Greg’s 40K to Far Away mistakes (yep, he’s already made a few) #40Kfaraway


I’m not excited about our 40K to Far Away Challenge.  “Excited” is too mild a word.  “Obsessed” is more accurate.  Nick, Stephen, and I each have 40,000 points and $400 and a goal: go as far as possible.  For this challenge, we didn’t define “far”.  Do we win by traversing the most miles?  Do we win by visiting the most places?  Do we win by doing the most activities?  We don’t know.  In the end, we’ll summarize each trip and we’ll run a poll to let you decide who won.

This challenge strikes me as being similar to a puzzle, video game, or board game.  Like many games, there are countless strategies and approaches one can take.  Unlike a game, this one has real life consequences.  Whatever we figure out now, we will have to actually do.  It’s one thing to devise a theoretical use for 40,000 points.  It’s quite another to actually travel that route.  And, unlike video games, there’s no reset switch.  Once we’re locked in, that’s it.  We will have to make the most of what we’ve planned.  When things go wrong during travel, we’ll have to figure out a way to cope.

I fully expect things to go wrong during travel.  What I didn’t expect was that I’d make mistakes now.

As a reminder, we plan to unveil the trips segment by segment as we go.  So, I can’t yet reveal what I’ve booked so far.  When writing about my mistakes I have to be coy about the details…

Vague background

While I’ll be traveling to a number of places, I’ve had one key destination in mind.  And I found two good ways to get there:

  • Option 1: Easy.  The easy option involved a single carrier, departed from the city that we will launch from, and included a terrific layover option.   Best of all, the easy option was easily bookable with the points available to me (Chase Ultimate Rewards).
  • Option 2: Cheap, but complicated.  The second option appeared to be cheaper, but it was more complicated.  I would have to position to another city and use multiple carriers to get to my ultimate destination.  Plus, to make this option cheaper, I had to find a way to book a super cheap Norwegian flight despite the fact that the Chase travel portal didn’t offer this price.

The trouble started when…

Last week, I called Chase to see if option 2 was possible.  Was there any way at all that I could use Chase points at 1.5 cents value to book a Norwegian flight that didn’t appear in the Chase travel portal?

As you probably already know, the answer was yes, I could book that cheap flight.  I wrote about it here: How to book the cheapest flights with Chase Ultimate Rewards.

I was so excited about this find that I went ahead and booked it over the phone.  My decision was madeOption 2 (cheap but complicated) was the winner.

Then, more than 24 hours passed by before I realized the mistakes I had made…

Mistake 1: Paying entirely with points

When you pay for travel with Chase points, you have the option to pay partially with points and partially with cash.  In the heat of the moment, I chose to pay entirely with points.  This decision locked me out of some award flight options that I may have otherwise considered.  With most award flights, you don’t have the option to decide how much of the award you’ll pay with points vs. cash (BA and Avianca are two notable exceptions that do often let you choose).  So, for example, if I spent 10,001 points on my flight instead of 10,000 points, that meant that I was left with 29,999 points to work with instead of 30,000.  That could easily be the difference between being able to book an award flight or not.

Luckily this mistake didn’t turn out to be a major issue, but I should have thought it through before jumping in.

Mistake 2: Not checking award fees

Option 2 (the one I went with) results in arriving in my destination continent in a different country than option 1.  Either way, I knew that onward award flights were available for the dates I needed and both involved the same carriers, so I saw those two arrival countries as being somewhat equal (especially since neither requires a visa for a US citizen).

Somehow, even though I had checked award availability, I had failed to notice that option 2 involved much higher award fees.  I now believe that the option 2 country imposes a departure tax which is passed along to award bookings, even by United.

Once I account for this extra award fee and the extra cost (although minor) to position to the departure airport for option 2, it turns out that option 2 is slightly more expensive than option 1!  That’s right, I made my plans significantly more complicated and more expensive by going with the “cheaper” option.  Bah.

Mistake 3: Bad assumptions with option 2B

Once I realized mistake 2, I set about finding ways to correct the issue.  And I found a great one.  Or so I thought.  I found an even cheaper connecting flight to my destination continent.  And this one arrives in a country with cheap departure awards.  This option, which I’ll call 2B, would save me a ton of points and money over option 1!

There was a catch.  The country I would fly into requires an expensive visa.  So I made an assumption:  I assumed that even without a visa I could fly into this country’s airport on a Friday night and depart Saturday morning without leaving the airport.  I wasn’t looking forward to this option as it meant sleeping (or not sleeping) overnight in an airport where the only lounge wasn’t scheduled to open until 3am.  And I’m dubious about it really opening at that time.  But still, the savings would be huge.  I could suck it up for one night.

I worked out the details of option 2B for almost a week.  I was getting ready to book my flights when I realized a couple of potential issues.  I emailed a friend (Stefan Krasowski, AKA Rapid Travel Chai), who I was sure would know the answers:

  1. Is there any chance that they won’t let me board from XXXXX to get to YYYYY because I don’t have a visa for YYYY?
  2. Is there any chance that they won’t let me hang out in the YYYY airport overnight without a visa?
  3. Any other likely gotchas besides being very uncomfortable overnight?

His answers:

  1. Yes, a good chance you won’t be able to board. [He went on to give details which I won’t share because it would reveal part of my journey]
  2. Yes, even if you are staying on the same airline or think you are checked in with a boarding pass, they may still chase you out. [He went on to describe his own experience with this at the same airport. I knew I could count on him to know!]
  3. [I can’t publish any of the third answer since it will reveal part of my journey, but basically the answer was that I definitely don’t want to transition through this country]

OK, so even if Stefan was wrong (which is doubtful), his answers freaked me out enough to completely discard option 2B.

If you ever need answers to questions like these, simply join Stefan’s Facebook group, Every Passport Stamp, and ask there.

Where this leaves me

I’m going forward with option 2.  It is significantly more complicated than option 1 and slightly more expensive, but I’m locked in.  I stupidly waited more than 24 hours after booking the first flight to do the rest of the required research.  Otherwise, I could have cancelled for free.

So, I’m down, but not out.  Not by a long shot.  The added complexity of option 2 may be its saving grace.  It means that I’ll have the chance to visit more places and take more modes of transportation.  And it will require more creativity.  You’ll give me points for that, right?

Don’t forget to check this post for the latest updates regarding our challenge: 40K to Far Away. What’s New?.

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