A few years ago, Daniel Gillaspia, a 30-year-old attorney, thought he had set an ambitious goal: to fly to Europe in business class—for free. He'd gotten the idea after reading about travel hacking and how travel credit cards helped other people pay for vacations with nothing more than credit card points and air miles.
Gillaspia never made it to Europe. But as his travel hacking knowledge grew, so did the scope of his trip, until he eventually planned out an unforgettable two-week getaway (worth $52,000) that took him to luxury lounges, first-class flights and 5-star hotels in 6 cities and 3 continents around the world—all for about $400.
Here's how he did it.
The hard part: earning his wings
Careful planning was the key to Gillaspia turning his trip of a lifetime into a reality. He didn't want to earn points that didn't apply to his travel route, and he didn't want to travel to destinations where airline miles couldn’t be used. "We made sure to only seek out cards that offered points that aligned with our travel plans," he told ValuePenguin.
He also gave himself some guidelines: to earn enough points within about a year, and to use his credit cards to pay only for expenses he’d normally incur; after all, paying for a trip with points only counts if you don't go into credit card debt to do it.
The fast-track to points: signup bonuses
Once he'd hammered out the details of his trip, he focused on finding the best credit card signup bonuses available. "For the most part, we wouldn't jump on a credit card offer unless it was an all-time-high offer," Gillaspia said. With a little luck, he stumbled upon some great deals, like a 100,000-point signup-bonus, which helped cover a large chunk of his expenses just for signing up and hitting a minimum spending amount.
Strategic credit card spending
After signing up for about 15 different credit cards, Gillaspia mapped out where and when to use each one. If he was going to earn enough points and miles to cover his trip, he needed to charge every last expense. Over the course of a year, every recurring bill he received was paid for with a card, including rent, auto loans, insurance, utilities and student loan payments.
It's worth pointing out that some companies will charge you an extra fee—typically around 3% of your total payment—to pay bills with your credit card instead of using a check or bank account transfer. Since these charges helped Gillaspia meet minimum spending requirements necessary to receive one-time signup bonuses, it made sense in his case.
But simply using his cards wasn't enough. Gillaspia also tracked the bonus categories offered by his credit card companies, so he could earn extra rewards on things like groceries and travel expenses during certain months.
Shopping through credit card portals
The last thing Gillaspia did to maximize his rewards was to shop through credit card portals whenever possible. By paying for things like dining or travel tickets through a credit card portal, such as Chase's Ultimate Rewards portal, you can earn even more rewards or receive significant discounts.
Taking the vacation of his dreams
After about a year of planning and earning rewards, Gillaspia had enough to embark on his voyage around the world.
Los Angeles to Tokyo
- Actual price: $4,444
- Gillaspia's price: $68 and 131,750 KrisFlyer Miles
Gillaspia's trip began at LAX, where he and his companion relaxed in the Star Alliance Business Class Lounge before boarding a Singapore Airlines business class flight to Tokyo.
The flight featured wide, reclining seats, a gourmet dinner and wine.
InterContinental Tokyo Bay (3 days, 2 nights)
- Actual price: $1,000
- Gillaspia's price: $0 and 100,000 IHG Points
After landing in Tokyo, Gillaspia headed to the InterContinental Tokyo Bay hotel, where he was upgraded to a deluxe corner room with a stunning view of Tokyo Bay.
From the window they could see the Tokyo SkyTree—the second tallest structure in the world—as well as some stunning sunrises.
While in the city, he took a sushi-making class from a sushi master. Later, he attended a traditional Japanese green tea ceremony, where his hostess led him through the ceremonial steps of brewing ground matcha tea.
The next day, he visited Sensoji Temple and explored Tokyo's narrow alleyways dotted with hanging paper lanterns and hidden restaurants.
And, of course, he tried some more delicious food.
Tokyo to Singapore
- Actual price: $11,660
- Gillaspia's price: $108 and 102,000 KrisFlyer Miles
After enjoying Japan, Gillaspia headed to Singapore on a flight fit for royalty. And if it weren't for his air miles, the tickets would have cost more than a king’s ransom (or somewhere north of $11,000).
The Singapore Suites program doesn't just give you more legroom. You get an entire suite of your own, designed by French luxury yacht designer Jean-Jacques Coste. After boarding, you don't need to worry about loading your baggage into the overhead bin.
The only decision you'll have to make is which champagne you'd prefer to start with.
Before dinner, Gillaspia was served hors d'oeuvres—caviar and biscuits. For dessert, he enjoyed Gianduja chocolate cream, vanilla ice cream and rose jelly on top of a dish of sable crumbs.
And when it came time to freshen up, he was given a designer amenity kit by Salvatore Ferragamo.
After dinner (and a few more glasses of champagne) Gillaspia donned the designer-brand pajamas provided to him, converted his suite into a bedroom and drifted off to sleep. "The service from Singapore Airlines in first class is probably the best I've ever received anywhere, doing anything," said Gillaspia.
At this point, you’re forgiven if you assumed Gillaspia's $52,000 vacation culminated with this flight. But he was only halfway through.
Marina Bay Sands Hotel (2 days, 1 night)
- Actual price: $450
- Gillaspia's price: $0
The next destination on Gillaspia's trip was Marina Bay, Singapore. The Marina Bay Sands Hotel is connected to a museum, a casino and a luxury shopping mall. You can even ride a sampan down the man-made canal that runs through the building (something of an East Asian take on Venice).
But his favorite part was the rooftop infinity pool. The water runs up to the edge of the building and overlooks the Singapore skyline.
Singapore to Johannesburg, South Africa
- Actual price: $7,676
- Gillaspia's price: $0, travel credits and 38,250 KrisFlyer Miles
After his Singapore Suites experience, no flight will ever feel the same to Gillaspia. But his business class flight to Johannesburg was nothing to write off. It featured spacious, brand-new seats and a personal television.
From Johannesburg, he had a $500 connecting flight to Cape Town—paid for with points, of course.
The Westin Cape Town (5 days, 4 nights)
- Actual price: $1,160
- Gillaspia's price: $0 and 40,000 SPG points
In Cape Town, Gillaspia enjoyed great meals and a fantastic view from the Westin hotel.
His room came with club access, which meant he was able to enjoy complimentary food and champagne on the house.
One day, he took a cable car to the top of Table Mountain to see the gorgeous view during sunset. Later in the week, he swam with great white sharks and played with wild penguins.
"These little penguins aren't very shy, and will waddle up right next to you," Gillaspia said.
To finish his visit, he took a helicopter ride around Cape Town to get a breathtaking view of the city.
Johannesburg to Abu Dhabi
- Actual price: $4,040
- Gillaspia's price: $104 and 110,000 AA Miles
The next leg of Gillaspia's trip was to Abu Dhabi. His business class seat on Etihad Airways wasn't as spacious as previous flights, but his seat reclined all the way back and came with built-in seat massagers. Of course, he had champagne as well.
The W Dubai (3 days, 2 nights)
- Actual price: $534
- Gillaspia's price: $0 and 40,000 SPG points
Upon arriving, Etihad provided complimentary transportation to the 5-star W Hotel in Dubai. "The rooms looked like something out of Star Trek," said Gillaspia.
At the Dubai Mall Aquarium, Gillaspia swam with sharks—again—only this time he wasn't in a cage. Fortunately, these sand tiger sharks are less aggressive than the great whites.
Later, he and his companion took a jeep out to explore the Dubai desert. Gillaspia got a little car sick, but he didn't let that ruin the view.
The next day, they went to the top of the Burj Khalifa. At 2,722 feet, it's currently the world's tallest building.
When their time in Dubai was done, the Etihad chauffeur returned to bring them back to the Abu Dhabi Airport, where they would experience an unparalleled first-class experience even before boarding their flight.
Abu Dhabi to New York City
- Actual price: $18,000
- Gillaspia's price: $104 and 180,000 AA Miles
Gillaspia entered the airport through a private entrance, where he enjoyed the first-class lounge and spa. The lounge offered fine foods, complimentary haircuts, massages and even a whiskey and cigar room.
After boarding the plane, Gillaspia was led to his apartment. Yes, you read that right: an apartment. On an airplane.
It came with a comfy chair and sofa, a vanity, a TV and a mini bar. In the evening, the apartment converted into a bedroom. But that wasn't the most impressive part of his in-flight experience. Gillaspia's favorite feature was the fully-functioning lavatory—with a shower included. How would you like to rinse off at 40,000 feet?
The Ritz-Carlton New York—Battery Park
- Actual price: $1,900
- Gillaspia's price: $0 and free-night certificates
The final leg of Gillaspia's journey was New York City. The Etihad chauffeur took him to the Ritz Carlton at Battery Park, where he was upgraded to a room with a view of the Statue of Liberty.
To cap off his trip, Gillaspia saw a Broadway show, explored Manhattan and visited the top of One World Trade Center.
After two weeks of living like the rich and famous, it was finally time for Gillaspia to return home to Houston. And he did so by flying economy on Southwest Airlines. The flight to Houston cost $450, which Gillaspia paid $24 for. His entire trip came out to $52,294, but Gillaspia only paid $408.
After that bucket list-worthy trip, Gillaspia started writing about travel and getting the most out of credit card points on his blog, UponArriving.com.