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What I realized on my last weekend trip to Honolulu: it’s all essential to vet my travel partners.
Not because it was a disaster but because it was awesome. I’m thinking a survey would do, maybe with a question like, “Do you have the aplomb to horseback ride through the Jurassic Park valley, swing by the local fish shop for a poke bowl, catch a few waves in an Outrigger canoe, search out the best Mai Tai in Waikīkī, then clean up to be island-chic for happy hour in under 22 minutes?”
Long Weekend Trip to Hawai’i
You already know that Gaby is one of my travel friends, but with this trip to O’ahu, we might have done quite possibly my favorite girls’ trip of ever. We set off on a long weekend — three and a half days — of action, adventure, eating, and cheers-ing, Aloha style. I’ve never thought of doing a long weekend in Hawai’i, but this trip made me realize it’s closer than I think and I am now counting the days until the next trip.
Yes, I’ve been to O’ahu a lot since I met my Hawaiian husband over a decade ago, but I love going back because it’s super dynamic. There’s always something new and all the stuff I love: independent boutiques, quality cocktails, creative food, as well as all the classic hikes and markets I so love. And, since we were in town for the Hawai’i Food & Wine Festival, I got to meet many local chefs and mixologists and see what they’re up to now.
O’ahu Long Weekend Itinerary
On this trip, we were on a mission to earn our eats by working out all day and partying all night. That meant I went on some epic adventures, including swimming with dolphins, hiking to my favorite lookout, riding horses through ancient valleys, and even trying my hand at Outrigger canoeing (which I’m pretty much in love with, by the way).
Here’s how to do a long weekend in Hawai’i yourself (gal pal not included):
Day 1: Friday
We started the trip out bang by swimming with the dolphins! Early in the AM we drove to O’ahu’s west side ( about 1 hour west of Waikiki) and boarded a boat chartered by Wild Side Specialty Tours. The next few hours were spent searching out sea turtles and dolphins. I haven’t spent that much time on this side of the island (aside from when I got SCUBA certified there), so it was a chance to get to know it better.
My day with Wild Side was a mix of education and fun, like how there’s this underwater shelf on the West Side of O’ahu that makes dolphins very happy, that there is a method to how to best swim with dolphins and sea turtles, and that we should all swim with dolphins at least once because it’s pretty special.
As it was the month’s start, we took part in First Fridays In Chinatown. Yes, you can get your culture on and gallery hop to check out the local art scene, but I also wanted to head there because some of my favorite boutiques are in this part of Honolulu.
One of my favorite food scenes in Hawai’i is centered in Chinatown, so we had to do dinner there. And it’s hard to talk about the Chinatown food scene without mentioning Jesse and Dusty, who now have three restaurants in the area. We headed to their second restaurant, Livestock Tavern, for some Happy Hour action before hitting up their sister restaurant, Lucky Belly, for some of the best ramen around (go big and do the Uni Gnocchi, followed by the Beast Bowl).
Day 2: Saturday
My weekend ritual anywhere I travel is to check out the farmers’ markets; this trip was no exception. So, as soon as we woke up, we beelined for Kapiolani (aka KCC) Farmers Market. There are other, more local farmers’ markets on Oahu, but if you’re only in town a few days and want to graze for breakfast, this is the place to head. I went for fresh-pressed juice, some local mango bread, and a breakfast sandwich from The Pig & The Lady.
Of course, we ate way too much at the market, so we headed outdoors to work it all off. First, we hit up the Makapu’u Lighthouse Trail—it’s a short, not too steep hike but has some incredible views of the island’s east side at the top (and was kinda perfect after a few too many cocktails in Chinatown the night before).
After the hike, we headed around the corner to Makapu’u and Waimanalo beaches for some quality beach time. Both beaches have beginner-friendly waves, so we went longboarding and body surfing for a few hours.
For sunset, we headed over to one of my favorite spots, The Modern Honolulu, for some poolside drinks (my all-time favorite is always and forever the Frozen Coconut Mojito). I’ve woken up at the crack of dawn to go to the Honolulu Fish Auction, so I can tell you that someone representing Morimoto Waikiki staff is usually there bidding for the freshest fish on the island. And yes, the sushi and sashimi are stellar there, but I insist you start your meal with the tableside tofu that’s pretty much life-changing.
Even if the Mai Tai isn’t even from Hawai’i, it’s pretty much illegal to hang in Waikiki without ordering at least one. So we finished the night off over at the Mai Tai Bar at the so-stunning-I’d-move-in-there Royal Hawaiian Hotel. As you can guess from their name, they have all sorts of Mai Tais on their menu, but the Ali’i Mai Tai (with muddled pineapple and aged rum) is my personal pick.
Day 3: Sunday
Food is a serious business in Hawai’i, but I don’t think any meal is taken more seriously than brunch. Locals line up for their favorite breakfast and brunch spots, and one place that always has a wait is Koko Head Cafe.
We started our Sunday off with brunch at Chef Lee Anne Wong’s Koko Head Cafe and pulled out all the stops ordering everything from the dumpling of the day to the specialty skillets and seriously addictive crunchy French Toast.
Yes, it’s that Kualoa Ranch where Jurassic Park (and many other films) were shot, but I’ve always wanted to head there to go horseback riding. I grew up horseback riding but had never managed to go to Hawai’i, so I was majorly marking this one off my bucket list. We headed back into the depths of the ranch that are so lush and green; you’d mistake it for Kaua’i if you didn’t know better.
The horseback riding adventure was super fun, but I was waiting all weekend for this afternoon because we were heading out on an outrigger canoe ride. My husband grew up competitively rowing outrigger canoes, but I’d never managed to go out on one. The crew over at Faith Surf School totally set us up, teaching us the basics and even helping us to catch a couple of waves. I was totally hooked and kinda think I could have a bright future in canoeing (just sayin’)!
Day 3.5: Monday
I have a rule I created back when I started dating Chris that I have to get into the water every day that I’m in Hawai’i. And it was especially easy on this trip since staying in Waikiki meant I was steps away from very friendly surf. Seeing as I’m an eternal beginner when it comes to surfing,
I appreciated being able to wake up at sunrise and head out into the surf for one last water session before heading to the airport. That last morning I also got one last acai bowl and a pour-over coffee down the street from our hotel at Gorilla In The Cafe. The only problem with this trip is that I really didn’t want to leave!
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Sponsored Post: A special thanks to Oahu Visitors Bureau, Outrigger Resorts, and Hawaiian Airlines for making this trip possible. As a guest, we were treated to many of the services and adventures on this trip; however, all coverage and opinions are our own!
Hawaiian Diacritical Marks: In an effort to be accurate and respectful of the Hawaiian language, we use diacritical marks in our articles on the region. For more about which marks are used in the language and how to find proper spelling, refer to this Hawai’i Magazine article.