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Plan Ahead to Snag the Best Travel Deals on Cyber Monday With These Steps

A happy couple and their two young children take a selfie at a picturesque seaside spot.
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Cyber Monday is coming.

Have your passport and budget ready because the steady roll of deals waits for no one.

The annual online shopping event that happens the Monday after Thanksgiving promises fleeting bargains, including discounted airfares, cruises, cars, hotels and vacation packages.

The hard-to-pass-up deals mean you have a chance to book your dream vacation on sale, find a cheap rental car or fly somewhere new affordably.

Whatever the destination, Cyber Monday is chock full of deals that budget-savvy travelers won’t want to pass up.

How to Prepare for Cyber Monday Travel Deals

Postcards sit on a rack in Los Angeles
Chris Zuppa/The Penny Hoarder

No need to go into debt for Cyber Monday and do the Aruba, Jamaica, ooh I want to — drain my bank account.

Follow these tips to help you make the most of your travel budget in a world of deals.

Step 1: Plan Ahead

“If you’re looking to score a travel deal on Black Friday or Cyber Monday, start planning now,” said Alexis Tiacoh, a spokeswoman for Expedia.

Seems like a Captain Obvious move, but it will seriously pay off if you’re looking to maximize your digital spending on travel deals.

Just like Black Friday, some Cyber Monday deals have limited quantities available, so you’ll need to plan ahead to make the most of the shopping event. Follow Steps 2 to 6 before the big holiday weekend approaches.

Step 2: Budget

How fun is that vacation really gonna be if you know it’s putting you in debt? Keep it stress-free by making it something you can afford.

“Set your budget and stick with it,” Tiacoh said.

Let your budget be your purchasing guide. Say no to deals that exceed it, else it’s gonna be an in-the-red Tuesday.

Try adding a Honey extension to your web browser. It’s free and can help you save more money at checkout.

It automatically researches all online coupons, promo codes and discounts available to ensure you’re getting the lowest possible price.

Step 3: Have a Destination in Mind

Select a handful of locations to search from your bucket list or look for deals in cities where you have friends and family, or go home for Christmas.

Shave time off your searches by knowing where you want to go instead of aimlessly wandering from site to site, unless you enjoy that sort of thing.

“Narrow down your destination and figure out what you’ll need to buy,” said Tiacoh.

For instance, if you want to go to New York City, do some advance research on potential flight routes, airlines, hotels, rental cars and any shows, tours or other activities you may want to do.

Websites like Expedia, Orbitz and Travelocity let you save a trip itinerary in advance and access it later, which is super convenient when Cyber Monday checkout time rolls around.

If you don’t save a trip, at least you’ll know exactly where to look and what to look for — and how much you can spend.

Flight deals will come and go quickly, so it pays to do your homework and be prepared for when a deal breaks.

Step 4: Sign Up for Accounts and Follow Social Media Ahead of Time

Travelers walk through an airport.
Aileen Perilla/The Penny Hoarder.

Start hunting for your preferred Cyber Monday websites, hotels, airlines, cruises or aggregate service now.

Download apps, register for accounts and newsletters, join loyalty programs, follow your favorites on social media and bookmark everything. Bonuses abound when you sign up early and get your feeds ready. You can unsubscribe, unfollow and delete later.

This will spare you from the tedious details of registering for an account during the crunch time of a sale — plus, you’ll get first dibs on exclusives.

Skyscanner, a travel-fare aggregator, spokesperson Dana Cohen said airlines are likely to announce flash sales via email.

Apps like Expedia will offer incentives like in-app coupons and exclusives as well as double reward points for booking.

Step: 5 Set Price Alerts

Many apps like Skyscanner, Hopper. Momondo, and Hipmunk let you sign up to receive price- drop alerts on flights you’re watching. You’ll get a notification on your phone, or via email if you decide to watch fares using an online service like Google Flights.

You can track routes in tandem with other travel services to ensure you get the best price on a flight or service you’ve been eyeing.

Step 6: Look at Last Year’s Deals

If you’re eager like me and making a Cyber Monday travel plan already, you’re probably finding that many airlines, hotels and cruises have yet to release their deal details.  

Unfortunately, many won’t release their deals until Thanksgiving week.

A way to combat this is to find out what they did last year. Do a quick Google search of the company name and “Cyber Monday 2017.”

This will give you a ballpark idea of what to anticipate this year.

Day Of: Shop Around… But Not Too Much

A young couple take enjoy the sun and breeze on the deck of a cruise ship.
Pekic/Getty Images

Deals, deals, deals. So many swimming around that it’ll be tough to tell a good one from a gimmick.

Not all deals are created equal. Cross-reference prices of providers and resellers to get the best one.

But be careful not to stall too long.

“Don’t second-guess yourself because flight deals can go quickly. Book the flight; figure out the logistics later,” Cohen said.

Skyscanner will post updates in real time for Cyber Monday flight deals and Cyber Monday hotel deals in one convenient place if you’re trying to shop around fast. They’ve even calculated the best time of day to book flights.

Deals will come and go by the hour and day. Keep refreshing and updating your searches.

Day Of: Be Flexible

It’s not always as simple, or affordable, to go from Point A to Point B. Keep an open mind about indirect alternatives.

“Consider flying out of farther-away airports; they may have bigger discounts on certain routes,” Cohen said.

If you find a great deal but don’t love the destination, consider where else you can travel nearby,” she added.

For example, you can find a cheap flight to New York City and then hop on a train to Philadelphia, Boston or Washington, D.C.

Day Of: Read the Fine Print

That steal of a deal may not include carry-on baggage. Or it may require you to travel before the busy summer travel season.

Many deals will have blackout dates, other exclusions and worse — they may not include additional fees like a resort or city tax.

Don’t let the excitement of a bargain make you skip the fine print.

Day Of: Use a Credit Card for Protection and Rewards

Some credit cards offer price protection in case you find a cheaper deal, request a refund later or need to file a claim.

Use a credit card with rewards, points, miles or cash-back perks on any travel purchases.

Put these perks toward a future vacation or on another a big purchase. Squeeze as many benefits as possible out of every purchase.

Vacation Packages

Consider broadening your search to include bundled vacation packages. These combine flight, hotel and car in one convenient purchase.

You’ll find these deals through travel booking websites, agents or discounted services like Groupon Getaways.

This approach has the potential to save you hundreds of dollars on a trip.

Happy hunting for Cyber Monday travel deals.

Stephanie Bolling is a staff writer at The Penny Hoarder. Seeing the aurora borealis is on the top of her bucket list. Read her full bio here or say hi On Twitter @StephBolling.

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