The Worst Mistakes You Can Make When Booking a Vacation Online

Learning from these mistakes could save you money—and major headaches—on your next holiday.

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Mistakes to avoid when booking travel online - Couple on Caribbean beach

Not checking the user reviews

Travel sites like TripAdvisor provide a wealth of user-generated reviews and candid trip photos, but if you limit your perusing to positive reviews only, you’re overlooking a crucial resource: the “stealth-positive” feedback.

How to avoid this mistake: “I research using the negative reviews as much as the positive ones. You can determine the resort’s vibe by reading quotes from people who’ve rated it Poor or Terrible. I knew I’d found the right resort for us when I read people complaining about the lack of a swim-up pool bar, no kids’ club, and no nightclub,” says Amanda Eaton of Toronto.

Eaton recently booked a getaway to St. Lucia with her husband and three kids, and was pleased with the quiet, low-key resort they chose—one several disappointed party people had rated Poor on TripAdvisor.

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Mistakes to avoid booking online vacation - Influencer on palafito in Bora Bora

Believing everything travel writers say

Here’s a dirty little secret: influencers and contemporary travel writers wouldn’t exist were it not for the “press trip” or “familiarization trip.” That’s where a resort, resort chain, visitors and convention bureau, or other entity with a vested interest, hosts influencers and writers at their destination, picking up the travel, accommodation, activities and meal costs.

While sponsored trips are necessary—most magazines and websites don’t pay writers well enough to cover trip expenses—do be aware why a specific resort is featured in a story or social feed.

How to avoid this mistake: Use influencers and travel features as preliminary research—not booking guides. Research competing accommodations. Resort Y may be just as wonderful and better priced—only lacking Resort X’s PR and marketing budget.

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Tips for booking vacation online - Woman with suitcase in hotel room

Thinking a “sell-off” room is the same as a regular room

Although third-party sites like and the last-minute section of can offer amazing deals, these rooms are often “leftovers” for a reason. “You will not likely be in the penthouse or on the club floor—last-sell rooms mean least-desirable rooms,” says Tom Waithe, Director of Pacific Northwest Operations for Kimpton Hotels. Think: sub-optimal view, close to the elevator, low floor.

How to avoid this mistake: There’s no need to avoid this “mistake” if a small crash pad and extra spending money trump splurging on a luxe room. But if you want to try your luck, see if you can use a great third-party rate as leverage with a hotel. “Call the hotel, and say ‘Hi, I saw a rate of XXX on a web site, would you honour the same rate over the phone?'” says Waithe. It doesn’t always work, but it doesn’t hurt, either.

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Mistakes when booking vacation online - couple with travel agent

Not considering a travel agent

“Travel agents often have insight into possibilities and best practices when visiting a specific destination: how much time to spend in one place versus another, how long it takes to travel between two locations, for instance. They also have access to discounts through their relationships and partnerships that simply aren’t available online,” says Jennifer Raezer, of, a series of downloadable guidebooks.

How to avoid this mistake: Consult a travel agent for ambitious or complicated trips, like your first backpacking trip across Central America, or your whirlwind around-the-world jaunt. (Don’t sweat it for a one-week resort trip to Cuba, though.)

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Tips for booking vacation online - travellers wandering souks of Marrakech

Not hiring a tour guide

Exploring a foreign city can be overwhelming, even without a language barrier. But throw that into the mix—along with other factors including a tight timeline, urban sprawl, confusing public transit, and in some communities, potential crime—and going it alone can be inefficient, or downright dangerous.

How to avoid this mistake: Hire a tour guide, or join a group tour. You don’t have to sign on for a multi-day commitment, just try a half-day tour to get the lay of the land. The best tours are ones geared to your interests, say, an architectural tour of Chicago, or a culinary tour of Puerto Rico. In certain historic sites, or rugged conservation sites, there may even be local regulations stipulating a guide is necessary. Get recommendations from your hotel.

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Booking vacation online - woman holding model airplane

Not buying third-party trip insurance

Online vacation sellers make it easy to add insurance onto your vacation—but is it the type of coverage you need? Think before you check that opt-in box, suggests Damian Tysdal, founder of online insurance comparison site CoverTrip. “Booking sites use simplified language like ‘Protect your investment in case you need to cancel.’ This doesn’t clarify that there are specific covered reasons for cancellation, such as illness of a child, death in the family, or a burglarized home. If you simply decide not to go, or the weather looks bad for your vacation week, these are not covered reasons,” he says.

How to avoid this mistake: “If you’ve already opted in and want to cancel, you may be able to if you are within the ‘Free Look’ period. This is a time frame in which you are able to cancel travel insurance—every reputable insurance company offers between 10 and 15 days to cancel,” says Tysdal.

Next, investigate third-party insurance options using comparison sites like SquareMouth. Choose a package that covers medical emergencies, evacuation, lost baggage, and 24/7 worldwide assistance, in addition to trip cancellation, advises Tysdal.

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Booking vacation online - Canadian passport at the airport

Not checking the expiration date of your passport

Think you can squeeze in one more trip before renewing your soon-to-expire passport? Think again. Many foreign-entry requirements stipulate your passport not expire for three, even six months, after the date you plan to depart from the country you’re visiting.

How to avoid this mistake: Visit the Canadian government’s Travel Advice and Advisories menu for country-by-country travel reports including entry and exit requirements. If necessary, renew your passport prior to booking your trip (use your new passport number when booking).

Now that you know the mistakes to avoid when booking a vacation online, check out the best Caribbean beaches for every type of traveller.

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