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9 Travel & Vacation Planning Mistakes That Can Cost You Money


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When it comes to travel planning, the Internet is an incredible resource – but, let’s face it, there is a lot of conflicting information out there. I love going on vacation, but organizing my trips is enough to give me some serious anxiety. From timing plane ticket purchases for the best possible deal, to waffling over hundreds of hotel options, getting the most bang for your travel bucks can be overwhelming.

Whether it’s the curse of indecision or inflexible dates, you can sabotage your ability to snag the best vacation deals before you even hop on a plane or gas up your car. By educating yourself about common spending traps, you can better allocate your money and set priorities before starting your search for vacation deals.

Costly Travel Planning Mistakes

1. Booking Too Late, or Too Early

Finding the perfect sweet spot to purchase airline tickets or reserve a hotel room can make a huge difference in how much you pay. If you book too far in advance, you could miss significant sales in which airlines discount tickets based on availability. If you wait too long, you could be stuck with low supply and pay much more for the same ticket. In fact, if you polled other folks on your flight, what you each paid for your tickets could vary by a significant margin.

The best time to buy is three to six weeks before your trip. In the six weeks prior, an airline is more likely to discount unsold tickets, resulting in other airlines following suit. As you close in on three weeks before your trip, you’re cutting it close. Airlines usually require a 21-day advance purchase for discounted seats, otherwise you could end up paying a premium. If you want some advice on when to pull the trigger on your tickets, try using the Price Predictor. It’s not always perfectly accurate, but can help you decide if you should buy immediately or hold off for a few more days.

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2. Booking at Night

When is the best time of day to get a deal? Well, if you’re waiting until you get home from work, you might be in for a rude awakening. Fare sales and specials are more likely to be released and copied by other airlines in the morning. This usually leads to a rush of purchases, leaving you with the more expensive leftover seats when you try to get the same deal at night.

Instead, look for fares on Tuesday morning. After a weekend of sales, airlines assess availability and demand, pushing out new sales early Tuesday morning, often just past midnight. Your best bet is to roll out of bed and start searching as soon as possible, or risk getting stiffed on a great sale price.

3. Being Inflexible With Dates

Sometimes, you just can’t be flexible with your dates. If you’re traveling for work or with friends and family members, you might be stuck flying on specific days. However, those firm dates could really cost you, especially if you’re slated to fly on a Monday, Thursday, or Friday. If you have a little flexibility, you’ve got a better chance for an amazing deal.

By choosing to fly on a Tuesday, Wednesday, or Saturday, you may be able to get steep discounts. Use websites that offer pricing calendars, such as the Low Fare Calendar. also offers a low fare calendar, while sites such as Orbitz and Travelocity provide a flexible dates tool, which allows you to see prices between one and three days of the dates you search for. It’s easy to see which days offer the best deals and then plan your vacation itinerary accordingly.

4. Paying for Too Much Insurance

Having travel insurance in place for a pricey vacation makes sense – you wouldn’t want to be in the red if you have to cancel your trip. However, before you choose certain types of coverage, make sure you’re not adding insurance on top of insurance that you already have.

Many credit cards offer trip, travel, and rental car insurance as part of their cardholder agreements, as long as you purchase with the card in question. Therefore, if you agree to even more insurance, you’re wasting money – and may potentially void better coverage through your credit card provider. For example, even basic cards offer insurance (all Visa cards, for example), but you must waive the insurance offered by the rental car company in order for the credit card insurance to cover you.

Because cardholder agreements vary, you should always check with your provider before you make decisions on insurance. Just call the number on the back of your card to find out your travel insurance options before adding extra cash to your trip package.

Paying Too Much Baggage Insurance

5. Ignoring Extra Fees

Hidden travel fees such as for baggage, resorts, and parking can add up. If you ignore them, you might think you’re getting a great deal, only to find out that you ended up paying more on the back-end. Don’t stick your head in the sand when it comes to paying extra fees. Knowing what you owe upfront can help you make better decisions and weed out the phony deals from the truly great prices.

My younger brother recently flew across the country for the holidays. After searching for the best deal, he found an airline that was significantly cheaper than its competitors by about $100. He was so excited that he booked the flight, no questions asked. Fast-forward to his return flight. Unbeknownst to him, the airline had strict baggage weight rules – charging for every pound above the limit. After weighing the baggage, my brother was forced to cough up an extra $200 to get his suitcase home.

Lesson learned: Read the fine print and add fees into the total price of your vacation so you don’t end up with any unpleasant surprises. What might seem like a deeply discounted fare or deal may not be so great after you add up the extras.

6. Buying at a One-Stop Shop

Buying a complete vacation package from one website or agency is a lot easier than scouring a handful of resources – but that doesn’t mean it’s cheaper. While some agencies brag that they can score better deals by bundling your airfare, hotel, and rental car together, you need to do some sleuthing on your own to confirm that.

Always price your vacation both as a package and separately to make sure you’re getting the best deal, because each situation is unique. Just make sure you also add up taxes and fees as part of your estimate to get a complete picture of the price. You often pay more when you have one website or agency put together your entire vacation, so while purchasing separately may take a little time, it may be worth it.

7. Being Overly Loyal to Brands and Companies

While you may have had several excellent trips on a certain airline, don’t be afraid to shop around and see if another airline has better fares – and the same goes for hotels. Unless you’re absolutely firm on where you want to stay, check around, read reviews, and look at amenities before you make your final decision.

The only time that loyalty to a particular brand really pays off when traveling is if you do it often. The average traveler taking one vacation per year isn’t going to rack up a ton of hotel loyalty points. However, if you do travel frequently, start collecting airline miles and opening loyalty accounts along the way.

I travel several times per year and collect miles through six different airlines. That way, I’m accumulating potential rewards, but I never feel like I have to fly exclusively with one airline.

8. Using a Credit Card to Fund Unaffordable Travel

Can’t pay for your vacation in cash? Don’t put it on your credit card. While it might seem like a good way to rack up points, get extra insurance, and enjoy your annual excursion, you should only use a credit card if you’re absolutely certain that you can pay back the amount within a month or two of booking.

If you were to charge a $2,000 vacation to a credit card with 18% interest and only made the minimum monthly payment, it would take 10 years to pay it off in full. Suddenly, that week in the sand doesn’t seem worth it, does it? Even if you do receive points or cash back, the rewards are minimal when compared to the overall expense.

If using a credit card is your only way to pay, reassess your vacation plans. Consider sticking closer to home, or opt for a camping trip over a vacation at a fancy resort. While it may not be as luxurious, you can skip the shock of receiving a massive credit card bill when your trip is done.

Using Credit Card Fund Unaffordable Travel

9. Missing Out on Membership Discounts

If you’re a student, military member, senior citizen, or a member of certain organizations (such as AAA or AARP), you may be able to score discounts on travel. Contact any association you belong to for a list of airlines, hotels, and car rental companies that offer discounts. Or, simply look online. Sometimes, booking sites provide boxes to check if you have a membership in a qualifying organization.

Final Word

Planning a vacation should spark anticipation and excitement and be a fun part of the overall process. However, approaching it from an uninformed or lazy perspective could turn your relaxing time off into a total nightmare. By being budget-conscious and understanding the most common spending traps and planning mistakes, you can navigate the mine field and rest easy knowing that your short-term trip doesn’t become a long-term problem.

What are your best vacation planning tips?

Jacqueline Curtis writes about edtech, finance, marketing, and small business strategy. With over 14 years of copywriting experience, she's created content and scripting for organizations such as GE, Walgreens, Overstock, and MasterCard. She lives in Utah with her husband, three kids, and an overzealous springer spaniel named Penelope.