40K to Far Away… It’s On!

Frequent Miler's 2019 40K to Far Away Challenge is done! Greg, Nick, and Stephen competed to see who could go farthest with 40,000 points and $400! Click here for contest results and next steps.

a collage of a man and a map

This is it… We’re off and away! This morning Nick, Stephen, and I set off on our 40K to Far Away adventures. Any guesses as to where we’ll end up? As I write this, all we know for certain, so far, is the first leg of each journey:

Greg flies United Airlines this morning from Washington Dulles to Lewisburg, West Virginia.  Yes, you’re right, that’s not far at all.  What in the world am I planning?

Stephen will board a Greyhound bus later this afternoon to go from Union Station to Newark airport.  Obviously, it seems to me, Stephen has plans to fly far from Newark.  I have absolutely no idea to where.

Nick flies United Airlines this morning from Washington Dulles to Honolulu, Hawaii (with a brief layover in Chicago).  We all saw this one coming, but it’s an extremely impressive start especially considering that he will have completed this journey to Hawaii for only 7,500 Citi points!

Posting as we go

We plan to post photos and videos as we go, so the trips will unfold in near real time on Instagram and Facebook. We’ll also publish blog posts about our adventures and once a day one of us will publish a summary: Who’s gone where? What wen’t wrong? How hungry are we? Who slept on a park bench?

Destination Hints

We’re each planning to publish hints to our final destinations. These will be found in our Instagram and Facebook stories. Stories are those circles that appear at the top of the app or web page when viewing Facebook or Instagram.  In Instagram or Facebook mobile, look for this:

a man smiling in a circle

In Facebook, via desktop web, look for something like this:

a man taking a selfie

Business Not As Usual

Over the next 10 days or so, this blog will not run “as usual”. Usually, we try to publish one major article every morning. That’s not going to happen. Usually we publish many Quick Deals throughout the day. That’s also not going to happen. Yes, if we notice a smoking deal we’ll publish it if we can, but we can’t promise anything. Each of us will be without internet for extended periods of time while we hop around the globe with only 40,000 points and $400.

Instead of business as usual, most posts will cover our 40K adventures, and new sweet spots or travel tricks that we’ve uncovered along the way.

Stay tuned!

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Parts Unknown

Would anyone be surprised if Stephen rode the Greyhound back to DC?


Safe travel guys, we’ll all be waiting with bated breath!


Finally, you guys are off…excited to see how where you guys go on this accessible budget.


Will Stephen’s burger posted on facebook count in the budget? ^_^

Traci Money

Looks like Nick is off to strong start but looks can be deceiving… #teamstephen


You guys inspired me to show up at the airport today & randomly pick a destination for a coupla days using all points. Godspeed!


Just got back from TLV ($$$) on the 25th went to Masada but no Vineyards but 2 in Crete . I’ll book airfare to Greece (ATH) next month for Sept.. I found no deals to TLV ( Best Beaches Ever) and a Nice safe Place to visit ..


Good for you, CD! I ended up in New Orleans for my 2-day random vacay (literally threw a ball of paper at the Departures Board & wherever it landed!). My Lyft driver into the Garden District had just moved from Tel Aviv, & we were swapping stories. Cannot wait til next Sept when AA starts direct svc from DFW – will be on the first flt! A friend took me to the top of Masada back-when by helicopter, the views & sense of history were palpable.

Let us know how the Greek wine is, safe travels.


Thanks for the post you travel very well . I Love Greece I booked my return trip 9/1>ATH $44 .My friends Don’t travel can u give me any ideas . I hit 3 tiny ports in one day on a Athens cruise and 2 cites in Crete (6 nites) . But I want to do 4 islands by ferry (cheap) then fly to ATH >ORD . What Islands would u recommend to see stuff and stay near the ports then take inland tours ??
Thank You


Thanks, CD, but Greece is still on my bucket list. It has repeatedly been jinxed for me for a myriad of reasons, including periods of civil unrest, but that will make finally going someday that much sweeter I suppose.

I think the islands are overall safer than Athens, so that is where I would head, too. I am not big on cruising, but in this case I would book (maybe with URs with Chase Travel?) a sailing/small ship island journey of as many of the islands as possible.

Sounds like we are on the same page but sorry I have no actual experience to supplement your travel goals. Other readers here certainly might. Let us know how you fare, bon voyage!


Thanks look @ the times on a cruise (been on 16) in port as in No Thanks .I felt very safe there and TLV too.. Look @ the Athens Rivera I was back before I knew what it was HaHa .The cost is HALF of TLV,Rome or Paris great dinners on the beach .That’s why I’m going back a DEAL !!!!


Thx for the info & tips, CD!

Nick Reyes

This is awesome.


GREG: You should have turned the blog over to me for 10 days. It would be renamed The Travel Snob by the time you returned


That picture of Nick is just the greatest. It looks like he’s the driver for The Beverly Hillbillies


Good luck!!!!!!!!!!!!!!!!!