Lee Huffman hosts the weekly ‘We Travel There with Lee Huffman’ podcast. His freelance work has been published on many popular websites, including Forbes, Investopedia, FinanceBuzz, NerdWallet, SlickDeals, and more, and he also maintains his own travel website at BaldThoughts.com.
Lee lives by the motto “Travel More. Spend Less. Live Better.” and helps his listeners and readers to use miles, points, mistake fares, and an assortment of additional strategies to travel the world for pennies compared to what traditional travelers would normally pay.
1) Four years ago, Erik Paquet from Abroaders and I discussed the basics of travel hacking, so let’s start on the assumption our audience understands the concept. For those looking to test the waters in 2022, what’s your advice for someone just getting started?
The number one thing: anytime you’re talking about travel hacking and earning miles and points, you don’t want to just jump in haphazardly. You want to be intentional with whatever strategy you use. So I always tell people, start off with: where do you want to go? Like Stephen Covey says, “Start with the end in mind,” right? I love Southwest Airlines, and I’ve had their companion pass every year since 2007. But if you want to go to Europe, if you want to go to South America or Asia, it doesn’t matter how great their points are; you’re not going to be able to redeem Southwest points to get to those destinations.
So wherever you want to go when you are first starting out, you have to take a look and see what airlines fly there and what hotels are at that location. Wherever you want to go, you want to be able to redeem miles and points that reduce the cost of your desired travel. We went to St. Kitts a couple of years ago before the pandemic. Using St. Kitts as an example, I can have as many Hilton points as I want, but when we were there, the accommodations consisted of boutique hotels, a Hyatt, and a Marriott. I could have five million Hilton points, and it doesn’t matter; I will not be able to redeem them for a stay on St. Kitts. So, in short, start with loyalty programs that will help you reach your initial goals.
2) Once someone gets started, what are some of the potential pitfalls and landmines one should look out for and strategies to avoid them?
So with all credit cards, whether you have four cards or 45 like me, you have to look at the benefits and features every year because they change regularly. Credit card benefits, in general, change on a regular basis. Annual fees sometimes increase, like the American Express Platinum recently increased to $695 a year. They threw a whole bunch of extra benefits in there, like a $300 annual credit towards an Equinox health club membership. Well, there’s no Equinox here in Nashville, so that benefit has zero value to me.
Every year, conduct a “performance” review on your cards. Before you pay that annual fee, say, “Is this card earning its paycheck? Am I getting the right benefits from it that I can use, based on the way I travel or how I spend?” If it’s not performing, call the credit card company and let them know you are not getting enough value from the card. Say, “This card really isn’t justifying the annual fee anymore. Is there anything you could do for me?” Sometimes they’ll say no, and if that’s the case, call back and at least talk to somebody else to confirm that’s true. Sometimes the second person will be able to help you, sometimes not, but that way you get confirmation that they can’t do anything for you.
When someone can help: Sometimes they’ll be able to waive the annual fee, sometimes they’ll say, “Hey, if you renew it, then we’ll give you some extra points.” Or sometimes they’ll say, “I normally know you get one point per dollar whenever you spend. For the first however many dollars you spend after renewing, we’ll give you some additional bonus points.” It’s like (Wayne) Gretzky says, “You miss 100% of the shots you don’t take.” So if you don’t ask, you’re not going to get anything, right?
It costs credit card companies a lot to acquire a new customer because they have to give new customers the “welcome” bonus. That said, never straight up say I’m going to close the card because then most customer services agents will say, “OK, thanks,” and then they’ll hit the buttons, and your account’s closed immediately. Just say, “I’m thinking about closing the card. Can I speak to the retention department?” Retention departments have a lot more leeway about what they can do to keep you as a customer.
So every year, do an annual review on your cards. Also, to avoid pitfalls and landlines, when you first sign up for a new card, make sure you take a screenshot of the initial offer. This way, you have a screenshot of what the actual offer was on the day of the application. Make sure you know how long you have to earn the welcome bonus and how much you have to spend, so you don’t miss out on the bonus.
The biggest opportunity that you ever have with a card is when you first apply, especially right now, a lot of cards are offering 100,000-plus point bonuses, and you really want to try to maximize that if you can. So keep track of what was promised.
Take a look at all the other different benefits that you have with a specific card. Sometimes people just focus on, “Oh, I can earn X number of points on spending. I can get the welcome bonus.” Then that’s all they pay attention to. There are a lot of other benefits that cards offer, like global entry or TSA pre-check reimbursement and airport lounge access. I have Amex Platinum, and before the end of the year, I have to use the $200 hotel credit. Basically, I can book a hotel through Amex travel, and I’ll get $200 off my bill. Pay attention to those other card features and benefits. You don’t want to lose out on the benefits you’re paying for if you can help it.
For many people, the big concern is that they’re going to overspend because they get caught up in the excitement of earning the bonus or earning the points. Next thing you know, you spend a lot of extra money that you wouldn’t have spent otherwise, just because you got so excited about earning miles and points. Now you overspent your budget, potentially carrying a balance from one month to the next and paying really high-interest charges. If you are going to play this game, you have got to be able to have some control over your spending to make sure you don’t go overboard. That’s why a lot of people are hesitant about miles and points and getting credit cards with rewards. They’re fearful of overspending.
Lastly, you don’t have to play the game with the goal of completely getting travel for free. Maybe you’re going on a week-long vacation, and you only cover three, four, five nights of the seven nights. That’s still a huge win! Don’t beat yourself up, something like, “Oh, these miles and points weren’t effective because I wasn’t able to pay for the whole trip.” Look at how much you actually did save. If you cannot use points for the whole trip, look at the trip’s cash prices online. Sometimes it’s more beneficial to pay for the weekend nights at a hotel, or if the hotel is in a business district, the weekday nights, because those are generally going to be the more expensive days to stay. Cover the expensive nights with points, and then pay cash for the cheaper nights.
3) I love your content because you use your penchant for making travel affordable and accessible to open up opportunities to make meaningful memories with your kids. What advice do you have for folks specifically looking to maximize their ability to create travel opportunities centered around family?
One of the ways to get the most amount of points is to double up with your partner. I can apply for a new card and get the bonus points, and my wife can apply for the same new card to get the bonus points. Some programs allow families to combine or pool points into one account without any fees. When you can’t combine your rewards, I’ll book some flights using my account some flights using her account.
For hotels, I pay for a couple of nights using my points and a couple of nights using her points. Then, when I arrive at the hotel, I let them know I have two reservations, it’s all the same family, so they don’t have to worry about moving us—whenever the reservation shifts from one person to the next, the worst thing that happens is that they have to redo your electronic keys midway through your stay.
Another thing you can do is get your family involved in the planning. My kids are now six and ten, and they’re at the age where they have opinions as far as where they want to travel, what they like, and what they don’t.
Even if they don’t pick where you’re going, get them involved by picking out different activities. Part of the fun of traveling with children is they see things from a completely different perspective. So you’ve got to try to incorporate some time in there where you don’t have anything planned and just walk around and see what they’re really into and just let them lead. It makes them feel really good because they’re “in charge” of the day, or planning, or at least that activity, and it helps build up confidence.
Lastly, renting a timeshare can be a big money-saver because they generally have full kitchens. Even if it’s just a box of cereal or a carton of eggs, having that in the morning saves you from having to buy breakfast every day. And for me, when using miles and points to pay for travel and hotels, food is one of our biggest travel expenses. So by staying at a timeshare, we actually are able to reduce our expenses considerably whenever we travel. You don’t have to own timeshares either; they are easy to rent on sites like endlessvacationrentals.com, tug2.net, and RedWeek.com.
4) An area that’s really been growing is using credit card points for experiences rather than travel. I call this “fun” hacking. Do you have any specific advice for those looking to explore rewards that transcend simple travel?
The reason why a lot of that’s happening is that these points hold liabilities on the books of the companies that supply the cards. Once these liabilities start getting too high, they go, “OK, well, we’ve got to encourage people to spend these points.” The card companies’ balance sheets get out of whack if folks don’t use their points—so cards partner with entertainment companies to create amazing opportunities to get you to use your points.
A few years ago, before COVID hit, I used points to book a couple of seats in a suite at the STAPLES Center to catch a Lakers game with my buddy. It was a wonderful experience, but a word of caution, you have to understand the valuation of what your points are worth so that way you can translate the value of an experience into a cash cost.
For example, Marriott points are worth about 0.8 cents each. Understanding the value of points and translating points value to a cash value helps you determine, “OK, I’m giving up $400 worth of points. Would I pay $400 to go have this experience?” Some experiences, like seats at the GRAMMYs, might be worth any price, but at least you know the opportunity cost.
Some of the big travel hacking websites, like The Points Guy, NerdWallet, and ValuePenguin, have valuation pages. On these sites, you’ll be able to see what they value your miles and points at to help you better understand an experience’s true cash value.
5) You just named a few already, but after Bald Thoughts, what are some additional resources you’d recommend for anyone looking to expand their opportunities?
There’s a tremendous amount of resources out there: NerdWallet, ValuePenguin, The Points Guy, FinanceBuzz. The best thing to do is, whenever you’re looking for inspiration, whether it’s for a destination, or whether it’s to make use of your credit card miles and points: go to Google and enter “best uses for American Airlines miles,” and read some of the articles there. It’s simple, but it does require a little bit of time to read a few articles on the topic to learn what’s possible.
Let me give you a couple more tips. Go to a portal first before you shop at any website. My wife shops a lot at Target. Before you go into Target, there’s a site called cashbackmonitor.com. Type in Target, and it’ll tell you all the different programs that you can earn miles and points at Target and other places (this is in addition to what you’re already earning on your credit card). So now you’re getting twice the rewards. Cashback Monitor is like the Expedia of online shopping, where you type in whatever store you’re going to, and it’ll show you all the different portals that offer additional rewards.
The other tip is to register your credit cards to earn automatic rewards. If you go out to eat a lot or if you’re out traveling and you happen to stop at different restaurants, there are two different programs that you can register your credit cards with to earn additional rewards on top of what you’re earning already.
The first is dining rewards, which partners with several airlines and hotel loyalty programs. Say you want American Airlines miles, just google American Airlines dining rewards, find their website, and then you can simply sign up. If you happen to dine at a restaurant that’s participating in the program, you’re going to get additional rewards automatically.
There is also an app called Dosh. Dosh has a cashback app that stacks on top of the dining rewards and whatever you’re earning already through your credit card. So now you’re earning points three different ways!
Generally, you’re going to earn anywhere from five to 10% cashback with Dosh, plus the miles you’re earning from dining rewards, plus what you’re earning on your credit card. You literally can earn 15 to 20% back on your meals between cashback, miles, and points.
