Many people wonder how Caroline and I ended up living out of hotels. We’ve been married for 4.5 years and we’ve gone to 20 countries a year, 4 years in row, and we stay in luxury hotels (best hotels of 2014, 2013, 2012).
But how did we get here? And the truth starts back before we were dating. Which is fine, because I’ve been wanting to tell our personal story on the blog… but just never got around to it. So I’ll share our story now, and tie it in with how and why we live in hotels.
Caroline and I met in Charlottesville, VA, my hometown, but she had moved back to Amish country Ohio – her home “town”.
One thing I’ll add that will give some context is that I dropped out of high school when I was 17. Years later (2010) I was taking classes at the community college, and a few classes away from getting my associates. I dropped out of college, again, with the goal of traveling the world.
I didn’t tell my friends explicitly that my goal was to travel around the world, as it would have seemed a little crazy. After all, I had very little money.
But my philosophy has always been that free travel is possible if you don’t have a timeframe. Walking, biking, or even hitch-hiking are free… and that’s what I did.
I went to visit Caroline in Ohio, since she had recently moved back home… and it goes from there.
My plan was to travel the States visiting friends, and then travel the world. But so far the trip involved Ohio.
To be honest, it was the first time in our friendship that we were both single, and at that point in time it was incredibly clear we were meant to be.
I mean, in hindsight it was insanely clear. We were two dreaded hippies, with extremely similar beliefs and values, who dreamed of one day traveling.
I’d never met someone who so clearly valued kindness and helping people about themselves. And to this day I would say I’ve never met someone more selfless than Caroline. But even on day one of dating, I knew. I knew for 100% certain we would get married.
Although this created a problem I’ll talk about in a minute.
It wasn’t clear how the next year would play out for a number of reasons, but I did want to continue traveling around the US. I hitch-hiked around the US. In fact, I once shared the stories of hitch-hiking from Ohio to my cousin’s in Nashville – which was crazy (read that here).
I kept going until I got to my parents’ house, which at the time was in south Texas.
At this point in time I had a predicament.
I knew I wanted to marry this girl… but, I also knew I wanted to keep traveling and didn’t have money.
Honestly, my plan was to hitch boat rides and camp/sleep outside. For whatever reason, I 100% assumed I would be fine doing this alone, but didn’t want to drag someone else into it. I seriously had nights thinking about worst-case-scenarios.
Ironically, now I’ve actually traveled the world and we have hitch-hiked together in Thailand, Germany, Austria, Chile, Rarotonga, etc… I know it’s actually not that dangerous. But at the time, I was getting cold feet.
During my time at my parents’ house, I went on a quest to find out how to travel for free… but I didn’t learn of anything new. Hostels were never my thing, especially if I was married, and nor were they free.
In fall 2010 Chris Guillebeau had just come out with the book, the Art Of Non-Conformity, and he must have been promoting it via guest posts on travel blogs.
The book opened my thinking to the idea of making money online, which seems obvious now… and in general it was about alternative ways of doing things. One way he mentioned in the book, was buying $1 coins on miles earning credit cards to get free miles.
The $1 coin thing lead me to Flyertalk.
It was a crazy time. You could order $1,000 of one dollar coins from the US Mint, and they would give you free shipping. It was basically a promotion to circulate the use of $1 coins, I guess?
You’d buy the coins, earn the miles, then take the coins to the bank and deposit them. The glory days.
At that time the US Mint limited orders to $1,000 per 10 days.
What they didn’t realize is that they only limited the $1,000 based on credit card numbers… which we quickly had multiples of.
The true symbol of the glory days is the following:
- We signed up for 100,000 mile credit card bonuses
- We’d order $1,000 in Amex gift cards via a rebate portal where you’d get like 5% back
- There were promo codes to get free shipping
- The Amex gift cards would come in, and you’d use those to order $1 coins
In other words, Amex gift cards was a way to get unlimited $1 coin orders, and you’d make 5% back via cashback portals.
The biggest credit card bonus I got was 100,000 Amex points, that I transfered to 150,000 British Airways miles (they weren’t called “Avios” yet). If I spent $5,000 to get the miles, thats $250 profit.
Earning cash and 100,000 miles at this time was super easy. Travel wasn’t free, it was profitable.
But imagine what my in-laws must have thought of me. This guy with no job, and dreads, has Caroline signing up for credit cards while they’re dating.
I made my way back to Ohio, and eventually popped the question. 2 months later, in May of 2011, we got married. Yes, we were only engaged 2 months. And yes, most of our dating was with me somewhere else. But for the next years, it would be rare if we weren’t in the same room.
We got married in an old theatre in Killbuck, Ohio. The theatre was still closed but the owner said we could use it for $100. Caroline’s parents wouldn’t let us do a pot-luck, so they provided some food. And Caroline’s dress cost $25 from a thrift store. Those were the only expenses, and that tells you a lot about us. We’re both extremely frugal, but then again, we didn’t have much choice.
Our first four months of marriage were hardly normal, but we did have “normal” jobs. But yeah, that only lasted four months.
Then we used our miles to book a oneway ticket to Asia. Stopover in China.
The Travel Begins
It wasn’t really a plan. It wasn’t a gap year, and it wasn’t a plan to travel forever.
It was just a oneway ticket, millions of miles in our stash, and a goal to see the world.
The trip started by us visiting a friend in China, who was now teaching english. This is the story of the worst day of my life (read here). Basically, I assumed it would be easy to connect, and wrote down my friend’s address in English. We wandered around town trying to find taxis or people who could read the address and point us in the right direction. The few people who attempted to help sent us in the wrong direction.
It was a crazy trip, to say the least.
Then we went to Bali, and fell in love with the place. Maybe I was just glad to be out of the cold. From there we “backpacked around Asia”.
These were by far the craziest travels of our lives.
First of all we were super broke.
We hitch hiked at times, and on a few occasions slept outside. (All of our “craziest places we slept” stories, came from these months).
You’ve never met more frugal people. Hostels were too expensive. I remember one time in Bangkok we found a place locals stayed where you could get a private room the size of a twin mattress for under $3. The owner of the place thought it was the funniest thing ever that the two of us shared the room.
We also met and stayed with locals in Bali, Malaysia, Cambodia (although they were expats), Hong Kong, etc…
I’d be surprised if we spent $10 a day for the two of us. I wouldn’t believe it.
Stories from this time also include:
- Being taken to a fake border, between Thailand and Cambodia.
- Being stamped out of Cambodia and not having a visa into Vietnam (actually stuck in no-man’s land).
- Sleeping in a really old rental car we rented in Guam
- Until we made a friend who let us stay at his house
- The time we landed in Rarotonga with no place to stay, found out even hostels were $60 per person per night, and the person who picked us up hitch hiking offered her rental house (in between leases) for the two weeks for $200.
Also, our two weeks in Sri Lanka included tons of stories. Amazing cultural ceremonies, these riots/protests that blocked off the road, and sharing a van with a local family across the island all night because they were taking a family member to the hospital to reattach whatever was chopped off.
The list goes on and on.
When we started the hotel thing
Even before our first flight, we had millions of frequent flyer miles earned for free from the $1 coin thing and a ton of credit cards.
But I rarely bothered with hotel points. Paying anything above $5 a night wasn’t an option for a long time.
There was a rare exception June 2011 when a promo by Club Carlson was ending. Stay one night, and get 50,000 points. And 50,000 points was worth more then.
We needed a hotel and this promotion was good enough that we justified the hotel. After we got to the hotel, I read up more on the promotion and then looked at the award chart. The hotel, which wasn’t that expensive, would earn as many as 5 nights elsewhere.
So I created an account in Caroline’s name, enrolled in the promo and booked the same hotel. A different lady checked us in this time, but when we switched to our new upgraded room, I can’t imagine what the staff was thinking when we rolled across the lobby. It had to be clear that just the two of us, had two rooms… one empty.
Well, this worked out really well not long after. Our 100,000+ Club Carlson points were put to good use when we got to China, because they ran a promotion that gave 9,000 points back, per award reservation. That’s right, 9,000 points refunded on any stay, and free nights started at 9,000 points.
There happened to be a cheap Radisson Blu in Shanghai at the time, and we alternated nights so every night the other was checking in. This meant every night got back the 9,000 points.
It wasn’t until later, in early 2012 that we did our second promotional earning. IHG ran the first promotion giving 50,000 points for 3 nights. Well, in Chiang Mai, Thailand, the Holiday Inn was bookable for $30 at the time. The 50,000 points cost us no more than $100.
What did we do with the 50,000 points that cost us $100?
It was that May that the InterContinental Fiji went on PointBreaks – a sale where all the hotels on the list are only 5,000 points a night.
Being our anniversary, we spent 40,000 of those points for 8 nights at the InterContinental Fiji. The hotel was going for $400 a night, and we used like $80 worth of points.
I couldn’t stop running the numbers. Forget the fact the hotel was $400 a night. But think about the fact that we needed 3 nights in Thailand anyways, and that $100 got us 3 nights in Thailand, and then enough for 10 nights in the more expensive Fiji.
When something was a really good deal, we would start to justify it. But it was still rare. I had yet to think about scaling it up.
We switched from Asia and the Pacific to South America. See, back then British Airways miles were region based and allowed unlimited stopovers on a oneway. And better yet, Easter Island was a part of the same South America region. And better yet, a oneway ticket at the time would cost 20,000 miles.
In other words, a oneway ticket from Santiago back home, with stopovers in Easter Island, Peru, and Miami was only 20,000 miles. And remember, I previously got 150,000 BA miles from one Amex card.
Right before the big devaluation I offered some friends a free ticket to join us on the route. Chile, Easter Island and Peru. My friend Ben joined, and Caroline’s sister joined.
After they left, we decided to spend over a month in Peru. But we would have to visa run at some point, so we went near the border of Bolivia.
At this point in time, I can not tell you in words how broke we were. I can tell you in stories, but it can’t paint the feeling of desperation. $5 started to seem like “the expensive hotels”, and we wound up in the sketchiest of places. We kept getting sick in Peru, and I could tell Caroline wanted to go home, although she definitely never said it… I just knew. Who wouldn’t? It was cold, and didn’t feel like the Balinese adventure experienced earlier that year.
I’ll never forget the day in Puno.
We went down to the bus station and got our ticket all the way to La Paz, Bolivia. It was less than $5.
We got our snacks. We waited for the bus. Then we waited in line to put our backpacks under the bus.
Before we put our bags in, the guy asked to check our passports. Then he wanted to know where our visa was. However, it didn’t matter because it was visa on arrival. It took a minute for him to communicate, because my spanish is poor, but after a few attempts it was clear. Bolivia charges a $160 fee for the visa (a reciprocity fee), and he was telling me that I need to go in to the ATM and get the $160 each before we could get on the bus, because there’s no ATM at the border.
I was crushed.
That was more than a month’s budget.
Plus, we needed to leave Peru to extend our 30 day visa before our flight home.
We walked over to the ATM and stood there…
Then I turned to Caroline and said, “let’s go home”. I’m not sure she knew what to think. I repeated, “let’s go home”. I don’t remember what she said exactly, but I could tell she was more than willing.
We didn’t bother trying to refund the $5 ticket, we just walked all the way back to the little homestay. We got on the wifi, loaded Skype credits, and called British Airways to move up our ticket.
For whatever reason, BA didn’t even bother charging us a fee. They just changed our ticket.
The next morning we went to Arequipa, where our flight out left the following morning. Then we flew home.
Taking a break
We went back to Charlottesville, (where we had first met) and stayed on friends’ couches until we got real jobs, and found a house on craigslist that did a 6 month lease. It wasn’t really on purpose that we got such a short lease, the guy just wants his lease cycle to be near the UVA student cycle. Summer.
This point in time was desperate in another way. The blog started getting traction, and I realized how much I hated working for other people. I was an idiot, who thought he could run everything better than my boss. Which, wasn’t true, but it was the narrative in my head.
It’s funny, because Carrie and I have always talked about what business we would one day start, but we never thought the blog we were writing would be that business. Although, the problem with most business ideas is that we wanted to do something we thought was super meaningful – mainly, create a technology that increases wealth (not just makes us money).
But, the blog started making money.
And then I started getting job offers… and I wasn’t really in a position to decline them. I was working my job in Charlottesville, coming home and working for other people’s websites, and then writing my own website.
Very little sleep was involved at that stage.
Our lease ended in July 2013, and at that point we had to decide. Was this a short break, or a new way of life where travel was something we did on vacations.
That spring was really the first time I got any income at all from the blog.
At that point we annualized how much money we’d make from the blog, set a budget for our travels (which didn’t leave much room for savings), and we took off again.
At this point we announced we’d be posting our stats publicly and what our goal was.
It was early June that I first saw a picture of Zakynthos, Greece. It was so stunningly beautiful that we just booked a ticket. After all, you have to book 21 days in advance with AA to avoid the close-in fee. We were going to go somewhere and we picked ZTH.
This is the context for the video we did on Zakynthos, Greece. There weren’t points hotels and we were on a budget, so we did couchsurfing. It’s one of the two times ever, and it happened to be that the host owned the best restaurant I’ve ever eaten at… ever.
I love food. Like before we go someplace I imagine and highly anticipate what the food is like, and this was the best food ever.
This was like winning the lottery to me. Exploring this awesome island on a scooter, and eating amazing local food. The trip was off to a good start.
Full-time travel 2.0
Before when we traveled we had zero income. None. And even though it wasn’t a ton of money for the two of us, it was more than zero! It was a sustainable system, and that took a lot of stress off of us.
It means sometimes we just work, and we don’t go out and see the sights. And because of that, it means we travel a lot more slowly, so we can do both. We generally spend a week at a time every time we go to Budapest, for example. In Bali, we spent a month when we returned.
Also, at this point I spent a lot of time thinking about sustainable points strategies, and keeping track of stats helped us understand this.
It was clear going into it that living out of hotels would require large amounts of hotel points, and therefore earning hotel points would have to be scaled up. On the rare event that a great hotel promotion came along, I would have to jump on it as big as I could. Things like that became rules, because we’d always need the points.
Before, we rarely did hotel promotions, and now we’d survive on hotel promotions.
It’s crazy to think that July 2013 was 2.5 years ago already. Like just round two was that long ago. Zaknythos feels like yesterday.
Everything since then has been documented on the blog, and even on video. Like every trip is on video (we’re still a year behind on video, but they will be!).
And here are some videos (the ones in bold are my favorites):
- Taking my mom to London
- Mileage running to South Africa
- The Real Bali (and their weird holiday)
- Balinese food
- Things to do in Bali
- The doors to our Indian train were locked!
- 3 Unique Cultures in India
- Surprising Caroline with Phi Phi Islands
- Grand Canyon
Actually, that’s quite far behind, but hopefully in the next couple of months we can get back to editing those. We have dozens more countries to do just to catch up.
Over time, travel started to look a lot less like homelessness, and a lot more like jet setting.
Largely, this has to do with sustainability. You don’t get anything done at a “hotel” that is $2 a night, and sometimes you don’t enjoy it.
Us to Africa, to Asia, back to the US, back to Europe, then Africa, then to Asia, etc…
Suddenly, it felt normal to be in a 5 star hotel, or an overwater bungalow.
Now, it’s normal to be in the middle east, or eating street food.
Our first time in Hong Kong, I remember seeing a specific part of town and being sketched out. Hong Kong was our stopover on the way to Indonesia, this is that first trip to China in 2011. We were in Hong Kong, then China for a month, and then Hong Kong again.
What’s funny, is that the second time in Hong Kong we saw that same street and were totally not sketched out. In fact, everything in Hong Kong looked like the Ritz Carlton to us, the second time.
Fast forward a few years later to our most recent country visited, Myanmar.
Myanmar is soooooo cool. We stayed with our friends who live there now, and outside on the dirty streets at 8am you can hear the yell of a woman getting louder and louder. Well, not a yell, but more of a chant.
Then a little bit later, you hear this guy chanting a different word, and with a different melody. Turns out it was the milk man. He walks up and down chanting at the top of his lungs the word for milk.
Then the trash man goes by yelling “trash”.
Then the water guy came by and my friend Andrew jumped up to get his 5 gallon water thingy.
Such a cool and fun way of life.
Also, we went out to eat and ordered our lunch- we both got a curry and milk tea. We were seated across from two old men, and as weird as it would be to be seated at someone else’s table in the US, it’s normal in Asia. Anywho, one of the guys paid for us and then communicated that he paid for us while leaving.
Now, our meals together probably came out to 1 US dollar, but it was two people’s worth of food for him!
On the other end of things, on our recent trip to Bora Bora it felt relatively normal. It definitely wasn’t our first polynesian island nor luxury hotel. When I remembered the room was overwater, it was cool… but the rest of the time it was relatively normal.
All this to say, it’s totally weird that it’s all normal.
I’m used to being seated at someone else’s table in Asia, or going into restaurants that don’t have english menus and ordering, or going into crowded restaurants with stools and no walls. It’s normal.
Finding our hotel using public transit, without previously looking it up? So normal.
Getting a random bus to a place I can’t pronounce to people who can’t speak english? Totally normal.
It seems odd, but getting around in non-english speaking places is normal. Even without a taxi or looking up how ahead of time. Different is normal.
Think about it. How often do you go to the grocery store? A couple times a week? Is it hard?
Well, that’s how often we switch hotels or even cities.
People are always surprised that I don’t plan ahead at all, but at this point it’s auto pilot. I land and I go, and it’s normal.
We’re only 28 and 29, but we’ve already seen the entire world. Which is crazy if you consider that we got married in 2011 and hadn’t really done any travel. I had been to Mexico with friends, and Carrie had been to Europe… but not much else.
Then basically overnight we were all in. No learning curve, just pushed in.
We didn’t read blogs on what to pack or how to get around to our destination. We just assumed we didn’t need that much, and that we’d figure out the rest as we went.
It’s been that for over 4 years.
When I think of all the experiences we’ve had, I’m almost emotional. From overwater bungalows, to boat rides in Bali, to Safaris in Africa, to swimming in a heated pool in the snowy alps. It’s truly unreal.
There’s probably much more I could have shared about our personal lives, or specific travels if this weren’t already so long.
But at this point I should emphasize how grateful I am for the readers here. Like, it’s absolutely crazy that some people think to use my links when they need something. Since they aren’t in the posts, I know they aren’t “impulse buys”, but instead signs of support.
Wow. For that I’m honored.
And I also have to thank frequent flyer miles.
In 2014 we stayed in 4 to 5 star hotels and spent about $7,000 on hotels. You could spend $7,000 in one month of 5 star hotels! The fact that it’s what we spent in an entire year, is crazy. That’s less than rent in Charlottesville! Can you believe that?
And to be able to fly around the world on a whim, well I don’t know if I could add up the value of that. Our last First Class flight was probably more than our year’s budget in terms of retail value.
I’m still far away from my goal of seeing every country, and yet feel as though we’ve seen the entire world.
Perhaps I should take some time to be introspective and come up with a better ending to this post. But the last years have been a roller coaster. It’s like I blinked and woke up 65 countries later. That’s how it all feels, a dream.