Aloha! We just returned from Hawaii and spoiler alert… it was my favorite vacation yet! In the past, Jeremy and I have typically cruised through the Caribbean – which is great – but Hawaii is just next level. TBH, we had a teeny tiny tiff over where we honeymooned to andddd
(surprise), I won. We went to the Mediterranean even though Jeremy had his heart set on Hawaii. So it was his turn to pick and there’s no time like chilly January to head to paradise!

After a ton of research, we settled on a Hawaiian cruise in order to see as much of the state as we could on our first trip. It was surprising to learn that only ONE ship cruises the Hawaiian Islands and that same ship is the only cruise based out of America. We’d also heard that Hawaii is notoriously expensive so a cruise seemed like a win-win!

Day 1: Oahu

The Pride of America sets sail from Honolulu so thank goodness we got to Oahu a couple days early because this island has THE MOST. We lucked out with a direct flight from Atlanta and although we were hella jet lagged, we were excited to explore Waikiki. We checked into the Laylow Hotel and y’all, this place is ME in design aesthetic – pink and palm-leaf print everything. It’s a block over from Waikiki Beach and you are surrounded by every store you’ve ever wanted to shop at and a ton of amazing restaurants. We cleaned up and went next door to the Paia Fish Market for shrimp tacos and a beer before exploring Waikiki.

It was already evening on Oahu, but that didn’t stop us from popping over to the Royal Hawaiian Hotel to check out its gorgeous decor. We took a quick walk on the beach, but unfortunately didn’t have enough time to enjoy Waikiki Beach in the daytime. Jetlag set in early and we made sure to catch some zzz’s to make the most of our only full day on Oahu.

Day 2: Oahu

Lanikai Pillbox Hike: Since we were five hours ahead of Hawaii time, we woke up bright and early (I’m talking 5 A.M.) and hopped in our car to head 30 minutes across the island to Lanikai. I would highly suggest starting this hike early because not only is parking a little tricky, but the Pillboxes get busier and busier as the day goes on. We parallel parked on a residential street around 265 Kaelepulu Dr, Kailua, HI 96734 and walked uphill towards the country club. Keep an eye out for the hand-written sign that marks the trailhead (sharing a picture of it below). Prepare for a steep start to the hike, but the tricky part is over quickly and the views throughout the rest of the trail are worth the huffing and puffing. This is one of the best ways to kick off your Hawaiian vacation and easily one of my favorite activities on the trip!

Coverup: J.Crew | Swimsuit: Nordstrom Rack | Hat: Brixton

North Shore: From Lanikai Beach, we drove West toward the North Shore. With no exact destination in mind, we had left the afternoon open to trying as many food trucks as possible and catching sight of its famous waves.

We first stopped at Waimea Bay and watched surfers for a time. The waves were far too large for any of us to feel comfortable swimming, but it was a beautiful place to relax in the sand. From there we went to Giovanni’s Shrimp Truck for its shrimp scampi we’d heard so much about! We followed it up with fresh pineapple and a couple coconuts. We enjoyed spending the rest of the day driving a bit, stopping to check out views, beaches, and more before returning to Waikiki.

The Brewseum: We were beyond ready for a drink when we returned – most of the dining on the North Shore is stands and trucks so little to no alcohol – so we went straight to The Brewseum in Honolulu. While their made-in-house beers weren’t the best (opt for a mai tai), the establishment more than made up for it! This unique bar features a speakeasy upstairs and a World War II museum downstairs. You’ll get to have a couple drinks while time traveling back to the 1940’s.

Day. 3: Oahu and Cruise Embarkation

Pearl Harbor: Bright and early is the theme of this trip (which was honestly pretty badass and the opposite of my actual life) so we were up-and-at-em, packed up, and on our way to Pearl Harbor by 8:30 A.M. We’d heard about lines, but since we arrived fairly early we didn’t have to worry about them. It’s free to watch a 20-minute video about the attack and then board a ferry to the U.S.S. Arizona memorial. The viewing area is currently under construction, but the ferry spent quite a bit of time cruising slowly nearby the memorial while allotting us a moment of silence in rememberance.

You could easily spend a whole day at Pearl Harbor – there are a ton of things to see – but since we were on a time crunch, we opted for a tour of the U.S.S. Missouri, the ship in which the Japanese and Americans signed a treaty effectively ending World War II. The Arizona and Missouri are situated bow to bow to mark the beginning and end of the war. The whole experience was so emotional; we all teared up at one point or another. If you are on Oahu, you can’t miss the opportunity to pay your respects at Pearl Harbor.

Ho’omaluhia Botanical Gardens: Since we didn’t have to be on the cruise until 5, we had enough time for one more Oahu activity and I urged the group to pop by the Ho’omaluhia Botanical Gardens. The grounds were gorgeous and we all enjoyed feeding the insane amount of fish in the lake, but as this stop had us cutting it close for boarding the cruise, it’s one activity we could have skipped.

Day 4: Maui

The best part about the Pride of the America itinerary is that it features two overnight stops – one in Maui and one in Kauai. This allotted us a full day with no time restraints to explore the island. Equipped with all that time, we decided to do the Road to Hana.

Road to Hana: We took a free shuttle from the port to the airport to rent a jeep. Between the rental and gas, the price clocked in a little under $200 for the day, which split between five people isn’t too shabby for a day of exploring. The Road to Hana (mile marker 1) begins in Paia, which is quite close to both the port and the airport. We followed THIS GUIDE for reference and set out on our journey. Since there is very limited service on the road, be sure to screenshot the mile markers you want to see because it’s easy to miss various turnoffs.

If you have motion sickness, I would NOT suggest driving Hana Highway. There are over 600 sharp turns and countless one-lane bridges and steep drop-offs. But goodness gracious, it is beautiful! Our favorite stops were Ho’okipa Lookout (mile marker 9), Halfway to Hana Stand (mile marker 17) for amazing banana bread, Hana Lava Tube (mile marker 31), and Wai’anapanapa State Park (mile marker 32), which is the famous black sand beach. Be sure to plan to leave Hana a couple hours before sunset as this is definitely not a drive to do in the dark. Suffice it to say, we all went to sleep pretty early after a day full of exploring Maui!

Check out the second half of our trip HERE!

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