3 Hawaii proposal ideas that are over-the-top

All you have to do is ask, "Will you marry me?" These resorts take care of the rest.
engagements hawaii

For many travelers, just flying to Hawaii and popping the question on any of its pristine beaches is exciting enough, but what these resorts and tours have up their sleeves take the tradition up a notch.

Propose on Maui, then fly to Oahu to pick out the ring

maui proposals
The Cliff House at Montage Kapalua.
Photo: Montage Kapalua

Hawaii’s most over-the-top wedding proposal this year appears to be happening at Maui’s Montage Kapalua Bay. The resort recently partnered with the House of Harry Winston to put together a proposal package called Love Is In the Air, a $20,000 experience (ring not included—we’ll get to that in a second) that starts with penthouse views of Kapalua Bay, a private helicopter ride to Oahu, engagement photo sessions, gourmet meals and other romantic activities in between.

It’s presented as a new take on the traditional way of presenting the ring—you don’t. Instead, you pop the question, then extend a Harry Winston box that’s empty inside. Lovebirds are then flown away to Oahu via Blue Hawaiian Helicopters to fill that void with a stop at the House of Harry Winston salon to select said engagement ring (purchase of ring is at an additional retail cost) with a private consultation.

Hop back on the helicopter for a ride back to the Montage and dinner for two at the resort’s Cane & Canoe restaurant.

For full package details and reservations, visit Montage Kapalua Bay. Package is not bookable online, must call reservations at (808) 662-6600 and mention the “Love is in the Air” to reserve.


Propose on the estate grounds of a romantic Hawaii Island inn

holualoa inn
Holualoa Inn, Hawaii Island.
Photo: Holualoa Inn

Holualoa Inn, an elegant bed and breakfast tucked away on the slopes of Mount Hualalai near Kona, makes for a the perfect backdrop to pop the big question. Perched 1,400 feet above sea level, this inn, featuring four guests rooms, two suites and a historic cottage, is prepped with various private corners across the estate to get down on bended knee and ask: “E male ana ʻoe iaʻu?” (“Will you marry me?”) Whether that’s in the Rooftop Gazebo or the lanai of the Zen Buddha Garden, Holualoa Inn has two engagement packages to choose from depending on your interests—a proposal package for the adventurous couple, or couples who prefer to be pampered.

In the former, upon check-in, you go on a ziplining tour with Hawaii Forest and Trail in Kohala and have a romantic lunch overlooking Pololu Valley. In the latter, indulge in a 90-minute couple’s massage, then enjoy a sunset sail with some wine. When you return from either, the inn’s Love Affair Package, which includes rose petals on the bed, a bottle of chilled champagne, chocolate-covered macadamia nuts and a fresh tropical flower bouquet will greet your loved one after you pop the big question.

At breakfast the next morning, receive congratulatory lei to wish you a happily every after together.

For full package details and reservations, visit Holualoa Inn.


Propose with the help of a professional Disney photographer

disney aulani
Aulani, a Disney Resort at Ko Olina.
Photo: Disney/Aulani

If you want your proposal to feel like a dreamy fairy tale then Disney’s Aulani resort on Oahu in Ko Olina is the one (they would be the experts after all, right?). Let the concierge assist you in crafting this magical memory by soliciting their PhotoPass Cast Members to secretly document the picture-perfect moment you surprise him or her with the ring.

Or, if you want to make it even more custom, consider going on any of its guided tours, like a day horseback riding at Kualoa Ranch followed by an exclusive catamaran ride to a private beach or a guided tour of the North Shore and catered picnic lunch. The cast members are experienced in custom-tailoring engagements for their guests and photographing them to make the moment a tale as old as time, something you and your loved one can remember forever.

For more information on planning a wedding at the resort, visit Disney’s Fairy Tale Engagements & Weddings.

Categories: Travel Tips