Life Is a Trip: Escape on an Oʻahu Friends Getaway

When you imagine getting away somewhere with one (or a few) of your friends, what kind of place comes to mind? Southern charm? The lights and chaos of Las Vegas? A desert oasis? International travel? For me, it would be escaping to the Hawaiian Islands, preferably Oʻahu. Located just below the Tropic of Cancer, this Island has it all, which means you don’t have to be a typical tourist and take the beaten path in order to enjoy everything it has to offer.

It may be one of the most remote locations on Earth — complete with remarkable topographic diversity — but it’s the prime paradigm of paradise.

Oʻahu is alive with the spirit of Aloha. When you’re on an island in the middle of the Pacific Ocean, it’s like a tropical refuge for the soul, where everything seems to make sense. And no, it’s not just the Mai Tai’s talking. Maybe it’s the spirit of the Island or the personality of the people that truly bring it to life.

It doesn’t matter what kind of goal you have in mind for your trip; all of your needs, desires and expectations will not only be met, they will be exceeded. In the Heart of Hawaii, there are endless things to see, do, eat and drink, as well as various options for those who feel like doing much of nothing at all. Year-round, the weather is inviting and perfect for planting yourself on the beach with your toes in the sand.

Whether you and your friends are well-heeled foodie travelers who wish to dine on authentic eats, the type to get outdoors and see the sights, or simply feel like all you want to do is party all day whilst watching the waves crash along the shoreline and all night beneath the full moon and fireworks, it is evident the moment you step off the plane that you’re in for a treat.

I used to think that if I was going to plan a Hawaiian getaway that I needed at least two weeks to work with in order to feel like the time spent was substantial, but this recent trip changed all of that. It was a four-day, non-stop adventure that required an up-for-anything attitude, lack of complaint, enthusiasm and the ability to get back to my hotel room to clean up (and try my best to look well put together) in just a matter of minutes. Trust me: It’s doable.

You seriously only need a three-day weekend to get a taste of the good life, one that will leave you wanting more from this living, breathing paradise.

Here are the top 10 things we recommend doing on an Oʻahu Friends Getaway to have the greatest vacation of your life.

1. ARRIVE in “first class style” by booking a reservation with Platinum Limousine. Their drivers are courteous, professional and are there to share some insights about the Island you probably won’t get elsewhere. Dee Yajima, the company’s manager, made sure to get me to my destination safely and on time. Our best advice is to not rent a car. Let others do the driving for you. That way, you won’t have to deal with figuring out directions, dealing with traffic and you can sit back and relax. Isn’t that what vacation is all about? (First… you’re on an island.  Second… don’t read a map or app while driving.)

2. UNWIND while taking pleasure in happy hour at the RumFire Sheraton Waikiki. Good eats, tasty drinks and a sunset view to-die-for, especially if you happen to be half-submerged in the hotel’s infinity edge pool.


3. CHECK-IN at The Modern Honolulu. This place reinvents what it means to travel in style — think island vibes meets Miami Beach. Other places may have more history, but this hotel is making history of their own. They pull out all the stops, without a doubt. It was recently named Honolulu’s “Best Boutique Hotel” by readers of Hawaii Magazine. Relax poolside, dine, grab a stiff drink at The Study (a lobby bar hidden behind a bookshelf), or party like you mean it at the hotel’s award-winning A-List nightclub, Addiction. On Friday night, start your weekend off with a bang on the Modern’s pool deck, the best place to get a glimpse of the fireworks show that Hilton Hawaiian Village puts on. If you have the opportunity to connect with Passion, the hotel’s Marketing and Communication Manager, she’ll fill you in on everything you need to know to make your visit one to remember.

modern honolulu

Interested in staying somewhere not-so-swanky, but still offers a quiet, restful sleep? Reserve a room at Shoreline Hotel Waikiki. This hotel is a short stroll to the beach, restaurants, shops and my all-time favorite: people watching. There’s even a rooftop swimming pool.

4. GET OUTSIDE and marvel at the natural majesty of Oʻahu with Hiking Hawaii. Whether you’re a professional adventurist, passionate hiker or someone that has never seen a trailhead in your entire life, going on a guided hike or tour with Hiking Hawaii will show you the Island’s breathtaking beauty. You should also make time to journey out on your own with a visit to Makapu’u Point Lighthouse Trail. Views from the observation decks are marvelous.

get outside

You can’t come to Oʻahu without getting in the ocean. Take a surf or SUP lesson with Hans Hedemann Surf School while enjoying the breathtaking backdrop of Waikiki and Diamond Head. Waikiki Beach is the best spot to take a beginner surfing lesson. It’s also the same location where the great Duke Kahanamoku was credited with the riding the longest wave ever ridden.

5. EAT like you mean it at Morimoto Waikiki and prepare to pick your jaw up off the floor. This place is simply incredible. One bite in this luxurious, culinary journey might encompass some roasted kahole lobster with lemon crème fraîche, while the next might feature a crispy whole fish with pickled papaya salad and spicy tofu sauce.

morimoto feature

Another hot spot for dinner is 12th Ave Grill, where the diversity of American cuisine is made simple and from scratch. You must try the Shinsato Farm Pork Belly Confit with poached Ka Lei egg yolk and Maui dark rum as a starter or the Coriander-Lime Seared Big Island Kampachi Crudo with house pickled serrano pepper chimichurri.

Interested in lunch with a view? Hit up the Shore Bird Restaurant & Beach Bar at Outrigger Reef on the Beach. You won’t be disappointed.

6. EXPLORE southeast Oʻahu early Saturday morning by making a stop at Hawaii’s largest farmers’ market. It’s a delectable treat, especially if you get caught in the warm morning rain. There’s nothing like eating an OnoPop while raindrops roll off your nose. 

7. ENJOY Island life like a local — visit Waimanalo beach. This place is a world away from the crowded beachfronts of Waikiki. Take a dip in the warm, turquoise waters, then allow yourself to be in awe of your surroundings. After working up an appetite (either from a long walk on the beach or soaking up the Hawaiian sun), cruise down the street and grab some food at Sweet Home Waimanalo cafe and market. Try their fish tacos with bok choy slaw, pineapple salsa and lime cream sauce. Talk about mouth-watering! Wash that down with a chilled Hibiscus Mint Iced Tea. Perfection.

waimanalo feature

8. TOUR the bits and pieces of Honolulu most folks, including the locals, have never seen or heard about with Pedal Bike Tours. There’s no better way to see the hidden gems of Honolulu than to go on a tour with this company. So professional, knowledgeable and all around good vibes. The best part (other than visiting historical monuments such as Iolani Palace and iconic Kamehameha Statue)? Checking out the street art in the city’s warehouse district, called Kakaako. There is some serious out of sight talent here.

pedal bike tours

9. GATHER for a food festival unlike any other. If you happen to be on Island during the first two weeks of September, you must — I repeat, you must — attend at least one Hawai‘i Food & Wine Festival event. Truthfully, if you’ve ever called yourself a “foodie,” you belong here. Not only is it the “premier epicurean destination event in the Pacific,” it’s where cuisine and culture collide. World-renowned chefs, top wineries and mixologists, as well as top-notch culinary memories.

After attending, your friends will be begging you to come back the following year. It’s that amazing.

hfwf feature

10. REMEMBER – And lastly, remember to Hang Loose! After all, you’re on vacation.

Mahalo nui loa to Oʻahu Visitors Bureau, Hawaiian Airlines, The Modern Honolulu, Shoreline Hotel Waikiki and Stryker Weiner & Yokota for making this unforgettable trip possible.