No. Buying insurance for flights or hotel rooms—which often costs about 10 percent of what you’re paying for tickets and lodging—isn’t usually worth the money in the long haul. Even in an emergency, you can usually get by without the benefits. You can cancel hotel reservations with 24 hours notice, you can usually change your flights for a fee in case of inclement weather, and the airline already covers your bags for up to a few hundred bucks.
That said, there are exceptions. Here are four situations in which I would consider insuring my trip.
ON BIG, EXPENSIVE TRIPS OF A LIFETIME
Suppose you’ve been saving your money for five years for a big safari in Africa. You’ve planned every last detail, and furiously squirreled away cash by forgoing luxuries like partying with friends on Friday nights and cable TV. You’ve spoiled yourself by buying business class plane tickets for your overseas flight, and plunked down non-refundable cash to reserve a posh hut at one of the world’s finest eco-lodges.
Then, on the day you’re supposed to depart, a triple crown of calamity hits: a blizzard blankets your hometown airport, torrential rains are forecast for the next week in the nature reserve where your safari will be, and you break your leg. If you haven't insured your trip, you'll probably regret it.
WHEN YOU BOOK A TRIP DURING BAD-WEATHER SEASON
Imagine that your best friend is getting married in the U.S. Virgin Islands in September, during the height of hurricane season. In the event that an epic storm strikes, you’ll likely be able to reschedule without penalties. But what if a hurricane is lurking—its path not confirmed—so you preemptively cancel? You’re out of luck. Same goes for traveling to cities in the colder half of the country during February.
WHEN YOUR SCHEDULE COULD BE IN FLUX
You've made plans for a four-day salmon fishing trip to Alaska next month, but at about the same time your sister is due to give birth to her first child. If you know in advance that another important event may impinge on your plans, it's not a bad idea to hedge your bets.
I’m not a fan of floating sick boxes of any kind, but if you are taking a cruise, get insurance to cover your trip. A vacation on a boat involves a lot of moving parts.
First, there’s the issue of flying to your port. If your flight is cancelled or delayed, you’re out of luck. Then there’s the mechanical condition of the ship. If the cruise is cancelled after two days, or altogether, you don’t want to be left holding the bag. There's also the possibility of sickness or injury during a port visit; The ship isn’t waiting around for you. Go with third-party insurance because it’s invariably more comprehensive than what the cruise lines offer with their in-house policies.