Here’s How to Pop the Question Without a Hitch

You’ve got the ring. You’ve picked the perfect vacation. And now, you’re ready to turn that dreamy getaway into one of the most unforgettable moments of your life. A destination proposal combines the thrill of travel with the romance of asking your partner to spend forever with you—but it does come with a few extra logistics.

From keeping the ring safe in transit to finding the right moment and photographer, we’ve gathered the top dos and don’ts—courtesy of the pros at Be Inspired PR—to help your travel proposal go off flawlessly.

The DOs

Pop the question early in the trip.

If you’re carrying an engagement ring, the last thing you want is to be anxiously guarding it all week. “When it comes to proposing on vacation, we highly recommend proposing at the beginning of the trip. After proposing, you will be so much more relaxed and can use the vacation to celebrate together, instead of being nervous the whole trip!” says Jamie Bohlin, owner of Cape Cod Celebrations.

Enlist local expertise.

Planning a proposal in a city (or country!) you’re unfamiliar with? Hire a planner based in the destination. “Planners can take care of hiring a photographer in the style you’re after, curating a florist for the vibe and aesthetic you’re looking to create, source live music, paper goods, catering, ensure your hotel room is set for celebration when you return…the list is endless,” says Ashley Lachney of Alston Mayger Events. All you need to do is show up and shine.

Start the ring process early.

Timing is key. Kaeleigh Testwuide of The Diamond Reserve recommends visiting multiple jewelers at least six weeks before your departure and placing the final ring order no later than four weeks out to avoid any delays.

Ensure the ring before you fly.

Before wheels up, submit your appraisal to your insurance provider, Kaeleigh of The Diamond Reserve adds. It’s a step that’s often overlooked, but essential for peace of mind when traveling with such a valuable (and sentimental) item.

Book a photographer in advance.

You’ll want to relive this moment for years to come—so don’t leave photography to chance. “You’ll be so wrapped up in this whirlwind moment that you and your partner will appreciate having these images to help you remember every sweet detail,” says Jenna Miller of Here Comes The Guide. Start researching local photographers a few weeks before your trip and secure your date early.

The DON’Ts

Don’t stress over perfection.
Travel throws curveballs. “Obstacles often pop up that are out of your control,” says Carli Fernandez of The Concierge Travel Group. She encourages you to embrace the imperfections—they’re part of the story.

Never check the ring.

Repeat after us: the ring goes in your carry-on. To avoid blowing the surprise at airport security, wrap the box with a note that reads “This is an engagement ring—please open discreetly.” It’s a tip straight from Kaeleigh of The Diamond Reserve, who’s seen more than a few TSA-induced proposal spoilers.

Don’t leave the ring unattended.

Once you arrive, keep the ring with you at all times or lock it away in the room’s safe. Leaving it in your luggage in the hotel room—or worse, poolside in a bag—opens the door to theft or loss. 

Don’t keep staff in the dark.

Thinking of proposing at a resort or fine dining spot? Give the staff a heads up. They’ve likely witnessed dozens of proposals and can offer thoughtful touches like champagne, rose petals, or a well-timed dessert. “They may be a wealth of valuable information during your proposal planning,” Miller says.

And finally—be careful about who you tell ahead of time.

As tempting as it is to tell all of your friends and family, AJ Williams of AJ Events warns against it. “One too many ‘Did anything exciting happen today?’ texts could give the whole thing away.” Keep the circle tight and enjoy the big reveal after the moment is yours.
Planning a destination proposal isn’t just about choosing the right place—it’s about creating the right experience. With these expert-approved tips, you’ll be set up for a stress-free, heartfelt, and momentous occasion you’ll cherish forever.

Photos courtesy of (in order of appearance): Karen Loudon Photography (1st); Katy Weaver Photography (2nd & 3rd); Andrea Mariño (4th)