Keys to Pulling Off the Perfect Vacation Proposal

By Crystal McCormick

You and the love of your life are enjoying a dreamy sunset on a Caribbean beach or trekking through a tropical rainforest, and despite enjoying sensory overload in every delicious way, the only thing you can really think about is how lucky you are to be so enamored.

And then in the middle of a sandbar or under a canopy with the sun peeking through, just when you think it could not get any more romantic, he drops to one knee…

There’s nothing quite as romantic as getting away and exploring a new place together – except, that is, for proposing while on your vacation.

The latest trend when it comes to popping the question, a destination proposal is the ultimate way to enrapture your partner. With engagement season in full bloom, there’s no better time to start planning. While it’s true that when in love it doesn’t matter where and how you propose, don’t fool yourself; the engagement story is a pretty big deal.

If you want to make sure it’s a day both of you will never forget, there’s a couple of things you need to keep in mind.

Protect the Ring

Let’s face it, the ring is the star of a perfect proposal and chances are, you spent a lot of time (and money) picking out the perfect bauble just right for your boo. So, it would be pretty much be disastrous to land at your destination only to find out that the ring didn’t make the trip.

Protect the engagement ring (and the surprise) by packing it in a safe box in your carry-on luggage to prevent TSA from accidentally spilling the beans when you walk through security. Also, if the ring cost a pretty penny, having an insurance policy on it is a good idea. That way, you can at least ensure you can cover a replacement ring if the worse does happen.

Back Up Plans and Getting Help

2. Have a Back Up Plan

If proposing while vacationing in the Caribbean, you’re probably envisioning getting down on one knee under a clear sky with the sand between your toes - but, as in marriage, the weather doesn’t always go as planned, so make sure you have a plan B in place.

When the weather forecast for your big day is ominous, don’t fret; you can still have a night to remember. Bring the surprise proposal indoors at a quaint restaurant or with a romantic dinner for two like those available at Palace Resorts. Between a decadent dinner, champagne, and her favorite desserts – she’ll be so overwhelmed with the proposal, she won’t even notice it’s raining cats and dogs outside.

3. Enlist Help from the Hotel

People love romance and witnessing the perfect proposal come to fruition – including hotel and resort staff. In fact, some resorts even have coordinators on staff, such as at Palace Resorts, for example, where wedding experts can help assist with every detail to make sure the proposal goes off without a hitch.

If you’re looking to do an intimate proposal, have the resort staff turn off all the lights in your luxury Palace Resorts suites and make a trail of rose petals and candles leading to a heart of light and flowers positioned around the ring. Sure, it may seem cliché –but there’s a reason why this tried-and-true bedroom proposal makes its way into pretty much every romance flick.

Plan to Think Outside the Box

4. Think Outside the (Ring) Box

You´ve already proven you don’t want a boring and expected proposal, so why pop the question with the traditional ring box?

When popping the big question beachside, take advantage of the tropical ambience and present the ring in a seashell – or, if you plan on proposing at a romantic dinner, have the restaurant staff place the ring in a champagne glass or in her favorite dessert. Yes, another nod to cheesy romance movies, but a sure winner, nonetheless.

 5. Planning is Key

The old adage: failing to plan is planning to fail is not only good life advice but it’s true in proposals, too. And most likely, her engagement story ranks up there with life events like having a baby and the actual wedding - so, make sure you plan it perfectly.

Don't wait until you get to your predetermined spot to plan the specifics for the perfect proposal. From making dinner reservations at the most romantic restaurant to choosing the best stretch of sand for a sunset proposal, getting your ducks in a row ahead of time could make the difference between an Instagram-worthy proposal and a total engagement fail.