The Ultimate Travel Hacking Guide

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Travel hacking is a hobby. It’s finding insights and/or beating the system to maximise your enjoyment.  We’ve scored discount Business Class flights & errantly priced hotels. We’ve also researched insurance inside out, and so much more.  It’s a hobby I’ve dedicated countless hours to. This blog post, The Ultimate Guide To Discount Travel is my free gift to you. Enjoy!

Types of Deals

Error Fares (Airlines & Hotels)

How to find error fares and cheap flights

The holy grail of bargains, are error fares. Exactly as they sound, this is when an airline or hotel chain simply type the wrong price into their listing.  Usually they catch them quickly, but while it’s listed, it’s free to book.

If you find an error fare, book it immediately. Errors only last a very short period of time. It could be minutes, maybe hours. Don’t miss an error fare, they are what travel hackers live for!

Error fares are honoured 90% of the time. For example, a recent roundtrip Vancouver to Melbourne business class airfare for only $700. The airlines figure it’s better to be talked about in a positive light, than face angry customers.

In the adjascent image, Virgin Australia

The best Flight errors sites are:

  1. Hack The Flight – Hot Deals
  2. Holiday Pirates – Pricing Errors

Hotels also make errors. I find most of my hotel error deals here:

  1. Secret Flying – Hotel Deals
  2. Hack The Flight – Hot Deals

Note: Hack The Flight deals appear in my browser as push notifications. They can be distracting, but for computer addicts like myself, they are a godsend.


Sales & Clearance Deals

Secret FlyingOther times, Airlines & Hotels simply need to clear flights, or promote their brand.  In NewSecret Flying WebsiteYork we scored a $65 deal from NYC to Dublin. The flight was from Norwegian Airlines, promoting their regional airport and bus service.  It was a brilliant experience, worth every penny.
Sale fares are not only discount stock. Around the world fares are also common, including Business Class.  Virgin is famous for ridiculously good business class world fares. Subscribe to their newsletter to be kept in the loop.

Hack The Flight

For those who like to learn, checkout this forum:

Business Class:
Economy Class:

Note: Also keep an eye on Hack The Flight & Secret Flying (subscribe to FB notifications for best results). These guys are the best in the business. For US residents, try The Flight Deal

Australian’s keep an eye on: OzBargain Travel


Skip Leg flights – ITA Matrix

The ITA Matrix is incredibly powerful.  It’s a free software that scans all possible flights showing you the cheapest way to book. If you spend the time to learn how to use it, you can save huge amounts off your travel.

In the above video, I show you how to find skip leg flights. This is when you find a flight that goes through your desired location. Instead of re-boarding the flight, you just get off the plane there.  In the above example, I saved close to 30% off my flight.

There’s only two tricks to this system:

  1.  It’s much easier with carry-on only baggage
  2. Get on the flight early to avoid your bags being checked below

Learning to use ITA Matrix can you save a fortune.  To make it easy, here’s a link to all of the world’s airline codes.

Special Note: Thanks to @thatonethere from the OzBargain community, who pointed out that you need to book Skip Leg flights as one-way fares, as the remainder of the flight is cancelled when you fail to re-board.

Cheapest Day to Fly

When you do find a deal fare, you’ll often have to massage the dates to suit your schedule. Know in advance you will be able to do this, but you’ll need to put in some effort. Not all days are the same, and prices will vary depending on demand.

One trick I love is using Google Flights to scan for the cheapest days to fly. Keep in mind, Google flights is in US dollars (usually) and will often not see the sale fares you find. Use this tool to find the cheapest days to travel the route you are researching.

Google Flights

The above picture shows Google Flights in action. You can quickly scan the prices for every day of the month. This is also great for researching average prices, seasonality and connection flights.

Frequent Flyer Points

Frequent Flyer Points

Contrary to popular belief, you don’t need to own a business to earn millions of frequent flyer points. In fact, if you earn $45k per year, you have more than enough to make it rain points. The trick to point usage is making sure you spend them on upgrades. Once you factor in taxes, upgrade flights net you a much higher rate of return. Find out more here: Point Hacker

How do you make points?
There’s lots of ways to score a handful of points. Things like your shopping flyer cards will bring in a little each year.  However, there is one way that all point hackers swear by:  credit cards.

Taking advantage of the credit card signup deals can net you 500,000 or even a 1,000,000 points per year. Simply follow one of the many sites that outlines credit card details, and signup to the best value ones.  In many instances, they waive the first year fee.  Simply signup, meet their purchase goal (eg. $1,000 in the first 3 months), and then cancel the card. It’s easy!

Most point hackers will signup to the same credit card every 12 to 24 months, depending on the T&C of that company.

Contrary to popular belief, having multiple credit cards does not damage your credit rating. In fact some studies have shown it increases it. What you want to ensure, is you always pay it off in time.

Best credit card deal sites:

  1. Point Hacks
  2. The Points Guy
  3. OzBargain (Australians only)

Pay someone else to do it all

You might also want to consider a service like ‘I Fly Flat‘.  I’ve talked to their CEO, Steve Hui. His business is based around making point saving easy for you. Their team also helps plan your future trips. So if you know you need to get to a specific location, they will set you up with a plan to save the points for the right airline. They also help you book the fare!

Rent an Airline Ticket (when you don’t have a plan)


Bare with me here, this one is unusual.  Sometimes you enter a country without a plan to leave. The problem here, is that most countries require you to have an exit date and a flight booked.  Now you can buy a full refundable ticket, but as I found out first hand, it’s not always quick or easy to get these refunded.

The solution is a system called FlyOnwards. For $10, these guys buy your onward flight for you, and rent you the service for 48 hours.  They they get then refund themselves, saving you the hassle and cash flow.

The cool thing is, the tickets are 100% real.  You can go online and check.  When you get to customs, you present the paperwork and thy let you in.  Easy as that!

Myths about discount deals

There’s a lot of disbelief around travel hacking. Let me assure you, it’s all myth.  A ticket is a ticket, there’s nothing past that.  Below I’ve covered a few of the objections (myths) I hear often.

    1. They will give me crappy seats
      Absolutely false. The person working the desk doesn’t know what you paid, only that you have a valid booking.  Sure, if you book a discount airline, don’t expect silver service.  You will be treated like every other customer.
    2. They will cancel last minute on me
      Once the airline issues your tickets, you are golden.  This is when you know you are set. Once the ticket arrives, it’s yours to keep.
    3. I won’t get the frequent flyer points
      Once you have the ticket, check the airfare class. This tells you how they grade your flight, and if you get 50%, 100%, 200% or 300% worth of miles.  Each airline is different, but a quick Google and you’ll work it out.
    4. Return Flights are always cheaper
      This certainly used to be true. Now computer price modelling has taken over the airlines, there’s many more bargain one-way fares.  While not as common, always checkout one-way flights just to be sure.

Myth Summary
In my experience the people that put up the most objections, are the people who put in the least effort.  By very nature of you reading this, you’re ahead of the pack. Please leave a comment about any deals you score. Show them how easy it is.


Skills &Technology you need


    1. Patience. Patience. Patience
      Pricing specials don’t miraculously appear when you ask for them. You have to start looking ahead of time, and be patient enough to let them materialise. In 2017 we flew an 11 leg flight for under $1,000*.  This took me over 3 months of searching to piece together. Be prepared to look daily for a while.*11 leg flight: Cancun, Vancouver, New York, Dublin, Munich, Zurich, St Remy, Malaga, Barcelona, Lisbon, Toronto
    2. Know your goals & your prices
      If you spend just 5 minutes every day studying deals, you’ll soon learn what is a good, great and incredible deal.  You’ll also know when to act.  I recommend you write a bucket list of places to visit, and your availability therein. When a deal comes up, pounce like a tiger.
    3. Have you passport & credit card details on you always
      When a sale fare arises, you may have mere minutes to book it. Always have access to both your details, and that of likely travel partners. I strongly recommend buying the password and detail keeper “1password“. This handy iPhone & Desktop app saves you time and money by storing your personal details, website logins, memberships and credit cards all in one secure place.
    4. TripIt app
      Easily the best travel app, and it’s FREE.  Tripit allows you to store all your booking information in one place. Recommended to all travellers. View Trip It here
    5. Noise Cancelling Headphones
      Spend good money on good headphones.  I strongly recommend the Bose QuietComfort 25s. I own these myself, and they make flying a dream.  They block out all the outside engine noise, leaving you alone to your thoughts… or some sweet tunes.
    6. High quality VPN
      Most people don’t understand how valuable a VPN is.  It allows you to hide your location and pretend to be anywhere in the world.  I’ll write a full section on this below, but make sure you checkout this post: VPN Guide & Deal
    7. Uber & AirBNB
      If you aren’t using these two tools, have you been living under a rock?  Simply the cheapest and best way to travel.  Uber in particular ensures you won’t be ripped off by greedy Taxis.  AirBNB cuts the cost of hotels, and usually provides much more value.  If you don’t have them already use my referral links:
      – AirBNB Signup Here
      – Uber Signup Here
    8. A curious mind
      Finally, keep an open mind. Many people are too ‘A to B’ oriented. Open your mind and consider a longer flight path, and you’ll find a world of opportunity. At the time of writing this I could buy a flight from NYC to Melbourne (Australia) for around $1,500. Alternatively, I could fly NYC to Bangkok for $600 + $200 to Melbourne.  This flight not only gives me a nice stop in BKK, but also goes through Shanghai on the way home, allowing for a quick stopover to explore.

Why You Need a VPN

Virtual Private Networks are totally misunderstood, and 100% required for your travel.  To understand it, in one click you can encrypt and hide your digital footprint.  This allows you two major advantages:

  1. It makes using public WIFI safe. Particularly for banking or sensitive data you might be accessing.
  2. Piracy.  Yes, I know this is a grey area, but if you do pirate, do so safely.  A VPN hides your identity. Do it.
  3. Access to country specific content. I love US talk shows, which are often geo-blocked.  With one click, I can pretend to be in the USA and access all that sweet content.
  4. Sneaky plane WIFI trick. I do a lot of flying, and nowadays WIFI on flights is getting pretty good.  If you use your VPN, you can get around their protection systems, and access high bandwidth content like Netflix.
  5. Cuba & China. Both countries use an internet filter that stop you accessing basic tools like Skype. Having been trapped there without any access to funds, I can tell you, a VPN saved my life.  Using it, I could access Skype and call home for help.

Don’t hesitate.  For $30 per year (using this special deal), you will have a great VPN on your desktop, mobile and partners’s devices.  Just follow this link for the special deal -> Special 50% off discount deal

Haggling on AirBNB

AirBNB Haggle 2

AirBNB has revolutionised travel, allowing you to access beautiful properties, and paying less than a hotel.  Plus, for savvy travellers, there’s a chance to save even more money and score ridiculous deals.

Unlike the sophisticated hotel industry, AirBNB hosts tend to have no idea when it comes to pricing.  As such, there’s a few ways to score great deals.

  1. Search for new listings
    Often when listing for the first time, new users will list their property miles below it’s true value.  We’ve scored crazy deals in apartments worth hundreds per night, paying only $50. The key is to look every day, twice a day.  When the new listing goes up, jump on it!
  2. Search Midweek start dates
    AirBNB hosts are using pricing software more and more.  This means every day of the week will be priced differently.  If you can’t find the right property for the exact dates you want, consider staying nearby for a couple days over the weekend, and then renting your perfect property midweek and onwards.To be clear, I’m not suggesting you change accommodation constantly. What you often find, is AirBNB hosts take bookings for the weekend, but struggle to move it on the weekdays.  We often find, adjusting our dates slightly, can open up a lot more accommodation options.
  3. Haggle on the price
    AirBNB owners want the money, and psychologically are more scared of missing a sale, then they are excited of receiving one.  Use this to your advantage.  I send the same note to prospective AirBNBs, asking nicely for a discount. I use copywriting and negotiation best practices, and as a result have saved a fortune.  There’s two key tips here:

A. Never round your numbers

It has been studied in business classes around the world, when you suggest a round number, people don’t believe you.  Offer a price like $51 per night, and it seems well considered and thought out.  You will always have a higher strike rate.

B. Offer Value

Don’t just ask for a discount like a bum, prove you are worth it.  You want them to feel like you are the perfect tenant, and that discounting their price is worth it, because you will look after everything well.

Example haggling template

Hi ___,

We love the look of your property, what a beautiful place!

My girlfriend and I will be in ______ for __ weeks, and would love to rent it.  Unfortunately, coming to the end of our travels, we are running low on funds, and it’s just a little bit outside our allocated budget.

I realise asking for a discount puts you out, but I want to assure you, we are the perfect guests. We are very quiet, super respectful people.  We will mostly be out exploring the stunning city architecture  and exploring the cities cafes.  You can see our over 100 positive reviews in our account.

I’ve crunched the numbers, and we could afford $51 per night, for a total AUD$XX for the __ day period.  If you could agree to this, we would be extremely grateful, and promise to treat your apartment like our own.

We looking forward to hearing from you,

Joshua & Tuscany

Insurance for Australian’s

This is a MUST have. No questions asked. A decade ago, it saved my friend Kelvin’s life. We were celebrating in a 2nd level bar in Vietnam. Kelvin tripped out the window (don’t ask) and fell face first onto the concrete below.  It required emergency hospitalisation, business class airfares & 3 rounds of reconstructive surgery to fix him. Insurance covered it all.

In recent times, I’ve cut my leg open paddle boarding. Smashed my laptop & iPhone. Had bags stollen, and visited the doctor. All of these have been covered in full by my travel insurance. As I said at the start, this is a must have.

Best Travel Insurance for Australians & Kiwis
Without doubt, the best and cheapest coverage is from Southern Cross Travel Insurance (SCTI). I’ve researched this extensively, and they always come out on top.  Their service is A grade, and they payout super quickly with a minimum of fuss.

Score a 15% discount with SCTI by signing up for their newsletter and watching for promotions. I’ve calculated they run their special roughly once every 3 months. Also keep an eye on OzBargains – SCTI section.


Travelling More Than 12 Months
World Nomads
If you are travelling for more than a year without returning home, then you’ll need World Nomads.  Look through the discount sites and you’ll find yourself a coupon. They will still be more expensive, and their coverage is not as good as SCTI, but they do cater to nomad travellers like me.


Credit Card Insurance
If you have a good credit card (see point hacking section), then you may already be sufficiently covered for short trips away.  Usually less than 3 months is covered with a very high level of cover.

Make sure you read the fine print, and make all your travel bookings through the same card. I also recommend you call them and triple check before you leave.  If something goes wrong, you want to know who to contact and how to claim.

Credit Cards & Debit Cards for Travel (Fee Free)

It costs a fortune to use your debit or credit card overseas.  You may not see it, but your bank is converting into local currency at an very unfavourable rate.  You usually lose around 5% per transaction, and often there are withdrawal fees on top.  Travellers Cash Cards are even worse.  Even the best ones like Qantas Cash are ripping you off.  So what should you get?


28 Degrees Credit Card

28 Degrees Travel credit Card

Made specifically for travel.  This card is free (no annual fee), and converts into local currency at the market spot rate.  They literally don’t charge you anything!

The only costs you ensure are $2.50 fee if you clear your card early using BPAY. However you can avoid this by setting up direct debit to pay off the card on the due date.

Full review here


  • No annual fee
  • Swaps currency at spot rate
  • Works with Apple Pay


  • Paying your bill costs $2.50 if using BPAY
  • No frequent flyer points
  • Interest rates on unpaid fee circa 21%

This card is a must have.  Unless you really want the frequent flyer points, you simply must have this card. I have used mine for years and have everyone I know on it. You can apply here


Citibank plus bank account & debit card

Citibank plus travel cardATM fees also cost a fortune overseas. There is often a machine fee, plus they gouge you on the international transfer fee.  Enter Citibank. This daily account provides you with an international debit card that is FEE FREE.  That’s right, you get the spot rate and pay nothing else.  It’s incredible.

There’s no need to do a pro/con list here. It’s simply a must have.  I’ve had multiple people verify this, and use it myself for years. Citibank is the gold standard for debit cards and travel accounts.  You can apply here


Transferwise’s Borderless Bank Account

Special Bonus signup deal – Use this link and receive first $500 transfer

For travellers and business people alike, the new Transferwise Borderless Bank accounts are a game changer.  Particularly if you plan to receive or send money overseas. I can tell you personally, not being able to send a friend $20, or getting killed on fees when receiving payment is a killer!

Transferwise Borderless Bank Account

The account has

  • No setup fees,
  • No monthly fees,
  • No international receiving fees
  • No exchange rate markups

If you use PayPal, this will save you at least 5% per transaction

Apply here and receive your first $500 transfer free


Life is meant to be enjoyed. Read my other article about how travel hacking across the world changed my life. I found my paradise in the Caribbean, who knows what it will bring you. I encourage you to open your eyes, see the world, and experience everything life has to offer.

At the very very least, download 1password and store your details in it.  Then setup accounts with the 3 credit card / bank account providers I mentioned above. When you do choose to travel, you will be prepared.

If you liked these tips, please share this blog on your social media. I also encourage any feedback or recommendations. This article will continually be updated, but I need your help!

Travel well friends.


Never afraid to swim against the tide. I believe in questioning the norm, and finding new, more efficient solutions to problems. Don't accept a life that is average, chase your dreams and be the person you aspire to be.

5 comments On The Ultimate Travel Hacking Guide

  • Pingback: How I Found A Better Life Travelling ()

  • Hey Josh, great guide! In regards to error fares, I personally subscribe to a paid service from there’s a free version as well but the paid one gets you the deals first (time is of the essence with these things). You can select the departure cities of interest and Scott’s team send you deals and error fares for those. (ps. I have no affiliation with them, just thought it might be useful)

    Manny –

    • Hey Manny,

      Thanks for the comment. I also subscribe to Scotts Cheap Flights, although so far I haven’t found much value from it. I’ll be interested to see if this changes, but thus far I’ve been emailed deals with overstated comparison value, or error fares I saw on Hack The Flight first.

      Have you had better experience with them?


      • Hey Josh, I’m generally on the lookout for business class error fares so in that aspect Scott’s list is a bit poor, I have had 2 notifications so far. But i figured that for the price, it might be worth it even if it means I managed to secure 1 flight thanks to it. I agree that most of it they’re sending aren’t exactly error fares but still handy to see what sales are on.

        • Yep, you are right. I also signed up for $50 on the same principle. Plus, I shouldn’t sell them completely short. I’ve just booked a trip to Cuba because of their email. It turned out a found a better deal than the one they advertised, but I wouldn’t have looked if it hadn’t been for their email… so I’m already in the black with them 🙂

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About Joshua Strawczynski

About Joshua Strawczynski

Joshua is obsessed with efficiency. He tests and trials different ideas and technologies to share them with you!

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