Picture this. A sun-drenched, golden coastline and delightful breeze. Shirtless volleyball players glisten on the sand. Tanned, hardbody surfers ride gentle waves.
I say closer to home because Hawaii is technically a part of the United States. However, when your plane lands on Oahu and you feel that island breeze hit your face, you’ll quickly realize that Honolulu is worlds away from the Mainland.
With so much to explore on Oahu, you could easily spend an entire week here and still leave parts uncovered. That’s why I recommend dedicating at least one full day of your trip to fooling around Waikiki.
One day in gay Waikiki
When looking for a stay in Honolulu, you’ll discover that the majority of your options are located in Waikiki. Airbnbs are outlawed here, so you must pick a hotel. No worries, there are hundreds to choose from, all at a moderate price with unbeatable hospitality and amenities.
Though if you are looking for something truly unforgettable, an experience that will live rent-free in your head for the rest of your life, book a stay at Kaimana Beach Hotel. Overlooking Sans Souci Beach, with sweeping views of Diamond Head Crater, Kapi’olani Park, and the Outrigger Canoe Club, Kaimana Beach Hotel offers travelers world-class accommodations and dining in a stylish, eclectic setting.
Since completing renovations in 2021, Kaimana Beach Hotel has received a handful of awards, positioning it as one of the most coveted stays in Honolulu. This inclusive oceanfront property celebrates its original mid-century architecture with a modern, boho aesthetic worthy of its own HBO series. It creates a great backdrop for a honeymoon or destination wedding.
The hotel’s success is due in large part to its openly gay General Manager Ha’aheo Zablan, a native Hawaiian, who runs a tight, yet fabulous ship. As Director of the Hawaii LGBTQ Legacy Foundation, Ha’aheo also ensures his hotel is a happening place for Honolulu Pride in October. Throw in its close proximity to Hawaii’s most popular gay bars, Kaimana Beach Hotel is the ideal launchpad for a gay island escape in Waikiki.
An early start
Begin your day with the breakfast of champions – delicious, hot malasadas from Leonard’s Bakery. I’ll note, the early bird gets the worm here. To avoid the wait at this iconic Honolulu eatery, it’s best to arrive right when it opens or just after 11 am.
After breakfast, grab a towel and work on your tan back at Sans Souci beach. Located in the quieter part of Waikiki, this aptly named stretch of sand is the perfect place to forget your worries and finish that book on your reading list.
You might be surprised to learn that the majority of Oahu’s beaches are nudist-friendly. Topless sunbathing is permissible on beaches (unless it’s within the confines of a state park.) That being said, most people decide to stay clothed in Waikiki. When you’re ready to let it all hang out with fellow exhibitionists, Polo Beach on the North Shore is worth a visit.
Island shop hop
Once you’ve perfected your tan, it’s time to work on your island look. Perhaps you forgot to pack an extra pair of sliders in your suitcase, or you want a full-on shopping spree – Kalakaua Avenue has everything you need.
Despite Hawaii’s remote location, Waikiki is a retail hotspot, housing every major designer brand imaginable. If you take away the warm weather and abundant palm trees dotting the avenue, you could mistake Kalakaua for Chicago’s Magnificent Mile or San Francisco’s Union Square. Among the big department stores and iconic fashion houses of Luxury Row (Prada, Balenciaga, and Louis Vuitton, just to name a few), you’ll find trendy outfitters like Kith, Stussy, and Free People in the mix.
Once you’ve shopped ‘til you’ve dropped, it’s time for lunch. And oh boy, does Waikiki have a lot to offer on that front. You could try your luck at Muragame, Tokyo’s udon king, though you might have to wait in its notoriously long line. You could eat an obligatory Hawaiian plate lunch at Paia Fish Market or Kono’s, two local chains. If you have a picky group, you’ll satisfy every appetite at Kuhio Food Hall inside the International Market Place.
If I had to pick just one place for lunch, it would have to be the unassuming poké outpost on Kuhio Avenue – Maguro Spot. Don’t let its hole-in-the-wall aesthetic fool you, this place is a cut above the rest. It has the best poké in town, with each bowl made custom and fresh to order.
After lunch, it’s time to pick up souvenirs for your friends and family back home. By now, you’ve probably spotted a few gift shops and ABC Stores that would do the trick. Instead, I encourage you to pay a visit to the open-air markets on Duke’s Marketplace. Tucked behind Duke’s Lane, the entrance to the alleyway can be a little tricky to find. Once you’ve located it, meander through the maze of pop-up shops and get tchotchkes, ukeleles, locally made crafts, Hawaiian shirts, and all the kitsch your heart desires.
Leaving the alley, you’ll run into Moana Surfrider (one of the first hotels to be built in Waikiki), Kuhio Beach Park, as well as Kapaemahu, The Healer Stones. These four stones were placed as a tribute to four mahu, a Polynesian term for third-gender individuals who identify as neither male nor female, but a mixture of both in mind, heart, and spirit.
Resting on the banks of Waikiki Beach, Kapaemahu has to be one of the most serene LGBTQ landmarks in the world. If you would like to learn more about mahu and The Healer Stones, check out the exhibit at the Bishop Museum in Kalihi.
Dinner and a drink
At this point in the day, you’re probably ready for more R&R. If it’s time for pau hana, aka happy hour, head on over to Hula’s Bar and Lei Stand for a cocktail. Hula’s is the most popular gay bar in the state, so you’re always bound to run into some fun. I like going there for happy hour because you get a spectacular sunset view from the patio while avoiding the cover charge at the door later in the evening.
Hula’s is the place for cruising, in every sense of the word. Not only does the bar play host to a delightful array of visiting eye candy, but Hula’s also organizes a catamaran tour every Saturday, the best gay boat tour Waikiki has to offer. Be sure to book your cruise in advance as it tends to fill up quickly.
Hau Tree at Kaimana Beach Hotel
Now that you’ve worked up a healthy appetite, satisfy your hunger back at Kaimana Beach Hotel’s restaurant Hau Tree. This stunning beachfront restaurant is the most recent culinary concept to hit the scene in Waikiki, and one of the only places where you can dine literal steps from the sand. Serving delectable, farm-to-table dishes for brunch, lunch and dinner, Hau Tree is a noteworthy dining destination in its own right.
If you prefer to drink your dinner, you’re in the right place. Local mixologist Jen Ackrill has transformed Hau Tree into one of the best spots in Waikiki for sunset cocktails. She nods to the classics, like the 1944 Mai Tai, and elevates beach favorites, like the Waialua Honey Ginger Daiquiri or the frozen rosé or, as I like to call it, frosé.
Out in Waikiki
As the sun sets on Waikiki, new wildlife emerges – the night owl. The sidewalks of Kalakaua trade croc-clad travelers for musicians, b-boys, and street performers. Kapi’olani Beach Park, an urban green next to Honolulu Zoo, swaps its soccer moms for fire spinners. A stone’s throw from hostel row, on Queen’s Beach, an influx of rowdy party-goers meets at dusk for the pre-game. A paradise for beach lovers and shopaholics during the day, Waikiki delivers just as much fun and excitement at night.
A wild gay night out in Waikiki should always start with karaoke at Wang Chung’s. While this cozy bar lacks a bit of elbow room, it compensates with strong drinks and a charming, welcoming atmosphere.
Once you’ve sung through the entire Britney discography, rendezvous at DECK on the third floor of Queen Kapiʻolani Hotel. From its sprawling namesake deck, you’ll have one of the best views of Diamond Head Crater during the day, and the commotion on the street below at night.
If you’re ready for round three, you’ll find a younger crowd partying all night long at Bacchus, another lively gay bar toward the center of Waikiki.
Or just a few blocks down the street, get up close and personal with someone new at In Between. This cozy bar gets its name from its compact orientation between two buildings. And I really mean cozy. It’s so small that you can’t help but socialize with whoever happens to be there at the same time.
If you do end up meeting someone new, you’ll find all the party favors and supplies necessary to finish the evening strong at Velvet Video, just down the road.
Given its large concentration of gay bars and its welcoming aloha spirit, it’s easy to see why thousands of LGBTQ travelers flock to the island annually. In my book, that makes Oahu one of the gayest, if not THE gayest island in Hawaii. Perhaps the entire Pacific Ocean.