Aloha! My husband and I recently took a birthday/anniversary/2nd honeymoon to Hawaii! Aside from coming back with sunburn and sand in our luggage, we took with us an experience we will remember for a lifetime. Check out our day-to-day itinerary and best recommendations below! All opinions, photos and experiences are my own.
This hotel was close enough to the beach & food, but far enough away from the resort go-ers – it was perfect for us. With such a cool vibe, we couldn’t say no and the staff was so nice even giving us a complimentary bottle of wine since it was our first time to the island.
FRIDAY
We arrived on a Friday night. After dinner at Heavenly Island Lifestyle (which is connected to our hotel – excellent service!) we headed to Waikiki beach for fireworks! Unfortunately we did not make it to the best spot for seeing them, but it was the effort that counted. There were a lot of people, so plan accordingly to be sure you can get all the way down the beach in time. They have fireworks EVERY Friday night at 8 PM.
SATURDAY
We took a day to acclimate to Island Life and get a layout of our surroundings. This was a very chill day and a good way to start our trip – we highly recommend relaxing into vacation! We visited the beach for most of the morning, which was crowded at any given time, but there were enough areas available for lounging so it ended up being just fine. We ate at the Steak Shack just behind the Outrigger hotel and by far it was one of our favorite meals. They make their own Teriyaki sauce and this meal really hit the spot after a long morning spent trekking for breakfast and giving up (our 1st choice for breakfast was closed for a wedding).
After spending a day on the water, we went in search of a sweet beach treat at Banan. You can find this gem of a place in the alleyway by the Cheesecake Factory in Waikiki. When you see the lineup of surfboard storage, you know you’ve made it!
They make everything out of bananas and turn it into plant-based deliciousness. I highly recommend the Mana Smoothie. We returned more than once! For dinner we walked around the corner for some pizza and wings to bring back to our hotel room. A great ending to a chill day!
SUNDAY
On Sunday morning we woke up at a specific time to go to church. It was important for us to get out of “tourist nation” and there are zero regrets about that!
Oahu Church welcomed us with open arms and it felt good to worship with people who actually lived on the island. We recommend checking them out if you’re there on a Sunday. Our Uber driver on the way back to our hotel gave us some really cool recommendations, too. He was the bomb!
That evening we went to Chief’s Luau! It was one of the “must-do” items since it was our first time in Hawaii. The food was good and the entertainment was awesome! We ended up not spending money on the “Royal Paradise” Experience and I’m glad we didn’t. The only difference in those tickets were being able to have a man in your arrival photo with the staff instead of two women, and sitting closer to the elevated stage. Plus, we made some friends – Dalton and Krystal if you’re reading this hi! – and got all the same food and drink access as the Royal Experience. One thing I HIGHLY recommend is paying extra for the transportation there and back. It was nice not to have to worry about parking or if we were going to feel like driving after all the food and alcohol, and our bus chaperone, “Cousin Lisa,” was so much fun and really got the party started!
MONDAY
Per our Uber driver’s suggestion(s) on Sunday, we used a company called Zipcar (app) to take us around the island after having lunch at Steak Shack again.
We wanted to see it all and so we mapped out stops along the way, but eventually went as far West as we could and had to turn around. One place I wanted to spend a lot of time in was Kualoa Ranch because of all of the activities. However, if you want to do anything there make sure you budget plenty of money. We decided to save our money and I’m glad we did, but next time I’m on the island we definitely will spend money to do the ATV tour through Jurassic Valley!
Our Zipcar was a newer Hyundai Elantra. This company is so cool because it rents for about $10 or $12/hour, you have the option to set your pickup and drop-off location, and it cost far less than renting a car through a typical rental company. Especially since we only needed a car for certain things and not for everyday use (most places we got a good walk in or Ubered).
Another bonus: it came with a gas card, a parking deck card so we didn’t have to pay the fee to park and leave, and it unlocked with your phone through the app.
We walked from our hotel to a nearby resort and returned it after the day was over. This was the best experience we’ve ever had renting a mode of transportation anywhere and it felt good to be independent! Another service that we ended up not using due to the wait time to get approved was Hui. It’s the same idea, but less user-friendly in my opinion.
Our first stop was Valley of the Temples. Such a great view and only $5 to get in per adult! Make sure you ring the bell when you arrive. We also made a stop at Turtle Bay Resort for some snorkeling, but I opted to stay in the shade to avoid further burning. Dakotah was a little disappointed because he actually did not see any turtles while snorkeling in the bay. We didn’t stay but maybe an hour or so, but our friends form the Luau said they walked the beach and saw huge turtles!
From there, we drove as far as there was road. All in all, the trip around the whole island was not long probably a good 2 hours give or take, but we stopped a ton for food and water and to stand on vacant beaches. In “live-able” Hawaii there is so much beauty! Here’s a photo from when the road was blocked off by a gate and access was only allowed by permit. We were very curious about the other side of that gate, but remained respectful. We enjoyed the beach rocks, the sun setting, and drove back to our hotel.
That night we ate in Waikiki at Kuhīo Ave Food Hall. This wasn’t far from our hotel, we walked and both got something we liked. Dakotah got a burger from Banzai Burger and I got tequila and tacos from La Pina Cantina.
TUESDAY
This was the day I seriously underestimated our little stroll of a hike. It was in fact not a stroll. Please, if you’re going to hike Diamond Head eat breakfast beforehand! Don’t be like us surviving off of water and liquid IV. It was doable, and thankfully we did the hike between 7 AM and 8 AM, but DO BETTER!
We were drenched in sweat, but the views were worth it! Just know that there are lots of stairs and some steep inclines. It is a good way to wake yourself up. We had only woken up 30 minutes before our Uber driver arrived (poor planning on my part oops). Once Dakotah looked at the map at the beginning of the trail he laughed at me. I was not prepared!
For lunch we decided to ditch LiquidIV for Banan smoothies again! We walked back to the hotel from there to shower and take a nap. We were already pretty burned from the first day at the beach, so we wanted to sort of stay away from the beach, especially since we had a whole day planned at the end of our trip at a different beach on the West side of the island.
We hopped in the pool for some snorkel practice after showering off and it was really nice that no one was really up there with us so we just hung out and played in the water. This snorkel practice helped a TON for the next day’s activities.
WEDNESDAY
We started the day off with breakfast at Leonard’s Bakery. They are famous for their Portuguese donuts, which did not disappoint! We also purchased ham & swiss rolls which was my favorite part. The wait was about 30 minutes, so plan accordingly. We were headed to Kailua Beach for a self-guided day of events, but if we had chosen to be guided we may have lost our spot or our money since we ran behind a little bit. We made it to Kailua by 9:37 AM, and I made our reservation for 9:00 AM.
Kailua Beach Experience was our favorite excursion out of the entire trip! This was part of Dakotah’s birthday present, so we went all out and made sure to have access to all that we wanted. We found a deal online so it was less than $200 to have a locker, discounts in the store, meal ticket, kayaks, snorkels, fins, dry bags, life jackets, boogie boards, and bikes at our disposal. We started with boogie boards on the most beautiful beach I have ever seen and then walked the 2 minutes back to the shop to pick up kayaks and snorkel gear.
We chose to kayak the advanced trip to Moku nui Island. This was yet another underestimated trip! If you think you can kayak for an hour or two without stopping, so did we. If it wasn’t for our double-kayak situation I would not have made it and I am not being dramatic. It was so much fun though. Then we snorkeled and found some cool fish and several sea turtles to follow! They are very curious creatures and will poke their heads above the surface to say hello. Keep in mind that though they are beautiful and cool to watch it is illegal to touch them or disturb their habitat, so keep your distance, but admire away!
There are guided kayak tours available, and the ladies I saw with the guides did not seem as winded as we were. On the way back we were chanting about food as motivation to keep paddling. Another thing that’s illegal and hard to steer clear of if you’re not used to kayaking in the ocean: the reef. Do not kayak on the reef, you may run into it or hurt it and it’s disrespectful to the wildlife there. (We may or may not have done that. I may or may not have cried trying to avoid it.)
That night we met our friends from the Luau at a local sports bar for pizza and beer. We had so much fun! There are always lot of options around the hotels for food, drinks, and karaoke. The nightlife in Waikiki is thriving.
THURSDAY
We were set to take off in the evening from the Honolulu airport, and try as I might I could not get tickets to Pearl Harbor so we ended up taking the day to pack up, eat, and head to the airport early. Our airport food was expensive, so just know that you will shell out $50+ for two people to eat burgers and fries, and since things were still opening up after Covid our options were limited.
Overall, Hawaii was one for the books. One thing is for sure: when we return, I’m adding cage diving with sharks to the list of things we want to do. Is Hawaii on your bucket list? Got questions about our trip? Comment below!
Wherever you are and wherever you’ve been doesn’t matter. What matters is wherever you wanna go, & Ken We Go Now?
Kendyll Weeks 