Travel Guide: Oahu, Hawaii

Good morning and happy ALMOST Friday, friends! I’m back today with my Travel Guide to OAHU, Hawaii! My family visited Oahu over Christmas – I’m rounding up the outfits I wore first, but scroll down to the bottom for my full review!

Tularosa bikini top // bikini bottoms // gold necklaces // self-tanner (in “dark)

The below photo was taken at our hotel, the Royal Hawaiian. I just loved all the pink umbrellas and beach towels dotting the landscape!

Nina bikini top // Thessy bottom (this bikini comes in a bunch more colors! See more here)

The view from our hotel pool. We had to save beach chairs at 6 a.m. every morning because they’re first-come, first-serve!

floral print bikini top // bikini bottoms // pom pom bag // Dior sunglasses

blue polka dot dress

My mom and I with are floats 🙂 As you can see, Waikiki Beach does get a bit crowded!

on my mom: Vince Camuto swimsuit // on me: bikini top // bikini bottoms // Dior sunglasses

My new sandals that I brought with me on the trip!

floral print cover-up // “Greece” sandals

floral print cover-up // “Greece” sandals

The view from Lanikai Pillbox Hike – it was INCREDIBLE, however it was a pretty scary climb!

Tularosa Frances dress

Lunch at ARVO – we were dying to find some avocado toast on the island!

PilyQ white dress // pom pom bag // Dior sunglasses

My whole family usually goes somewhere fun for Christmas, and the past couple of years we went to Lake Tahoe (a winter wonderland!). This year we wanted to stay somewhere a little warmer, and Hawaii seemed like the natural choice: it had been on our bucket list forever, it’s always warm, and you don’t even need your passport! I did a ton of research to figure out which island we should stay on, and finally ended up with Oahu! It seemed like there was the most to do in Oahu, and you can explore pretty much the entire island by car since it’s only a couple hours drive from top to bottom.

Where to Stay

THE ROYAL HAWAIIAN: We stayed at the Royal Hawaiian and LOVED it! Just a short drive from the airport and located in the heart of Waikiki, this historic hotel is also known as the “Pink Palace of the Pacific.” It literally is a huge pink palace, with tall ceilings and elegant decor, plus the wafting smell of gardenia wherever you go and a common “pink” theme throughout (even our hotel robes were pink!). We stayed in the Historic Building – the rooms were spacious, comfortable and decorated with beautiful Hawaiian prints. If we go back, we would probably choose to stay in the “Tower” since those rooms offer a beautiful view of the ocean and Diamondhead (and our rooms offered a garden view). One of our favorite parts about the hotel was breakfast! The breakfast buffet at Surf Lanai was out of this world, with all kinds of breakfast favorites mixed in with traditional Japanese food. My husband said that the breakfast was better than any trip we’ve ever gone on, even our honeymoon! The Royal Hawaiian also had a nice pool (the chairs are first come first serve, so we alternated waking up at 6 a.m. to go save our pool chairs). You can also pay to reserve beach chairs for the day, but you’ll want to book them in advance because the spots fill up quickly! Although we did drive around and explore Oahu, we spent three really lazy days at our hotel just lounging at the pool or by the beach. My husband and brother rented surfboards one day and attempted to surf, while I floated in the ocean or read my book. Overall, we really loved our hotel, we found it charming and elegant, while the service was amazing. The only downside, I would say, is not a critique of the hotel itself but rather Waikiki – and that is, the entire area is SUPER crowded and touristy. Whenever we wanted something to eat, our options were to eat at our hotel, or go to one of the many chain restaurants nearby. While the Royal Hawaiian felt very authentic to Hawaii, the surrounding stores, restaurant chains and crowds of tourists did not.

AN AIRBNB: Now that I know more about Oahu and have visited once, I would probably choose to stay in an Airbnb if I returned to Hawaii. My very favorite part about Oahu was actually the North Shore – the beaches are breathtaking, it’s a lot less crowded, and there are no huge high-rises dotting the landscape. Instead, there are neighborhoods and cute little beach houses, mixed in with food trucks selling delicious cups of coffee along with acai bowls made with real acai. You could also rent an Airbnb at Lanikai Beach, names one of the top three prettiest beaches in the world. My brother and I went one morning to check it out, and it is gorgeous, with soft white sand, clear water and a couple of visible islands in the distance. It’s also a residential area, so it’s free of hotels and the throngs of tourists.

What To Do

  • Visit the Botanical Gardens: The Ho’omaluhia Botanical Gardens are only a 30-minute drive from Waikiki, and absolutely beautiful. There are 400 acres of tropical plants along with a man-made freshwater lake, hiking trails and a campground, all for free. Definitely bring your camera! You’ve probably already seen pictures of the gardens on Instagram without realizing it.
  • Visit the North Shore: The North Shore is absolutely gorgeous and definitely worth seeing. During the winter, the biggest waves are at the North Shore, so of course, it’s where all the surfers hang out! We set up camp on one of the beaches and then watched surfers catch waves. Be sure to visit the Sunrise Shack while you’re there, as well as head into Haleiwa for more food trucks and little shops. We heard the best shaved ice on the entire island is in Haleiwa, called Matsumoto. Nearby is a little cluster of food trucks including Crispy Grindz, where I had the best acai bowl of my entire life!
  • Lanikai Beach: Lanikai Beach has been voted one of the top beaches in the world, and I can definitely see why! If you want to visit the beach, you’ll have to park along the street in a neighborhood, so I would recommend going early in the morning (and be prepared to parallel park!). It seemed like a great place to rent an Airbnb, too – it’s a residential area but there are some little shops and restaurants nearby, even a Whole Foods!
  • Try surfing: Pretty much every hotel in Waikiki offers surfing lessons, or you can rent a surfboard and try it out on your own. There were plenty of people surfing right outside of our hotel, and some of them were pretty talented! My husband and brother tried it, and said it was much harder than it looks, although both of them did manage to get up on the board and catch a wave!
  • Hike: There are tons of hikes to do in Oahu. We did the Lanikai Pillbox hike – there’s an old WWII bunker at the top with an amazing view. Overall, it’s a pretty short hike, but it is pretty strenuous. It was a little frightening on the way back – you are climbing down a really steep incline and the mud was slippery. All of us almost fell at least once! (Definitely don’t hike any of the mountains if there’s a chance of rain.) The other hike we really wanted to do was Crouching Lion – but that one is even more intense!
  • Shop: Although I did complain a bit about how touristy the Waikiki area, it is home to some amazing shopping. Gucci, Dior, Louis Vuitton, Chanel and other high-end stores line the streets, along with more affordable beach stores and boutiques. One store we went to over and over again was the ABC Store, which was more like a general store in Hawaii. There was one right next to the hotel, so we went a lot to pick up bottled water, bandaids, and other random stuff.
  • Explore! There is SO much to do in Oahu, you could keep busy for a month! The North, West, South and East side of the island are all pretty different and each boast their own beautiful beaches, hikes and attractions. You could hike Diamondhead (a dormant volcano), visit Pearl Harbor, hit up Hanauma Bay (a nature preserve with a beach and turtles), zipline at Kualoa Ranch, or simply spend all day at your hotel soaking up rays by the pool. The cool part is that you can tailor your Hawaii vacation to you and your family’s needs/wants. We chose to relax half of the time, and explore the other half!

One last thing, is that I would definitely recommend renting a car if you come to Oahu. You will probably want to get around the island while you’re there. You could rely on Uber, but that would be a lot more expensive! I used this website to find a jeep rental in Oahu – nothing feels cooler than riding around Hawaii in a jeep, hhaha! We didn’t take the top off of ours, but it was still really fun. Overall, I would 100% recommend Oahu for your next vacation!

If you have any questions about Oahu, let me know in the comments! You can check out my other travel guides HERE. xoxo

Leave a Comment


  1. Such pretty pictures! I’ve always dreamed of going to Hawaii – hope to go sometime soon!


  2. Diane

    We love Oahu! Of course, it doesn’t hurt that we have family stationed there with the Army. We’ve been lucky enough to visit several times in the past few years and hope to return at least once more before they return stateside. Did you try a Mai Tai at the Pink Palace? It’s supposedly where the drink was invented. It has been fun comparing all the places that claim that honor. I agree about the crowds in Waikiki, but it is still lovely. We’ve also done the Airbnb on the North Shore. You can definitely find your “thing” somewhere on the island. On our first trip we drove the circumference of the island and just stopped to explore when we saw something interesting or for fresh pineapple, macadamia nuts, amazing coffee, and the list goes on. Can’t wait to get back!

  3. Loved this! It’s my dream to visit Hawaii one day, thanks for the great guide Cait!

    I hope you have a wonderful Thursday,


  4. Laura Leigh

    Looks and sounds like an absolute dream! My in-laws are heading there next week so I am sending this their way! Love every single one of your swimsuits gal!

    xo Laura Leigh
    Louella Reese

  5. Aww, now I want to go back to Hawaii! We stopped in Honolulu for three days on our way back from Australia a few years ago – spent the Fourth of July at Pearl Harbor then watched the fireworks on Waikiki Beach! Great memories!

  6. Tes, I was waiting for this travel guide! Oahu Looks and Sounds gorgeous and Hawaii has Been on my bucket List forever. The swimwear you Wore is too cute and I wish it was a Little Bit warmer Right now haha – i am such a Summer Child!
    Xx Janine

  7. The picture with the white dress is breathtaking! I see it is simply a dream there!
    xx from Bavaria/Germany, Rena

  8. Jessi

    Hello there! Where did you find your high waisted jean shorts (2nd pic from top)? I love them!

  9. Trish

    Thanks for these! My husband and I want to go to Europe – specifically England, France, and Italy – this spring and have no clue where to start with housing, destinations, etc. I saw you were recently in England and being so well traveled, in general, do you have any tips and/or must-see’s?

    • Kate

      @Trish, my mom and I travel to Europe almost annually. We’ve found that sites like HomeAway, FlipKey and Airbnb are your best bets for room and board. We also pick a home base and then travel from there using public transportation (trains & buses, mostly). I would suggest the French Riviera, Cinque Terre, and Amalfi Coast, to get started. Flights between cities in Europe are very cheap, so flying from Paris to the French Riviera may be 50 euros one way. We’ve also used GateOne Travel and Viking River Cruises to plan everything, and all we had to do was show up. I hope this helps!

  10. Hawaii is so amazing!

    || The Neon Factor, by Diana 🦄 ||

  11. Olivia Schueller

    Beautiful pictures!! So jealous.

  12. Catherine

    I got engaged in Kauai! Definitely try to visit there or Maui next! I think they are even more stunning than Oahu, if that is possible! Love all the cute swim suits!

  13. Samantha

    This is so cute!! I looks like you had a blast!!

  14. The second last photo of you is completely stunning – but also – oh my goodness it gives me the scaries too! GET BACK FROM THE LEDGE! 😉

    Rebecca |

  15. Michelle

    We’ve stayed in Honolulu a couple of times. It’s fun but too busy fir me when I’m on. Aviation. We love Maui and have stayed there several time – more relaxing and low key.

  16. So much fun! You look really pretty in your first swimsuit the best!


  17. Elena F

    Heading to Oahu in Monday. This was helpful. We’re staying at an Airbnb and renting a car and hopefully we’ll get to learn more about their culture that way, hotels like you said are where the tourist are and hotels just show what they want to show about the culture of the place. Love your outfits!

  18. These photos are so cute!! Love that first one of you and Chris in the water <3

  19. Hawaii is high on my list to see! Totally saving this guide!

  20. What a beautiful place! Loved all your insta pics you were sharing while there and here. I haven’t been to Hawaii yet but I will definitely remember this post when planning! Thanks for the guide 🙂

    Amanda @ Cupcake N Dreams

  21. Kate

    There’s also zip lining on the North Shore. My mom, who is 70, and I did that in August 2018, and it was absolutely amazing with beautiful views of the North Shore and the mountains. ClimbWorks was the name of the zip lining company. I highly suggest zip lining on Oahu!!

  22. Lauren

    Hi Caitlin! We just got back from a New Years trip to Hawaii too! Except instead of going to Oahu, we went to the big island and stayed on the west side of the island at a VRBO condo resort 18 miles north of the Kona airport. If you are looking to go back to Hawaii ever, I would HIGHLY recommend the big island! I think Maui and Oahu are very popular right now so they get a ton of tourist activity….the big island is A LOT quieter and has very few chain anything! The VRBO we stayed at was a 3 bedroom, 3 bathroom condo with a FULL kitchen and two lanais and was right on the ocean with a restaurant and salt water pool. It was truly incredible for 6 adults (2 couples and my siblings) staying together. There is TONS to do on the big island too. Hapuna State Park is rated one of the best beaches in the world and it was gorgeous….sounds a LOT like Lanaiki beach on Oahu. There’s also tons of hiking to see waterfalls, Volcano National Park, star gazing on Mauna Kea, surfing (my brother and sister took lessons), snorkeling and coffee plantation tours! The best part of all of it was the no crowds….it truly felt like we were residents of the island and really got to enjoy the natural beauty without having to shove past people or be anywhere to early for fear of missing out on something! I can’t recommend the big island enough for a return trip!!

  23. Alaina

    Thank you for this post! We are spending a week in Oahu in May. Safe to say that the Lanikai hike would not be suitable for a 3 year old? Loved that picture.

  24. Lovely!!!!

  25. Nice review. I used to live on Oahu and agree with most of your recommendations. I’m partial to Honolulu personally though- I love the city-on-an-Island feel but how close it is to Kailua side for the day.

    Fifteen Minutes to Flawless

  26. Jor

    Pictures are beautiful, I saw the camera you have is canon 5D mark iii, can I ask what lenses you recommend? I just had a baby last year, and are looking for good portrait camera/lenses

  27. Obsessed!! Amazing review & can’t wait to plan a trip to Hawaii.
    Love reading all your travel guides – always an amazing job!

  28. Hawaii is on my bucket list too! I love to hike and always up for adventure so even more excited to go after reading this post!

  29. Ashley

    Hawaii looks absolutely breathtaking! It’s definitely on my bucket list to visit someday. It looks like you had an amazing time and all of your outfits were gorgeous! Stunning Cailtin!


  30. Hi dear, loved your pictures! I have been on Oahu as well in November. We had such a good time 🙂 Shared a travel guide as well 🙂 loved to see your pictures!!!! makes me wanna go back quickly :)) xx

  31. Oh wow what a gorgeous spot! Also that photo on that roof edge 😛 gosh.

  32. fancyrock

    I’m going to Oahu next week — all your tips are great! (Although I bet I will have a slightly different experience than you had, considering as how my husband and I will be taking our 6 kids along….) :o)

  33. If you did research on Hawaii and had to recommend to go for your Honeymoon, would it be Oahu? We’re going to Hawaii for our Honeymoon but I’m unsure which island! I’ll do more research but I love how I can refer back to your post when it comes to deciding where.

    @happilyeveralanis | Happily Ever Alanis

  34. Aimee Leisenring

    Beautiful photos! I currently live on Kauai and as some people have already mentioned, the tourism is waaaay less here. The beaches are not as crowded, the hotels are absolutely stunning and beauty is everywhere! It’s a very low key relaxed island, I highly recommended visiting for a non-high paced vacation. Spring is especially beautiful since all the plants and plumerias trees are in bloom!

    Xo Aimee

  35. Catherine

    Would you say the “greece” slides run true to size?

  36. Hi Caitlin,
    Thank you for all the info and beautiful photos that you’ve shared 🙂
    I heard that Airbnb is not legal in Hawaii but you recommend one? And is car a must in the island?
    Thank you in advence,

  37. Catherine Diloreto

    Which company did you use for your keep rental? I checked the website and it list several options. Heard some companies were a nightmare in HI so thought I would ask since you rented from there recently. Thank you So much!