Aloha 🙂
Unlike many other places that I have traveled to before, Hawaii has made a special & lasting imprint in my heart. After visiting the beautiful & enchanting island of O’ahu, I fully understand why two of my cousins have decided to make Hawaii their home state.
Apart from the breathtaking views, and the immense amount of lush greenery everywhere, the people-the Hawaiians, also impacted this lasting impression. Prior to visiting Hawaii, I spent time learning about the history behind the islands, and I was quickly angered and able to relate to some of the injustices that were brought upon Hawaiians. I was reminded of the injustices that my ancestors experienced as a both black and Cherokee people. I share all of this because I am a firm believer of learning about the culture and the history of any destination that you are traveling to. Choosing to watch a documentary, or planning to visit a museum that specifically teaches on the culture, is important to do as it’ll eliminate ignorant traveling.
If you’re desiring to adventure off to Hawaii, or hope to immerse yourself into one of the most beautiful locations within the U.S., then keep reading for a day by day ‘Four Day Travel Guide to O’ahu’.
Within this travel guide, I am going to share some popular must do things (I promise that they won’t be cheesy), and then a few activities that were shared by a local (my cousin).
Hawaii also has INCREDIBLE food, so if you’re a foodie like myself, then prepare to discover some of the best places to eat as well. If you’re hoping for more food images, check out my Instagram and review my ‘Oahu’ highlight for full plate pictures, and the tagged restaurants.
Where to Stay:
One of my least favorite things to do when exploring a popular place, is being amongst other tourists. I know- high risk of sounding ridiculous here- but I really do want to get a local’s lifestyle as much as I can. When traveling, I try to find a hotel that is not in a tourist hot spot, but visiting O’ahu made this a little difficult. Thankfully, I was able to stay one night in Kaneohe, which gave me the chance to be secluded from all of the tourism and immersed into life as a local. We spent the rest of our time in Waikiki, at the Aston Waikiki Beach hotel.
As you research the best accommodations for your budget & preference, you will quickly realize that most of the hotels are located in Honolulu, HI. From what I have been told, this has been done purposely, and there are limited option for Airbnb’s. Yet of course, there are some exceptions, and I stumbled across a few places away from all of the craziness in Waikiki (Honolulu).
Less crowded resorts & hotels-
Paradise Bay Resort in Kailua (I am planning to stay here next time)
Turtle Bay Resort in North Shore
Courtyard by Marriott in North Shore
If you’re patient or even desire to be amongst all of the other travelers on their vacation, here are a few locations in downtown O’ahu, also known as Waikiki-
Aston Waikiki Beach Hotel (the pic below is featured on our Ocean King room balcony)
Another incredible idea is to find an Airbnb located on the north or the east side of the island.
What to Pack:
Hawaii is probably one of the easiest places to pack for when taking your four day vacation. If you have been to an island before, or the tropics, then you already know exactly what I am referring to. Here is exactly what I packed and what I recommend on this four day travel guide-
Beach Gear & Attire-
Swimsuits- Pack at least two to four swimsuits, and a few cover up’s to go with it.
Towels- Double check to see if your hotel will provide beach towels, and if they don’t bring some with you.
Swim shoes- This is important if you want to NOT step on random shit in the ocean. Most of the beaches have clear water, but there are a few that you’ll want swim shoes for.
Speaker- Of course pack your speaker for good music while on the beach.
Waterproof bag- We actually got rained on while in the ocean (it was MAGICAL), so bring a waterproof bag to protect your gear.
Sunglasses & goggles- If you want to be a little mermaid in the ocean, bring goggles. You will LOVE being able to see the beautiful ocean.
Sunscreen- Hawaii sun is no joke. Load up & bring the sunscreen with you.
Snacks- Yes, you will find food along the way or even afterwards, but I wish that I packed some snacks because I ended up leaving the beach due to being hungry 🙁
Toiletries- For after your quick beach shower, and while you’re in there, you will need toiletires Pack sanitizer, deodorant, baby wipes, a dry towel, and some body spray.
Change of clothes- Your adventure will not stop at the beach. Bring clothes to change into so that you don’t have to go back to the hotel.
Miraflora CBD– YES, please grab some Miraflora CBD Immunity gummies. I personally got thrown around in the waves and had I not brought these gummies with me, I would have been SO sore. It was also nice to have another source of immunity protector with me 🙂
Other Outfits & Things to Bring-
Camera gear- if you can buy a drone ahead of time, please do so. This is my major regret 🙁 I would also recommend a GoPro so that you can film underwater and on hikes. And of course, your vlogging camera 🙂 you will absolutely want to capture your memories here.
Dresses- bring at least 2-3 dresses with you, one being your cocktail (sexy) dress, and the other two being selections that you can easily dress up or down. You will have at least one night where you have a bougjie dinner, and need to match the vibe.
Athletic wear- PACK IT ALL. A lot of the activities are being spent outside. If you’re traveling to Hawaii and wanting indoor entertainment, book elsewhere. You will spend a majority of your trip outside, and most of that involves being active. So pack your cutest athletic fits and biker shorts.
Sneakers & sandals- Bringing both is crucial. When at the beach, you want sandals as they won’t capture a lot of the sand (a pain to clean out of your rental car btw). You will also want some sneakers and/or hiking shoes for the trails that are worth hiking.
Negative COVID test or vaccination card- Without either one of these, you will NOT be entering that plane to Hawaii. For more information on the travel requirements, visit https://hawaiicovid19.com/ and please follow every last instruction on it.
Day One:
Kailua: Close to where my cousin lives, this is a residential area which means you will not see tons of tourists over here. I would recommend the following for day one, as they are all within this area.
Breakfast at Boots & Kimo’s– this is the best breakfast that I have had in a LONG time. Get here early as the wait can get long.
Leonard’s Bakery Malasada truck– You can’t say you went to O’ahu and not try Leonard’s Bakery. Rather than wait in Waikiki for Leonard’s bakery, stop by the truck to get the same options without the long line.
Morning Glass Coffee at Key Project– Grab coffee from this place but also their breakfast burrito. They have the BEST burrito.
Ho’Omaliuah Botanical Garden- Featured as the background in the picture above with myself and the pineapple, this place is MAGNIFICENT. You will be so in awe with how lush the mountains are, and the beauty of nature meets you as you’re driving by the garden.
Hike at Nu’uanu Pali State Park- After going through the botanical gardens, squeeze in a hike to soak in some of the best coastal cliff views.
Dinner in Waikiki: Head back to your hotel to change, and to get ready for a fun night in Waikiki. I would start off with dinner and then go for a walk or a drive in Waikiki for your first night in O’ahu.
Hula Grill- This is a perfect time to bring out one of your cute cocktail dresses, and ask for a waterfront table. We had the best sunset view of the ocean front, while eating really incredible food. I’d also try their Honey Nut Shrimp to start with- it was SO good.
Day Two:
For day two, you will drive around a bit, yet stay within a 20 min proximity to the areas listed below.
Honolulu Coffee- Start your morning by grabbing coffee and an almond croissant (SO GOOD) from Honolulu Coffee. I’d also grab a water bottle, because a quick hike is next 🙂
Lanikai beach & pillbox hike– While we weren’t able to hike the 1.6 mile pillbox trail, we recommend that you try to do so if you can. From what I have seen, the views are amazing, yet this is a well known hike so you can anticipate crowds. The beach is also a popular area, with many people choosing this beach to relax at.
Makapu’u tide-pools and beach- Surprisingly, a lot of people weren’t at this beach or the tide-pools. This made me SO happy. I was also so intrigued by the ocean, that I didn’t want to leave. The picture above was taken from my iPhone, and it is unedited. Gorgeous right!? Another must do thing is to take a swim in the tide-pools. Just know that you will need to be safe, as the current from the waves can be strong.
Waimanalo Bay- While I wasn’t really a fan of this area (the waves were so crazy), it is perfect if you want to bring your family as there are a TON of families around. This is also a local area as well. We didn’t see a ton of tourists and my cousin suggested this beach for that very reason.
Evening in Honolulu After spending time on this side of the island, head back for a bougjie dinner in Honolulu.
Dinner at Chef Chai- If you travel like myself and my bff, then you want at least one fancy dinner while on vacation. If you have that desire, Chef Chai is exactly what you need. Wear a nice dress, bring out the heels, and order a bottle to celebrate your time in Hawaii. They also have a 3 course meal for $75 that you will absolutely enjoy.
Day Three:
North Shore: You will want to get up early for an hour drive to the North Shore. We packed our beach gear and athletic wear to change into after the beach. You can plan to spend your entire day on this side of the island and you can also expect to LOVE it.
Sunrise Shack– The mouthwatering acai bowls that you see in the picture above were from the Sunrise Shack. THE BEST ACAI BOWLS THAT YOU WILL EVER TASTE IN YOUR LIFE. Also, this place is SO cute and perfect for your IG pic (you can see mine below).
Sunset Beach– Also known as the “surfer mecca”, Sunset Beach is a MUST when visiting Hawaii. To start with, the water is beyond beautiful. It’s clear, warm, and the sun hits you just right. You can also expect few crowds here- which makes this area even better.
Halewia: Near the North Shore with tons of shops and restaurants as well.
Uncle Bo’s – Take advantage of their happy hour if you can- Mai Thai’s were only $7 and I was not mad about it 🙂 As far as the food is concerned, this restaurant wasn’t super impressive (yet not disgusting either).
Heading back to Honolulu: take the scenic route on the west side of the island for coastline views and because you have a few stops to make on the way.
Coconut Girl & Guys LLC- THE BEST SHAVED ICE you will ever get in your entire life. I’d also recommend getting the ice cream in it as well. Please stop by here and support local 🙂 Tracy is the owner and she is so sweet!
Order online and pickup your food from Bob’s BBQ. By the time that you have spent the entire day out, grabbing this food to go will be perfect. You’ll also get to say that you experienced Hawaiian BBQ 🙂
Day Four:
If you’re able to, I would recommend getting a flight that departs after 2pm, so that you can enjoy Hawaii for a few more hours before returning to your reality. If you’re able to make this happen, I suggest getting up and checking out of your room by 8am, so that you have enough time to say goodbye.
Farewell views at Diamond Head- If you’re ambitious and able to do so, wake up early enough to watch the sunrise at Diamond Head. You can drive up to the top, but expect a minor hike for the best views.
Panya Bistro in Honolulu – After saying goodbye by soaking in the views at Diamond Head, grab a quick and tasty bite at Panya Bistro. The food is so flavorful, and the perfect way to end your trip in Oahu.
Overall:
Transportation: Please get a rental car to full experience all of Hawaii. If you’re planning to book a rental, use Turo as they have less expensive options. We were able to rent a BMW for 4 days and it was cheaper than going through a rental car company.
Friendliness: We experienced the most welcoming natives while we were visiting. As you should when traveling anywhere, be respectful of the locals and always remember that you are only visiting. Don’t expect for people to hand you the moon & the stars because you’re on vacation.
Solo Travel Safety: I would totally come back and do solo trip to Hawaii! Yet I also see myself always coming back with a friend, because experiencing this with my bff made it more fantastic.
Final Thoughts: Have you ever traveled somewhere and thought “omg I could totally live here” the entire time? That is what happened while we were in Oahu. Hawaii is one of the most peaceful, serene and beautiful places that I have ever been to. I see why both of my cousins are living on two of the islands in this mesmerizing state.
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