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How To Plan The Perfect Destination Proposal

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Are you planning on proposing on holiday? Sorry US folks – I mean, are you planning on proposing on vacation? Then this quick blog should help.

In it, you’ll find a step-by-step guide on how to plan the perfect destination proposal, as well as real-world insights and experiences of how I proposed to my wife in Iceland back in March 2017.

How To Plan The Perfect Destination Proposal [A Step-by-Step Guide]

How to plan the perfect destination proposal

Step #1: Decide whether to take an engagement ring abroad with you or use a placeholder

You should decide whether you want to take an engagement ring abroad with you (which has its own risks) or use a placeholder to propose with – the idea being that you choose one together when you get back.

A placeholder could be something as simple as a Haribo ring, an empty ring holder or just a standard cheap ring – either way the gesture remains the same!

We’ve heard of lots of proposals that have succeeded with either method — do whatever you’re most comfortable with!

When it comes to actually buying the engagement ring, make sure you get the right size. Women’s ring sizes can be pretty tricky to work out on your own.

It helps if you and your partner have discussed getting engaged in the past and she’s already mentioned what her ring size is. But if you’d rather it be a complete and utter surprise, then you could also print out a ring sizing guide and measure one of her other rings against it.

Just remember that her ring finger is likely to come up smaller than most of her other fingers.

If you do get the sizing wrong, don’t panic! Jewellers see this type of thing all the time and are usually perfectly happy to resize a ring for you, although sometimes this means paying a small fee.

Step #2: Get insurance for your ring!

Whether you’ve bought the ring in advance or plan to buy it together, get insurance for it as soon as possible… especially if travelling with it.

If you already live together, you may be able to get it added to your home contents insurance (although only do this if you’re the main person on the insurance policy to reduce the risk of being found out).

Otherwise, you’ll need to take out specific cover for your ring, which many insurance companies offer. The guides listed below are pretty useful for working out what level of insurance you’ll need and where to buy it:

Justine's engagement ring on top of a silver heart

Step #3: Find a good hiding place for the ring

My advice would be to try to time buying the ring a few weeks before your holiday.

This provides a decent buffer time in case of any delays, while not being so far in advance that you risk being found out because she accidentally discovered it.

And on that note, make sure you find a really good hiding place… ideally somewhere she’s unlikely to go. And come up with a good cover story in case she tries to look where it’s hiding.

In my case, when I bought Justine’s ring, I hid it inside my backpack that was under my side of the bed. There shouldn’t have been any reason for her to go in there as she’s got her own bag and thankfully, the ring lay undiscovered inside my backpack for several weeks.

That is, until she suggested that we use that very backpack as our cabin bag on the proposal trip!

Thinking quick on my feet, I made some excuse that it had been damaged or messed up in some way and convinced her to use her own backpack instead.

Step #4: Take your engagement ring through security (and remind security or TSA agents to be discreet!)

Make sure you keep the ring with you at all times.

Ideally, you’ll keep it inside its box and within your jacket pocket as there should be little reason for your fiancée-to-be to have your jacket, whereas she may try to carry a shared cabin bag.

To avoid any mishaps with being found out at this stage, it would be worthwhile sticking a note on the ring box (if using one) to ask the security or TSA agent to be discreet should they need to unpack your belongings for any reason.

Security agents see engagement rings go through the machines all the time but it never hurts to remind them that you actually want this destination proposal to be a surprise!

Here’s what I wrote on Justine’s ring box:

“Please be very discreet!”

Engagement ring box that says "Please be very discreet!" on it

Step #5: Propose early on in the holiday

Right… onto the proposal.

Feeling nervous?
Yeah. I get it.

To avoid sweating too much (or worse, getting found out or even losing the ring!), it’s better to propose early on in the holiday… ideally within the first day or two.

And think of it this way… it’ll also give you both the entire holiday to celebrate!

Step #6: Make sure you have a Plan B

Ahead of proposing to Justine, I had a brilliant destination proposal idea.

We were travelling to Iceland for the first time together and so I’d imagined proposing to her somewhere in the deepest depths of Iceland with the Northern Lights dancing overhead… maybe even with a Prosecco in hand.

Pretty romantic, huh?
Well that’s what I thought…

Until I realised that she wouldn’t be able to see the ring with it being so dark… doh!

At this point I didn’t have a Plan B. And so I spent the next couple of days waiting for the perfect moment within our jam-packed schedule. Instead, I wish I’d come up with a few ideas before the trip in case my first plan didn’t work out.

My point is — hatch a Plan B, maybe even a Plan C before your trip in case the inevitable happens and things don’t go according to plan.

Step #7: Nothing going to plan? Be spontaneous!

So what happens when your Plan A, B and C don’t work?

Be spontaneous!

Some of the best proposals have happened this way. The main thing is that you and your partner have just created a magical memory together.

Take me and Justine for example…

When I realised the Northern Lights idea was just not going to work, and as we know, I didn’t have a backup plan, I had to be spontaneous. And actually everything turned out way better than my original idea!

We’d made an unexpected detour in our itinerary to head to a black sand beach along the south coast of Iceland – little did we know it was actually Sólheimasandur Beach. Now, on the surface, this doesn’t seem like the ideal proposal spot; I mean for one, there was a plane wreck on this beach and lots of tourists around!

But we ventured just a couple of minutes away from the plane, over a sand dune, and were hit with miles upon miles of black sand, snow-capped mountains in the background and not one single person around.

I took a punt and thought it would be the best opportunity for me to pop the question.

Justine and Scott getting engaged in Iceland

And I had no clue before the trip that it was even going to turn out that way!

My point is that you’ll just know when it’s the right time, moment and place for you both. And trust me, it’ll all work out if you just throw caution to the wind and propose when it feels right!

Step #8: Try to capture the moment on camera

Unless you’re lucky enough to have a photographer following you around… I mean personally, I still don’t understand how you can be inconspicuous in this case!

But anyway, you can totally capture the moment on camera yourself if the time and place suits.

Had Justine and I been caught up in the moment of the Northern Lights then we might not have caught the actual proposal on camera. We would have gotten the perfect “after” shot but that’s it. Not that it’s massively important, but it’s a nice thing to have.

Instead, I had yet another genius idea to pretend that I simply wanted to get a photo of both of us with the mountains in the background by using our tripod.

As it’s usually just me and Justine travelling as a couple alone together, and we rarely ask strangers to take our photo, this didn’t seem weird. So Justine had no clue… literally no idea… she didn’t even see me get down on one knee as she was still looking at the camera!

But what this meant was that we caught the exact moment on camera when she said: “Are you joking?!” in response to my proposal. Like I said, not everything goes according to plan.

Thankfully, she realised fairly quickly that I wasn’t joking and said “Yes!” and I know she’s pretty cut up that her first response was so… well… unscripted!

But it was our moment.
Our most wonderful travel memory.
And our special destination proposal caught on camera.

I hope these tips and insights into how I proposed to Justine help. If you’ve got any unanswered questions, then just leave me a comment below or send me a private message

Want more couples travel inspiration? Check out these romantic quotes and fun travel puns >>>

Good luck… however you choose to propose, I’m sure it will all work out.

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Scott Jenkins

Scott is one half of the married couple behind the Wanderers of the World travel blog. He lives in Bristol, UK and has travelled extensively around the world since his childhood. Since 2014, Scott has joined his wife, Justine on hundreds of trips throughout the UK, Europe and beyond. He's responsible for some of the photography you'll find on this site and most of the "tech stuff". He also writes the occasional blog post about proposals or skiing (having done the latter since he was 8 years old). Aside from travelling and having epic outdoor adventures, he runs a 3D printing business and enjoys learning about technology and electronics.

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