This travel hacker paid $400 for a $52,000 round-the-world trip - here's how he did it

Charles Clark

Nov 10, 2016, 18:24 IST

Flickr/Dan Gillaspia

Dan Gillaspia paid $108 to travel in Singapore Airway's First Class suite.

Dan Gillaspia is an attorney based in California, but in his spare time, he's a travel hacker. He's seen the globe and experienced some of the world's best First Class cabins and five-star hotels.

His most recent vacation was a $52,294 round-the-world trip which took him to Tokyo, Cape Town, Dubai, and other far-off destinations.

It was the trip of a lifetime, but Gillaspia isn't a big spender.

So when it came to planning his trip, he employed every trick and some serious "travel hacking" to whittle his bill down to as low as possible.

In the end, he paid just $408.

After months of meticulous planning, he and his partner, Bradley Darnell, gamed the system and accrued 1 million air miles through various credit cards schemes and deals.

We asked Dan, who runs the travel blog UponArriving, to let us know more about how he managed to pull it off.

Dan and Bradley's first flight on their epic journey was from Los Angeles to Tokyo. They flew Business Class on Singapore Airlines which should have cost $4,444 — he paid $68.

Dan first became interested in travel-hacking about two years ago after looking at other travel blogs including "The Points Guy" and "The Frequent Miler." He told Business Insider: "I spent months learning everything I could about travel hacking and eventually started to put my own plans in motion for an aspirational round the world trip."

Dan and his partner stockpiled roughly 1 million air miles through various credit card schemes which reward you with miles for spending or signing up. In total, they used 15 credit cards from banks including Chase, Amex, Citi, and Barclays.

An example of this is Virgin Atlantic's American Express credit card, which offers 3,000 bonus miles on your first card purchase within 90 days of your account opening. On Dan's first flight, he was treated like royalty. Dishes, including the pictured shrimp and prosciutto, were all served on china plates.

Their first stop was a deluxe corner room in the InterContinental Tokyo Bay hotel for two nights. Guests would usually have to pay $1,000 for this privilege — they paid $0.

Of course, it wasn't all about fine dining and five-star hotels. It was also an opportunity to experience different cultures. Here's a woman demonstrating the ceremonial steps to turning ground up matcha into green tea.

"We did take advantage of a few select loopholes that were offered at the time," says Gillaspia, "but it mostly came down to a lot of planning to make sure we were strategically signing up for credit cards with the best sign-up bonuses that also fit perfectly into our travel goals."

Between them, Dan and his partner have around 45 credit cards, but he insists that his credit rating is as strong as ever. He uses up to four cards regularly, and organises the others in spreadsheets.

After Japan, his next destination was Singapore. This was a chance for the veteran traveller to sample what he called "one of the best First Class products in the world," the famous Singapore Suites.

For a mere $108, he and his partner were assigned a First Class suite designed by French yacht designer Jean-Jacques Coste.

Chilled Dom Perignon is available throughout the flight. This particular bottle from 2006 usually retails for around £110.

He says the service on Singapore Airlines is the best he's ever received anywhere while doing anything, and he assures readers on his blog that the Dom continues to flow even in the face of turbulence.

Speaking to Insider, Dan said the key to racking up the miles is to keep an eye out for the best offers. While some cards offer thousands of air miles as an incentive to sign up, others "send them home with a free rotisserie chicken" from Walmart.

When Dan and Bradley arrived in Singapore, they managed to bag a free stay at the famous Marina Bay Sands hotel for one night — a total saving of $450.

The view from the infinity pool on the roof is incredible. The pool is the longest of its kind and stretches over the city at 57 stories.

Dan told us he wouldn't necessarily recommend this form of travel-hacking to everyone. "It takes a high degree of discipline to avoid running up large credit card balances, and a lot of organisation and attention to detail to successfully manage so many different cards."

After Singapore, Dan and his partner's next stop was Cape Town, South Africa. They flew Business Class on the smaller A350.

The aircraft was smaller but felt extra fresh since it was only one month old. Dan bagged this $7,676 flight for free.

While in Cape Town, the pair enjoyed beautiful views of Table Mountain from their hotel suite which, again, they paid $0 for.

Dan and Bradley took the cable car 3,000 feet through a layer of clouds to the top of Table Mountain. He writes on his blog that the sight is so stunning, it’s recently been named one of the new seven wonders of the world.

They also went cage diving in nearby Gansbaai, where he encountered several great white sharks.

Dan says the great thing about using miles and points to book all your airfares and hotels is that you're left with more cash to splash on the fun things — like this helicopter ride over Cape Town...

And this visit to Boulders Beach, where thousands of wild penguins live. However, Dan does have a word of warning. "If you’re not careful and knowledgeable, you can end up getting 'hacked' by the credit companies yourself," he told us, "and end up in over your head with mountains of credit card debt and a damaged credit score."

His second-to-last stop was Dubai. For this leg of his journey he flew Business Class with Etihad Airways. The seats weren't quite as comfortable as Singapore Airlines' First Class suites, but still came equipped with built-in seat massagers. Dan and his partner paid just $104 for this flight from Johannesburg to Abu Dhabi.

Etihad provided Dan and his partner with complimentary transfers to their accommodation in Dubai's W Hotel, where the rooms wouldn't look out of place in a sci-fi movie.

Even the lobby, which is on the 30th floor, is fitted with hypnotic lighting. As always, they paid $0 for their two nights here.

The couple checked out the famous sand dunes. They even managed to capture this epic selfie at sunset.

Dan admits that even after his trip, it can still sometimes be quite time consuming to keep up with everything because "things change so quickly with credit cards and hotel and airline loyalty programs, but the return in value for time spent can’t be questioned."

Of course, no trip to Dubai would be complete without a selfie in front of the world's tallest building, the Burj Khalifa.

Dan and Bradley saved the best till last. They decided that for their final flight from Abu Dhabi to New York City, they would spend their time in an Etihad apartment, often considered one of the best First Class cabins in the world. The terminal entrance had a separate entrance for First Class passengers, where their bags were immediately taken away before they were shown to their check-in desk.

Dan says there was so much space in his apartment that he didn't know what to do with himself. There are cabinets, closet racks, a television, and a mirror display.

"Instead of spending money only to be slumped over in crowded economy for hours on end, we not only fly in style, but we use the funds we saved to experience more extravagant forms of travel like private helicopter rides and shark dives," Dan said. "It's a real game changer."

If you get restless, Etihad's planes house a lounge area known as “The Lobby” that you can hang out in.

In keeping with tradition, Bradley and Dan paid $0 for their final hotel stay in the Ritz-Carlton in New York City. Dan says the more credit cards you have, the better, so long as you can keep track of them.

You can check out Dan's blog, UponArrival, for the latest news and developments in credit cards and airline reward schemes.

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