What Should I Do When...
...I MISS MY FLIGHT?
Get to the airport right away and ask to be put on the next flight. If an agent gives you grief, explain why you missed the flight—particularly, why it wasn't your fault (snarled traffic, for instance). Airlines are more likely to ask for additional payment if an agent thinks you missed the flight simply because you wanted to change your ticket without paying a change fee. With a little luck (and a sympathetic agent), you'll be on a flight later that day at no extra charge.
Worst case: Paying the difference between your new ticket and the original fare, plus a ticket-changing fee of about $150 for domestic flights.
When all else fails: Realize that no matter what the official policy is, agents can cut you some slack. Mentioning that you belong to the airline's frequent-flier program can't hurt. May we also suggest crying as a tactic?
...THE AIRLINE LOSES MY LUGGAGE?
Take the obvious first step and contact the airport's lost-and-found. File a bag-claim form and ask about the airline's policy for reimbursing you for toiletries and other essentials. Most bags are recovered and will be shipped to you (at home, a hotel, wherever—and at the airline's expense), so stay polite.
Worst case: About 2 percent of delayed luggage disappears forever. If your bag vanishes for good, file a form that itemizes what was inside it. Most airlines won't pay for precious items, including cash, artwork, electronics, and jewelry. So don't pack them in luggage. For covered items, you'll be paid for the depreciated value, not what it would cost to buy brand-new gear (including the bag itself). Sometimes you'll even have to produce receipts. On domestic flights, a carrier's liability maxes out at $3,300 per passenger. Weirdly, liability on most international flights is even less—about $1,700 per passenger.
When all else fails: Instead of looking for receipts for items purchased years ago, bring in printouts of the current value of comparable items for sale as "used" on Amazon. Overall, the moral is: Never pack anything of value in your checked luggage.
...I CRASH MY RENTAL CAR?
After the accident (here or abroad), insist on calling the police (even if it's a minor fender bender), and make copies of the report. If you declined collision damage waiver insurance coverage, your auto-insurance policy should cover damages. If you declined rental coverage and don't have auto insurance, the credit card you used to pay for the rental should pay for damage to the vehicle.
Worst case: You didn't check for loopholes in your policy's fine print, and now you're stuck with a huge bill. Coverage provided by your credit card or auto insurer often doesn't apply to vans and luxury vehicles. Rentals in some countries, such as Ireland and Jamaica, may not be covered either. That's why you need to call your credit card company and check the fine print before you depart.
When all else fails: Never agree to pay anything to the rental company on the spot. If you've looked into all the other options and it looks like you're on the hook for thousands of dollars, call a lawyer.
...MY TOUR OPERATOR GOES OUT OF BUSINESS?
Hopefully, you paid with a credit card, which you should always do because it offers the most protection. If so, call your card company and explain what happened. Your money can be refunded if you contest the charges within 60 or 90 days of when your statement is mailed to you.
Worst case: You paid with a check and didn't buy travel insurance that specifically covers the financial default of a tour operator. In which case, you're not getting your money back.
When all else fails: Contact the United States Tour Operators Association (ustoa.com) to see if the tour operator was a member of their group—and as such, would have been required to keep $1 million in reserves to refund to customers.
...MY PASSPORT IS STOLEN—AND I'M THE VICTIM OF A CRIME?
For most crimes except minor pickpocketing, call the police. If you've been hurt or robbed, or your travel plans must be changed, the police report will help you file claims with health and travel insurers. Cancel any stolen debit and credit cards, too.
Worst case: Your passport was stolen, and without it you won't be allowed back into the country. Contact the nearest U.S. embassy or consulate ASAP. With luck, you normally either travel with a photocopy of your passport, which will help speed up the process of getting a new one, or you've e-mailed a scan of your passport to yourself at a Web-based account you can access.
When all else fails: Bust out your emergency stash of traveler's checks, which you brought along for just such an occasion—and which should hold you over until you get your hands on new cards and a new passport.
...MY CHECKED LUGGAGE IS ROBBED?
You'll probably never get your stuff back, but you should file reports anyway. Why? They increase the chances that the thieves will eventually be caught. If there's a slip in your bag stating that the TSA inspected it, file a claim at the TSA website (www.tsa.gov).
Worst case: There's no slip of paper from the TSA noting that your bag has been inspected. So file a claim for reimbursement for lost and stolen items with the airline directly—and quickly, because claims often must be submitted within as little as 24 hours of an incident. Ironically, airlines won't pay for the most-likely-to-be-stolen items, such as jewelry and electronics, and they impose caps on their total liability per passenger.
When all else fails: File claims with the airline, the airport(s), and the TSA. To be safer next time, put a TSA-recognized lock on your bag to prevent the half dozen, non-TSA workers who handle it from being able to pry it open.
...I GET SICK WITH A BUNCH OF OTHER PASSENGERS ON A CRUISE?
If your cruise is interrupted or postponed because of an outbreak, you should expect to be given the option to cancel for a full refund or to reschedule at a discount of up to half off.
Worst case: Cruise ships are not required to compensate passengers for illnesses. If you and a small number of passengers get sick on an otherwise uneventful sailing, don't expect a refund.
When all else fails: Call the cruise line's customer-service department and request a discount on a future sailing, explaining that your vacation was ruined and that you'd like to give the experience another shot at a discounted rate, or with credit for on board purchases.
...I NEED EMERGENCY MEDICAL HELP AT MY DESTINATION?
Most U.S.-based health-insurance plans offer some coverage overseas, but only for emergencies, such as broken bones or heart attacks—anything that would send a reasonable person to the ER. Chances are you'll have to pay the hospital or doctor directly and get reimbursed later, so keep all receipts. In some rare cases, health plans work with doctors and clinics overseas, and if your treatment occurs in-network, your insurer may be able to pay the bill directly, saving you the trouble of paying out of pocket.
Worst case: You have no insurance and rely on Medicare or Medicaid. Neither program will protect you outside the U.S. Be sure to buy supplementary travel insurance in advance of your trip. To scout out the policies of multiple established, well-regarded providers, use insuremytrip.com.
When all else fails: Get to a doctor or hospital and worry about payment later. In many parts of the world, medical treatments cost far less than in the U.S. And in countries with socialized health plans, medical bills have a way of disappearing, even for foreigners.
...I'VE BEEN ARRESTED OVERSEAS?
Drugs are involved in roughly one-third of the arrests of Americans abroad, so it goes without saying to just say no. Legal systems vary widely around the globe, however, and to avoid getting in trouble because of an unusual foreign law—in Singapore, for instance, you can be fined for not flushing the toilet—study up on your destination's peculiar regulations in guidebooks and at travel.state.gov.
Worst case: You're facing serious jail time, or worse. When speaking to the police, be respectful and apologetic without necessarily admitting wrongdoing.
When all else fails: Tell everyone who will listen that you demand to speak with a U.S. embassy officer, who can help you navigate that country's legal system, find a local attorney, and send messages to your family.
...I'M CAUGHT IN A NATURAL OR MAN-MADE DISASTER? Serious emergencies can happen anywhere (see: London, Haiti, Chile, Mumbai, New Orleans), so it's a good idea to e-mail your itinerary, including flight and hotel info, to a friend back home. Register your trip with the State Department for free at travel.state.gov, so that the government will know where you are and will be able to help get you to safety in a crisis.
Worst case: If you're fortunate enough to have life and limb intact, money shouldn't be a concern: When true emergencies occur, hotels and airlines are generally very sympathetic to travelers and waive cancellation and change restrictions.
When all else fails: Figure out a way to get yourself to a U.S. embassy or consulate, which can provide safety and coordinate evacuations. Getting home may take time, so be patient, and try to console the travelers around you, who may become your new best friends.
CORRECTION: The link for registering a trip with the U.S. State Department has been corrected. Sorry.