10 reasons to vote for Greg for #40KFarAway

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.

two men holding cups and sitting on a bench

Now that the Frequent Miler team has completed the 40K to Far Away Challenge, we will soon publish a poll to let readers decide who won.  With that poll, we’ll publish summary results: where did we go, what did we do, how much did we spend, etc.  But lists and statistics only tell part of the story.  To really understand our accomplishments, I think it is best to hear from each of us why our trips were so special.  For that reason, we are each publishing our own plea: the reasons to vote for me.

And, without further ado, here are the top 10 reasons to vote for me (Greg):

I went crazy far

a map of the world with red lines
Image courtesy of Great Circle Mapper

Sure, Nick technically went a bit farther, but come-on, South Africa is far.  The Seychelles are far.  Traversing the three furthest reaches of Africa is, by any definition, far.

I previously posted that I could have easily built a trip that covered 35,000 miles by nesting multiple cheap round trip flights, but it would have been a sucky boring trip.  I opted instead to go far (just not as far) to awesome places and to build an awesome trip.

I used points in creative ways

a man with a beard and a beard with a beard and a beard with a beard and a beard

Do you remember my Ultimate Rewards Battle Plans post?  There I detailed the advantages I’d have over Nick and Stephen thanks to being assigned Ultimate Rewards points (hey, they picked the other currencies, not me).  One of those advantages is the ability to transfer points to United.  And while United is low on sweet spot awards at the moment, they have one killer option: Excursionist Awards.  It’s hard to wrap one’s mind around what these Excursionist Awards are, but suffice to say that they provide a way to get a free one-way flight when you pay miles for a one-way flight before and another flight afterwards, and bundle it all into a single “round trip” award.  The primary rules are that the “before” flight must begin in the same region that the “after” flight ends, and the free flight must be in a different region.

In order to make the most of this Excursionist Award benefit, I had to find the cheapest possible “before” and “after” award flights so that the excursion flight would be a true bargain.  Towards that end, I found that flights within Japan are just 5K one-way.  I also found out how to find 5K awards within the US.  The latter was key to my making my plan work.

Next I looked for qualifying regions where I could use the free one-way to maximum advantage.  I created maps to help visualize each United Region.  With those maps, it quickly became clear that traversing Africa would be my best use of a free excursion flight.  United usually charges 17.5K one-way within central and southern Africa.  By embedding the flight within a 10K round-trip award, I saved 7,500 points.

Of course, if one excursionist flight is good, then two are better, right?  Yep.  So, I booked two 10K awards for a total savings of 15,000 points.  With the first award I flew all the way from the north-westernmost point of Africa (Dakar) to the southernmost country in Africa (South Africa).  With the second award I flew all the way from southernmost South Africa to the farthest reaches of Africa to the north-east: the Seychelles.  And who doesn’t want to go to the Seychelles?

a beach with palm trees and a boat in the water
The Seychelles was a great place to relax after my big journey!

I pushed my points to the limits

retention call

In addition to the creative use of United miles described above, I was determined to get the most out of my remaining Ultimate Rewards points.  Since I have the Sapphire Reserve card, I can use points for 1.5 cents each towards travel as long as that travel is booked through Chase. On two occasions I ran into major obstacles doing so.

The first obstacle was when I found a $140 Norwegian flight from NYC to Madrid.  Chase’s travel portal showed a price of around $190.  The difference was that Chase was showing the “LowFare+” price (note the plus) whereas I wanted to book the “LowFare” price which didn’t include food or a checked bag.  So, I called and persisted when told no, and was finally successful in booking the price I wanted with points at 1.5 cents per point value.  See: How to book the cheapest flights with Chase Ultimate Rewards.

My next obstacle came when I wanted to book a rental car at the Johannesburg airport to be later dropped off the same day at the Johannesburg train station.  This proved to be a double obstacle.  The first issue was that Chase’s travel portal didn’t show any cars available in Johannesburg either at the airport or otherwise.  The second obstacle was that even competing travel portals didn’t show Park Station as a valid drop off location.  Anyway, I persisted like crazy and was ultimately successful in overcoming both obstacles.  For a full account, please see:  Ultimate Rewards: How to book with points despite online limitations.

I had amazing experiences

two men holding cups and sitting on a bench

At every stop on my journey I had terrific experiences.  I think that the videos I created do a great job of showing many of the highlights.  If you only watch one, watch the Johannesburg video.  Really.  Do it.  Others worth watching: Train from Johannesburg to Cape Town, and Cape Town Wine Tasting and Penguins.

For those who prefer to read rather than watch, here’s a written list of highlights:

  • Library of Congress in DC: I thoroughly enjoyed my first ever visit to this amazing historic building.  I was lucky too that I happened to visit on Mahatma Gandhi’s 150th birthday since the library offered a fascinating one-day-only Gandhi exhibit.  The exhibit was more relevant to me than usual in that I knew I would soon be in the country were Gandhi first campaigned for civil rights (South Africa).
    a large building with columns and a tiled floora sign next to a door
  • Madrid Self-Tour: I fell in love with Madrid during my brief visit.  I walked all over (maybe not as far as Stephen, but still quite far) and also enjoyed riding the clean and efficient metro.
    a building with towers and lights at nighta stone structure with lights at night
  • A traditional Senegalese meal: We sat around a small table and ate directly from a single shared dish.  The meal was delicious and the company was terrific.
    a group of people sitting at a table with food
  • Sunrise chef-prepared breakfast: Chef Bjarne prepared a picnic breakfast which we ate at sunrise atop Northcliff Hill overlooking Johannesburg.
    a couple of men kneeling on a bench
  • Rosebank Sunday Market: The market happened to be celebrating their 6th birthday.  We toured the market with the market-owner, tasted authentic South African foods, and spent time talking to and learning from African artisans.
    a man with his arm around another man

I made real connections

a man in a white shirt cutting food in a kitchen

When I think about great travel experiences, sometimes the beauty of the destination stands out (hello Swiss Alps!), and sometimes exciting experiences come to mind (like the time a baby whale was playing tirelessly in a small inlet in Maui).  Most satisfying, though, are the interpersonal connections.  That is, travel is most fun and memorable when I make new friends (or reconnect with existing friends).

In Madrid, I had time to get to know my CouchSurfing host José as we talked before, during, and after dinner.  Will I ever see him again?  I don’t know, but I’ll certainly message him when I visit Madrid again.  Hopefully he’ll let me buy him dinner.

In Dakar, I got to know Penelope as we talked during and after our shared meal.  She is from Canada and is pursuing her MBA.  She likes living in Dakar, but she seems ready to move on to the next stage of her life.  Will I ever see Penelope again? In person? I have no idea. On Facebook, I feel like we’re already staying in touch.

In Johannesburg, I spent a solid 6 hours with Chef Bjarne and now count him as a true friend.  I’m now determined to figure out how Bjarne can earn frequent flyer miles in South Africa (it’s not as easy there as in the US) so that he and his husband can fly first class suites (like I did recently).  I know they’ll love every second of it.  And hopefully I’ll have a chance to show him around Ann Arbor or to meet him in a big city when he next visits the US.

On the train to Cape Town I made a number of friends.  Most live in South Africa, but one couple is from Indiana.  I invited them to visit me in Ann Arbor.  And with others I’m in contact via email.

a group of men sitting at a table a group of people sitting at a table

In Cape Town I reconnected with an old friend and, for the first time, got to know her husband — a great guy.  I only got to spend a short time with her 7 year old son, but it was enough to bond over Minecraft discussions (thanks to my son for having been a Minecraft addict for several years).

I ate well

a group of people sitting at a table with food

Thanks to my new friends José, Penelope, and Bjarne; and to the Rosebank Sunday Market; and to my friend in Cape Town, I had the opportunity to eat local dishes from each of my destinations (and to drink local wine in Cape Town).

Even though I never left the airport in Ethiopia, I ate well there too.  The Star Gold lounge was a complete dump except for one redeeming feature: the Ethiopian food was excellent.

I slept well

a bed with a canopy over it
My bed in Dakar

I slept in beds in 4 of the 7 nights of my trip. For three of those nights, thanks go to José who’s couch was made up with sheets and a pillow and was more comfortable than most beds (plus it was in a separate room with a door); and to Penelope who provided me with a beautiful private room with en-suite bath; and to my friend Kate who provided me with a complete guest room.  The other night in a bed was on the train from Johannesburg to Cape Town.  Despite having brought my own bedding on the train, I was very comfortable!

On the other 3 nights I slept sitting up, on airplanes, in economy.  I have Ambien to thank for getting good sleep on those nights.

I enhanced my experience through status matching

United offers a free status challenge for those with elite status with certain other airlines (found here).  I knew that I would be flying Star Alliance for most of my trip, so I figured that it would be helpful to have meaningful status.  I requested a match/challenge from Delta Diamond status and was granted 90 days of United’s near-top-tier 1K status.  This gave me the ability to change and cancel awards for free, free access to Star Gold lounges when travelling internationally, priority security lanes and boarding, and more.

a group of people sitting in a room
Star Gold lounge at Addis Ababa airport (ADD).  Yes it was crowded, but the food was very good.

The ability to go to the shorter lines when flying Ethiopian and South African was very nice, but the key killer benefit for me during this trip was Star Gold lounge access. In the Addis Ababa airport (ADD) this benefit was huge.  There are no Priority Pass lounges at ADD and my itinerary had me laying over there twice (once on the way to Johannesburg and once on the way to the Seychelles).  Thanks to my borrowed elite status, I was able to get into the Star Gold lounge and eat very well… for free.

I went outside my comfort zone

a man standing on a couch

I’ve known about CouchSurfing for years, but I never thought I’d actually do it.  CouchSurfing is a website/community where people basically let each other sleep on their couches or spare beds, for free.  There is a bit of a “pay it forward” aspect to all of this, but I think that many hosts do it primarily because they enjoy it.  They enjoy making new friends and showing them around the home town that they’re proud of.

Once I scheduled the bulk of my travel, I realized that I had almost no money at all left for lodging.  This was largely due to the fact that award taxes coming out of Senegal are very high.  I wrote about this dilemma (without mentioning Senegal by name) in this post: Greg’s 40K to Far Away mistakes.

So, with my cash budget shot and all points spent, I had to turn to CouchSurfing.  Luckily, any fears I had going in were quickly extinguished.  I found that it was easy to search for hosts who spoke English, offered a private room, and banned smoking; and to select only those with many positive references.

I quickly received a few hosting offers in Dakar, but Madrid proved to be a much harder nut to crack.  I relaxed my criteria.  OK, I don’t need a private room…  Still nothing?  OK, I can live with second hand smoke for one night…  Hello?  Maybe I’ll be less picky about the number of references…  Still nothing?

It turns out that there’s intense competition for free lodging in popular cities like Madrid (seems obvious in retrospect!).  So I planned instead to find a cheap midnight movie where I’d pretend I was on an airplane: pop an Ambien, put on eye-shades and earplugs, and call it a night.

Fortunately for me, José came to my rescue with a last minute hosting offer (and when I say last minute, I mean I was already in Madrid starting to look up movie times).

I stayed within budget

I detailed all of my spend here: How Greg toured Madrid & Africa for 40K points and $400.  The net result was that I spent a total of $397.08.  With that spend, I earned 811 Ultimate Rewards points which credited to my account early enough to use for the challenge.  I spent all 40,000 of my budgeted points plus 811 points earned from my credit card spend.

In other words, I used every scrap of my budget except for $2.92.  And with that meager budget, I enjoyed an amazing trip.

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Nick visited Auckland, NZ  but no LOTR movie location visits (tsk, tsk) but I am truly impressed how he travels with all his hats – I struggle traveling with those style hats -but I wear them as well.  We are planning on riding the train from Wellington to Auckland next year and hitting Hobbition and a few other LOTR sites.  Almost got my vote.

Stephens trip reminded me too much of backpacker trips of the 20th century, truly impressive with the breadth and width of what he did with his miles and money,  but more walking and trolls than I care for (I get my troll fill whenever I visit Reddit, lol). Yet I enjoyed his creative money creation and staying under budget. Almost got my vote but just to frugal for an European visit; now if it was M.E., Africa or Asia then we have a contest.

…For the Win:

Staging to return Via Etihad First Apartments- I would have voted for anybody that relaxed on return after the end of the contest traveling in a Eithad 1st Apt for 80K AA ( that wasn’t a short flight).

So Kudos finishing in the Seychelles to return home via Etihad First Apartments for 80K AA -You win -we used 80K AS miles for F seats on BAs A380 -JNB – LHR ($590 fuel surcharge) but F rest of the way LHR to PDX.  I think you got the better Hard/Soft product on Eithad.

Win also, since we are spending 16 days this December to visit SA, we’re touring the Mother city (CPT) and region for almost a week – renting a car for 4 days for Safari north of Jozie – then 3 day urban weekend staying in Melrose Arch (Suburb of Jozie)  using up the last of our  SPG biz SUBs from 2018 on our Hotel stays while in ZA.  Planning on visting the Rosebank sunday market and apartheid museum while in Joburg 

RE: Train ride
Premier Classe train was awfully tempting to spend a day traveling the SA countryside on a luxury train ride – but in the end we booked seats on BA JNB-CPT-JNB  (for AS miles of course).  Since DW has finite amount of PTO for 2019. Makes me glad now that we booked travel via air- as all it takes is one train to breakdown to have an issue.

[…] 10 reasons to vote for Greg for #40KFarAway […]

[…] I used my points creatively and pushed them to their limits. Within the budget I traversed the African continent twice and was the only one to travel long distance by a mode of transport other than plane. I had amazing experiences and made new friends. I ate well and slept well. I truly enjoyed touring Madrid and Africa, and ending up in the Seychelles was awesome. For more, see: 10 reasons to vote for Greg. […]

Is Europe Far Away?

I don’t see the case for Steven’s trip at all. Regarding $ vs. Points, Converting MR to cash is better for a cheap europe destination trip or “sorry, but I could find know good uses of MR points conversion”… Really???

Time to call BS.
Amex MR offered a 40% points bonus for British and Iberia transfers; an offer they run this offer like clockwork for the last how many years at the same time (so if you researched you would know it was coming). You can fly to MAD from a host of cities on the east coast for 17k + $73 — that’s 13k with the transfer bonus. He’d still have 27k MR and and $327 to do whatever; e.g. another IB fight out of MAD to South America, Africa, China or Japan or a host of other places and still have MR and $$ left over.

Or if not demonstrating a use of flight points that, what about a Hilton night for 2.5K MR– there are still a few 5k Hiltons left and you can transfer 1MR for 2HH. There are many, many more cool frugal MR point opportunities then these and only wish he could have demonstrated one or more.

Lastly, does anyone really consider travelling to Western Europe “Far Away”; because that’s as far as he got (and they’d written previously that getting home was not the objective, so why is this now even being considered). and if you want to know how to get there on the cheap, then you can subscribe to Scott’s Cheap Flights newsletter and if slumming around Euope on the cheap is your interest then there’s a bunch of backpacker blogs that do that really well. Me? I thought this blog was for miles and points and that writers here would instruct of good, creative uses and if I can find them, then why can’t someone who writes here?


Loved following this. Awesome itinerary, with equally great experiences. Hard to beat. Congrats on a great competition.


Greg wins this for me, but with some reservations. I wish he hadn’t relied so much on Couchsurfing and free meals from friends, but in the end he had a fantastic trip and showed how some of these services can be enjoyed and valued, so that’s a plus. Great job Greg! Nick probably would have won in my book if he hadn’t gone so far over the budget, because it seemed like the most enjoyable trip. Stephen’s trip was impressive too, but some of his decision making was questionable (sleeping in a rental car instead of choosing a hostel downtown in the city center) and his challenge seemed more like “$950 and Far Away” instead of “40K and Far Away”.

Overall, this whole series was very, very enjoyable and gave some great point-using strategies, and I hope you guys do something similar in the future! Maybe combine your strategies into a joint trip for you all and your families?


“Far away” was specifically defined as not necessarily distance. Greg and Stephen are both in the running. Nick was DQ d by his overspend. I am impressed that Stephen got there and back on his budget. I want to read his case for a vote but i definitely lean in his direction.

Marriott Marty

As the goal was to go the farthest (within budget) with the other factors less important, you are the winner. The ex we use was fascinating though and all should be proud. Perhaps next time the factors should be given equal weight. Of course for a Miles and points community the use of miles and money for travel Is the focus. No need to count housing next time unless you have a contest for the best cheapest commercial places to sleep. To all well done


Although this one-way trip was definitely a work of art (and perseverance), I cannot accept the premise of spending as little as possible to go as far as possible only to rely on the crutch of having unlimited resources for the return trip. Sorry, even though this was designed to be a one-way contest, this stark contradiction just rubs me the wrong way. Thus, my vote is going to Stephen.


So because you dislike the contest they created, you won’t vote for the people who followed the rules that they created? If you don’t like the contest, why did you even follow along? I’ll never understand this type of thinking.


Darn right, Lisa! As a follower, and per the rules, I get to vote any way I want using the criteria of my choice. And for the reason that I stated, my vote goes to Stephen.

But I will also say that I really appreciated all the work these guys did to put together their trips, and I’d vote for each of them over that copycat exercise at TPG in which all 3 contestants went to BKK and back without spending any time visiting the destination.


Other people essentially provided much of your food & some lodging for you, albeit a legit free “service.” I don’t see much difference between that & hopping around to different friend’s homes. Still, your itinerary was well-structured, more interesting, & overall a happier feel than Nick & Stephen’s + you met all initial criteria. Congratulations on a trip well done!


I think I had heard of couchsurfing.com previously, but had forgotten about it. Having read Greg’s experience, I would definitely consider it. Traveling solo (without wife/kids) I might give it a go … though I am not in a great position to reciprocate on the other end (no real couch, and our spare bedroom is in use by a foreign exchange student). I have a conference to attend in Vegas next March and I am now considering a couch surfing side trip to southern Utah to visit Zion again (or something similar). Sounds like a perfect way to visit many places on a shoe-string budget, which is what this contest was all about.


Nick clearly cannot win since his blew the budget. Stephen did great, but his lack of being able to very far hinders him even though he did some really cool stuff. I agree, Greg is hands down the winner.

I know you guys talked about doing a biz/F type challenge…….but I have to admit, I may enjoy another 40K to far away with each having to use different currencies.

Janet Weiden

I can’t vote because I’m your Mom. Nevertheless I am so impressed with how interesting you made your trip. IMO you are amazing. To be fair, I think Nick and Stephen made you proud to have them on board with you. Both created terrific trips. Congratulations to the 3 of you.

Tom Mackay

Greg I think you abused the “free food from friends doesn’t count” option. I think you need to account for more of your meals. Nick has my vote


Yes, I also feel the “pay it forward” idea puts somewhat of a liability on the books. Like paying for a hotel room/meal with a credit card but since not owed back during the contest period isn’t counted as a cost!

I think Greg should ideally have assigned some kind of value to the couchsurfing freebies & then deducted that from the $400 allotted for parity.


Great job, great read…but Nick always lends such a rakish air to a story…hmm…


Greg wins because he owns the blog and anything else would result in the firing of the winner. Do you guys really want to be responsible for someone being fired?


Seems like a slam dunk win for Greg to me. Unforuntately, while this contest was really interesting, it was difficult to follow via the posts on the website and facebook. While it was interesting, it had a lot more potential to be more but was hard to follow.

Regarding my vote, Stephen ended up back in Virginia after spending some time meandering around Europe. Ending back up in Virginia just seems like poor planning for a “FarAway” journey. Definitely not worthy of the “FarAway” challenge. He also did not show any creativity to use of the Amex rewards points. Simply reserving them for dollars is boring and did not provide a learning opportunity for readers.

Nick went a long distance and provided some useful information for redemptions, but totally blew the budget, Definitely not deserving of the win.

Besides going a respectable distance and ending in a far away place, Greg showed us the real value of points and creativity with the United excursionist awards. My only wish is that he had spent a bit of time in Lewisburg, WV instead of just turning around for the return trip. Seems like a waste of a trip just to step off the aircraft, go through security and reboard the same plane. It would have been so much more interesting if you had spent the day in WV.


Ding ding! We have a winner.