For some frequent travelers, the first step off the plane and onto an island paradise, or the familiar feel of their own pillow after a grueling business trek, are all the travel rewards they need.

But for a growing number of cost-conscious globetrotters, it’s not about the destination, but the journey. And that journey happens to be managing and maximizing travel rewards points, miles, freebies and upgrades. It’s a world where status is everything, and optimizing itineraries among multiple credit cards, rewards and travel affinity programs is a hobby with huge pay-offs.

Because of the increasingly complicated landscape of travel rewards, it may seem daunting and even overwhelming to get started. That’s why we’re here, to offer a primer for getting started, scoring small victories and building the skill necessary to soak in that view of first class knowing you paid next to nothing to sit there.

Should You Be Pursuing Travel Rewards?

Pursuing travel rewards isn’t for everyone. And by that, we just don’t mean that some folks would rather book a trip and then jet without dealing with the tedious details of managing points.

Some travelers simply may not be in a comfortable spot financially to take on all that comes with travel rewards management. What is comfortable?

“I define this as: paying on time and in full every month and not spending more money just because you are using a credit card,” said Brad Barrett, founder of Richmond, Virginia-based RichmondSavers.com. Barrett and his site have been featured in The New York Times for developing a step-by-step guide to traveling to Disney World nearly for free.¹

“I would also suggest that you have a credit score well into the 700s so you can qualify for all of these cards,” Barrett told Allianz Global Assistance. “And you must be able to hit the ‘minimum spending requirement’ on the cards in order to earn the massive signup bonuses that carry the real value.

Barrett added that travelers planning major purchases within the next 18 months should also be wary of taking on any potential risk to their credit.

That said, not all travel rewards programs are run through credit cards; most travel sites, airlines, rental car companies and hotels offer reward programs simply for consumer loyalty that can be measured in dollars spent, miles traveled or stays completed.

Getting Started

Once you’ve cleared yourself of any potential financial bumps and bruises that pursuing travel freebies and upgrades could potentially cause, it’s time to get a lay of the land.

Perform a self-assessment by asking some questions:

• What are my spending and travel habits? This can help dictate which credit cards and other affinity programs you consider pursuing. Regardless of which credit cards you choose, look for programs that offer generous sign-up bonuses for instant gratification. This strategy is suggested by Brian Kelley, a business-traveler-turned-rewards expert who runs ThePointsGuy.com.²
• What are my goals? Travelers who simply wish to put an end to letting accumulated points expire before they cash in will likely have less aggressive objectives than those who want to finance an overseas dream trip exclusively through travel rewards.
• How will you get your questions answered? There are a number of blogs, Twitter handles and message boards helping to power the thriving community of travel rewards, including FlyerTalk.com and MilePoint.com. For example, FlyerTalk’s MilesBuzz forum includes insider tips ranging from how to claim 10K Lufthansa miles by subscribing to The Economist to details on Home Depot’s one-day Delta Sky Mile offer.³

“When someone is getting started, the tendency is to read all the travel rewards blogs and it can quickly become overwhelming,” RichmondSavers’ Barrett said. “The truth is, there are a lot of details and you can almost never learn everything. But you don't need to know everything to get a lot of value out of this strategy!”

Travel Rewards Concepts to Understand

A lot of the travel rewards rules, lingo and culture makes perfect sense. That said, here are three key concepts to look closely at when evaluating any program or offer:

• Expiration dates: It’s a bad word in the travel rewards community. Expiration dates range from generally from one to several years after rewards are accrued. And it’s critical to note, track and flag these dates; as they could be different for all your programs. When deciding which perks and points to use for a particular trip, an upcoming expiration date may trump a higher value discount simply because you don’t want to lose a reward.
• Availability: It’s no longer the airline’s dirty little secret that not all miles are the same – and that free miles earned through rewards program activity often face more stringent black-out dates and other constraints. Likewise, AMEX has a sterling reputation and customer benefits that dwarf many other credit cards, but there is also a more limited number of retailers and restaurants that accept the card. And hotel rewards may exclude Friday and Saturday stays. Always explore and anticipate potential limitations when vetting and cashing in on rewards programs.
• Redemption value: What is the value of the rewards you’re receiving? In other words, while Travel Rewards Program A may accrue points faster than Travel Rewards Program B, the rewards that Program B offers may require far fewer points. Do the math and dig a little deeper before falling for a program that looks too good to be true.

Getting Organized and Staying on Points

Never take on more than you can manage. The whole point of travel rewards is to reap value for your loyalty to specific brands. If you’re overwhelmed and in over your head, then you may start to miss out on low-hanging-fruit opportunities and defeat the purpose pursuing travel rewards in the first place.

Organization is personal, and while no solution is tailored for every traveler, the likelihood is that there is a system that can help you.

This is one of The Points Guy’s first pieces of advice to all beginners: pick and use an online mileage and/or points manager.² AwardWallet.com is one of the more popular tracking sites. While AwardWallet tracks more than 50 billion miles and points for members across 600-plus programs, other points management sites include Tripit.com and Usingmiles.com.⁴

RichmondSavers.com’s Barrett chooses a more old school approach to staying organized. “Being organized is very important, but it doesn't have to be difficult,” he said. “I use a simple spreadsheet to track all my hotel and airline account logins and another worksheet to track the credit cards I've opened. It has the following information: card name, bank name, which person opened the account, bonus info, required spending, date opened, date bonus earned and date closed.”

Savvy travel reward managers grimace at the following stats: 10 trillion frequent flier miles are currently being left on the table. That’s a value of more than $165 billion.⁴

With a little patience, tenacity and knowledge, you can enjoy the rewards of frequent travel from credit card companies, airlines, travel portals, hotels and others without added to this number.

Save travels – and don’t forget to read the fine print.