Luxury or Laid Back: We’ve Got Two Perfect Waikiki Itineraries For Your Next Trip

The mere mention of Hawaii conjures images of swaying palm trees, golden-torched sand, and tourists attempting to surf with all the grace of a newborn giraffe –- and of course, their selfie sticks in full effect capturing said surfing.

Waikiki isn’t just for first-time honeymooners – I can attest firsthand that it’s also a playground for the luxury traveler who enjoys the finer things in life: luxury hotels, world-class dining, indulgent spa experiences, and, of course, a Mai Tai that costs roughly the same as one month’s rent. It’s also a place you can embrace the local culture and feel your soul peacefully ease back into place.

If you’re going to do Waikiki right, here are two unique ways to experience all the hot spots along with two hotels, each perfectly suited for any discerning traveler.

The Perfect Waikiki Itinerary for the Casual and Creative Beach Lover

Set this perfect itinerary to “Island in the Sun” by Weezer for an effortlessly laid back and breezy beach vacation.

If there was ever a hotel made for writers or creative types, Romer Waikiki at The Ambassador is THE one. And if we’re being honest, it isn’t just fit for travel writers like myself, but creatives in general.

Recently renovated top to bottom, this is a loud property in a quiet neighborhood located in the heart of Waikiki. You’ll love everything about this hotel like their colorful and happy wallpaper, their corner store with local artisan pieces and their monthly drag show, to name only a few.

The hotel is an easygoing gathering place with everything that Waikiki has to offer mere steps away. If you’re traveling with a group or kids, take advantage of their cute bunk rooms (and if you’re not, check out their sister property for an adults-only hotel in Waikiki).

Start your morning with a three-minute walk to Rise & Grind Café. It’s set in the back of a food truck park, and it’s well worth the morning walk.

Spend your sun-filled days at Waikiki beach or on-site at the Waikiki Swim & Social Club, then grab a takeaway lunch at Kono’s a few blocks down. This favorite spot began on the North Shore and popularity helped add it all around the island, so do yourself a favor and order a bomber.

During the day, go for an early hike at nearby Diamond Head, then head out for the most unique espresso martini at HIDEOUT at the LAYLOW. The Hideout Signature Espresso Martini is the perfect blend of Big Island Coffee Roasters Espresso, Pau Maui Vodka, St George NOLA Coffee Liqueur, and the best part: Macadamia Nut Espresso Foam. Insert drool here.

If you still need more cocktail suggestions, hit up Favorite Son at Romer Waikiki at The Ambassador and try their island famous POGstar Martini with Absolut Vanilla Vodka, Chinola, Passion Fruit, Orange, Guava Summer Club Sidecar. If you don’t want alcohol, order a POG juice, a favorite on any island.

For an after-dinner and chill vibe, check out the Green Lady Cocktail Room. Picture a cutesy little speakeasy bar set behind a bamboo wall at White Sands Motel, where the drinks are great, but their playlist and moody vibes are even better.

I don’t normally coffee shame people, but if you drink Starbucks in Hawaii, just don’t. Please don’t. I highly recommend Ali’i Coffee Co. a few blocks away from Romer. The Mac Nut Cold Brew with banana milk is a must-try (or add a banana milk floater to any iced latte) and the friendly staff will help guide you through their binder of drinks and cheeky descriptions.

Opt for casual sushi in a beachy maxi dress at Katsu Midori Sushi, inside Prince Waikiki. There are no frills here, the menu is large enough to be overwhelming, you order from an iPad, but it’s worth the stop and you will not get a seat without a reservation.

The Perfect Waikiki Itinerary for the Fancy and Elevated Traveler

While the Renaissance Honolulu Hotel & Spa isn’t necessarily beachfront, you came to Hawaii to be pampered and you’ll get that as this 39-story luxury hotel. Enjoy floor-to-ceiling glass windows from most guest rooms with a perfect view of Oahu’s natural beauty, including a stunning glimpse of the ocean.

You don’t have to go far for an incredible and luxurious massage – be sure to ask for Mina, who has some of the most experienced hands around. Afterwards, hit up the hotel’s heated saltwater pool or soak in one of the two hot tubs, or lounge poolside with cocktails. You have options without even leaving the hotel.

Located across from the Ala Moana Center, the world’s largest open-air shopping center, you’ll have your pick from designer stores like Celine, Louis Vuitton, and more. Take it up a level by booking personal shopping services and be sure to bring your Platinum card in your beachy clutch.

For dinner, enjoy Mediterranean cuisine at MARA, an award-winning seaside-esque oasis at the Renaissance. Specialties like tapas and shellfish are served family-style at this Honolulu restaurant, but the real stunner is the Manoa Chocolate Sokolatina, a soft and moist chocolate cake served with salted caramel ice cream. This was probably the liveliest restaurant we visited during our seven-day trip, which may have had something to do with their killer espresso martinis (garnished with an orange peel, IYKYK).

For the best Mai Tai’s in the area, head out to The Beach Bar at Moana Surfrider and choose from three variations. If you’re feeling extra fancy and don’t want an alcoholic cocktail, you’ll feel plenty fancy sipping afternoon tea on the veranda like the effortlessly classy traveler you are.

For yet another exquisite sushi dinner, head to Sushi Sho for their intimate omakase experience at The Ritz-Carlton. You’ll find only ten seats, a master sushi chef, and the freshest fish you’ll ever taste—so, yes, reservations are mandatory.

A staple for over 70 years, you can also grab dinner reservations at Hy’s Steakhouse & Cocktail Bar where they are known for their dimly lit restaurant and dark mahogany interior along with their artful theatre of tableside service for nearly every dish.

Take the luxury up to even higher standards by booking a private yacht charter or even a helicopter tour around the island to look down on down on the peasants (me, I’m the peasant).

Waikiki, But Do It Your Way

Waikiki is often associated with packed beaches and touristy luaus but make no mistake—this is also a destination that caters to every kind of traveler, whether you’re the luxury traveler who appreciates the finer things in island life or the creative type who is looking to get their groove and work-life balance back. You’ll find all that and more on O’ahu.

And in case you didn’t already know, no visit to O’ahu is complete without at least two days on the North Shore, but that’s a different article for a different day.

For now, a hui hou (until we meet again).