How to get a great holiday on a cheap budget

Holiday Pirates is a great find for anyone looking for a holiday bargain.How to get a great holiday on a cheap budget

It was first introduced to me by someone I used to work with, he quickly made that evolution from Work Acquaintance to Colleague to Work Mate to Mate to Friend, typically each jump happened while enjoying some golden beverage or aromatic curry. To further up his valued friend status, he introduced me to Holiday Pirates. At first I was hesitant, I thought between Upgraded PointsHead for pointsMomondo and Seat Guru most of my travel optimising needs were being met. But being a fellow explorer of the world, I tend to take his suggestions with more than a little passing feigned interest.

In a nut shell they keep a look out for outstanding deals in terms of flights and holidays (being a single traveller, holidays are not usually of interest as they are per person).

But for all great deals, you are likely to need to take a hit on at least one of the following:

  1. Booking months ahead
  2. Booking last minute
  3. Being flexible with your destination (often a plus with all the choices out there)
  4. Being flexible with departure dates/times (Tuesday is far more likely than a Friday)

In short being flexible is key to finding a great deal.

My personal experience:

As you may know I left the corporate world to follow my passion project of starting Reaching Aspiration to help fast track people to success. As it was self funded, I had at the time a very real need to become far more budget conscious. Although I am originally from South Africa, my immediate family all immigrated to New Zealand. New Zealand! Living in the UK, that is pretty much the furthest spot on the planet and on the way to…well, nowhere really, perhaps the North Island could argue it is on the way to the South Island and the South Island is on the way to Antarctica. With flying via Asia or the US is roughly the same amount of flying time.

So I was on the look out for a budget friendly ticket to New Zealand. Then the world (Holiday Pirates & Thai Airways specifically) gave Dave a little wink by advertising a return flight to Auckland starting from £350. That certainly piqued my interest with, as reasonably timed flights out of season tickets typically ranging from £700-£800. So this was less than HALF.

Steps I took to get the right deal for me:

Step 1 – Check dates & Airline – There were plenty of dates to chose from. I chose dates that roughly worked for me and checked the price, was this one of those starting from £350 but really £650 unless you want to forgo luggage, food, a seat and less than 5 hours connection times. Price check – £352. I also did a quick review of the airline and found no show stopping red flags. In fact generally really good.

Step 2 – Play with itinerary – I was hoping to leave London a week earlier, so I added a stop over in Bangkok to test drive a digital nomad lifestyle. One week should do for a test case. Price check -£355

I also have a mate in Melbourne that I hadn’t seen in far too long. So I added a split trip, land in Melbourne, depart from Auckland, make my own way from Melbourne to Auckland (BA points on Qantas). Price check – £390 (including week stopover in Bangkok)

Step 3 – Confirm accommodation – Family in New Zealand good with the dates. Mate in Melbourne good with the dates and excited. Nervous Price check – £390 six hours later (a life time in terms of deals this good).

Step 4 – Booked for £390 – Checked my seats on Seat Guru to get the best available seats in economy. Locked in a bargain. I then added my comments below the deal and the next day Holiday Pirates were active enough to adjust the deal to show the stopover option (great for breaking up a long trip, seeing somewhere new & usually for the same price, I did a similar thing on a previous trips, for example stopping in Hong Kong, a place that should be on everyone’s bucket list) and split destination (Works because airlines often group by zones rather than specific destinations).

So is it a bargain for all? Perhaps not, but certainly was for me. They have a life long fan and evangelist in me.


  • Be flexible with destinations
  • Check regularly (or use there alert function)
  • Act fast <- These specials and deals move fast. Umm’ing and Aah’ing costs money.
  • For those with inflexible jobs <- make them flexible, fly on a Thursday and then work remotely the first day (Are you at home or in the Caribbean?). Alternatively ask to work a little extra (you are probably doing it already) and then take it in Lieu.



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