Protecting the Ring (and the Surprise) Through TSA

The engagement ring is arguably the most important item in your luggage — and how you pack it can make or break the surprise. “The best place for your ring is in your carry-on, whether that’s a backpack, roller bag, duffel, or crossbody,” says Chang.

While it may feel safer to keep it on you, she cautions against slipping it into a pocket before security. "Going through TSA with a ring in your pocket isn’t going to fly — and taking it out for screening could ruin the surprise.” Her advice? Store it in a small pouch or interior pocket of your carry-on, never in checked luggage or a pants pocket. Kolanović-Šolaja also recommends insuring the ring before flying and taking photos for documentation, just in case any issues arise during security or customs.

Planning the Moment Without Raising Suspicion

Pulling off a surprise proposal on a shared trip takes strategy — and a little restraint. Chang suggests working the moment naturally into your plans rather than building the trip around it. “Keeping the proposal a surprise is about sticking to your travel itinerary and then weaving your proposal into it based on your partner and what you think they’d most enjoy,” she says. “If you know you’re heading somewhere beautiful or having a particular dinner or doing an activity your partner is most excited about, think about how you can play off that for the proposal.”

She also recommends timing it early. “I would also highly suggest you do it on the front end of the trip, ideally within the first day (or two). This allows you to enjoy the trip and not have to feel nervous and anxious the whole time.”

Keeping the Secret Safe (Digitally)

Kolanović-Šolaja recommends taking extra precautions to make sure no notifications or messages give away the surprise. “Act as a magician, meaning use the art form of misdirection to lead to the surprise. Have one itinerary for you both as a couple, but keep the real itinerary with the proposal plans on your phone only.”

Her final piece of advice: manage your tech carefully. “Turn off all push notifications and/or get a privacy screen for your phone. Nothing is worse than a notification from the hotel, a concierge sending you a message on WhatsApp, and your fiancé reading it by accident.”

Working with the Hotel and Local Partners

Hotel staff can be invaluable in pulling off a seamless, surprise proposal — as long as coordination stays discreet. “Depending on what you have planned, bringing in some help from the hotel, restaurant, tour company, or car driver can be very useful,” says Chang. “They can help you with ideas, physical setup if needed, or staging, or just playing a part to help move the proposal where you’ve planned it.” Still, she cautions against overcomplicating things. “The fewer people you have involved with the proposal, the less chance of something slipping or a mistake occurring,” she adds.

For travelers who do want a bit of behind-the-scenes support, the concierge is often the best place to start, says Kolanović-Šolaja. Per the pro, “Most [hotel] concierges would be delighted to help you plan from the hotel to the restaurant, through to the excursion,” she says. “When you are upfront about your plans and let everyone know the proposal is a surprise, everything stays under wraps.”

How Far in Advance to Plan

Proposal timelines vary, but both planners agree that timing should fit naturally into the broader trip-planning process. “Unless you want to do something very specific on a specific day, which requires reservations months in advance, there is no required amount of time that you need to plan a destination proposal,” says Chang. “If you’re planning a destination proposal in conjunction with a trip you’ve been discussing, then you should be thinking about the proposal as you plan the trip.”

Contingency Planning

Even the most thoughtful itineraries can go sideways — from bad weather to missed connections — so having a backup plan is key. Chang recommends thinking through possible disruptions before departure. “Think about what the likely derailments would be and have a plan B and a plan C if you’re forced to change your plans,” she says. “This is also a great time to utilize the help of your contacts at your hotel, restaurant, or tour company.”

For example, if you’ve arranged a romantic beach dinner and the forecast calls for rain, work with the hotel to secure an indoor space or move the setup to a covered terrace. The goal, says Chang, is to keep the moment relaxed and memorable — even if it unfolds a little differently than planned.

Capturing the Moment

Deciding whether — and how — to capture the proposal can be almost as important as planning the proposal itself since it is such a personal decision. “You have to know how you feel about it and, more importantly, how your partner feels about it. You do not want your partner to feel uncomfortable," says Chang.

After all, there’s no one “right” way to document the moment — it all depends on your partner’s personality. Kolanović-Šolaja adds, “Does your fiancé love details and aesthetics? Then take the time to hire a local planner or designer to make the proposal look amazing. Does your fiancé get anxiety when they have to give a speech? Then skip the photographer and keep it intimate.”

Explore more romantic getaways across the Benchmark Resorts & Hotels portfolio, a collection of more than 50 distinct, independent properties by Pyramid Global Hospitality. Located in diverse destinations across the globe, Benchmark’s resorts and hotels reimagine immersive travel, inspiring guests to create memories born from meaningful exploration, authentic moments, and innovative experiences – no matter the occasion. Benchmark guests can earn complimentary gift cards, on-property perks, and destination experiences through the collection’s signature Mosaic Rewards program.