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Winning at Travel, Every Time

The Points Guy shares his strategies for making the most of your travel budget

By Robert DiGiacomo

If you've finally reached the stage in life when you can travel when you want and where but don't know how to get started, or just want to up your travel game, Brian Kelly, founder of The Points Guy website, can help.

Exterior view of a patoe looking out into the ocean. Next Avenue, travel, rewards
"Points are meant to be used, so don't hoard them."   |  Credit: Georgi Kalaydzhiev

In his new book, "How to Win at Travel," Kelly offers his best tips and tricks for everything from finding the most affordable flights and managing airline, hotel and credit card loyalty programs, to overcoming travel anxiety and handling jet lag. The book also addresses topics like buying travel insurance and dealing with accidents and health issues while on the road, both key concerns for older travelers.

"Getting into the points and miles game, especially in your empty nest or retirement years, will exponentially increase your travel opportunities ..."

"We're living in the Platinum Age of travel, where travel is more affordable and accessible than ever before with the right tools and information," Kelly tells Next Avenue. "Getting into the points and miles game, especially in your empty nest or retirement years, will exponentially increase your travel opportunities, and it's not as daunting as some may think."

Here are some top takeaways from Kelly's new book to help you plan your next travel adventure without breaking the bank:

Use Credit Cards to Play the Travel Points Game

Credit cards are at the top of the list when it comes to earning rewards for travel, according to Kelly, who says he has 28 cards and a "near-perfect" FICO score. Instead of earning elite status with just one airline or hotel, you can transfer credit card points to a variety of different travel partners, so you'll enjoy more flexibility and still be eligible for first class and room upgrades. Some of Kelly's picks for cards that deliver the most benefits include American Express Gold, Capital One Venture X and Chase Sapphire Preferred.

"Not only are credit cards the quickest and cheapest way to accrue points, especially in the U.S. when the average person has 3.84 credit cards, but individual airline and hotel loyalty programs just don't have the same weight they used to," he says.

Keep a Spreadsheet to Track Your Miles, Points and Loyalty Programs

Be sure to include a tab for any special spending requirements or perks that come with each credit card, so you can take advantage of them. Kelly also likes to dedicate a tab to track his redemptions, so he can see the value from each transaction and each card.

Headshot of Brian Kelly, author of How to Win at Travel. Next Avenue
Brian Kelly  |  Credit: Jonno Rattman

Set Aside Time Each Month to Manage Your Points

Once you set up the spreadsheet, you can probably stay up to date by checking it once a month. You can also automate the process by using a site like AwardWallet, which tracks more than 600 loyalty programs and enables you to monitor expiration dates, earnings, reservations and other details.

"The great thing about points and miles is that you can make it work for you, based on your personal preferences," Kelly says. "You can keep it simple by having just one or two credit cards in your wallet and becoming very familiar with whichever cards you choose."

Being Flexible with Dates and Destinations Will Reap the Biggest Travel Rewards

Trying to plan a bucket list trip with your children and grandkids? Google Flights is Kelly's go-to, free tool for finding the best fares. The site lets you compare prices across different travel dates and use its "Explore" feature to determine which destinations are going to get you "the most bang for your buck."

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"My first time playing the points and miles game was when I was 12, and my dad tasked me with booking a trip for my entire family using his miles, so I'm no stranger to multigenerational vacations," Kelly says. "Now I have my own kids, and I've loved using points and miles to take them all around the world with me."

Book Flights with Miles to Maximize Your Travel Dollars

Retirees start with a big advantage – flexible schedules — compared with people who are still working and/or have kids in school. If you can book flights with airline miles, Kelly says, you get the equivalent of a refundable ticket, since many carriers let you cancel for free (or a small fee) and receive the miles back.

Book cover of How to Win at Travel by Brian Kelly. Next Avenue

"Not only does this give you greater flexibility in changing your travel schedule as needed, but this can come in especially handy in the event of unexpected delays," Kelly says. "I always use my points to book a backup flight if I'm worried about delays and cancellations."

Don't Forget to Check for Senior Travel Discounts or Airfares

According to Kelly, some airlines offer senior fares, but you often have to call to verify your eligibility. You should also keep an eye out for valuable, limited-time discounts, like the 55% off for 55+ promotion that Frontier Airlines ran this past fall. An AARP membership, which starts at $12 a year, is another tool to unlock discounts on hotels, airline tickets and rental cars.

Use Your Travel Points Whenever and Wherever You Can

Never say never, but Kelly says it's hard to imagine a situation where you wouldn't want to book with points or miles in mind. In his view, accruing points and miles provides more security, because he knows he could book a flight at the last minute under emergency circumstances and probably not have to pay for it.

"Points are meant to be used, so don't hoard them," Kelly says. "They usually decline in value over time, so always use them for flights and hotels, and save your hard-earned cash and retirement savings for activities and experiences."

Robert DiGiacomo is a veteran Philadelphia, Pa.-based journalist who covers food and travel, arts and entertainment and personal finance. He has written for The Washington Post, USA TODAY,  The Penn Gazette and Fodor's. Read More
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