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The 5 Worst Trip Planning Mistakes (and How to Avoid Them)

The 5 Worst Trip Planning Mistakes (and How to Avoid Them)

Throughout history, millions of vacations have gone askew for variety of reasons. Remember the Griswold family’s cross-country drive to Walley World? (Fiction, yes, but no doubt representative of many real family road trips.) Naturally, attacks from crazy relatives can’t be stopped by any measure of good planning — but more common travel mishaps, like busted trip budgets or overpriced flights, are easily avoided if you plan right. Below are five all-too-frequent trip planning mistakes made by even experienced globetrotters.

1. Being Inflexible with Your Dates

Choosing set dates for your trip and then refusing to budge is a surefire way to pay too much for your flight. You can save hundreds of dollars on airfare by pushing your travel dates around by just a few days. Ticket prices tend to be lowest on Tuesdays and Wednesdays, and the most expensive on Fridays and Sundays, but this may vary. Play with your dates, and use your booking engine’s flexible search option if it has one.

If you’re planning to fly during high-traffic holidays like spring break or Christmas/New Year, be prepared to pay top dollar for air transportation. Budget travelers may want to seek alternatives to holiday travel, whether it means taking the kids out of school or begging the big boss for some extra vacation days.

Although the dates of your hotel stay are probably at the mercy of the travel dates you set for your flight, keep in mind that flexibility pays off at many hotels as well. Whether it’s weekday specials at B&Bs or low off-season rates, a bounty of hotel bargains exists for the traveler who’s willing to move his or her travel dates around.

2. One-Stop Shopping

The days when most travelers would call up a travel agent, book a trip, hang up the phone, and be done with it are long gone. Now, the internet is a hodgepodge of hundreds of competing travel provider sites, all of whom are touting the “best deals” and “lowest prices” — and 9 out of 10 times it’s a mistake to book the first thing you see. While I can’t guarantee that a single travel site will always give you the lowest rates, what I can promise is that a thorough search of the major airlines and travel providers will almost always yield the best rate for your trip.

Aggregators like or TripAdvisor Flights scan multiple airlines to serve up a buffet of fares in one easy place. (TripAdvisor is SmarterTravel’s parent company.)

Unless you’re staring at a jackpot fare that is mind-numbingly affordable — say, something like a $500 roundtrip ticket from the West Coast to Europe in the summer (jackpot!) — keep looking. You can always come back. (Well, almost always. We’ve found that some airfares posted on airline websites can change in a matter of minutes … which brings us back to the point about jackpot fares.) See Tips for Finding Cheap Airfare and How to Hack Your Way to a Cheaper Airfare for more help.

3. Going Deal-Crazy

I’m a big advocate of the travel deal. But, as with most things in life, one can take the deals thing too far. Travel deals often work against the consumer, and this is exactly how some businesses can afford to offer certain types of promotions.

Beware of discounted tickets or passes that you may not actually use. Also beware of discounts or special offers for hotels, cruises, or packages that you probably wouldn’t book in the first place, or that exceed your budget even with a percentage off or a free night’s stay. Sure, it feels like you’re getting more value for your money if you’re paying less than the original price for accommodations. But if you’re still paying more than you would at a comparable, cheaper place, what’s the point?

4. Cramming Too Much In

If you’re dropping several thousand dollars on your vacation, I don’t blame you for wanting to get your money’s worth by stuffing an extensive schedule of sightseeing into your itinerary. But it’s key to leave plenty of room for the unexpected in your trip, whether it’s a missed connection in Chicago or a broken-down bus in Costa Rica. (It’s also smart to leave some space for spontaneous adventure. You could come across a fantastic deserted beach or undiscovered locals-only cafe when you least expect it.)

In particular, too-tight flight connections are a big travel mistake. I once booked a multi-leg flight on that included less than 60 minutes between connecting flights at Charles de Gaulle Airport in Paris. My first flight was about 20 minutes late, and I ended up sprinting for 15 minutes through the airport to my terminal, where I was faced with a long, snaking airport security line. By this time I was sweating profusely and pretty certain that I wouldn’t make it onto my next flight. I got lucky when a Frenchman in the security line noticed my hysteria and got out of line to tell airport security, in French, that I was about to miss my flight. (When I had previously attempted to communicate this in a mishmash of English and lapsed college-level French with an American accent, security had instructed me to stay put.) Thanks to the kind stranger, I was allowed to bypass the line and made it onto my flight with only minutes to spare.

Keep in mind: That itinerary was originally created by Expedia, which, like a lot of travel providers and airlines, doesn’t always give travelers enough time in between flights. Always leave plenty of time for connections. We recommend at least an hour between domestic flights and two hours between international flights. This may vary by airport or time of year.

5. Under-Budgeting

Even travelers who carefully draw up a budget before their big trip can end up with financial plans slaughtered by baggage fees, airline surcharges, costs of airline meals and snacks, ATM fees, hotel service charges, car rental fees, internet charges, taxes, tips, local payments, and other pesky little (and big) fees. Overlook the surcharges and your trip could cost hundreds more than you bargained for.

The nickel-and-diming airlines are by far the worst offenders, but hotels, cruise lines, all-inclusive resorts, and car rental companies aren’t far behind. Your best bet is to always read the fine print and to ask your travel provider to outline exactly what is and what isn’t included in the price. Don’t let phrases like “all-inclusive” or even “free” fool you. Plus, be aware that many hotels and B&Bs, especially overseas, list rates per person, per night as opposed to per room, per night.

Unexpected mishaps like the theft or loss of an important item can also destroy a well-planned budget. Sarah Schlichter, Senior Editor at SmarterTravel, says she always budgets an extra $25 to $50 per person, per day for miscellaneous expenses when traveling. If you leave some wiggle room in your budget for extra fees you didn’t consider, like an unplanned cab ride or a battery charger for your camera to replace the one you lost, you’ll be less inclined to fret over the expenditure (and most importantly, you’ll be able to pay for it!).

For more tips and information, read Hidden Hotel Fees.

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Editor’s note: This story was originally published in 2017. It has been updated to reflect the most current information.

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