Our Oahu + Maui Hawaii Trip: One Week in Paradise 🌺
Updated: 4 days ago
If there is one trip I already want to do all over again, it’s this one.
We spent a full week in Hawaii for my birthday and our first wedding anniversary, splitting our time between Oahu and Maui, and it ended up being the perfect combination of exploring, beaches, amazing food, sunsets and actually slowing down for a few days.
I’m SO glad we decided to split the trip between two islands. Oahu gave us more of an adventure-packed few days, while Maui was where we slowed down and really felt like we were on vacation. We both had never been to Oahu either, so it was fun to visit this new island together.
Here’s everything we did!
Planning a Hawaii trip? 🌺 Before we get into this trip, I have a couple more Hawaii posts you might want to save! If you’re planning to drive the Road to Hana, you can read my full Road to Hana guide from our 2021 trip here. The Road to Hana takes a full day and we didn't have time to do it again this time around. And if this is your first time visiting Hawaii, you can read all about my first Hawaii trip and everything we did here.
DAY 1: ARRIVING IN OAHU + WAIKIKI 🌴
We flew from LAX to Honolulu on Tuesday morning and landed around 11 a.m., which basically gave us an entire first day in Hawaii.
We stayed at the Prince Waikiki for two nights, and after dropping off our bags, changing and getting settled, we spent part of the afternoon enjoying the hotel pool and taking in the marina and ocean views. I also got a birthday massage from my mom at the hotel...and it was SO relaxing.
That evening, we decided to walk from the Prince Waikiki to the Royal Hawaiian, and I’m SO glad we did.
It was our first time seeing Waikiki and Honolulu, so walking through the city instead of immediately getting into an Uber gave us a chance to actually take everything in. It was such a fun introduction to Oahu and made the Royal Hawaiian feel like a destination at the end of our walk.
And obviously, one of my first priorities was visiting The Royal Hawaiian — aka the iconic pink hotel. 💗
As someone who will choose a pink hotel every single time, I had been so excited to see it in person. We walked around the property, checked out the beachfront area and, of course, took approximately one million photos
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From there, we headed to SKY Waikiki for drinks, apps and sunset. The sunset rooftop views over Waikiki were absolutely gorgeous, and it was such a fun way to kick off the trip. We just walked in since we weren't having dinner here.
Our original plan was to grab dinner at Paia Fish Market afterward, but it was closed for repairs while we were there. Instead, we ended up at Kai Poke, which was the perfect casual first-night-in-Hawaii dinner.
After a very long travel day and our first night exploring Waikiki, we headed back to the hotel because we had a VERY full day planned the next morning.
DAY 2: OAHU ROAD TRIP — LANIKAI + THE NORTH SHORE
Our second day was basically our see-as-much-of-Oahu-as-humanly-possible day.
We left Waikiki around 7 am and drove over to Lanikai Beach, which was one of the places I was most excited to see. The water and views were gorgeous, and getting there early made it feel even more peaceful.
Afterward, we stopped in Kailua for breakfast at sunrise shack for acai bowls before continuing our drive around the island.
We made a quick stop at the Halona Blowhole and then continued up the eastern side of Oahu toward the North Shore.
And honestly, the DRIVE itself was part of the experience. This was one of those days where I was constantly looking out the window because every part of the island looked completely different from the last.
Once we made it to the North Shore, we stopped at Jenny’s Shrimp Truck for lunch. Garlic shrimp in Hawaii just feels mandatory, and having it from a shrimp truck on the North Shore made it even better.
We spent the afternoon beach hopping and exploring, including Waimea Bay, the Banzai Pipeline area and Laniakea Beach, where we were hoping to spot sea turtles.
By late afternoon, we started the drive back toward Waikiki because we had one more thing planned for our final Oahu night: drinks at House Without a Key.
This ended up being such a pretty, classic Hawaii evening. Live music, drinks, palm trees and the ocean in the background — exactly what I wanted from our last night on Oahu. We got the special mahi mahi fish and it was very good.
After fitting what felt like an entire Oahu vacation into approximately 48 hours, it was time for island number two!
DAY 3: OAHU TO MAUI 🌺
Thursday morning, we walked around the famous Waikiki beach and had breakfast by the water at Goofy's before heading to the airport to return our rental car.
We flew from Honolulu to Maui.
This was where the entire vibe of the trip changed.
We picked up our rental car and headed toward the west side of the island, where we were staying at Hale Ono Loa at an airbnb near Kāʻanapali.
Our condo was right on the ocean, and one of my favorite parts of staying there was honestly just sitting outside and watching the water. At one point, we spotted five sea turtles from our balcony. FIVE. Every day we saw sea turtles...it was amazing.
I could have sat there all day.
We got groceries and settled into our new home for the next few days before heading out to explore at a beach.
While snorkeling at Kapalua Bay Beach, we saw some of the coolest marine life of the entire trip. I spotted a little spotted eagle ray and a spotted pufferfish. The snorkeling here was super easy and the water was crystal clear.
Then other people started saying they had seen HUGE rays farther out.
My reaction was essentially: absolutely not. 😂
Brandon's reaction was the complete opposite.
I got out of the water while he went looking for them, and he eventually came back saying he had found three massive spotted eagle rays that were around seven feet wide.
I was simultaneously jealous and very happy that I had remained safely on shore.
That night, we had dinner at Monkeypod Kitchen, which was one of the restaurants I really wanted to try while we were in Maui. It was also officially my birthday eve, so the trip was already feeling extra special.
DAY 4: MY BIRTHDAY IN MAUI 🎂🌺
I turned another year older in one of my favorite places I’ve ever been, and I genuinely could not have planned a better birthday.
We kept the morning slow — one of my favorite things about vacation.
I love going to bed early on trips and waking up early without an alarm, so I spent part of the morning watching the sunrise, reading and journaling while Brandon made us breakfast on our patio.
It was exactly how I wanted to start my birthday.
Of course, we couldn’t spend my birthday in Maui without getting in the ocean, so we squeezed in a snorkeling trip at Honolua Bay. The water was so clear, and it was such a fun way to spend part of the morning before heading back toward Kāʻanapali.
After snorkeling, we stopped at Miso Phat Sushi for my birthday lunch. Sushi is one of my absolute favorite foods, so this was obviously the perfect birthday meal before the rest of our afternoon plans.
I had also ordered the CUTEST custom birthday cake from a local Maui baker: a soft pink Funfetti cake with white and pink florals, pearls and white sprinkles. Obviously I had to turn it into an entire birthday photo shoot before we left for the afternoon. 🎀
Later that day, we walked over for our sunset cocktail sail off Kāʻanapali. Book the sunset sail we did HERE. It had open bar and very good apps.
This was easily one of my favorite experiences of the entire trip.
Being out on the water on my birthday, watching the Maui coastline and then seeing the sunset from the boat was one of those moments where I just kept thinking, I cannot believe this is my life right now.
It was such a special way to celebrate my birthday and our anniversary trip together.
After that we stopped by kareoke at the Westin, which is my favorite thing to do.
DAY 5: SOUTH MAUI + SNORKELING + ULU KITCHEN 🤿
Saturday became our South Maui adventure day.
We started with breakfast overlooking the golf course in Wailea before heading toward the beach.
One of my favorite parts of Hawaii is that I can spend HOURS looking for things in the water, and this trip absolutely delivered.
While we were in Wailea, we also stopped by the Grand Wailea, which was a really special stop for Brandon. His family used to travel to Maui almost every year when he was growing up, and he wanted to take me around the resort and show me a place that held so many childhood memories for him.
After walking around the property, we spent some time hanging out at Wailea Beach right outside the resort. It was such a sweet little full-circle moment getting to experience a place Brandon remembered from his childhood together — and, of course, we’ll take any excuse for a little more beach time in Maui. 🌺🌴
We spent more time exploring the Wailea area, walking along the coast and browsing The Shops at Wailea before eventually making our way back.
That night, we had dinner at Ulu Kitchen, which was another restaurant we had planned for the trip and such a nice way to end our South Maui day. This was our favorite food of the trip.
DAY 6: WEST MAUI, SHOPPING + ALOHA MIXED PLATE 🌴
By Sunday, we were ready for a much slower day.
One of the best things about this trip was that we didn't feel like every single hour needed to be scheduled. We had already packed SO much into Oahu and the first few days of Maui that it felt good to just wake up and decide what sounded fun.
We woke up early as we did most days here and went to Black Rock Beach.
We spent more time around the beaches near where we were staying and headed toward the Kāʻanapali/Lahaina area.
We also went to Whalers Village to shop for a while. There was some rain that day, so shopping ended up being the perfect way to wait it out.
For lunch, we went to Aloha Mixed Plate, which was exactly the kind of casual local Hawaii meal I wanted to fit into the trip.
We also drove through Lahaina, which was incredibly emotional to see in person after the devastating 2023 fires. So much of the historic area was destroyed, and seeing the empty spaces where businesses, homes and pieces of the town once stood really puts the scale of what happened into perspective.
One very important discovery from this trip was also SHAVE ICE.
We found a local shave ice spot near where we were staying, and I genuinely don't think I can ever look at a regular snow cone the same way again. It was life-changing. Ululani’s Hawaiian Shave Ice at the Westin was amazing and so was Maui Matcha there. Highly recommend.
Not being dramatic at all.
Okay, maybe a little.
But seriously — get shave ice and matcha in Maui.
DAY 7: ONE LAST MAUI MORNING ✈️
Our flight home wasn't until the afternoon, so we were determined not to waste our final morning sitting inside packing.
We woke up, enjoyed the ocean one last time and soaked up as much Hawaii as we could before checking out.
Leaving was genuinely depressing.
Seven days sounded like a long trip when we booked it, but by the end I felt like I could have stayed another week.
OAHU VS. MAUI: WHICH DID I LIKE BETTER?
This is SO hard because I liked them for completely different reasons.
Oahu was amazing for exploring. I loved being able to drive around the island, see Lanikai, eat garlic shrimp on the North Shore and then be back in Waikiki for drinks that night. If you want a trip with beaches, restaurants, shopping and a lot to do, Oahu gives you all of it.
Maui, though, felt more like an actual escape.
Watching sea turtles from our balcony, snorkeling, going on our sunset sail, waking up next to the ocean and having slower mornings made Maui feel incredibly special.
If I did this exact trip again, I would probably give myself even MORE time on Maui.
SOME OF MY FAVORITE MOMENTS
There were so many little moments from this trip that I don't want to forget: walking through Waikiki together on our very first afternoon, seeing five sea turtles from our condo balcony, Brandon finding giant spotted eagle rays while I waited safely on shore, my pink birthday cake, watching the sunset from a boat on my birthday, our early mornings together, driving around Oahu, live music in Hawaii, the beaches, and finding shave ice that I will now be thinking about indefinitely.
The trip also came at such a perfect time in my life.
I've been thinking a lot lately about change, what's next and learning to enjoy where I am without constantly trying to rush into the next chapter. Spending my birthday in Hawaii was such a good reminder that even when some parts of life still feel like they're in-between, there is already so much to be grateful for.
I got to celebrate another birthday with my husband, travel somewhere beautiful, spend an entire week outside and near the ocean, and make memories that we'll be talking about for years.
And considering I started looking up when we could go back approximately five minutes after getting home...
I think it's safe to say Hawaii has officially become one of my favorite places. 🌺
Until next time, Hawaii. 🤍
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