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Everything You Need to Know to Plan an LGBTQ-Friendly Hawaiian Vacation

Oct. 19, 2018
20 min read
waikiki beach
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Though traveling as an LGBTQ individual, group or family can be challenging for a number of reasons, one destination where folks don’t have to worry is Hawaii. The Aloha State is one of the gay-friendliest places not just in the US, but in the world. Same-sex marriage has been legal there since 2013, and many resorts now specifically cater to LGBTQ travelers, weddings and families.

There are plenty of ways to use points and miles to book a trip to the islands, too, whether you’re drawn to the bustling shores of Waikiki, the rugged splendors of Kauai or the family-friendly vibe of Maui’s beaches. No wonder Hawaii is one of TPG readers’ favorite places to maximize their points. We’ve also seen plenty of flight deals lately, including fares as low as $311 round-trip from the East Coast and $247 from the West Coast.

An aerial photo of Tunnels beach. Tunnels is located on Kauai's North Shore and is named after the "tunnels" that snorkelers and divers can observe when navigating the reef. This is one of many great snorkeling spots in Hawaii, and also one of the better surfing beaches. (Photo by bjonesmedia/Getty Images)
Photo by bjonesmedia/Getty Images.

What’s more, the major airlines and hotel chains operating in Hawaii tend to score very high on the Human Rights Campaign’s Corporate Equality Index, which rates US businesses on their treatment of LGBT employees, consumers and investors. Among the airlines that received a perfect score on the latest report were Alaska Airlines, American Airlines, Delta Air Lines, United and Southwest (which will hopefully launch flights to the islands next year). In the hotel world, Hilton, Hyatt, IHG, Marriott and Wyndham, among others, all received perfect scores, too, so LGBTQ travelers have plenty of choices for where to spend their points or cash.

Photo by Jakob Owens on Unsplash
Photo by Jakob Owens on Unsplash

If you’d like more background information on gay history and travel to Hawaii (albeit a little dated now), pick up a copy of "Rainbow Handbook Hawaii: The Islands’ Ultimate Gay Guide" to read on the plane. Hawaii’s LGBT Legacy Foundation site is another great resource on gay travel, programming and events in Hawaii. You can also peruse Purple Roofs for listings of LGBTQ-friendly accommodations, travel agents and tour operators.

With options for every taste, you just need to decide what kind of vacation you want, and which island is right for you.

Oahu: Cultural Attractions 

Hawaii’s most populous island, Oahu, is home to the state capital of Honolulu, as well as the major international airport, Daniel K. Inouye International (HNL), making it a smart place to start for Hawaii newbies. It’s also a great destination for LGBTQ travelers in particular for a number of reasons, not least of which is Honolulu Pride. This year, the Honolulu Pride Parade and Festival is taking place on Saturday, Oct. 20, though events run all month long, including special exhibitions, speaker panels, singalongs, pool parties and more.

Getting There

Although it’s right around the corner, there still seems to be a lot of award availability on various flights from the West Coast to Honolulu. I found awards in both economy as well as business class with American Airlines. Though you could redeem 20,000 AAdvantage miles or 22,500 Alaska miles each way for these flights in economy, the better option would be redeeming just 12,500 British Airways Avios each way. The program is a transfer partner of American Express Membership Rewards and Chase Ultimate Rewards, so you have various ways to top up your account, especially if you can take advantage of a limited-time transfer bonus.

Where to Stay

Several of the festival’s hotel partners are also offering special packages with discounts and added perks for folks who want to fly in for the fun. Aqua-Aston Hospitality, for example, has 21 properties on Oahu that offer “Out and Proud” packages not just during pride, but all year round. Guests receive a discount that varies by date and property, and free welcome beverages at Honolulu’s best-known gay bar, Hula’s Bar & Lei Stand. The catch is you actually have to book by phone, calling 855-945-4092 and mentioning “Out and Proud.” I called to find out what was available over Pride, and learned their rates were $20 to $40 per night lower than the standard ones on the Aqua-Aston website.

Honolulu's Pride parade marches through Waikiki. Photo courtesy of Hawaii's LGBT Legacy Foundation.
Honolulu's Pride parade marches through Waikiki. Photo courtesy of Hawaii's LGBT Legacy Foundation.

Castle Hotels & Resorts has 18 properties across the islands, including the Waikiki Shore and the Waikiki Grand Hotel on Oahu. The group is offering 15% off rates for stays booked by Oct. 20, and completed by June 30, 2019 using the promo code “prideweek” at select properties, such as the Waikiki Grand.

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Not sold on Honolulu Pride? The good news is Hawaii has pretty much perfect weather all year round, so you can plan your trip to Oahu whenever suits your personal calendar. When you do, the options for points hotels abound.

For instance, you’ll need just 50,000 Hilton Honors points per night to stay at the Hilton Waikiki Beach this fall, or 58,000 to 60,000 points at the Hilton Hawaiian Village Waikiki Beach Resort, which is better for families.

Have Hyatt points? Your options are the Hyatt Centric Waikiki Beach (20,000 points), the Hyatt Regency Waikiki Beach Resort and Spa (20,000 points) and the Hyatt Place Waikiki Beach (12,000 points).

Marriott Rewards members, meanwhile, have 10 hotels to choose from, including some true classics like The Royal Hawaiian, a Luxury Resort Collection Resort (60,000 points), the Sheraton Princess Kaiulani (35,000 points) and the Moana Surfrider, A Westin Resort & Spa (60,000 points) — all on Waikiki Beach.

Things to Do in Oahu

Can't make it for Pride? Year round, Oahu offers travelers an unmatched mix of beach, nature and cultural activities. Travelers can people-watch on Waikiki or try sports such as surfing or outrigger canoeing with an outfitter like Waikiki Beach Services. There are numerous hikes around the island, including the steep walk up iconic Diamond Head, or to more remote places like the Makua Cave or the Pali twin waterfalls. Other great hikes include the Koko Crater Railway Trail and the Lanikai Pillbox Hike, on the windward side of the isle.

Photo by Melanie Lieberman.

For a bit of history, visit the somber Pearl Harbor Visitor Center or the stately Iolani Palace, the only royal palace in the US. The Bishop Museum has some phenomenal exhibits on Hawaiian history and culture, while Shangri-La, the former estate of the late tobacco heiress Doris Duke, is an incredible collection of Islamic art in a gorgeous setting.

UNITED STATES - AUGUST 02: "Iolani Palace" in the capitol district of downtown Honolulu, Hawaii (Photo by Carol M. Highsmith/Buyenlarge/Getty Images)
Photo by Carol M. Highsmith/Buyenlarge/Getty Images.

Honolulu is also where you’ll find the only serious gay nightlife scene on the island. Try long-running mainstays like Hula’s Bar & Lei Stand, Bacchus Waikiki and Wang Chung’s.

Travelers should also watch out for regular LGBTQ events, including the annual Rainbow Film Festival in August, and the SuperSlyde Pool Party in October.

Maui: Easy Beach Getaway

The so-called “Magic Isle” is indeed full of magical experiences, including historical luaus, breathtaking volcanic landscapes, scenic drives and rainforest hikes, not to mention accommodation options ranging from budget to truly lavish. That makes Maui the perfect choice for folks who want a laid back vacation that includes everything from sunning on the beach to getting out on the water or up the slopes of a volcano. Gay offerings are much more sparse here than on Oahu, however.

Beautiful sunny day at a beach in Wailea, Maui, Hawaii.
Wailea Beach on Maui. Photo via Getty Images.

Getting There

The same tips for Oahu apply here as well. While Maui's Kahului Airport (OGG) doesn't have the same volume of fights as Honolulu, there are still many nonstop options from the US mainland. This includes Alaska service from Anchorage (ANC), Bellingham (BLI), Los Angeles (LAX), Oakland (OAK), Portland (PDX), San Diego (SAN), San Francisco (SFO), San Jose (SJC) and Seattle (SEA); American flights from Los Angeles, Phoenix (PHX) and Dallas-Fort Worth (DFW); Delta routes from Los Angeles, Salt Lake City (SLC) and Seattle; Hawaiian flights from Los Angeles, Oakland, Portland, San Diego, San Jose and Seattle; and United from Chicago-O'Hare (ORD), Denver (DEN), Los Angeles and San Francisco.

Where to Stay

Among the hotel options, the Andaz Maui tends to have a more sophisticated, adult vibe compared to Maui’s myriad family-focused resorts. The Andaz hotel is home to Morimoto Maui and the Awili Spa and Salon where guests can custom-blend products for their treatments using local ingredients in the spa “apothecary.” It also has five pools, including one just for adults.

Though award nights there are hard to come by, they’re not impossible to find, and will cost just 25,000 points each. Which is a good thing, considering room rates tend to run between $500 and $600 per night.

Families love the Grand Wailea, which has been a member of Hilton’s Waldorf Astoria luxury brand since 2006. The resort’s standout amenities include the 20,000-square-foot The Rock facility, which houses the Camp Grande kids club, a gaming lounge with Ninendo Wii and Sony PS3 stations and The Spot club for teens and adolescents complete with a snack bar and games. The resort also has a huge complex of pools, including the Wailea Canyon Activity pool with five intertwining slides, a white-water rapids slide, a rope swing, a sand beach, six waterfalls, three Jacuzzis, four jungle pools, an infant pool and a swim-up bar. You get the idea.

Photo by Peter Rothbart.

Room rates here tend to range between $350 to $800 per night, but award nights are readily available for 95,000 points each. The resort also tends to field a variety of special packages with perks, such as the fifth night free.

Things to Do in Maui

Although Maui’s beaches beckon you to stay put and relax, travelers who simply can’t sit still will find tons of activities to get you out and about on the island. The old whaling town of Lahaina is a charming place to spend an afternoon and is also home to the Old Lahaina Luau, which is practically a cultural institution at this point.

Photo courtesy of the Lahaina Luau.
Photo courtesy of the Lahaina Luau.

For nature lovers, Haleakala National Park has some of Hawaii’s most spectacular hikes and mountain-biking trails, while the Maui Ocean Center is a great place for kids and adults alike to learn about Hawaii’s unique marine environment and creatures.

Whale-watching season tends to last from mid-December through mid-May, and Maui is the best island from which to take tours like Pride of Maui’s whale-watching and snorkel tour, or Hawaiian Paddle Sport’s outrigger canoe and kayaking whale-watching tours.

And even though Maui has a quieter gay social scene than Oahu, visitors can still easily join the community. Time your trip to a Maui Pride Rainbow Dine Out — a bi-monthly event held at the Maui Brewing Company location in Kihei — and watch out for regular LGBT & Friends hikes. At any time of year, travelers can drop by a gay-friendly bar like Vibe Bar and Nightclub or Three's Bar and Grill.

Kauai: Relaxed Retreats 

The smallest and least-populated of Hawaii’s four main tourist islands, Kauai, is known as Hawaii’s “Garden Island” thanks to its lush landscapes and laid back pace. Kauai is the ideal option for LGBTQ travelers looking to get away from the crowds and to experience some of Hawaii’s most awe-inspiring scenery.

Photo by Getty Images.

Getting There

Luckily, it’s easier than ever to do so thanks to new nonstop routes from several mainland airports to Lihue Airport (LIH). These days, visitors can fly direct from Denver International on United; Los Angeles on American, Delta, Hawaiian and United; Oakland on Alaska and Hawaiian; Phoenix on American; Portlandon Alaska; San Diego on Alaska; San Francisco on United; San Jose on Alaska; and Seattle on Alaska and Delta.

Where to Stay

Most of the resorts here are on the island’s southern shore around Poipu, which tends to be sunnier than other parts of Kauai and is, as a result, better for families who want a reliable place to spend a beach holiday.

Among them, the Grand Hyatt Kauai was refurbished in 2015 and is a perennial favorite thanks to bright, spacious rooms and plenty of award availability starting at 25,000 points per night.

Grand Hyatt Kauai
The Grand Hyatt Kauai.

However, Marriott is the chain with the biggest footprint on the island, with a whopping nine resorts, so start saving your Marriott Rewards points now. They’ll come in handy, not only for nights at solid mid-range options like the Kauai Marriott Resort (50,000 points) and the Autograph Collection’s Koloa Landing Resort at Poipu (50,000 points), but also at standout luxury resorts such as the St. Regis Princeville Resort (60,000), perched on the precipices along Kauai’s northern coast.

The St. Regis Princeville. Photo courtesy of Marriott.

Travelers can also support gay-owned properties by booking a stay at a Parrish Kauai home, cottage or condo, or opting for a 17 Palms Kauai vacation cottage, owned by Ross Martineau and Jeff Demma.

Things to Do in Kauai

Among the natural sights that attract visitors here, Waimea Canyon is truly spectacular. Mark Twain called it "the Grand Canyon of the Pacific" thanks to its red rock cliffs and serpentine slopes. The island also has Hawaii’s only navigable river, the 20-mile-long Wailua River, on which you can take a boat tour or do a combination kayak paddle and hike to see beautiful fern-covered caves and the gushing Opaekaa and Wailua waterfalls.

Mark Twain called Waimea Canyon the Grand Canyon of the Pacific. Photo via Getty Images.

Kauai’s most famous natural wonder, however, is the Nāpali Coast. Its sheer, undulating cliffs are the recognizable backdrop from films including "Jurassic Park" and "South Pacific," and their peaks reach as high as 4,000 feet. Unfortunately, the park is closed indefinitely for repairs following unprecedented rainfall and landslides in April.

So, to experience the Nāpali Coast, travelers must opt for a leisurely boat trip along the coast from below, or a helicopter ride instead. Maverick Helicopters, one of the most established flight outfits in Hawaii, has actually just launched new tours out of Kauai, including a 50-minute Kauai Explorer itinerary that takes guests along the Nāpali Coast and over Waimea Canyon.

Apart from nature activities, visitors here can learn about local produce and cuisine on tours with Tasting Kauai, or go for a chocolate tasting at Garden Island Chocolate. Kauai also has some of the best golf courses in the US, including an oceanside one designed by Jack Nicklaus at Hokuala, a Timbers Resort near Lihue, and two cliff-top courses designed by Robert Trent Jones, Jr., up north.

The Big Island: Independent Adventure

The so-called Big Island certainly lives up to its name. It’s the largest island in the Hawaiian archipelago, and you could fit all the other islands combined into its landmass. The scenery here varies from fertile rain forests to alien-like lava fields, and from arid deserts to snow-capped volcanoes.

Hawaii's Kilauea Caldera at Twilight. Photo by Kevin Thrash// Getty Images
Hawaii's Kilauea Caldera at Twilight. Photo by Kevin Thrash// Getty Images.

Getting There

Unlike the other islands in the Aloha State, the Big Island has two airport options: Hilo International Airport (ITO) sits on the eastern side of the island, while the larger Ellison Onizuka Kona International Airport at Keahole (KOA) occupies the westernmost tip of the island. Hilo is served by just one carrier from the mainland (United from Los Angeles).

Kona, meanwhile, offers nonstop options on multiple airlines: Alaska from Anchorage, Bellingham, Oakland, Portland, San Diego, San Francisco, San Jose and Seattle; American from Dallas-Fort Work, Los Angeles and Phoenix; Delta from Los Angeles and Seattle; and United from Denver, Los Angeles and San Francisco.

Where to Stay

Although you’ll find major chain hotels like the Westin Hapuna Beach Resort here as well as luxury options like the Four Seasons Hualalai and the Fairmont Orchid, Hawaii Island is also known for its collection of gay-owned and gay-friendly inns and B&Bs.

The gay-owned Lava Lava Beach Club is located at the Kohala Coast’s Waikoloa Resort, near many of the major resorts, but offers a more casual, come-as-you-are scene.

Image courtesy of Volcano Mountain Retreat.
Image courtesy of Volcano Mountain Retreat.

The gay-owned Hale Ohia Cottages, meanwhile, are set on a secluded estate that dates back to 1931, and offer easy access to Volcanoes National Park, which is just a mile away. The adults-only Volcano Mountain Retreat is an intimate collection of bungalows about halfway between Volcanoes National Park and Hilo. There’s also the clothing-optional Absolute Paradise near Pahoa. Just be aware that this is near the areas affected by recent volcanic eruptions.

Things to Do on the Big Island

Like the other islands, Hawaii is a nature-lover’s playground with options ranging from water sports and ocean explorations to treks through Hawaii Volcanoes National Park, which recently reopened.

Entrance to the Thurston Lava Tube at the Hawaii Volcanoes National Park. Mount Kilauea [Photo by Yin Yang via Getty Images]
Entrance to the Thurston Lava Tube at the Hawaii Volcanoes National Park. Mount Kilauea. Photo by Yin Yang via Getty Images.

Hawaii Forest & Trail offers tons of excursions, including waterfall hikes, bird watching and more. Big Island Bike Tours can do everything from leisurely rides along the coast and through the interior to multiday trips to some of the island’s more isolated corners. Sunshine Helicopters will whisk you over the fiery vents of Kilauea and along the Kohala Coast, while the part of the island near Hilo is renowned for its waterfalls and rainforests. Visitors can also stop by Kona’s famous coffee plantations for tours and tastings, or book a horseback ride with Paniolo Adventures.

Say yes to Hawaii from 9,000 Membership Rewards points. (Photo by @mreyz/Twenty20)
Photo by @mreyz/Twenty20.

There’s plenty to do in the water, too, including diving with manta rays at night, snorkeling, scuba and whale watching with Body Glove Hawaii, and paddleboarding or outrigger canoeing with Kona Boys.

Hawaii has to be one of the friendliest destinations in the world for LGBTQ travelers. Of course, what else would you expect from the place that’s famous for its welcoming Aloha Spirit? The only hard part about planning a trip here is deciding which island(s) you want to visit, and what activities pique your interest.

Like all the best destinations, a visit to Hawaii will leave you wanting more. Luckily, it’s easy to use your points and miles to both get and stay there, so you can come back as many times as you like.

Featured image by Getty Images