A Cheat Sheet for Nailing Your Destination Proposal

Destination proposals are ultraromantic, but traveling can present some unexpected complications and curveballs

Updated 10/28/19

Photo by Quattro Studio

Some argue that proposing to your forever someone is almost—if not equally—as important as your wedding day. The gesture itself is monumental. It’s an outright proclamation of your love and a heartfelt invitation to take your relationship to the fully committed level. No matter where you pop the question, you want the day to be special and to go off without a single hiccup. Destination proposals are ultra romantic, but traveling can present some unexpected complications and curveballs.

Fear not—we asked a handful of experts to weigh in to make sure your travel proposal is flawless.

Pick a Destination You’ll Both Love

“Your proposal day will forever hold a special spot in your heart, so pick a place that is meaningful for both you and your fiancé(e)-to-be. Tailor the proposal around mutual interests, and don’t get boxed in by social expectations of what a proposal should be,” says Kathryn Money, the vice president of strategy at Brilliant Earth. "Be original and make your own memory."

Maybe it’s a locale you’ve both always dreamed of going, or maybe it’s a place you’ve visited before and where you have always wanted to return. It doesn’t have to be a quintessential romantic city, like Paris or Florence, and it doesn’t have to be over the top. What matters most is that you’re both excited to be there.

Tell Your Hotel or Resort What’s About to Go Down

This is optional, but a decision that might just elevate your proposal.

“Many all-inclusive resorts who are known for their romantic touches offer amazing proposal packages to take advantage of. Some may include a special celebratory champagne toast after you pop the question, while others provide an exclusive photographer to capture the big moment,” says Jennifer Avey, the vice president of marketing at Destination Weddings Travel Group.

She says that chances are, as long as your resort is aware of the special occasion happening, your suite will be decked out with romantic touches and amenities such as rose petals and breakfast in bed the morning after.

Do Your Research Before Jetting Off

Even if you’re normally a fly by the seat of your pants kind of planner, a destination proposal requires a bit more foresight. First, you’ll want to be aware of any cultural traditions or no-nos. One thing to note is that in many countries, proposing inside a sacred temple is frowned upon, and you’ll want to know about local hours of operation and the best romantic spots or scenic lookouts.

“[For example], if you’re planning to propose in a well-known tourist destination, it’s essential to think about noise levels of the proposal location and the crowds that will be present. Will you be interrupted by street vendors trying to sell you something? Will other tourists push past you to get the perfect photo of the site? If your fiancé(e)-to-be can’t hear you when the question is popped, or if there are too many distractions happening all around, it can certainly take away from the magic,” says Money.

Basically—think through all the logistics.

Insure Your Ring Before Boarding

“Things happen. A stone could fall out or, God forbid, your engagement ring ends up misplaced during your travels,” says Kristen Gosselin, the owner and creative director of KG Events & Design. “An insurance policy for the ring is not only financially responsible, but it protects the sentiment of the ring itself, which is priceless.”

She says you'll need to inquire at the jeweler or check with your homeowners’ insurance to see about adding the ring-specific policy. It’s a very small amount of effort with a huge peace of mind payoff. Also, you’re going to insure it eventually so you might as well do it the second it’s in your possession.

Don’t Put the Engagement Ring in Your Checked Luggage

Raise your hand if you, or anyone you know, has ever dealt with lost baggage. Though luggage usually turns up eventually—days or months later—losing the ring even temporarily can put a serious damper on your plans.

“If you’re getting on a plane, never ever put the ring in a checked bag. It only takes one set of prying hands to open your bag and get tempted by a ring box, or a lost bag to send you into a tizzy,” says Money. “With something this important, it isn’t worth the risk.”

Do Pop the Question Early in Your Trip

Unless you have a really good reason to wait until the end of your trip together, you may find that things go more smoothly if you propose early on.

“Not only does this lessen the chances of you [potentially] misplacing the ring, it also gets your nerves and jitters out of the way so you’re not a nervous wreck,” says Avey. “It’s going to be suspicious to your partner if you start acting differently throughout the trip if you wait until the end. Plus, the earlier on in the vacation you pop the question, the more time you have to celebrate your engagement in an amazing locale together.”

If you do get the jitters and you want to wait a little bit longer—or if you’re simply waiting for the perfect moment—keep the ring in a safe back at the hotel room. You’ll feel better knowing the bling is locked up while you’re exploring with bae.

Avoid Proposing During a Major Excursion

Proposing during an activity means you have many more moving parts to keep track of. The simpler you can keep things during a destination proposal, the better.

“First, you have to get the ring to your excursion site safely. Then, you need to bank on the fact that the ring size will fit perfectly, so it doesn’t fall off while, say, rappelling down a waterfall—or out of your pocket, for that matter,” says Avey. “We recommend a non-active setting to eliminate the stress of losing the ring somewhere you can’t get it back.”

On that note, Money notes that no matter where you’re traveling or where you’re going to propose, keeping tabs on your belongings (ring included) is super important.

And finally, she says, “Try to avoid flashing the ring around too much and leave the excess handbags and shopping bags at the hotel during the proposal so there are less things to keep track of while you’re celebrating your magic moment.”

Good luck out there—we know your destination proposal is going to be perfect.

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