How to Propose on Vacation

For many, a vacation proposal is the mecca of all things luxury and romance. Whether it’s on the beach in Mexico, under the Eiffel Tower in Paris, or just in a small town that you fell in love with early on in your relationship, a trip-turned-engagement is a great way to ask the question—and celebrate after!

While there are a few more components to consider when proposing outside your hometown, we’re breaking it all down so that you can head to the airport feeling confident in your plans. Here’s how to propose on vacation, in style and feeling stress-free, for a trip that you’ll cherish for a lifetime.

Plan Your Destination Accordingly

The first step toward planning a vacation proposal is to pick a destination. Whether you’re selecting a spot as a couple (and the proposal is just an added bonus) or the whole trip is a surprise, one of the biggest components is choosing a destination that you’ll both love. Don’t feel pigeon-holed in selecting a “classically romantic” locale such as Paris or Hawaii.

Instead, plan your trip to a spot that you’ve both always wanted to go to, or a place you loved and want to revisit without too much stress on whether or not it’s deemed “romantic” by society. All that matters is that it’s a place you both are (or will be) majorly excited about, and that it's safe (so you feel comfortable traveling with a ring and presenting it to your SO).

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Pack the Ring Right

As you’re getting ready for your trip, take extra care when packing the ring. First, make sure to pack it in your carry-on, as opposed to a checked bag. Almost everyone has dealt with a lost bag (which sometimes takes weeks to show up), and if your trip is centered around a proposal, it would be a big bummer to be waiting on the ring. While you might be afraid of a TSA agent searching your carry-on and ruining the surprise, there are a few precautions that you can take to avoid it.

First, pack the ring in either a watch box, shaving box, or a different container that doesn’t shout “something exciting is in here” in case your SO rummages through your bag for toothpaste or a sweater. Additionally, be sure to put the box in a compartment that you don’t need to access often (so you don’t accidentally knock it out).

Prior to flying, remove liquids, gels, and anything that could look suspicious to avoid getting flagged for a more thorough check (which could result in them pulling out the ring and flashing it to your almost-fiancé). If your bag is selected for a more thorough check, request to undergo it in a private room with your SO waiting outside to avoid having to propose at the airport on the spot.

Make Sure That the Ring Is Insured

You don’t want to think about the ring getting lost, stolen, or losing a gem (especially before actually proposing), but being prepared ahead of time is better than scrambling after the fact. One of the first things most couples do after getting engaged (and after popping a bottle of bubbly) is insuring the ring, so it’s something you’ll have to check off the list eventually. Doing it before traveling will give you peace of mind, should anything happen before the special moment. Check with your jeweler or homeowners’ insurance about adding the ring to a current (or new) policy.

Tell Your Hotel/Lodging About Your Plans

Proposals are exciting, not just for those getting engaged but for everyone around them, so don’t be afraid to tell your plans as you’re making reservations. Chances are that your resort or hotel will have packages you can add on, or ideas to elevate the proposal (or celebratory trip afterward) even more. If you don’t want to shell out extra money, the odds are in your favor that they’ll at least hook you up with some flowers, Champagne, or breakfast in bed. Even for things such as excursions, dinners, or shows, let them know that this is your proposal trip if you’re a fan of extra surprises.

Have a Proposal Plan...and a Plan B

Prior to traveling, make sure to have a plan in place as to where, exactly, you’d like to propose. While you might envision doing it at a popular tourist destination or on an action-packed excursion, it’s better to keep the actual proposal a little more lowkey. In crowded places, the chances of snagging a good spot (free from excessive noise or people pushing you to get a photo op) can be tricky, and if you’re on an excursion, you don’t want to risk losing or damaging the ring while swimming, hiking, or exploring.

Once you do have a spot in mind, consider coming up with one or two backup options in case the weather doesn’t permit, or you arrive and are underwhelmed by the original choice. This is a great way to utilize your hotel’s concierge or Airbnb host to see if they have additional ideas that are sure to “wow” your SO without running into snags such as too much tourist traffic.

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Propose Early

No matter how calm and cool you think you are, there’s a good chance that your SO will be able to tell that you seem a little off going into the trip.

Nerves will be high and the pressure is on, so if you can avoid prolonging the proposal until the end of the trip, all the better. That way, you’ll get to share the beautiful moment together and have time to celebrate together (stress-free) before heading back home and celebrating with your family and friends. This gives you a little bubble of romantic vacation time to soak up the excitement of the proposal, just the two of you, before including others. If you do plan to wait until later in the trip, keep the ring locked in a safe back in your room while out and about so that you don’t have to worry about it while exploring on your vacay.

So, whether you propose in an ornate hotel room, on a sunset cruise, at a romantic dinner, or just on a stunning beach, a vacation engagement is one of the most fun ways to celebrate the next chapter in your relationship. As long as you have a plan (and a plan B), keep the ring safe, and pack smart, you’re in for a perfect proposal—and one of the most memorable trips of a lifetime.