Reminiscing my 40K to Far Away (On Greg’s Mind)


While planning my strategy for the Frequent Miler team’s new 3 Cards 3 Continents challenge, I became more and more nostalgic about my trip from the previous big challenge: 40K to Far Away.  In that 2019 challenge Nick, Stephen, and I competed to see who could build the biggest one-way trip out of 40,000 points and $400.  I ended up in the Seychelles, which was cool (or, errr…, quite warm actually), but it was the journey and the people I met along the way that made the trip fantastic.  I’ve never before recounted my story from beginning to end, but if you’ll indulge me, I’ll do so now…

a map of the world with red lines

Rapid Summary

On the first day of my adventure, I flew to West Virginia and back, did a tour of the Library of Congress in D.C., Megabused to NYC where I met up briefly with a friend, and then I flew to Madrid, Spain.

In Madrid, I refreshed at a WeWork office and self-toured the city.  Madrid was the one stop where I had no plan for where to sleep.  Fortunately, I was saved by José after a list minute CouchSurfing plea.  He fed me an authentic Spanish meal and I slept very comfortably on his couch.

The next day, I flew to Dakar, Sengal.  There, I shared an authentic Senegalese dish with my CouchSurfing host and a couple of others.  Next, I toured Ngor Island before returning to my private bedroom room for the night.

Next was a full day of travel.  I flew from the northwest of the African continent (Senegal), all the way to the south (Johannesburg, South Africa) with a layover in Addis Ababa.  Lounge access at the Addis Ababa airport made it possible for me to enjoy an Ethiopian meal during my airport layover.

In Johannesburg, I enjoyed a chef prepared sunrise breakfast at Northcliff Tower overlooking the city.  Chef Bjarne then gave me a brief driving tour of the city with stops at Constitution Square and the Rosebank Sunday Market.  At the market we were given a tour by the market’s owner, and an artisan even made a Frequent Miler bracelet for me!

From Johannesburg, I took a train to Cape Town where I slept in a semi-private sleeper-car.  I had a great time making new friends and watching the desert scenery.  Then the train broke down.  The bus that took us the last part of the way literally blew its top, but we somehow made it to Cape Town anyway.

In Cape Town, I stayed with a friend and enjoyed getting to know her husband and son.  They took me to Table Mountain National Park, then on a driving tour of the Cape Peninsula.  That tour included incredibly beautiful sights, wine tasting, and even an opportunity to visit penguins (yes, we were so far south that penguins live there)!

On the final day, I flew from the southernmost tip of Africa, Cape Town, all the way to the Seychelles which are nearly as far east and north as you can get within the African continent.  There, I planted my figurative flag at the airport in the Seychelles.  I was done!  This was a one-way challenge and there was no more room in my budget to account for the taxi ride to my hotel let alone the hotel itself.

After the challenge was over, I rested up at the terrific DoubleTree Seychelles.  Then, I flew to London to meet up with my wife.  To get there, I flew Etihad business class to Abu Dhabi, and then Etihad First Apartments to London.  The latter was amazing!  See my review here: Etihad First Apartment Review – Simply Awesome.

If you’re interested in the details of how I went so far with only 40K points and $400, see this post: How Greg toured Madrid & Africa for 40K points and $400.  If you’re interested in more details about the trip itself, please see below.

I had such an amazing time with this trip that I find it hard to imagine how I can top it in the next challenge!  Even though the new  3 Cards 3 Continents challenge will have a much larger budget, I will have to accomplish much more to win (plus, the new challenge requires round-trip travel).

Day 1: West Virginia, DC, and NYC

On the first day of my adventure, I flew to West Virginia and back, spent a little touristy time in D.C., Megabused to NYC, and flew to Madrid.  For my original detailed account, see: Greg’s first day of #40K to Far Away adventures.

To West Virginia and Back

a brick building with windows
In one door, and out another. That was the extent of my West Virginia adventures.

All three of us kicked off our journeys from the Washington Dulles airport (IAD).  I started out by flying United to nearby Lewisburg, West Virginia.  In West Virginia, I deplaned, walked into the tiny airport from the tarmac, immediately went through security, and then walked back to the very plane that I had just arrived on.  I flew right back to IAD.  This purpose of this silly little excursion was to setup two free flights crossing the African continent.  Details here: Maximizing and Understanding United Excursionist Perks.

A tourist in D.C.

a large building with columns and a tiled floor

I took a bus from Dulles to L’Enfant Plaza, near the National Mall. From there, I explored the Library of Congress and took a free tour. 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).

Megabus to NY, Subway to JFK

a blue and yellow bus

After touring the Library of Congress, I walked to Union Station and boarded a Megabus to NYC.  I had managed to snag a $1 fare which really cost $4.25 after taxes. The bus ride was slow, but uneventful.  For dinner during the ride I ate a sandwich I had absconded with from the Air France lounge at Dulles airport.

two men taking a selfie

In NYC, my friend (and former contributor to Frequent Miler) Julian Kheel met me at the Megabus stop and guided me to JFK airport.  Originally he had hoped to go with me on the first international part of my journey, but he ended up backing out of those plans.  Still, it was great to see him for this short visit.

Norwegian to Madrid

a man holding a bottle in a plane

I had paid only $140 (9,326 Ultimate Rewards points) for this flight to Madrid. The plane itself was clean and nice (it was brand new).  I popped an Ambien and awoke the next day in Madrid, but with no idea where I’d sleep that night…

Day 2: Madrid

I had blown almost my entire budget on transportation and so I couldn’t afford to pay for a hotel in Madrid.  Instead, I had signed up for CouchSurfing (an app/website where people offer up their couches for free to visitors) and sought out someone to host me in Madrid.  Not a single host took the bait.  So, I entered Madrid with no idea where I’d sleep that night…


At the time of the trip (but no longer), Business Platinum cards offered free WeWork membership.  I used my free membership to gain entry to one of three WeWork offices in Madrid.  There, I took advantage of free coffee, free food, and free internet, and set about looking for where I could sleep that night.  I entered a plea into a Last Minute Madrid CouchSurfers forum and then looked up other options.  Was there a long late night movie I could go to? (not that I could find)  How about a bus that circled the city all night long? (maybe… I didn’t quite figure that out)  Could I stay at WeWork? (no)

It turned out that the Last Minute Couchsurfers forum paid off.  A very highly rated host offered up his sofa!  Even better, he sent me written directions to do a self tour of Madrid.

Touring Madrid

Originally I had signed up for a free walking tour of Madrid.  Even when I’m not on a strict budget I like to do these anytime I visit a new city.  Unfortunately, the free walking tour was cancelled because I was the only one signed up.  Luckily my last minute Couchsurfing host had provided a written guide.  I managed to see about half of the things on his list before I tuckered out.

Here are a few photos from my tour:

a large building with towers and a dome shaped roof a group of people in a plaza with Plaza Mayor, Madrid in the background a stone structure with lights at night

I’ve never been to Madrid before, but I loved it from the get-go.  The metro was super clean and reliable, and the city itself was charming and vibrant (at least the parts of the city I visited).

José’s house

a man in a white shirt cutting food in a kitchen
José, prepares dinner

That evening, my CouchSurfing host, José, whipped up a delicious Spanish meal which he shared with me and another CouchSurfer.  The other guest shared a bottle of wine.  I contributed in a tiny way by sharing treats I had grabbed from the Air France lounge at JFK.

a man standing on a couch
That’s me “CouchSurfing” on José’s sofa before it was made up into a bed.

José prepared his sofa with sheets and a pillow and so I was super-comfortable.  His living room actually had a door that closed to the rest of the apartment and so I had a private room to sleep in!

Day 3: Dakar, Senegal

On day 3, I flew to Dakar, Senegal. For this part of the trip, I found a CouchSurfing host well in advance. Penelope was originally from Canada but now lived in Dakar running a family business.

a group of people sitting at a table with food

Penelope and her two employees were delightful. They brought in a traditional Senegalese dish which we all shared.

I then traveled by boat to tour nearby Ngor Island, before returning to my host’s home where I stayed in a beautiful room with its own private bathroom.

a bed with a canopy over it
My CouchSurfing room in Senegal

For more details about my visits to Madrid and Senegal, see: Greg’s visits to Madrid and Dakar #40Kfaraway.

Day 4: Crossing the continent for free (ish)

I spent my entire 4th day flying across the African continent.  I flew from Dakar to Johannesburg with a ground stop on the way in Bamako and a multi-hour layover in Addis Ababa.  This incredibly long day of flying was sort of free.  I had made use of United’s excursionist perk to get this leg of my trip for zero miles (but I did have to pay taxes and airport fees).  This (and a later flight to the Seychelles) was the reason I had flown from Washington Dulles to West Virginia and back.  I explained all of this here: Maximizing (and understanding) United Excursionist Perks

a group of people sitting in a room
Star Gold lounge at Addis Ababa airport (ADD).

In the Addis Ababa airport I had access to the Star Gold lounge only because I had status matched from Delta Diamond to United Premier Platinum prior to my trip.  Even though the lounge was overcrowded, I was fortunate that it had very good Ethiopian food.  By this time I had eaten authentic and delicious Spanish food in Madrid, Senegalese food in Dakar, and Ethiopian food in the Addis Ababa airport.

Day 5: Johannesburg

I landed in Johannesburg (Jo’burg) at around 3am on Sunday.  I rented a car and drove to Chef Bjarne’s house.  I had met Bjarne on the CouchSurfing website which I used, in this case, to find locals who could give advice about what I could do on a Sunday morning in Johannesburg with only about 6 hours available.  Bjarne offered to prepare a sunrise breakfast at Northcliff Tower overlooking the city!  I paid for the ingredients.  After breakfast, he took me in my rental car for a tour of the city.  In addition to the breakfast and great fun hanging out with Bjarne, a big highlight was our visit to the Rosebank Sunday market.

Watching this YouTube video is the best way to get an idea of what my time in Johannesburg was like.  If you’re not interested in watching a video, though, you can instead check out the photos and captions that follow…

two men holding cups and sitting on a bench
Chef Bjarne and I clinked our coffee mugs as the sun rose over Johannesburg.
a person in a white car with a door open
Constitution Square and my rental car.
a man standing next to a statue
Constitution Square
a sign on a wall
The Rosebank Sunday Market happened to be celebrating their 5 year anniversary
a group of people posing for a photo
Rosebank Sunday Market. From left to right: Me (Greg), Donna (the owner and director of the market), and chef Bjarne
a man pointing at a menu
Bjarne points out braii meats (barbeque meats) at the Rosebank Sunday Market
two men posing for a picture
Mark, an artisan at the Johannesburg Rosebank Sunday Market, created this Frequent Miler bracelet for me!

Days 5 & 6: Johannesburg to Cape Town by Train (and bus)

One of the best deals I took advantage of for this trip is the ability to take a train all the way from Johannesburg to Cape Town, in a sleeper car, for about $50.  Along the way, I made a bunch of friends and enjoyed watching the desert scenery roll by.  Until the train broke.  Most of us switched to a bus and we were on our way.  Until a big part of the bus fell off.  Seriously.  Luckily, that bus part wasn’t too important as we were still able to make it to Cape Town, only about 6 and half hours late.

The best way to get an idea of what the train was like is to watch this YouTube video.  Alternatively, check out the photos and captions below…

a train in a tunnel
Shosholoza Meyl train in Johannesburg station.  A guard initially wouldn’t let me in because I was sporting a decorative wooden sword that an artisan gave me at the Sunday Market.  “No weapons allowed!”  I wanted to bring it to my Cape Town friend, though, so I walked away and shoved it deep into a bag I was carrying.  I managed to smuggle this weapon aboard.  Don’t worry… the weapon still has not been used to hurt anyone or anything.
two men sitting together smiling for the camera
My roommate on the Shosholoza Meyl train.  When traveling alone, they assign you a roommate.  Luckily mine was friendly and courteous (for the record: I was too).
a landscape with mountains in the distance
View from the Shosholoza Meyl train.  We sometimes saw animals like Ostriches and others that I can’t name.
a table with a white tablecloth and a vase of flowers on it
View from the Shosholoza Meyl dining car
a group of people sitting at a table
About to enjoy lunch with friends I met on the train.
a man standing in front of a train
The train eventually broke down.  We were given the choice to wait until it could be fixed or to switch to a bus.  Most of us switched to busses.  This picture shows where we got off the train and waited for our bus.
a man carrying a fallen tree on a road
The bus ride was scenic and pleasant until the bus blew its top.  This blurry image shows the bus driver and a guard carrying the top of the bus towards us.  They had walked down the road behind us to get it.
a man standing on the street next to a box
A better view of the piece of bus that fell off.
a group of people sitting at a table
A family I became friends with during the journey. They chose to stay on the train and wait for it to be repaired rather than taking the bus.

The next day, I emailed the father of the family shown above. Here’s part of the email:

Hi Ben, it was great meeting you and your family.

I hope the rest of your train ride went well. On the bus they stopped 4 times to let people off (we had been told there would only be one stop). Then we had to stop again when a big piece of the bus’ roof fell off. I’m not kidding. We still arrived by 9:30pm though.

Had a fun time in Cape Town today!

And Ben wrote back to let me know that switching to the bus was a far better choice!

Greg…awesome hearing from you…if pieces falling off busses was your problem then I think we win the worst trip award as we only arrived in Cape Town Tuesday morning at 02:50…with the locomotive smoking and on fire….as the brake pads of the train clamped up and we drove 220kms like that…Well we are here safe…and it was also great meeting you…

And separately he wrote:

My wife and I plus our eldest son got free food on the train due to the train running late and we all got food poisoning from it…this was a trip to remember.


Days 6 & 7: Cape Town

In Cape Town I stayed with a friend who has stayed at my house in Ann Arbor many times in the past.  She was very happy to reciprocate and I was thrilled to get to know her husband and son.  They fed me dinner and gave me a room to sleep in.  The next day, they gave me a great tour of Cape Town!  We visited Signal Hill at Table Mountain National Park, drove the beautiful coast, did wine tasting at Cape Point Vineyards, and visited penguins at Boulder Beach!  The best way to get an idea of our Cape Town tour is by watching this video.  If watching a video is not your thing, see the photos and captions that follow…

a man standing on a yellow frame with mountains in the background
Table Mountain itself was too fogged over to visit.  Instead we went to Signal Hill at Table Mountain National Park where we got a good view of the fog covering Table Mountain.  Other views from Signal Hill were more impressive.
a group of people holding wine glasses
We drove down the coast towards Cape Peninsula and stopped at Cape Point Vineyards for wine tasting.
a hand holding a booklet with penguins in the water
One highlight of the tour was a stop at Boulder Beach where a penguin colony likes to hang out and entertain visitors.
two penguins on a rock
I loved watching the penguins at the Boulders Penguin Colony!

Days 7 & 8: Cape Town to the Seychelles

After our whirlwind tour of Cape Town, my friend dropped me off at the Cape Town airport and I flew all the way to the Seychelles.  Specifically, I flew, Cape Town to Johannesburg to Addis Ababa (where I enjoyed more Ethiopian food), and then to the Seychelles.

At the airport in the Seychelles I declared that my 40K to Far Away journey was done.  This was intended to be a one-way challenge to see who could go the farthest with 40K points and $400.  I planted my figurative flag in the Seychelles at the airport.  I was done!  I would have liked to have made my way to the hotel before declaring my doneness, but I didn’t have enough money left in my budget to pay for the taxi ride.

After my “I’m done” declaration, I was free to spend real money and points.  I spent the night at the wonderful DoubleTree Seychelles, then flew to London the next day to see meet up with my wife there.  I flew Etihad business class to Abu Dhabi and then the amazing Etihad First Apartments to London.  See pictures below…

a pool with a beach and chairs
DoubleTree Seychelles Beach and Pool
a person's feet on a pool
Relaxing at the DoubleTree Seychelles pool after my thrilling and exhausting trip.  Ahhh.
a beach with palm trees and a boat in the water
DoubleTree Seychelles beach.
Etihad Guest Sweet Spots
Here’s my incredible Etihad First Apartment suite.  Wow!  See my review here: Etihad First Apartment Review – Simply Awesome.
a bed with a book and a magazine on it
Bed time! I found the bed to be very comfortable. See my review here: Etihad First Apartment Review – Simply Awesome.

The End

Thanks for indulging my reminiscences.  If you’re interested in the details of how I went so far with only 40K points and $400, see this post: How Greg toured Madrid & Africa for 40K points and $400.

Want to learn more about miles and points? Subscribe to email updates or check out our podcast on your favorite podcast platform.
Notify of

This site uses Akismet to reduce spam. Learn how your comment data is processed.

oldest most voted
Inline Feedbacks
View all comments

Love the post, keep doing what you’re doing!


I like the post, especially some newly shared pictures from that trip.


Nice walk down memory lane. Looking forward to what you come up with the upcoming challenge 🙂

M Khan

Ignoring the comment below.. – what an amazing post Greg! Love what you guys do here on the FM Blog – its amazing how you’ve managed to build your site and recruit the most amazing and likeable personalities along the way!! My first stop whenever I open my browser! I’m looking forward to seeing you at the Travel Summit in YYZ!

Last edited 1 year ago by M Khan

Why soooooooooooooooooooooooooooooo many pictures with Greg in them?
No offense but this is a big turnoff for me. It was why Million Mile Secrets became the laughing stock of this space in blogs community.


I meant no offense to Greg or FM staff, just being honest with my feelings. I know that many others in our meetup groups agree. Together we can make FM better!


Yes u did But the blog didn’t Like it -7 sorry ..I was very Worried about his Train Trip on that one. My friends asked me to Transfer Lots of funds in case I got Kidnapped on my trip, Way South…But I knew a Blog owner and few others who said the same as my Moscow Trip. Don’t Go You Idiot and I didn’t Go..In the USA u do what u want and Who cares what others Think or Post..

V Bernie
By the way at my hotel out front a Super Rich person got killed a year later as in Wise friends..

Last edited 1 year ago by Cavedweller
Jan W

I enjoy seeing you in action, especially on something like this. It’s more real that you “made friends” when we see you eating and touring with them. Plus it makes me imagine my face in there, having a great time and meeting new people! As Emily wrote, just my opinion…