If you were to dream of the most extraordinary millennial getaway, what would you picture? For me, it would include planting myself in the sand with a Mai Tai, cooling off in the clearest teal waters you’ve ever seen, and enjoying the local culture. The trip would be comprised of equal parts relaxation and adventure, and feature fresh seafood, tropical drinks, and the best photo opps ever. If a paradise like this sounds like your kind of retreat, too, I put together some of the best things to do on Oahu that made me feel like an influencer on my most recent trip. This way, you can easily recreate the trip for yourself.
When I received an invitation from the Waikiki Beachcomber by Outrigger in Honolulu, Hawaii to enjoy a five-day getaway courtesy of the hotel, I couldn't say no. The hotel billed the trip to me as the "ultimate millennial experience" and it didn't hurt that everything offered completely lined up with my dream getaway.
As soon as I saw the private balcony attached to my room, I couldn't resist snapping pics with the stunning teal ocean backdrop. This was the perfect opportunity for me to live like a social media star: waking up in a cozy bathrobe, enjoying a cup of coffee in my plush bed, walking the beach at night with the faded glow of tiki lights in the background, and watching the sunset from my floor-to-ceiling windows.
This lifestyle hotel is such an awesome, millennial-friendly place to stay while in Waikiki Beach. As I sat inside a plush poolside cabana enjoying a few refreshing happy hour cocktails, I had one thought: "This is how every millennial should kick off their vacation." And that was only the beginning.
After I was done lounging around, I had the chance to experience as much of the culture as I possibly could in my short timeframe. I took a hula dance lesson, enjoyed the most incredible poké ever, surfed with the locals, and took advantage of all the Instagram opportunities possible, including local craft beer, poolside yoga, and selfies in my lei.
Although I would have been happy as a clam never even leaving the hotel, there are so many awesome things to do on Waikiki Beach and beyond — such as canoe surfing, snorkeling, shopping at the Waikiki Beach Walk, going on a catamaran sunset cruise, savoring shave ice, and more — so I couldn't resist stepping outside for even more adventures. (My camera did not oppose, either.)
I grew up surfing at the Jersey Shore, but surfing in Hawaii brought riding the waves to a whole new level. My first day was spent at the beach taking a surf lesson with Faith Surf School. I couldn’t have been more pumped, and my instructor, Barney, was the GOAT. He had an awesome, hilarious personality that made my surf lesson one-of-a-kind, and he gave me great tips — such as taking my time when popping up on the board and not leaning too close to the front so the board nose-dived — and was patient when I was getting the hang of things. An instructor who makes a new, potentially challenging activity fun and comfortable can make or break the experience, and I'd definitely recommend booking a lesson with Barney.
Another dreamy activity I tried included stand-up paddle board yoga, which was a first for me. I love yoga, but I’ve never experienced it on the Pacific Ocean, or on a paddle board, and Yoga Kai Hawai`i made this an experience to remember.
My instructor made me feel like I was a pro and having these pictures to look back on will always inspire me to go for anything and everything in life I want to try. Living your best life should be a priority, and honestly, so should stand-up paddle board yoga in Hawaii. Even if you just want to have a unique yoga session in the most peaceful environment ever, I suggest giving this activity a try while you're on Oahu.
The waves along Waikiki Beach were pretty rough the day we went, so we headed to Magic Island Lagoon, which is quite possibly the most serene, picturesque place I’ve ever been in my life. (I captioned my pictures, “Nama’stay here forever,” and really wanted to.)
My instructor, a group of locals, and I were some of the few people on this gorgeous man-made peninsula, and when I brought my paddle board into the clear water, I was in awe of the sun-drenched, palm tree-lined backdrop. My instructor was as impressed as I was, and she captured the most amazing pictures for my ‘Gram.
I was also able to hike Diamond Head while I was on the island, which is a volcanic crater and extremely popular landmark of Hawaii with extraordinary views of Oahu. Let me tell you, the view from the top is definitely worth the trek to get there.
The hike itself is pretty moderate and took about a half an hour. If you love hiking, I highly suggest heading there early in the morning to beat the crowds and the heat. Once you reach the very top, you’ll be inclined to throw a couple of hearts up with your hands and have someone snap a bunch of pics.
After working up a sweat and feeling pretty accomplished with my climb, it was the perfect time to treat myself to some serious snacks. I’ve bean in love before, but Hawaiian Aroma Caffé — a charming, chic, and tropical coffee-lover's heaven in Waikiki Beach — really perked up my soul and my Insta feed when I needed a caffeinated pick-me-up.
As a major fan of doing it for the foodie 'Gram (but also savoring each and every bite), I had my fill of fresh fruit, shaved coconut, peanut butter, and local honey, and was very pleased with the adorable little umbrella that topped off my açaí bowl. If you're on the açaí bowl bandwagon, your tastebuds and Instagram aesthetic will fall hard for this afternoon treat.
When it came to immersing myself in the local music and beloved traditions of Hawaii, I enjoyed a hula lesson at the Outrigger Reef Waikiki Beach Resort. It's a free activity offered to guests through the hotel, so you can get a taste of the local culture during your vacay.
I've watched hula dancers before, but I never truly appreciated that hula is so much more than a beautiful dance and show until I tried it for myself. During my lesson, I learned that each movement tells a story through the dance and lyrics. As I danced to music from a live ukulele player, my body told a story about the flowers on the Hawaiian islands. I have never felt more graceful and more connected to a culture.
To complete my adventures, I went on an afternoon Holokai Tradewind Sail, which one of the local activities offered by Outrigger’s DISCOVERY program. By signing up to be part of the DISCOVERY program, you can peruse a list of really cool local experiences you're able to "redeem." They can be booked online ahead of time. I recommend this for any traveler who wants to make the most thrilling memories while on the island. Plus, it makes planning an epic itinerary nearly seamless.
The catamaran sail had a bar on deck for those who are 21 and older, which obviously I enjoyed to the fullest. As we sailed through the waves of the Pacific and got splashed in the front of the boat, I couldn’t help but stop, smile, and really think I was in a dream or starring in my very own version of a feel-good self-discovery movie. I mean, that was the point of this trip, right?
My exact getaway and itinerary felt like the perfect millennial statement vacay, and I felt like I did this beautiful phrase, "Oi kau ka lau, e hana I ola Honua," — "Live your life while the sun is still shining" — justice.