The INSIDER Summary:
• Daniel Gillaspia is a pro at managing airline miles, points, and rewards.
• He recommends using many credit cards carefully.
• Flying out of airline hubs and using companion passes also saves time and money.
When Daniel Gillaspia isn’t working as a full-time attorney in Houston, he and his partner Bradley Darnell travel around the world by expertly managing airline miles, points, and rewards from their 45 credit cards.
“Travel is naturally a pretty expensive thing to to enjoy, but I knew that there were ways to do so-called ‘travel hacking,'” Gillaspia said. “I started to learn the ins and outs of everything, and then I was like, ‘Alright, well, I’m going to put this knowledge into practice and see how far it can get me.'”
He now shares this knowledge on UponArriving, a website he runs that covers the latest developments in credit cards, airline and hotel award programs, and other travel topics.
INSIDER asked Gillaspia for his best travel hacks. Here’s his advice for making luxury travel happen at a fraction of the cost.
Make sure your finances are in order.
“The average American household has something like $15,000 worth of credit card debt, and if someone is prone to running up credit card balances, they should think twice about getting into this, because rewards credit cards almost always come with some of the highest APRs (annual percentage rates),” he said.
Choose cards with valuable sign-up bonuses.
“There’s the Chase Sapphire Reserve that offers a 100,000 point sign-up bonus, which could convert into $10,000 worth of first-class airfare, but you have people running into Wal-Mart signing up for cards that send them home with a free rotisserie chicken,” he said. “Not all cards are created equally.”
Keep an eye out for multiple sign-up offers on the same credit card.
“If you just search around a little bit more, you may find a sign-up bonus for the same card offering 20,000 more miles or something like that,” he said.
The more cards you have, the better — as long as you keep track of them.
Gillaspia estimates that between him and his partner, they have 45 different credit cards.
“A lot of people shudder when they hear that, they think our credit score is in the crapper,” he said, “But actually, our credit scores are as strong as they have ever been.”
The key is keeping track of them and paying them off fully each month. Gillaspia uses two to four cards regularly, and organizes the rest in intricate spreadsheets.
“The more credit cards you have, the bigger payment history you can build up over time. If you’re responsible and don’t run up a huge balance on your credit cards, pay them off each month and keep their utilization down to a minimum, you’re going to inevitably increase your score over time,” he said.
Think of points as a form of currency, and spring for deals that give you the best exchange rate.
“You don’t want your points to be redeemed for poor values, really low values,” he said. “You always want to maximise.”
Fly out of airline hubs.
Flying out of an airline’s headquarters means you will have more flight options, and thus save time and minimise extraneous connecting flights.
“It’s just a better, more efficient use of miles a lot of times, if you’re going through hubs,” said Gillaspia. “And it also saves time, especially for people like me who like to do weekend getaways.”
Earn a companion pass.
A companion pass allows another person to fly for free on any flight you book. It’s earned after reaching a certain number of points, depending on the airline.
Gillaspia’s companion pass allowed him and his partner to get away about every two weeks to explore places around the US and the Caribbean.
“I would say that while the first class experiences we enjoy are certainly our favourite way to fly, earning the Southwest Companion Pass was one of the best things we ever did,” he said.
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