Traveling the World One Point at a Time

Written by Kara Thompson

Have you ever walked out of a store and quietly asked yourself how one bag of groceries could cost $65? Have you set aside money to save for something special, like a classic handbag or nice golf clubs, only to feel a strong sense of buyer’s remorse when they’re left to collect dust in the back of your closet? We’ve all been there, but what if there was a way to ease the regret of those daily spendings and extravagant purchases by knowing that the money is going toward an experience you may not have otherwise. What if every time you pumped gas or went out to dinner, you were earning points that could score you a flight to Paris, an upgrade to first class, or a fancier hotel room?

Influencer and travel expert Lindsay Silberman has mastered the art of using credit card points to fund vacations across the globe. Using points, she’s flown round-trip to Tokyo for $45 and upgraded to first class to and from Lake Como for no additional cost. Later this year, she plans to visit Greece and the South of France and will only spend $117 in taxes on those flights.

Understanding how to earn points that can fund adventures like this might seem overwhelming, but Lindsay is living proof that if you just take a little bit of time to research, you’re sure to reap the benefits. “I always knew that I wanted to travel and I wanted to attempt to have first class experiences, but I certainly didn’t have $8,000 to spend on that kind of flight,” she explains.

Lindsay realized that if she was strategic with points and miles that she could hack her travel expenses and ultimately visit more destinations and have better seats than the average jetsetter. She started by reading about the different types of credit cards that were offered and took a deep dive into researching the benefits that would best suit her lifestyle. Her favorite tool for educating herself on the subject was The Points Guy—a travel website run by founder and CEO Brian Kelly that gets roughly 7 million unique visitors a month. Lindsay says that Brian’s site has taught her everything she now knows about traveling with points.

If you’re longing to get away for less like Lindsay, she recommends you start by comparing the sign-up bonuses on different cards, take note of the annual fees, and see what other offers you get as a cardholder. For example, the Chase Sapphire Preferred Card, which she pegs as a great beginner’s option, offers 60,000 bonus points after you spend $4,000 on purchases, gives you two times the amount of points when you spend on travel and dining, and one point per dollar spent on all other purchases. Another advantage is that the card’s annual fee is only $95, which is much less intimidating than many of its competitors.

For those of you with a wanderlust spirit who are looking to go all in, options like the American Express Platinum Card have higher annual fees but offer greater benefits. Sure, you might have to dish out $550 upfront, but a $200 airline credit, access to airport lounges, and monthly Uber discounts alone make it worth opening. “The annual fee is always a big turn off to people, but if you take a few minutes to look through the benefits and discounts they’re giving you, the fee pays for itself in a month or two,” Lindsay says.

Some cards will even give you two, three, or four times the number of points when you spend in certain categories, like hotels, airlines, and dining. “That’s how things add up quickly. If you spend $500 on a flight and you book it with a card that gives you three times the amount of points for travel, that means you’re really getting 1500 points instead of 500. In a lot of ways it’s like you’re being credited back money to put toward another trip.”

Cards aside, when it comes to getting the most out of a vacation, it’s also important to remember that doesn’t hurt to ask for upgrades. If you’re early to the airport, talk to the gate agent to see if there are better seats available on your flight, or when you check in to a hotel, ask the concierge about room upgrades. You might get both for little to no cost.

Similarly, if you’re going to be spending a lot of money on a special trip, like a honeymoon or anniversary, it’s always good to see what packages are available and see if the resort will offer any throw-in perks. “A lot of hotels tend to be more generous, particularly with honeymoon couples, because they know that those guests spend more money on average. They may give you a bottle of champagne, a free massage, or a better room,” Lindsay explains. “It’s the same for big trips or big spends in general. It’s always good to ask what they have available or see if there’s anything extra they can offer.”

Becoming an experienced traveler like Lindsay will take some time and accumulating points to cover round-trip vacations won’t happen overnight, but doing your research and finding the right card is a great first step. Spending is inevitable, but receiving perks on common purchases without having to think about them is a bonus that everyone could benefit from. At the end of the day, you’ll have a nice fund set aside that just might turn into the most lavish trip you could dream up. *

Lindsay’s Top 3 Travel Essentials

Noise Cancelling Headphones

I’ve tried several brands, but always go back to Bose Quiet Comforts. They are the only way I can 100% guarantee that I’ll have a calm, relaxing flying experience.” nordstrom.com

Sleep Mask

“If I’m on a red-eye, long-haul, or early morning flight, I swear by my Slip eye mask. Trust me: wearing one will significantly increase your chances of actually getting decent sleep on a flight.” cosbar.com

Facial Spray

“This Caudalie Beauty Elixir is a super light and refreshing facial mist that I have with me on every single flight. A few mists, a few deep breaths, and you’ve got hydrated skin and relaxation in one.” bluemercury.com