Tips for Proposing on Vacation

Amazing proposal tips from our Couples Travel Experts, Samantha & Ryan, of Our Travel Passport!

We got engaged in San Francisco right by the Golden Gate Bridge. It was magical and thoughtful and just the beginning of our life traveling together.

Proposing on vacation is incredibly romantic and thoughtful.

There’s nothing quite as romantic as getting away and exploring a new place together. It also makes getting down on one knee an even bigger surprise, because she (or he) will never expect you to propose when you’re in the middle of running from a museum to the beach to the best ice cream shop in town together.

Chances are, if you’re in love, it doesn’t matter where you propose, because your future spouse (pending they say yes) will be so excited to spend the rest of forever with you that they’ll hardly notice anything else but you. But if you are planning on proposing on vacation, there are a lot of things to prepare for…

so here are our tips for proposing on vacation, and making sure everything goes as planned!

Pack the Ring Properly

If you’re flying to your destination, be sure to pack the bag in your carry-on luggage in a way that security won’t ruin the surprise if they have to go through your bag. Put it in a longer box, like ones for necklaces, inside one of those false books, or put the ring box inside of another box, like one with your shaving kit.

Be sure to remove your liquids and gels and don’t carry on anything that would possibly be suspicious and make them have to check your bag.

Make sure the ring is in an inner zipper compartment, so it doesn’t accidentally fall out when you’re pulling out your laptop or headphones for the plane ride. Also, don’t pack it in your checked luggage, because that would be the worst “lost luggage” story of your entire life.

Be Prepared for Customs

If you’re traveling internationally, be aware of the customs process at your destination airport. When I visited Morocco, I was randomly stopped at customs and had every single one of my items removed for inspection. They even ripped opened the ziplock bags I had neatly packed everything away in.

Luckily, I wasn’t proposing there, but the same thing almost happened to my dad when he did propose in Mexico. I recommend asking to be inspected in a private room while your future fiancée waits outside.

The last thing you want is a customs agent holding up the engagement ring in front of both of you and asking you about it in a foreign language.

Safety

Always be thinking about safety. You have to find that balance between keeping it secure and keeping it hidden. The safe may be the best option, but only if you’re the only one using it.

Walking around a city all day with a diamond ring in your pocket not only increases your chances of losing the ring, but there’s a better chance that it gets spotted by the last person you want seeing it.

We recommend making the proposal one of the first things you do, that way you can enjoy the rest of your trip together as fiancés!

Have a Backup Plan

When I planned to propose, it was going to be on this gorgeous hill with the Golden Gate Bridge as a stunning backdrop. Well, it turned out to be way too foggy that day (thanks Karl the Fog), so my perfect backdrop had turned into a whole lot of misty nothing.

I had to quickly devise another plan and pick another spot. If you’re planning to propose outdoors, the weather won’t necessarily be your friend, so make sure to check the forecast on the morning of your big day, and if need be, resort to Plan B.

Ask Your Hotel for Help

People love love and making other people’s dreams come true. As soon as you get to the hotel, make sure to let someone know your plans and see what they can do to help make your proposal and stay even more special.

A lot of hotels have concierge services specifically designed for engagement and honeymoon packages, so chances are your hotel service will love to help. Also, make sure to tell the hotel when you’re planning on proposing, so they can deliver flowers and chocolates to your room for when you get back.

Be Thoughtful

If your significant other loves to get dressed up and take pictures, plan on finding a local photographer to hide behind-the-scenes and snap some shots for you (actually, we suggest you do that no matter what, because those pictures are ones you’ll cherish forever). And find a way to get her or him dress up without drawing suspicion.

For example, tell her you want to take her to a fancy restaurant (and then do it before or after when she least expects it!). Or tell her that you set up a photoshoot for the two of you.

If she loves the beach, propose underwater during a diving excursion or on a romantic sunset walk. Or if you’re super adventurous, propose on the edge of a bridge right before you go bungee jumping (just don’t drop it)!

Most importantly, make sure you’re thinking about the two of you and what’s important to you both, because this is one of those moments that you will definitely remember forever.