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That Island Life: 10 Reasons to Head to Honolulu, Hawaii, This Fall Travel

That Island Life: 10 Reasons to Head to Honolulu, Hawaii, This Fall

Written by Stephan Horbelt on August 05, 2019
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One of the many great things about Hawaii is that each of its islands promises a unique experience for first-time and return visitors. But I’ve long considered Oahu to be the perfect “starter island” of sorts for LGBTQ travelers making their maiden voyage to America’s most lush archipelago. More than Maui, Kauai or the Big Island, Oahu — specifically Honolulu — offers everything you’d want from a Hawaii vacation.

Honolulu has surf, sun and sand in spades, naturally, but those things are complemented with an amazing dining and bar scene, not to mention the state’s only real LGBTQ nightlife options, as well as unparalleled hotel properties and a ton of annual events that come in handy when timing your warm weather getaway.

Now is the perfect time to start thinking about a trip to Honolulu this fall. Here are 10 reasons you won’t regret heading to Hawaii for your next vacation.

1. Oahu is the only island with a bustling gay nightlife scene.

Every island in the Hawaiian archipelago offers visitors an amazing trip to remember, but only Oahu — specifically Honolulu — can help you not remember all of your trip thanks to its fun selection of gay bars. And there’s a bar for every type of partier, whether you’re a raucous karaoke fiend, an all-night dancer or are just looking for a quiet corner and a glass of wine.

honolulu hula's
Hula’s Bar & Lei Stand

Any gay heading to Honolulu has to put in face time at Hula’s, the city’s legendary, longstanding gay bar (over 40 years!), located literal steps from Waikiki’s gay beach. The local gay community’s go-to spot for dancing, drinking and a bite, it opens at 10 a.m. (and we hear sells scrumptious breakfast sandwiches) and has people on the dance floor late-night ’til 2 a.m.

honolulu wang chung's
Wang Chung’s (photo via Trover)

Karaoke fans will feel right at home at Wang Chung’s, a small bar where everyone’s a bit off-key, but it hardly matters after a few Mai Tais. If you’re with a group, call ahead to inquire about the private room in the back, offering a couch for your crew and a sneak peek right into the kitchen. (Maybe you can even get the line cook to join you in a duet of “Islands in the Stream.”) On Sundays the bar also welcomes local drag queens to host weekend brunch.

If you’re looking for the full club experience, Scarlet Honolulu is the largest nightclub in Oahu, packed to the gills every Friday and Saturday night with a young, hip island crowd looking to dance, slam shots and watch drag shows, often featuring past Drag Race contestants.

honolulu bacchus
Bacchus

The closest thing you’ll find to a “neighborhood gay bar” in Honolulu is Bacchus, most likely within spitting distance of your Waikiki hotel. Serving up a cute crowd and a more laidback vibe than the island’s other gay bar offerings, there’s never a cover charge here. And depending on when you visit, you may find the crowd having fun at a trivia night or Drag Race screening party.

2. You won’t go hungry in Honolulu, morning, noon or night.

honolulu leonard's

Far be it from me to tell you where to spend your mealtime in Honolulu, but there are a few customary spots that are must-visits, whether you’re a newbie or Hawaii regular. For instance, are you really eating breakfast in Honolulu if it’s not a malasada from Leonard’s Bakery? This downright delicious sweets shop has been around since 1952, and its malsadas (Portuguese donuts) are the stuff of legend. For something you’d never find off-island, try a malasad puff with haupia (coconut) filling, coated in li hing powder.

For lunch, find yourself a Hawaiian BBQ plate lunch (grilled chicken, katsu, rice and mac salad … yum!) or a local spot that specializes in super-fresh poke. If you’ve never had poke (diced raw fish tossed with sauce and veggies), this is the place to experience it; it’s just not the same on the mainland, and in Honolulu it also won’t cost you an arm and a leg.

honolulu shave ice

When you’re craving a mid-day snack, find yourself some shave ice (yep, shave ice, not “shaved ice”) from a spot recommended to you by a local. There’s a slew of shave ice stands and larger brick-and-mortar spots on every part of the island, but some are better than others. Those snow cones you loved as a kid can’t even compete with Hawaiian shave ice, which is the equivalent of eating a sweet, sugar-flavored cup of snow.

honolulu stripsteak waikiki

And maybe your upcoming Honolulu trip calls for one night out to a fancy dinner, where you and your friends can dress to impress and savor some of the island’s local delicacies. If that’s the case, StripSteak Waikiki is a great option, a classic American steakhouse by Michael Mina, found inside the International Marketplace. Head here for sexy craft cocktails and entrées, plus a sophisticated ambiance that somehow still maintains the island’s otherwise carefree “aloha spirit.”

And speaking of food …

3. Honolulu hosts a ton of food and drink festivals.

Oahu is truly a food-lover’s paradise, and this fall sees Honolulu host more than a few festivals dedicated to various food and drink specialties, each one alone worth traversing the Pacific to attend. The Joy of Sake Festival (Aug. 9) celebrates the Japanese fermented rice wine with a public tasting event after the U.S. National Sake Appraisal. September is National Rice Month, and the one-day ninth annual Rice Festival (date still TBD) celebrates our favorite carb. The Hawaii Chocolate Festival (Oct. 5) live entertainment, guest speakers and — most important — chocolate tastings from the state’s own local chocolate vendors.

honolulu food & wine

For true foodies, the month of October is a perfect time to visit Honolulu, as the Hawaii Food & Wine Festival (Oct. 5–27) invades the island, hosting a slew of events and receptions where world-renowned chefs from Hawaii and abroad (including festival co-chair Roy Yamaguchi) and locally sourced ingredients are the stars. Hungry yet?

4. You can soak in some culture while scoring the perfect selfie at these local spots.

There’s nothing wrong with heading to Honolulu and doing little else but catching a beachside tan, but for the traveler who likes to mix in the occasional cultural activity, Oahu offers plenty of that, too. Check out one of the many museums on the island, like the Honolulu Museum of Art, which features a surprisingly diverse, expansive permanent collection, from Van Gogh to Warhol.

honolulu shangrila
Shangri La

One of Oahu’s most awe-inspiringly gorgeous locales is (quite fittingly) called Shangri La. Now a museum of Islamic art and design, it’s a mansion built by famed heiress Doris Duke, located near Diamond Head. You can catch a guided tour from the Honolulu Museum of Art, and the interior and grounds of Shangri-La will offer you more opportunities for social media profile pics than any one person deserves.

Home to the very last monarchs to rule over Hawaii, ‘Iolani Palace was the official royal residence through the turn of the 20th century (the only royal residence in all of the United States). A national historic landmark that has been restored to the peak of its beauty, there’s no better place to take in the lush history of the Hawaiian islands.

5. Waikiki’s Surfjack Hotel & Swim Club is a (reasonably priced) hipster paradise.

honolulu surfjack 2

Sometimes it seems like Honolulu — Waikiki in particular — has more hotels than people to fill them, which makes it that much harder to find the perfect property for your trip. The Surfjack is a great option for those who can’t break the bank but also don’t want to sacrifice comfort.

honolulu surfjack
The Surfjack Hotel Pool (photo by Desmond Centro)

Located in Waikiki but far enough removed from the hordes of tourists walking the beach to still be considered an off-the-beaten-path oasis, the property has some serious mid-century Hawaii vibes, but mixed with contemporary creative touches. Rooms are spacious and offer everything you need for a beachside getaway, and its restaurant, Mahina & Sun’s, is one of Honolulu’s best ‘onsite hotel dining’ offerings.

6. Or you can splurge on a stay at The Four Seasons Oahu at Ko Olina.

honolulu four seasons
The Four Seasons Oahu at Ko Olina

When budget isn’t the primary concern during your Honolulu getaway, you’d be smart to look into this beachfront hotel, located on Oahu’s peaceful and lesser-tread western coast. An island resort in every sense, it’s impossible not to be blissed-out by the amenities at this Four Seasons property, from the onsite spa and tasty breakfast spread each morning to the adults-only pool (one of four pools onsite) not far from the crashing waves of the Pacific. When you’re up to your neck in that pool, cocktail in hand, watching the sun set over the water, there’s simply no better place to be.

7. 2019 marks the 30th anniversary of Honolulu’s Rainbow Film Festival.

For proof that Hawaii, and Honolulu in particular, has long been a haven for the LGBTQ community, look no further than this queer film festival, marking three decades this year (Aug. 8–18). Over 2,000 filmmakers, actors, locals and guests converge each year to celebrate a new crop of films. Parties take place around the city, while most of the festival’s films are screened at the Honolulu Museum of Art.

8. Get high in Honolulu while becoming one with nature.

honolulu diamond head

If your Honolulu trip doesn’t include stepping out to take in the island’s natural beauty, you aren’t doing it right. One of the best ways to ‘get high’ is by making the trek up Diamond Head, the volcanic crater from which there’s no better view of the ocean and all of Honolulu. (Bonus points if you complete the hike pre-sunrise to watch the start of a new day.) Hawaii Forest & Trail is one company that can set you up with a guide to get the most out of what you’re witnessing. Their “Honolulu Heights” tour includes a hike up Diamond Head and pairs it with a drive high into the Koolau Mountains, picnic lunch included.

9. Life is perfect while enjoying a sunset cocktail cruise.

honolulu sunset cruise

If you’re gonna head to Hawaii, do it right. That includes plopping yourself down on a boat as sunset approaches and watching the sun descend into the ocean with a cocktail in hand. Hawaii Nautical, a company dedicated to on-the-water activities in Oahu and the Big Island, offers a “Harbor Sunset Cocktails and Pupus Sail” that is quite literally the perfect way to begin or end your Honolulu adventure. Have a bite and get comfortable on the ship’s bow as you sail toward Diamond Head and let the worries of work and other “city stressors” fade away.

10. All are welcome to celebrate Honolulu Pride.

honolulu pride

The week of Pride is a fun-filled time anywhere you find yourself, but Honolulu Pride (Oct. 11–20) is easily one of America’s most friendly and welcoming celebrations. Still a fairly small event compared to the massive events that take place on the mainland, Honolulu Pride makes up for its smaller (but actually manageable!) crowds with a community that heartily supports the purpose of Pride: visibility, community and love.

honolulu pride party
Honolulu Pride party photo courtesy Lei magazine

Each year Waikiki is fully decked out in time for the Pride parade down Kalakaua Avenue, which gathers smiling locals and tourists alike to cheer on the many floats and marchers. Other Honolulu Pride events are focused on art, films and fashion, and an annual festival at the Waikiki Shell Diamond Head Greens sees people gather for food and live music as soon as the parade concludes.

So what are you waiting for? Head to Honolulu this fall and join the island life.

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