So, the ring is selected, the tickets are bought, and your palms are starting to sweat. You’ve planned this moment for months and now you are counting down the days until you pop the question on the beach in some tropical paradise. But wait! Are you sure you’ve remembered everything?!

I wrote last week about NOT taking your diamonds with you on vacation, but engagements are obviously an exception. How are you supposed to propose without The Ring? This is what you need to do to protect yourself before you take that valuable piece of jewellery on your trip:
Take Care of the Paperwork
- Get an appraisal, with a photo, from a reputable jeweller or appraiser. (We can help you with that!)
- Get the ring insured.
- Most homeowner policies have a jewellery component and most have a limit of around $6000. If the ring is worth more than, whatever that limit is, you will need to get a separate policy or rider on it.
- If the value of the engagement ring is less than the homeowners limit, you will still need to let your insurance broker know that you’ve made this purchase. They will probably want a copy of your appraisal too, so have that ready.
- Read the fine print on your insurance coverage. If it says up to $6000 coverage, but also says a maximum of $1000 per piece, then that glittering ring is only covered for $1000!!
- If you don’t own your home, you can purchase tenant’s insurance, which insures your “stuff,” but not the home itself. This tenant insurance (sometimes called “content insurance”) may have the same limitations as the homeowner’s insurance as explained above. Read the fine print and talk to your insurance broker to ensure that your ring is covered.
Have a Plan
- Think through how you are going to keep the ring with you for the trip, without her seeing it. What if you are the lucky one who gets chosen for additional screening and your bag gets unzipped in front of hundreds of people at airport security? She will be standing right beside you! On the other hand, you can’t keep the ring on you without putting it in the scanner or else you will set off the metal detector… Think it through.
- Do NOT put the ring in your checked bags. Too many bags get lost! Don’t mess with Murphy and his law!
- Think through what day you are popping the question. Where will you hide the ring until then? In the safe where she will be putting her wallet and passport? Hopefully she won’t be placing her other jewellery in the safe, if she is taking our advice to NOT bring it! Does your room even come with a safe? Is it in good working order?
Maybe you should plan to propose early in the vacation to avoid the risk of ruining the surprise or losing the ring.

Popping the Question
Again, a little planning goes a long way.
- We had a client who planned to hide the ring in a shell at the bottom of the ocean so that their snorkeling trip the next day would lead her to the ring. What??!! Um… What about the currents?! Fortunately, he chose a different way.
- Another client proposed in the cross country trails up at Big White. She loved the ring so much that she gave him a huge hug… And the ring went flying into the snow drifts, never to be seen again. True story!!
- And yet another story… Mr. Right hid the ring in the pocket of his swimming trunks (not in the box, just the ring), then put his wetsuit shorts on to go caving with his sweetheart. In the pitch black caves he had planned to make his move, so up went the wetsuit shorts leg, down into the pocket, out came the ring… all in the PITCH black… and down on one knee he went. Fortunately he didn’t drop the ring, nor did she, and all is well. A happy – lucky! – ending.
So, in a nutshell: appraise, insure and think it through! Well that’s my advice anyway. And, by the way, CONGRATULATIONS!!