year.

However, we have only visited during the summer and Thanksgiving and didn’t find the crowds to be that bad. But it definitely is busier than the other islands we have been to!

Getting to Oahu

The best (and only!) way to get to Oahu is to fly! Oahu is home to one airport, Daniel K. Inouye International Airport (HNL), which is located about 10 minutes from downtown Honolulu.

One of our favorite things about this airport is that it has tons of open air, outdoor spaces! So when you land you’re instantly greeted with that fresh Hawaiian air.

Where to stay on Oahu

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During our most recent trip to Oahu, we stayed in an Airbnb on the North Shore. We love the convenience of a kitchen and being able to cook meals (it helps us save a lot of money while traveling), as well as getting to stay in more local areas. 

However, since our visit, a lot has changed on the island with Airbnb. Oahu has passed a new law making Airbnb and other short term rentals illegal in many areas on Oahu (including our favorite areas–the North Shore and the East Side). 🙁 You can still rent an Airbnb in these areas, but for a minimum of 30 days.

What this means is that the only area on the island where short-term Airbnbs are legal is in Waikiki.

Regions of Oahu

Oahu Regions

There are four main areas that people will stay on Oahu: West side (Leeward Coast), Waikiki/Honolulu, East Side (Windward Coast), and North Shore.

Our favorite areas of the island are the North Shore and the East Side. These sides just feel more laid back to us and are close to some of the best beaches on the island!

There are not really hotels on this part of the island, but even with the Airbnb laws, there are still some options to stay in these areas, which we will cover below.

If you’re looking for convenience, Waikiki/Honolulu are your best bets, as the area is very central to the activities on this guide. Normally, our biggest advice in Oahu is to not stay at Waikiki.

While Waikiki is a super fun area, it is too busy and commercialized, in our opinion, if you’re wanting that true Hawaiian experience. However, with the change in Airbnb laws, it is the area with the most options of places to stay.

As long as you leave Waikiki most days to explore other parts of the island, you’ll still get to experience a more laid back Hawaii!

A great option if you’re looking for a family-friendly resort vibe away from the city is the West Side. The Ko Olina area on the West Side is one of our favorite areas of the island.

There are 4 resorts, including the Disney resort and two condo type resorts with kitchens, that give larger groups and families a great place to call home on the island.

The lagoons in this area are nice and calm, making it great for kids or for those who don’t want to get slammed by waves. There are also lots of restaurants and shops within walking distance, or a short drive.

Lodging Options

Here is a list of some lodging options for each of the four areas we covered above!

North Shore

Booking.com also has other options for condos on the North Shore!

East Side


PS: if it’s your first time booking on Airbnb, use our code to get $40 off!

West Side

Getting Around Oahu

Both times we have visited Oahu we have rented a car. We love having the flexibility to go anywhere we want during the day, especially because there is so much to explore on the island!

While this Oahu itinerary does include a bit of driving, the scenery while driving on Oahu is beautiful, so it goes by very quickly! We suggest turning on Da Pa’ina, rolling down the windows, and soaking up the views.

If you only plan to leave the area you are staying once or twice, there is Uber on Oahu. However, with how far some things can be, it may be pricier than renting a car for the day.

We recommend checking out Uber’s Fare Estimate tool to see what the costs would be and then decide if renting a car or Ubering is the best option for your budget.

Oahu Itinerary

In this Oahu itinerary we are splitting up the days by area so you can spend less time driving around the island all day and more time enjoying your trip! This itinerary is almost identical to how we spent our 5 days on Oahu, but you could definitely reorganize the days if needed to fit your trip.

Looking for other options of things to do and places to eat? Make sure to check out our “if you have extra time” section below!

Day 1: The North Shore

  1. Start the day with coffee at Brew & Foam. Make sure you try their coconut whipped cream!
  2. For breakfast, grab an acai bowl at Haleiwa Bowls. Bonus points if you take it to the beach!
  3. Spend the rest of the morning at Laniakea Beach, a gorgeous beach on the North Shore with beautiful views. If you’re lucky, you’ll see a sea turtle on the beach!
  4. After relaxing for a few hours, explore the town of Haleiwa! This area has a small town, surfer vibe and we love walking around the shops here.
  5. Grab lunch at Kono’s. We recommend their breakfast bomber or the pork lunch plate!
  6. Enjoy your first (of many) shave ice during the trip at Matsumoto Shave Ice. Don’t forget to get ice cream and a snow cap!
  7. Head to Kaena Point for sunset! Depending on how much time you have you can do the full hike, or just wander around for a bit.
  8. Heads up: a lot of spots close kind of early on the North Shore, but here are a few dinner options nearby or you can cook at your Airbnb!

Day 2: The North Shore

  1. Kick off the morning with a sunrise hike up to the Ehukai Pillbox! It’s a 2.1 mile roundtrip hike with a 675 ft elevation gain and great views of the North Shore!
  2. Fuel up after your hike at The Sunrise Shack. We LOVED this spot! We highly recommend getting their coconut bullet coffee (SO good, but very filling!)
  3. Spend the rest of the morning soaking up the sunshine at Waimea Bay. Warning: parking here is a nightmare, so make sure you get here early!
  4. For lunch, head to Ted’s Bakery (make sure to get some pie!) or Pupukea Grill (Note: Closed Mondays).
  5. Finish the day by relaxing and watching the sunset at Sunset Beach. Make sure to find the crooked palm tree!
  6. For dinner, check out a spot that you didn’t make it to yesterday or you can cook at your Airbnb!

Day 3: Honolulu

  1. First things first: COFFEE! Head to Ali’i Coffee or Olive & Oliver for some caffeine for the day. (Note: Ali’i Coffee is closed on Sundays)
  2. Now that you’re awake and caffeinated, it’s time for a sugar rush at Leonard’s Bakery. Leonard’s is famous for its malasadas and WOW they are good! So good that Kathryn cheated on her gluten free diet (which she NEVER does) in order to try a couple bites…and it was totally worth it.
    1. If you want a more traditional breakfast, head to Sweet E’s Cafe or Joe’s Grill Express, which is a hole in the wall, affordable spot with amazing breakfasts (so we hear).
  3. You may have just eaten a whole box of malasadas and that’s ok! Next stop: Hiking to the top of Diamond Head. This 1.8 mile round trip hike gains 452 feet and has some crazy awesome views of Honolulu and the East Side. It’s $5 to park (cash only) and it gets really busy and hot, so plan to arrive early!
  4. After hiking Diamond Head, grab a Hawaiian lunch! Here are some good options:
    1. Ono Seafood (Note: Only open Tuesday-Saturday)
    2. Helena’s Hawaiian Food (Note: Only open Tuesday-Friday)
    3. Rainbow Drive-In
    4. Alicia’s Market (Note: Closed Sundays)
  5. Make sure you save some room for shave ice! Head to Waiola Shave Ice to experience some of the softest shave ice we have ever had. As always, make sure to get ice cream and a snow cap!
  6. After eating tons of delicious food and going for a hike, it’s time to relax at Waikiki Beach. This beach, with its view of Diamond Head, is iconic and while very busy, you have to experience it while on Oahu! Make sure to stay for sunset!
  7. Finish the day with our Hawaiian tradition: dinner at Duke’s! We recommend eating at their barefoot bar (cheaper, less fancy food) overlooking the beach. Their salad bar is awesome too! And if you aren’t sugar-ed out from the day, get the hula pie.

Day 4: The East Side

  1. Get up bright and early to do a sunrise hike up to Lanikai Pillboxes. Wow, the view from this spot at sunrise is absolutely breathtaking! Make sure to bring a headlamp! Also, parking can be tough (it’s in a residential area), so please be mindful of signs and the residents. Read our detailed guide to hiking to the Lanikai Pillboxes!
  2. After seeing an amazing sunrise, enjoy breakfast at Over Easy in Kailua. Or if you’re craving another acai bowls (which is totally normal!), check out Makai Bowls. (Note: closed on Sundays)
  3. Next, head to ChadLou’s Coffee Roasters for some coffee. We loved their Ice Grinds, but warning, it has ice cream in it, so it’s more like dessert!
  4. Admire the views at the Nu’uanu Pali Lookout. It’s $3 to park and a quick stop, but the views are gorgeous!
  5. Go chase waterfalls at Lulumahu Falls. This hike is technically government property and trespassing without a permit. Most people don’t get a permit, but it’s only $2.50 and super easy to get, so we recommend getting one to be safe. Also, this trail can be a bit confusing, but follow the pink markers on the trees and the stream and you’ll eventually find it. We recommend packing a lunch to enjoy before or after the falls.
  6. Head back to Kailua to the Obama family’s favorite shave ice spot: Island Snow. They also have mac nut ice cream here…score!
  7. After a busy morning and afternoon, spend the rest of the day relaxing at Lanikai Beach.
  8. For dinner, check out Kalapawai Cafe & Deli in Kailua!

Day 5: The Southeast Side

  1. Start the morning with a beautiful sunrise at the top of Koko Head Crater. The trail to the top is a leg burner with 1,048 railroad ties (stairs) you have to go up, but the pain is totally worth it for the views. Make sure to bring a head lamp! Read our detailed guide to hiking the Koko Head Stairs!
  2. After a killer workout, grab breakfast and coffee at Island Brew Coffeehouse.
  3. Spend the rest of the morning snorkeling at Hanauma Bay. This is a gorgeous bay that is famous for being the best snorkeling spot on the island. It gets very, very busy and parking can be rough, so be prepared! You also have to pay $12 a person to enter, as well as watch a video on marine life and preservation. (Note: Hanauma Bay is closed on Tuesdays)
  4. Drive up the road to Halona Beach Cove, which is a beautiful cove you can hike down to that has been the backdrop for Pirates of the Caribbean, 50 First Dates, and an Elvis music video. There’s a cool cave at the beach and also a blowhole you can view from the parking area.
  5. Continue up the road a little bit to the Makapu’u Lookout. 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. We also recommend packing a lunch to eat while you’re there!
  6. Spend the rest of the day at Makapu’u Beach or Waimanalo Beach.
  7. For dinner, either make a homemade meal at your condo or check out one of the spots in our “if you have extra time” section.
  8. Cry because you have to leave Hawaii 🙁

If you have extra time…





  • Pretend you’re at Jurassic Park at Kualoa Ranch! You can do ATV tours, horseback tours, kayaking tours, a film and TV tour, and SO much more here!
  • If you’re a golf lover, play a cheap 9 holes along the ocean at Kahuku Golf Course. It’s not a glamorous golf course, but you can’t beat the price and views!
  • Check out the Kailua Farmers Market (They have two Farmers Markets–one on Thursday nights and one on Sunday mornings)
  • Tour Kahuku Farms and also grab a smoothie from their cafe!
  • Enjoy the lagoons at Ko Olina. We love this area–make sure to grab a Dole whip at the Disney resort!
  • Lay out at Makua Beach or Makaha Beach on the West side! These would be great beaches to combine with Ko Olina!
  • Visit Pearl Harbor: We have yet to visit Pearl Harbor and really want to, but just haven’t had enough time. (Note: The USS Arizona memorial is closed until March 2019, but you can still visit other areas–see status here)
  • Go on a helicopter tour! Kathryn’s brother did this on our first trip to Oahu and it looked like so much fun!
  • View the island from new heights by going skydiving! Kathryn’s other brother did this on our first trip to Oahu and the video and photos were INSANE!
  • Learn how to surf at Waikiki
  • Spend an evening at a luau! There are so many to choose from, but we would highly recommend Toa Luau or Experience Nutridge for the cultural experience.
  • Visit the Iolani Palace in Honolulu

There are many amazing hikes on Hawaii, some of which are private property. Since we are big rule followers, we are only including trails that are legal to hike.

Dreaming of a Hawaiian getaway?

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about us

Hi y’all! We’re Adam, Kathryn, and Kona, an adventurous married couple (+ pup!) living on the road in our self-converted sprinter van! You can often find us driving all around the US and Canada, scoping out the best coffee shops, eating tacos and ice cream (we’re a 5+ taco and 2+ scoop household), and enjoying nature.


affilliate disclosure

This website contains affiliate links from websites such as MileValue.com, Amazon.com, Booking.com, and Rentalcars.com. If you use the links provided and make a purchase, we get a small commission at no extra cost to you. This compensation may impact how and where links appear on this site. This site does not include all financial companies or all available financial offers. We only recommend products we truly love, actually use during our adventures, and think you can benefit from too!


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  1. Suzanne

    What a FUN trip…as always…reading your blog really makes me want to go and explore Oahu! Of course, I would want ya’ll to come with me to make sure I do and see all of these incredible places and more! When I say more…it would be great to go for 10 days! ? Thank you for making it possible for me to travel through you! ?☀️???‍♀️?

    • Kathryn Frazer

      10 days or a month or forever sounds good to us! ? We’re so glad you enjoyed the guide! ?

  2. Camille Nankissore

    Thank you for the tips! Did you go to a luau?

    • Kathryn Frazer

      You’re so welcome! We did not go to a luau on Oahu, but we have been to one on Maui and they are SO fun!

  3. Alexandra Mejia

    The pictures look absolutely breathtaking! Thank you for providing so many tips 🙂
    If you don’t mind me asking, how much would you say you guys spent on food? My sister and I are heading there in a couple months and I’m not sure how much to take…

    • Kathryn Frazer

      Hi Alexandra! You’re so welcome! 😀 According to my budget doc, we spent $467 on food AND groceries for 5 days, but that was for two of us. Also, we tend to eat more than the average human lol!

  4. Adriana

    I’m so happy that I found you right before our trip! Can you give any advice on activities for kids? We are staying in Waikiki, but are totally willing to rent a car and venture out.. thanks in advance 🙂

    • Kathryn Frazer

      Hi Adriana! We’re so glad you did too! 🙂 I am not sure how old your kiddos are, but Ko Olina is a GREAT spot for kids. The beach there is protected from waves, so it’s very calm for swimming. And bonus—the Disney resort is there too! Depending on your kids ages, the Lanikai Pillbox hike is likely doable. We saw small kids on that trail. You may have to help the up in a few spots but it’s not that bad at all! Diamondhead is also a great hike for kids. It’s not flat, but very well maintained. Waimea Valley has a beautiful waterfall and the path to it is super easy for all ages too! There’s also Kualoa Ranch, which is where a lot of movies have been filmed and they have some fun activities there for all ages. I hope that helps a bit! Let us know if you have any other questions!

      • Adriana

        Thanks Kathryn! My son is 8 and daughter is 6. We are super excited, but also a little bummed about the hurricanes bringing rain and thunderstorms 🙁 But, it’s all good. We’ll make the best of it!!!

        • Kathryn Frazer

          Oh no! We hadn’t even heard about the hurricane! If it makes you feel any better, when we honeymooned in Maui almost 5 years ago there was a hurricane (it got downgraded to a tropical storm) and we still had a blast! We used the rainy days as our walk around and shop days or tried to find an indoor activity. We hope the weather is decent for y’all!

  5. Paulette

    Do you know if Haunama Bay is still closed? When i look online it appears to be open.
    Thank you!

    • Kathryn Frazer

      Thank you so much for asking this! I had seen it had opened back up and meant to update this, but forgot!

  6. Tabitha

    This is really a well written article. thank you – my family will travel to Hawaii in 2020 and this just helped so much. thank you for your time.

    • Kathryn Frazer

      We’re so glad to hear that Tabitha! Thank you for reading and let us know if you have any questions before you go!

  7. Lidia

    What accommodations do you recommend in the East Side?

    • Kathryn Frazer

      Hi Lidia! There aren’t any hotels (to our knowledge) on the East Side and we used to have a bunch of East Side Airbnbs on this blog post, which would’ve been our top pick, but with the new Airbnb regulations on Oahu, the only legal Airbnbs are in Waikiki. However, you can still legally rent some condos through Booking.com and VRBO on the East Side (some do require a minimum 30 day stay). Here are some of our top picks!

      Option #1
      Option #2
      Option #3
      Option #4

      I hope this helps a bit! If you prefer a hotel experience, Turtle Bay on the North Shore is great! Also, Waikiki would be a good option. Although it is a bit busier to stay in Waikiki, it does have a lot of amenities and activities nearby and some really nice hotels and Airbnbs!

      I need update the blog post with these options, so thank you so much for reminding me to do so!

  8. Brittney

    Thank you so much! I based my entire weeklong stay on this blog post and it’s been amazing. I even found some other places I loved along the way. ?

    • Kathryn Frazer

      No way! That makes us so happy that this guide was able to help you plan your trip! What other spots have you loved?

  9. LOANN


    • Kathryn Frazer

      Hi Loann! So happy you found our guide helpful! A couple ideas of things to do would be to go north towards Kahana Beach or Turtle Bay and relax a bit (we recommend Seven Brothers for lunch up that way or Giovanni’s Shrimp) or you could go south towards Kailua and visit the The Byodo-In Temple, Lanikai or Kailua Beach, the Lanikai Pillboxes , and Island Snow for shave ice!

      There is also Kualoa Regional Park right by Kualoa Ranch! Hopefully that gives you a few ideas!

  10. Maddy

    This is super comprehensive! I am traveling with 3 friends but none of us can drive- do you recommend uber/public transport?

    • Kathryn Frazer

      Hi Maddy! You could definitely Uber. It would possibly cost a decent amount of money depending on where you’re staying and where you want to go, but if you’re staying in Honolulu/Waikiki, you can get to quite a few areas in a pretty short drive. The North Shore (our fav!) is accessible by bus, which would definitely be cheaper than Uber! We haven’t taken the busses there, but have had great experiences in many cities with public transportation!

  11. Jo

    Your blog is fire!!! This is the perfect blog. Thank you so so much for sharing this with the rest of the world. I’m definitely going to be trying these for my trip 🙂

    • Kathryn Frazer

      Thank you so much Jo, we are glad you enjoy it!

  12. Debbie

    Thank you so much for this blog. My husband and I just returned from a trip to Oahu (to visit our son and his family) and I used your videos and itinerary to make a list of must-see places. While there we all flew to Kona, rented a vehicle, and drove to Hawaii Volcanoes National Park where we were able to stay for several days while exploring the Big Island. We visited many of the same places you have listed. We particularly enjoyed seeing the glow of Kilauea erupting at night and hiking Kilauea Iki Crater and the Nahuku Lava Tube. The beaches and waterfalls were amazing on both islands, as well as the majestic mountains. I really enjoyed hiking to Kaena Point where we saw monk seals, Laniakea Beachand and the sea turtles, and the awesome views of the Pacific from Makapu’u Point and the Halona Blowholes.

    Again, thanks so much for all the work you do in preparing these wonderful guides.

    • Kathryn Frazer

      That sounds like such an incredible trip! We’re especially jealous of the volcano erupting! Thank you so much for letting us know how your trip went and we’re glad we could help out in some way!


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