What is the safest way to travel with an engagement ring?

The safest way is simple, and I'll tell you because nobody else does: wear the ring. Right through security, through the flight, through the taxi line. Not in a bag. Not in a carry-on. On your hand. If you can't wear it yet - maybe the proposal hasn't happened - keep it on your body. A neck pouch under your shirt, a zippered interior coat pocket, a slim ring box tucked flat against your sternum. Anything that puts a layer of fabric and your own awareness between the stone and the world.

Last May a client named Thomas flew from Seattle to Boston with a 1.43 carat oval in a velvet box, inside a sock, inside his carry-on. He took the bag out of the overhead bin at Logan and the box wasn't there. The sock was. The ring was never recovered. He'd taken the bag into the lavatory mid-flight - he thinks someone lifted it while he was gone. The claim with the airline went nowhere. His jeweler's block policy didn't cover unattended baggage, because carry-ons are considered unattended the second you put them in the bin. I set his replacement ring in December. He wore it onto the plane that time.

If you're traveling with a loose stone or a ring you can't wear, box it in something generic. A plastic flip-top gem jar inside a pill bottle. A foam-lined hard drive case. Anything that doesn't announce itself as a jewelry box if your bag gets opened at security. Put that container in your personal item - the bag that stays under the seat in front of you. Never the overhead. Never a checked bag. I've seen TSA open a checked suitcase and "inspect" a ring box by dropping it on the tarmac. The prong on a 2mm Tiffany-style setting isn't surviving that.

Get it insured before you leave. Not your homeowner's rider - a standalone policy from a company like Jewelers Mutual or BriteCo that covers mysterious disappearance. That's the exact phrase. "Mysterious disappearance" covers the Thomas scenario. Most policies have a 30-day waiting period for new items, so don't buy the ring on Monday and propose on Friday in another state. I tell clients to add the ring to the policy the week it leaves my studio, even if the proposal is months out.

At security, you have a choice. Wearing it through the metal detector won't set it off - gold, platinum, and diamonds don't trigger most walk-through machines. But if you get pulled for the body scanner, the ring won't show up anyway, so just leave it on. Don't take it off and drop it in the plastic bin with your wallet and loose change. I've heard a story about a 2.7 carat emerald-cut that went skittering across the floor at JFK because someone put it in the bin and the bin tilted. That's a sickening image and I think about it every time I fly.

For international travel, I'm more paranoid. Customs forms, different legal definitions of temporary import, the risk of being targeted. In those cases, I tell clients to wear a simple metal band - a $200 silver ring from a street vendor - and FedEx the real ring to the destination, insured, signature required, with a hold at the FedEx office near the hotel. It's an extra $85 and it's worth every cent. FedEx has better chain of custody than any airline.

One more thing: if you're proposing on a trip, have a backup plan for the ring box. The classic hinged box is bulky and recognizable. I've had clients use a leather coin purse with a bit of foam inside. Or just wrap the ring in a microfiber cloth in a zippered pocket. She's not going to care about the box. She's going to be looking at the stone and your face, probably in that order.