A wedding proposal used to just mean getting down on one knee in the living room, a romantic walk followed by popping “the question,” or—if you’re going all-out—perhaps a ring in a Champagne glass with dessert. But just as weddings have become grander affairs, so have proposals. Of course, there’s absolutely nothing wrong with a low-key engagement. But for those with a flair for the dramatic or want to ensure that this first big step together as a married couple is a story for the ages, it may be time to go big. Really big.
You can absolutely set about planning a wild proposal from scratch, but consider the logistics of, say, planting a ring in a glacier in Iceland or having an eagle drop a ring into your fiancée’s hands in Mongolia. (Yes, both of those proposals actually occurred.) Do yourself a favor and call in some expert advice. Whether it’s an engagement concierge to help craft a completely bespoke experience or a resort with some pre-planned extravagant proposals, here are a few ideas to get you started:
Jenifour Jones of event travel firm Go Get It created a seriously epic scavenger hunt through California for one soon-to-be groom: It included a trail of roses on a beach, a private flight, and a spa day, all capped off by a stay in a suite at Big Sur’s Post Ranch Inn where a commissioned mural of the couple’s journey together hung over the fireplace and a photographer was hiding to capture the “yes.” She has also hired actors to create Off-Broadway plays that set the stage for the big question. These services don’t come without a bit of a price tag: They start at $5,000 and can run north of $25,000.
If you have your heart set on a proposal in your favorite vacation destination, odds are, there’s a wedding planner or tour operator who can help arrange your dream day. In Iceland, boutique tour operator Pink Iceland “spent an entire evening hunting for the Northern Lights so the question could be popped under the dancing lights in the sky,” says co-owner Eva María Þórarinsdóttir Lange. The company also arranged a pop-up concert with the couple’s favorite band on a deserted island. “We prefer to find natural venues a bit far from the main sights—it’s better when there is a little challenge to get there!” says Þórarinsdóttir Lange.
Many hotels also have awe-inspiring engagement packages available or are happy to help guests craft something truly memorable. The Cove Eleuthera on an idyllic Bahamian island and the Amalfi Coast’s Casa Angelina both have expert teams on hand to help devise the perfect plan. And even if your desired location doesn’t have a dedicated engagement planner (or “romance concierge” as is the case of The Cove), many resorts have wedding coordinators on staff who can help craft a dream proposal. At Il Salviatino in Florence, Italy, the hotel’s local connections allow them, for example, to arrange a private dinner proposal at the Uffizi or a private day of ring shopping at the Ponte Vecchio’s famous jewelers before a candlelit dinner overlooking the Duomo.
If you’re heading to Hawaii, the Four Seasons Resort Oahu at Ko Olina has a standout proposal idea: a private helicopter ride to the Hawaiian Legacy forest on the Big Island for a private tree-planting tour, a meal in the forest, a glass of Champagne once it’s official, and even La Perla lingerie delivered to the Penthouse Suite that evening. Want a big bang? The Four Seasons Lanai can arrange fireworks after you get a “yes.” The Montage Kapalua Bay puts a spin on things: Prospective grooms propose with an empty Harry Winston box, and then, the couple takes a helicopter trip to Oahu for a personal consultation with the jewelry house’s team.
One&Only Reethi Rah in the Maldives constructed a maze for one couple that ended with a bridge over a man-made river leading to a private dinner table. Craving seclusion? Soneva Fushi, also in the Maldives, can set a couple up on a private sandbank for the entire night: Dom Pérignon and a multi-course, lantern-lit dinner give way to an overnight in a luxury tent with a boat arriving at sunrise to deliver breakfast.
At Angama Mara in Kenya, charter a hot air balloon for the big question or arrange to ask in the presence of a herd of wild animals. The picturesque destination also offers a private picnic option with bubbly on the very kopje (hill) where romantic scenes from Out of Africa were filmed decades ago. But if you just can’t wait to get to the destination before popping the question, you can propose mid-flight on Hong Kong Airlines, where they’ll work with the groom on timing, and deliver Champagne and cake to celebrate.