Four Days in Paradise, One Outfit

Picture this: you're standing at baggage claim in St. Lucia's Hewanorra International Airport. Outside the air is a civilized 82 degrees, the sky is that aggressive shade of Caribbean blue that looks Photoshopped even when it isn't, and the water is doing its best to justify every screen saver you've ever seen.

Back home in Maryland, it's single digits with a foot of snow sealed under jackhammer-grade ice. It has taken you two days to get here, including an overnight layover in Miami, but you finally made it to paradise.

The baggage carousel sputters to life. Bags tumble out. Travelers lunge with all the grace of a Black Friday doorbuster. One of your two checked bags appears.

Then… nothing.

The carousel slows. Stops. Empty. About two dozen of you remain, staring as if you can will it back into motion.

You cannot.

Welcome to my field study in lost luggage.

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The Packing Strategy That Almost Worked

Yeah, that was me in the baggage claim area at St. Lucia's airport just a few weeks ago. Janet and I made it to paradise, but one of our checked bags did not.

We tell our clients a simple truth: glitches happen. The key is minimizing how much they matter.

Janet's packing strategy for trips involving more than one checked bag is sound:

• Essentials in the carry-on (toiletries, meds, one change of clothes).

• Split belongings between checked bags so no one is entirely stranded if a bag goes MIA.

It's a system that has worked flawlessly for years. Which is to say: we've never actually had to test it.

On this particular trip we were staying at two resorts, so Janet improved the system. Resort One clothes in Bag One. Resort Two clothes in Bag Two. Unpack once per property. Efficient. Elegant.

Unfortunately, I had already packed under the old split-the-difference system. In a small but decisive act of defiance, I consolidated all of my clothes into the bag designated for Resort One.

Guess which bag stayed in Miami?

There I was in paradise with:

• The clothes on my back…appropriate for winter in Maryland, not the Caribbean

• Flip flops

• A pair of shorts

• Electronics

• Five days' worth of prescription meds for an 11-day trip

The refill medication? Also in the missing bag.

Of course.

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The Shopping Spree I Didn't Want

When we filed the lost luggage report, an agent from American Airlines assured us the bag would arrive "tomorrow." I have learned that in airline dialect, "tomorrow" means "at some point in the narrative arc."

Rather than lose vacation time waiting, I went ahead and purchased essentials at the resort gift shop as soon as we arrived. I'm glad I did. It took four days for the bag to find us.

You don't have to buy bargain-bin T-shirts to keep reimbursement reasonable. But you also shouldn't treat a baggage delay as a license to refresh your entire wardrobe. Buy what you need, keep it sensible, and move on with your vacation.

For me, that meant:

• Toiletries not in my carry-on

• A couple of T-shirts for the beach

• Casual dress shirts to satisfy the restaurant dress code

• Swimwear (at resort gift shop prices, no less)

• A hat rated for Caribbean-level sun

Total cost: $400

Time not spent leaving the resort to hunt down basics I shouldn't have needed to hunt down: Priceless.

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The Medication Curveball

Missing extra clothing is inconvenient. Missing medication is critical. I had five days' supply of my prescription medications for an eleven-day trip and no idea when, or even if, my missing bag would show up. I'll admit, the math didn't feel great.

On Day Two, with our bag still enjoying its extended Miami layover, I decided not to gamble. I asked our butler for help. Within the hour, a resort nurse reviewed my online prescriptions and arranged a 10-day refill from a local pharmacy. It was delivered to our room the next day, and I never had to leave the obnoxiously beautiful ocean views from our balcony.

No butler? A concierge or front desk can typically coordinate the same solution. Many travel insurance policies also include concierge assistance for exactly this kind of situation.

Was it stressful? Briefly. Was it solvable? Absolutely. It was also unnecessary, because I know better.

The experience reinforced a truth we emphasize constantly: essential medications belong in your carry-on. Enough for the duration of your trip, plus an additional week's supply in case your return trip is delayed.

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What Airlines Actually Owe You

After my bag finally arrived on Day Four, I turned my attention to getting reimbursed. Here's what I learned — some of it the hard way:

• You must file a delayed baggage report before leaving the airport. Get the claim number and the claim receipt.

• You are entitled to reimbursement for reasonable, documented essential purchases during a delay, and you don't have to wait to see if your bag will show up. As long as you have the claim number, you can begin to purchase essentials.

• There is no legally permitted fixed daily cap for reimbursement, but stick to essentials.

• If your bag is delayed more than 12 hours, the airline must refund any checked bag fee for that bag.

For domestic flights, maximum liability for a lost bag is generally up to $3,800. For international flights, compensation is capped lower under international conventions — a topic for another day.

Keep receipts and baggage claim tickets. Submit promptly. Don't wait to see what the airline does before notifying your travel insurance carrier — insurance policies have their own filing deadlines.

And don't double-dip. If the airline pays, insurance covers the remainder if applicable and only up to their coverage limit. Check your policy.

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Pro Tips from the Lost Luggage Trenches

1. Divide and conquer. One person gets in the baggage service line while the other waits at the carousel. Janet did this. It saved us an hour.

2. Photograph your bags. Exterior, size, brand. Also photograph your baggage claim tags. Claims move faster when you can be precise.

3. Keep a packing list. Not aspirational. Actual. It helps with shopping, reimbursement, and worst-case loss claims.

4. Pack like someone will go through your bags. Because they will.

5. Have your hotel address ready. So the bag comes to you — not back to the airport.

6. Assume "tomorrow" means "eventually." Adjust your expectations accordingly.

7. AirTags are wonderful… when they cooperate. Ours chose silence.

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The Silver Lining

Our bag was left behind in Miami due to a baggage conveyor breakdown. It was irritating, but certainly not catastrophic. Not even close. We made it to paradise on schedule — even if my wardrobe didn't.

The experience confirmed something we tell our clients all the time: travel disruptions are rarely what ruin a trip. Not knowing what to do when they happen — that's what does it.

Pack essentials in your carry-on, including medications for the duration of our trip (plus extras). Split belongings between bags. Act promptly. Keep receipts. Don't let inconvenience snowball into drama.

Would I have preferred a seamless arrival? Of course. But now when we tell clients how to navigate lost luggage, we're not speaking theoretically. I, for one, am speaking as someone who knows with unsettling precision the cost of a resort gift shop bathing suit.

And trust me — that's knowledge you want in your corner.

P.S. I just heard from American Airlines. They've agreed to reimburse me for everything I claimed, with the exception of the charge for the nurse to issue my prescriptions. They covered the prescription, just not the nurse's fee. So if you're keeping score: the airline will pay for your emergency swimwear but draws the line at the person who kept you alive. Now I'm off to file a claim with my trip insurance provider.