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Ever heard of ‘travel hacking’? No, it’s not got anything to do with hacking trains or airplanes. That’s deeply illegal.

Travel hacking is the art of exchanging air miles and credit card points for money off travel. While most other hacks make things easier, this hack is actually pretty complicated, but it also has better rewards than probably any other hack out there.

Travel hack king Daniel Gillaspia, for example, managed to fund a five-star trip around the world for just £329 thanks to it.

Dan describes himself as “a licensed California attorney with a passion for travel", which sounds super interesting, “and for learning the ins-and-outs of credit card and airline award programs", which doesn’t sound super interesting at all, but is actually the reason for this article.

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See Gillaspia’s Instagram ‘uponarriving’ shows snaps of five star suites on Singapore airlines, pictures with penguins in Africa and much, much more – and it’s his, err, “passion" for reading the terms and conditions that have got him there.

So, how did he do it? Firstly, Daniel took out 45 credit cards. Yes, you read that right. And no, that doesn’t bode well for the state of credit lending in the country. And yes, we understand that you’re probably put off this plan already. But just listen to the trip Dan got out of it:

  • LA to Tokyo flight (Singapore business class, on board one of the world’s best business class cabins): Actual Price: $4,444 Dan’s Price: $68
  • Tokyo, InterContinental Tokyo Bay hotel (3 days): Actual Price: $1,000 Dan’s Price: $0
  • Tokyo to Singapore flight (in the famous Singapore Suite): Actual Price: $11,660 Dan’s Price: $108
  • Singapore, Marina Bay Sands Hotel (2 days): Actual Price: $450 Dan’s Price: $0
  • Singapore to Johannesburg flight (Singapore business class): Actual Price: $7,676 Dan’s Price: $0
  • Cape Town, The Westin Cape Town hotel (5 days): Actual Price: $1160 Dan’s Price: $0
  • Johannesburg to Abu Dhabi flight (Etihad business class): Actual Price: $4,040 Dan’s Price: $104
  • Dubai, The W Dubai hotel (3 days): Actual Price: $534 Dan’s Price: $0
  • Abu Dhabi to New York City flight: Actual Price: $18000 Dan’s Price: $104
  • New York, The Ritz-Carlton Hotel: Actual Price: $1900 Dan’s Price: $0

Dan runs a blog which explains how he set himself very careful spending limits so he won’t end up getting eaten by loan sharks 10 years down the line, but he actually had to spend £34,000 on credit cards to rack up the required points.

https://www.instagram.com/p/BK8R8yFggVT/?taken-by=uponarriving

“Cheat!," we hear you shout, as you sharpen your keyboards and prepare to type profanities. But wait! This £34,000 doesn’t have to be spent on anything other than life essentials – food, drink, travel – if you don’t want it to be. You could still live just like you do and rack up the points to travel for free. It just might take fucking ages.

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Dan credits two websites for making all of this possible: The Points Guy and The Frequent Miler. Of course, the points don’t just appear out of thin air, as Dan admits, but as he points out “the return in value for your time and effort can be astronomical".

Daniel’s only £329 actually spent directly on his travels were on the occasional flight. His holiday all in all should have cost £42,000, but actually, it just cost £329, and more time and patience than we, or we imagine anyone else, is prepared to put in.

We’ll probably just stick to being poor and spending all our cash on travel. Hit Dan’s blog at uponarriving.com for much, much more on travel hacking.

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