by Brian Biros Why go? Who doesn’t want to get engaged in paradise? And with its jaw-dropping range of climates and activities, your proposal doesn’t have to stick to the tropical-beach cliche, either.
Tip 1: Most tourists go to the island of Oahu, but each of the Hawaiian Islands has its own personality, culture, and draws. Do your research and see what’s on offer outside Waikiki.
Tip 2: If you do want to do a beach proposal, avoid the tourist-ridden obvious ones and seek out the islands’ “secret” beaches instead.
You’ve been dating for years, the hints have been dropped, and you have a trip to Hawaii on the calendar. Let’s be honest: She’s expecting you to drop to a knee at some point on this trip. For the sake of your well-being after Hawaii, you won’t want to return to the mainland without putting a ring on her finger.
There is a reason a Hawaii vacation carries an expectation of a proposal. What woman wouldn’t want to be asked for her hand in marriage with a thousand-foot waterfall or glowing magenta sunset as her backdrop? You won’t be the first or last couple to get engaged in Hawaii, but that doesn’t mean you can’t be original or catch her by surprise.
Plus, because it’s part of the U.S., Hawaii makes for an attractive getaway that’s easier to fly to and more affordable than other tropical paradises like, say, Tahiti, Bora Bora and the Maldives. There are many direct flights to Honolulu’s Daniel K. Inouye International Airport from the mainland, and you can arrange relatively inexpensive hops from Oahu to the other islands. There’s pretty much no bad time to go to Hawaii (“winter” averages 78 degrees Fahrenheit, while summer is usually about 85 degrees, and though rainy season lasts from November to March, it’s usually nothing like a deluge), but high season for tourists is from December to April.
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Best Instagram Proposal in Hawaii: Kalalau Lookout, Kauai
Kokee Rd, Kapaʻa, HI 96746, USA
Millions of years of erosion have made the Na Pali Coast Hawaii’s most photogenic. While most of it is only viewable by helicopter, the best walkable viewpoint is the Kalalau Lookout, reachable from southwest Kauai at the clockwise end of the circular highway. Mid-morning is the best time for the visit. Clouds should be sparse that early, but the sun will be high enough to accentuate the dramatic cliff ridges. Weather can change rapidly, so if it’s cloudy, wait for it to clear. Your patience and the long drive out to this lookout will be rewarded with perhaps Hawaii’s most stunning backdrop. Find a clearing along the trail with an unobstructed panoramic view of the lush green valley and blue Pacific. This is where you take a knee and that stranger walking behind you with the big camera turns out to be the photographer you hired. (Photo by @brittneyamaral)
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Most Hawaiian Proposal: Luau Kalamaku, Kauai
3-2087 Kaumualii Hwy, Lihue, HI 96766, USA
A luau may be the most quintessential Hawaiian experience. It’s almost obligatory for couples to enjoy this outing of food, drink, culture, and dance. The script is the same every day and begins with a pig baked underground in a traditional imu oven all day long and guests are welcomed in the evening for a set, all-inclusive price. The feast prominently features the roasted pig along with a large buffet. Expect an open bar primarily featuring mai tais. Afterward, guests are treated to a traditional Hawaiian dance show with women in hula skirts and shirtless men spinning fire. The show rarely deviates from its script, but you have the opportunity to change that. Call far in advance and ask to speak to the manager of the luau. Tell them you would like to propose to your girlfriend during the show. Most will be delighted to take part in the experience and to even integrate it. It could go down like this. You grab front row seats for the dance portion of the luau. Performers “randomly” select you and your girlfriend to join them on stage as they teach you the hula, surrounded by fire dancers. As the music comes to a halt, you drop down to one knee and propose as the audience roars in support.
You have endless options of luaus in Hawaii for about $100, but it’s best to choose a more intimate experience that doesn’t feel like you’re on a factory line. In Kauai, try the Luau Kalamaku for its incredible dance show. (Photo by @flour_n_flowers)
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Luau: Experience Nutridge, Oahu
3280 Round Top Dr, Honolulu, HI 96822, USA
On Oahu, Experience Nutridge is smaller and more interactive than other luaus in Honolulu. (Photo by @experiencenutridge)
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Luau: The Feast at Mokapu, Maui
3550 Wailea Alanui Dr, Wailea, HI 96753, USA
The Feast at Mokapu luau at the Andaz Maui serves premium food and drinks for a premium price ($200), but it’s worth it for your engagement! (Photo by @wheretheproudthingsare)
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Luau: Haleo, Big Island
78-128 Ehukai St, Kailua-Kona, HI 96740, USA
Finally, the Big Island doesn’t have the luau selection of the other islands, but Haleo Luau at the Sheraton Kona Resort is your best option. If a certain luau cannot accommodate your special request, simply call the next one on your list. (Photo by @haleoluau)
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Best Restaurant Proposal in Hawaii: Four Seasons Resort Hualalai, Big Island
72-100 Ka'upulehu Drive, Kailua-Kona, HI 96740, USA
While there are plenty of delicious dining options across the state, you want something secluded, romantic, and uniquely Hawaiian for the biggest dinner of your lives. A private dining experience on the beach will set the mood the minute your feet hit the sand.
When you take her to the Four Seasons Resort Hualalai on the Big Island, she knows she’s in for a special dinner, but she may not know just how special. You’ll be escorted to a single table set up on a private beach surrounded by floral arrangements, candles and tiki torches. The sun will set over the ocean as you enjoy a four-course meal tailored from the chef himself. Any point during this immaculate dinner experience is the perfect time to drop to one knee. (Photo courtesy of Four Seasons Resort Hualalai)
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Affordable Restaurant Option: The Kahala Hotel & Resort, Oahu
5000 Kahala Ave, Honolulu, HI 96816, USA
If the Four Seasons price tag for its Dinner Under the Stars is a bit too hefty at $1,000 per couple, you have other options. The Kahala Hotel & Resort in Honolulu is another of the many hotels offering a private, oceanfront dining experience, and this one starts at $285 per person. (Photo courtesy of The Kahala Hotel & Resort)
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Best Proposal for Fit Couples in Hawaii: Hanakapiai Falls, Kauai
Hanakapiai Falls, Hawaii 96746, USA
The erosion that has shaped Kauai’s Na Pali Coast has also made it inaccessible by car. Therefore, it remains Hawaii’s rugged outback and an exclusive playground for the adventurous. From the northwest tip of Kauai, the Kalalau Trail is the entry point for most serious Na Pali Coast hikes. Do not confuse this with the Kalalau Lookout, which is accessible from the southwest — a two-and-a-half-hour drive around the island from here. Keep in mind a recent change in regulations means permits are now required to park at the trailhead ($5) and hike the Kalalau Trail. Be sure to start early, as this adventure will take most of the day.
From the trailhead, begin the difficult climb until the trail wraps around the first sea cliff, revealing stunning views of the Na Pali Coast. Keep hiking — this isn’t the spot, but the mood is being set. You’ll be surrounded by endless scenery on the two-mile hike, which eventually lands you on Hanakapiai Beach. Most hikers turn around here, but you’re only halfway there. Take a break on the beach with the echoing sound of crashing waves, then continue your quest and follow the upstream path into the jungle. The hike crisscrosses the stream, so be sure you are both wearing good water shoes. After two miles of backtracking the Hanakapiai stream, you’ll start to hear the echo. As you come to the end of the trailhead, finally taking your attention away from each step on the slippery rocks, you look up to find yourself in a massive canyon with the thunderous 300-foot tall Hanakapiai Falls pouring into the pool below.
This is the moment. Your lady will have her breath taken away by the awesome setting. Before she is able to catch it, drop to a knee. The series will be all too overwhelming for her. When she recovers — which may take a while — jump into the pool and swim underneath the falls. The cold water and rush of the falls will take her breath away once again. (Photo by @juliannavezza)
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Most Artsy Proposal in Hawaii: Pow! Wow! Hawaii, Oahu
327 Lana Ln, Honolulu, HI 96813, USA
If she’s a lover of the arts, time your visit during POW! WOW! Hawaii in February to see world-class street artists turn the walls of Honolulu’s Kaka’ako neighborhood into massive murals. The festival now tours the world, but it returns to its original home in Hawaii every year. Previous years’ murals have included a collection of tropical flowers emerging from geometric shapes, a panda sleeping on a bed of poinsettias, and a depiction of a neon sign that simply says, “Today was a good day.” You have a few hundred to choose from, including new murals that will debut this year. Decide which murals will speak to her, and be ready to speak those four words to her when you take her there. A picture of the proposal with the mural backdrop is half the reason you are doing this here, so make sure you’ve hired a photographer to be there and ready. (Photo by @emilylmahr)
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Best Holiday Proposal in Hawaii: Pu'u O Kaimuki Park, Oahu
951 Koko Head Ave, Honolulu, HI 96816, USA
“Mele Kalikimaka!” is how Hawaiians say “Merry Christmas.” During the holidays, expect to hear Bing Crosby’s famous Christmas song of the same name several times per day. The timeless holiday classic still perfectly captures the holidays on the islands, where Santa trims his suit to shorts and jingle bells are accompanied by a ukulele. In Hawaii, you get all the Christmas merriment but none of the cold so why wouldn’t you want to spend the holidays here? While it will already be a vacation to remember, you’re about to ensure she never forgets it.
Start the evening with a trolley ride through the dazzling holiday light display of Honolulu Hale City Lights and its 60-foot Christmas tree. Then, escape the crowds and head to the top of Pu’u O Kaimuki Park, famous for its rustic “floating” Christmas tree, which has stood year-round for decades but only lights up at Christmas time. After taking in views of Waikiki Beach and Diamond Head, walk her under the hovering tree. In the peaceful faint glow of the green lights with no one else around, you’ll have your chance. (Photo by @ukeboy808)
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Best Secluded Proposal in Hawaii: Manawaiopuna Falls, Kauai
Eleele, HI 96705, USA
The landscapes of Hawaii are unmatched elsewhere on earth, but much of it is completely inaccessible. This is why helicopter tours have become so popular. While a tour on any island is worthwhile, the helicopter tour on Kauai is most impressive, with jaw-dropping views of the Na Pali Coast’s sea cliffs, the lush, green crater interior packed with waterfalls, and possibly even a landing in front of a superb waterfall on private land, inaccessible to anyone else.
If the chopper tour feels like something out of “Jurassic Park,” there is good reason for that. Much of the movie was filmed on this island, right up to this exact waterfall landing that the tour mimics. Your lady will already be blown away by the hour tour around the rest of Kauai by the time you land at Manawaiopuna Falls. Walk to the base of the falls, where she’ll lean her head on your shoulder. As she takes a deep inhale, watching the 400-foot falls majestically tumble into the pool and absorbing all the natural beauty she just witnessed, you’ll take a knee and pop the question.
The helicopter tour that includes a landing at Manawaiopuna Falls is only offered by Island Helicopters ($342), meaning you will be alone. If you want to be the only guests on the tour, call the company to see about reserving the full chopper. Ensure the pilot is well aware of your plans. He can either be watching and ready to snap pictures as the moment unfolds, or he can stay back, ensuring this moment is experienced just by you two in magically surreal isolation. (Photo by @nanettezumwalt)
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Best Beachside Proposal in Hawaii: Kaimana Beach on Oahu
Kaimana Beach, Honolulu, HI 96815, USA
This is Hawaii. You have as many options for beaches as you had for the engagement ring. There is no “best” beach in Hawaii, but everyone has a favorite. The trick here is to figure out which beach would be her favorite. I’ll give you some of the best beaches in different categories, and you can decide from there.
Let’s start out with where not to propose: Waikiki Beach. While it is a nice beach, it’s hectic and crowded, and there are much better beaches across the state. If you want a beach in this area, walk down to the less crowded Kaimana Beach, where the locals hang out to escape the Waikiki tourists. (Photo by @silver.dapple0527)
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Another Beachside Proposal Spot: Makalawena Beach, Big Island
HI-19, Kailua-Kona, HI 96740, USA
Want a beautiful white-sand beach with even fewer people? The hike to Makalawena Beach on the Big Island weeds out most visitors. (Photo by @coconut_sports)
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Black Sand Beach at Isaac Hale Park, Big Island
13-101 Kalapana Kapoho Beach Rd, Pāhoa, HI 96778, USA
How about a black sand beach? The eruption of Big Island’s Mauna Loa volcano created a new black sand beach in 2018 at Isaac Hale Park. (Photo by @imjustupsidedown)
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Red Sand at Kaihalulu Beach, Maui
Kaihalulu Beach, Hana, HI 96713, USA
How does red sand sound? You’ll find an actual red sand beach at Kaihalulu Beach in Maui. Many people come to see it, though, so get here for sunrise to maximize romance and minimize company. (Photo by @leonie_2107)
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Green Sand at Papakolea Beach, Big Island
Naalehu, HI 96772, USA
Green sand? Yes, there is actually a beach with green sand called Papakolea at the southern tip of the Big Island. Again, it sees many visitors, so early a.m. is best. (Photo by @terrax)
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Clothing-Optional Proposal: Little Beach, Maui
Kihei, HI 96753, USA
Want to make the ring on her finger so special that it’s the only thing she is wearing? Little Beach is Maui’s not-so-secret clothing-optional beach. (Photo by @ashleechanning)
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Secluded Beach Option: Waipi'o Valley Beach, Big Island
Island of, Waipio Valley Rd, Honokaa, HI 96727, USA
If you’re looking for ultimate beach seclusion, every island has an option. Both Maui and Kauai have beaches nicknamed “Secret Beach.” On the Big Island, even those that hike down into Waipi’o Valley rarely cross the stream to the far end of Waipi’o Valley Beach. (Photo by @kona_6am)
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Secluded Beach Option: Halona Beach Cove, Oahu
Halona Beach Cove, Hawaii 96825, USA
Oahu’s Halona Beach Cove is practically begging for a proposal inside of it. (Photo by @lescooleursdumonde)
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Secluded Beach Option: Polihua Beach, Lanai
Lanai City, HI 96763, USA
And Molokai and Lanai see so few tourists that you can take your pick of beaches on those islands. But if you need an answer, you won’t see another soul on Lanai’s Polihua Beach. (Photo by @island_mum)
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Secluded Beach Option: Kawakiu Beach, Molokai
Kawakiu Beach, Hawaii 96770, USAMolokai’s Kawakiu Beach is another beautiful setting for a perfect proposal. (Photo by @sumu777)
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Most Unique Proposal in Hawaii: Under the Sea
1839 Kahakai Dr, Honolulu, HI 96814, USA
If you’re both fans of scuba diving, here’s an opportunity to catch her off guard with the question. Even if she’s expecting a wedding proposal on your romantic trip to Hawaii, she isn’t going to expect it under the sea.
To pull this off, it will have to be a group effort. Let the dive shop know beforehand so the divemasters can help by carrying the laminated sheets with the big question and any other special messages you’d like to lead with. They could also have fake flowers stashed for you. The ring, however, is your responsibility. She won’t be the least bit suspicious, because videographers on commercial dives are completely common. But this time you’ll actually be purchasing the footage.
Admittedly, the proposal will be a little more clumsy than above-water proposals. With faces contorted by dive masks and regulators, you’ll miss out on facial expressions. There also won’t be any talking or sudden movements. You will, however, be able to hold your breath long enough to pull the regulators out for a celebratory kiss.
A shallow shore dive may work best for the setting. Be extra careful with that ring. If you don’t trust handling it underwater, then pop the question and use a fake ring underwater. Give her the real thing when you return to the boat or to shore. (Photo by @travelwithmazur)
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Most Otherworldly Proposal in Hawaii: Haleakala National Park, Maui
Hawaii, USA
Climbing to the top of Haleakala volcano is like ascending to another planet. The Mars-like surface of this massive crater is not to be missed on a trip to Maui. Sunrise is the best time to witness it, especially for what you have in mind. You’ll need reservations for sunrise — $1 on top of the $20 national park entry fee (per vehicle). Rather than crowding into the packed sunrise viewing platforms, hike down into the crater. Keep in mind it will be completely dark and you’re 10,000 feet above sea level. Dress warm, and good shoes are needed. Bring a headlamp and extra layers and blankets. You don’t want the moment ruined by cold.
Be sure to arrive well before sunrise to allow time to hike down into the crater. When you find a good spot, cuddle up on a blanket with another wrapped around you sharing a Thermos of coffee or tea. The sky will begin to light up beyond the crater, and the sun will eventually rise above the horizon. The colors of the sky are only half of the show. The otherworldly landscape around you will emerge from the night revealing perfect red cones and craggy mountains. This breathtaking setting, just after sunrise, is your perfect moment to pop the question. (Photo by @engagedonmaui)
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Most Explosive Proposal in Hawaii: Magic Island, Oahu
Magic Island, Honolulu, HI 96815, USA
Every Friday night, with a start time between 7:30 p.m. and 8 p.m., depending on the season, fireworks light up the sky off Waikiki for 15 minutes. Tourists pack the beach and waterfront hotels while locals head out Magic Island (actually a peninsula) off Ala Moana Beach Park for a more peaceful show.
Bring a blanket, pack a picnic, and walk out to the park early. Stroll along the palm-tree-lined paths and set up for sunset as you enjoy wine and cheese. After the sunset glows fade to black, turn your attention to the fireworks. She may think the grand finale is happening over Mamala Bay, but you have your own grand finale planned right there on your blanket. After tonight, your future fiancée will have the perfect answer to where you got engaged — on Magic Island in Honolulu. (Photo by @tabcolette)
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Most Spiritual Proposal in Hawaii: Iao Valley State Park, Maui
54 S High St, Wailuku, HI 96793, USA
Is your girlfriend less interested in marriage and more interested in the spiritual union of your souls? Pack your daypack with kombucha and hemp seed energy balls and head for Maui’s sacred Iao Valley State Park, a land ancient Hawaiians reserved for royalty. Most tourists walk straight to the Iao Needle observation deck, but you want to penetrate deeper into this valley that is still said to be a source of divine energy, or mana. Follow the stream past any marked trails until she finds a synergetic spot where your energy aligns with the valley’s. It is here that you will place an amethyst band on your life partner’s hand, requesting a union to last the remainder of your spirits’ occupation of your mortal bodies, and beyond. (Photo by @lisahdr_)
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Most Name-Appropriate Proposal in Hawaii: Sweetheart Rock, Lanai
Puupehe, Hawaii 96763, USA
Sweetheart Rock is an iconic, 80-foot-tall rock island off the coast of Lanai. Hawaiian legend tells of a warrior who kept his maiden in a sea cave near the island. One day after a storm, he returned to find the maiden had drowned. Stricken with grief, he climbed to the top of the rock with her body. There he buried her then jumped from the rock, plummeting to his death.
Don’t make the same mistake as that warrior and keep your maiden high up on the cliffs opposite Sweetheart Rock. From the Four Seasons Resort Lanai, hike for 15 minutes up the path along the rocky cliff to the dramatic overlook. Sit and watch the waves crash into the massive rock and its smaller island neighbors, surrounded by turquoise sea. Keep an eye out for dolphins or even whales if you’re here in winter. Let the mood set in, and when the time is right, give your sweetheart that rock. (Photo by @spiritofastorm)
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Most Peaceful Proposal in Hawaii: Kuli‘ou‘ou Ridge Trail, Oahu
Kuli'ou'ou Valley Trail, Honolulu, HI 96821, USA
The Kuli‘ou‘ou Ridge Trail may not be the most popular or easiest to pronounce of Oahu’s hikes, but the ironwood trees are what make it special. When a gust of wind passes through, the needles on the trees make a soft “whoosh” sound, which can get deafening during strong gusts through this dense ironwood forest.
Tell her before that you want to do the hike in silence. As you climb the switchbacks hand in hand, you’ll enter the ironwood forest and hear the magically serene sounds of the wind. After the last switchback, you will see a natural elevated platform to the right that looks like an altar surrounded by ironwood trees. Walk her over to the platform, then place the camera as if you are putting a timer on for a still picture. In reality, you will be recording. After you pose for the imaginary picture, turn to her, get down on one knee and break the silence. (Photo by Brian Biros)
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Most Overrated Proposal Spot in Hawaii: Diamond Head, Oahu
Diamond Head, Honolulu, HI 96815, USA
I’ve already warned you about proposing on Waikiki Beach, but right next door is another spot you could get lured into thinking would be good for a proposal, sunrise at Diamond Head crater. It seems so appropriate: Give her a diamond in Diamond Head Crater! Problem is, the hike up to the crater rim for sunrise is on the itinerary of every tourist passing through Honolulu. The viewing platform at the top will be so crowded you wouldn’t even have room to take a knee. Even if you find a viewpoint along the trail that looks secluded, eventually another tourist will admire your spot and join you. (Photo by @wanderlusterprincess)
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A Perfect Alternative: Lanikai Pillboxes, Oahu
Kailua, HI 96734, USAFor a quieter alternative, drive out to Lanikai on the eastern shore of Oahu. The hike up to the Lanikai “Pillboxes” (old military bunkers) is well marked, although you will be doing it in the dark. The crowd is far thinner and the sunrise more spectacular than you find at Diamond Head. While you may not find an empty pillbox to watch from, there are plenty of spots along the trail ridge where you’ll be alone. (Photo by @annetteroma)
