Digital Nomad Life With Points and Miles: Caroline Lupini’s System
Most people picture digital nomad life as a beach, a laptop, and a lot of free time. Caroline Lupini’s version looks different. It is a full-time job, plus a second shift of laundry, grocery runs, flight planning, and rebuilding routines in new countries.
That is what makes her story useful. She has spent 11 years traveling this way, visited 128 countries, and built a points-and-miles system that supports real life, not a fantasy version of it.
The travel dream is real, but the work is real too
Caroline is from Michigan, but when this conversation was recorded she was in Amman, Jordan. She spends about 11 months a year outside the US, and she is the managing editor for credit cards and travel rewards at Forbes Advisor.Her biggest point was simple: full-time travel still includes full-time life. She works about 40 hours a week, sometimes more. On top of that, she still has to figure out where to buy groceries, how to do laundry, and how to function in places where she may not speak the language.
That is why many long-term travelers move more slowly than vacation travelers. Early on, she often stayed only three or four nights in a place. Now, two to four weeks is much more common, because work and logistics eat into the day.
She still likes the lifestyle. A grocery run in a foreign country can be fun. But she is clear that this is not nonstop leisure. It is travel built around sustainability.
How an engineer from Michigan ended up on the road for 11 years
Travel clicked for Caroline in 2011 after a Europe bus tour for travelers under 35. That trip was not booked with points, but it pushed her toward the question that changed everything: how can I travel more for less?
At the time, she was still in university. She graduated in 2013, took an engineering job, and found herself working in a lab with no windows and only 10 vacation days a year. She knew fast that she did not want that life long-term.
The next turn came through a breakup. She left her job planning to move to Baltimore for a relationship, flew there on her last day of work, and got dumped. Instead of forcing a new version of the same plan, she pivoted. An online MBA through Indiana University gave her structure, and then freelance work started to fill in the gaps.
First came award booking help. Then came freelance writing. Later, that path led to Forbes Advisor. Back in 2014, the term “digital nomad” existed, but she says it was not yet a lifestyle she saw all around her. It took a few years before she realized this could be long-term, probably around 2017 or 2018.
The points and miles system that makes the lifestyle work
Her first big points win came in 2014. After changing a planned Thailand trip into time in Cambodia and Vietnam, she flew home in first class on Thai and Lufthansa. It had taken three years of learning before she hit a redemption that felt huge, and it set the tone for what was possible.
Her style has changed since then. In the early years, she chased cheap fares, mistake fares, and economy tickets that let her stretch limited money. These days, she still wants a deal, but she prefers business class for long-haul flights when the numbers make sense. If first class space appears at a reasonable price, even better.
Some highlights stand out. She has flown JAL first class and Etihad first class. She also booked an Emirates cash fare from the US to Milan for about $3,000 roundtrip and earned 100,000 Alaska miles on it, which is the kind of play points people never forget.
Hotels are where her strategy gets even more practical. She loves a splashy redemption like Kalala Island, but she often gets more value from low-category Hyatt properties. In Amman, she booked two weeks at the Grand Hyatt for 70,000 Hyatt points total, then used Globalist suite upgrade awards for the whole stay. That meant a suite, lounge access, and breakfast at a Category 1 property.
She repeats this idea on purpose. Each year, she looks for Category 1 and 2 Hyatts in places like Doha, Bali, and India so she can work toward 60 elite nights. If you want to see how Hyatt status can play out in a very different setting, BoldlyGo’s look at Palazzo and Venetian booking options for Hyatt Globalists and Amex FHR guests is a useful companion read.
She is still deeply analytical, too. With Hyatt, she often looks for about 1.8 to 2 cents per point. Still, she does not stop there.
“It’s unfair to not consider what you would actually spend if you didn’t have the points.”
That means comparing the hotel to the real alternative, which might be a boutique stay or Airbnb, not the sticker price of a luxury chain hotel. For readers who like that kind of structured thinking, DeAndre’s luxury points playbook follows a similar systems-first mindset.
Choosing countries is only half the job, the logistics matter too
Caroline travels with her partner, Kevin, and both want to visit every country. So destination planning is part personal goal, part weather map, part award strategy, and part life admin.
Jordan is a good example. She had already been, but Kevin had not. They were coming from the Seychelles with her parents, wanted to stay in the Middle East before parts of Africa became hotter, and there was a Category 1 Hyatt in Amman. That overlap made the stop make sense.
Their year also has fixed points. They return to Michigan, Colorado, and Quebec in the summer. They go back to Bansko Nomad Fest in Bulgaria, where they met. Bangkok is another repeat stop because of a conference they like. They are also prioritizing harder destinations now, including parts of Africa and the Middle East, because those places may feel less realistic once they have kids.
The paperwork side is just as important. Caroline keeps US residency and avoids staying long enough elsewhere to trigger tax residency. She uses the Foreign Earned Income Exclusion, which requires 330 days abroad in a year. That is why she keeps US time to roughly a month, with a buffer in case plans change. Kevin, who is Canadian, took a different route and got residency in Paraguay as part of leaving Canada’s tax system.
Health insurance changed too. For years she relied on US employer coverage plus travel insurance. Recently she added a comprehensive global plan through Genki, at about $300 a month, partly because maternity coverage often requires a long lead time. Mail goes to her parents and to Traveling Mailbox in Texas, where envelopes can be scanned, opened, stored, or shredded.
She says the lifestyle is easier now than it was a decade ago because remote jobs are more common, co-working is easier to find, and Wi-Fi is better almost everywhere.
What 11 years on the road changed
Caroline still opens new cards, although much less aggressively than before. She has more than 50 cards total. Her favorites include the legacy Citi Prestige for 5x dining, Chase Ultimate Rewards for easy transfer options, and the Alaska card that earns 3x on foreign purchases. To keep the chaos under control, she tracks credits and deadlines in Todoist with tasks and subtasks for each card.
Even with that structure, burnout happens. The problem is not usually one giant issue. It is decision fatigue. Too many small choices pile up, especially in harder destinations. When that happens, she slows down, picks easier stops, reads more, and gets back to the gym.
Emotionally, she no longer feels rootless. In the early years, travel itself was the steady part of life. Over time, she built community within it. Many of her friends live similar lives, so she keeps crossing paths with them around the world.
She also says the lifestyle made her more open-minded. In many countries, when you ask someone what they do, they do not answer with a job title first. That shift changed how she talks to people, and how she thinks about identity.
After 11 years, the excitement is still there. Italy and Argentina rank high for scenery. Iraq and Afghanistan left the strongest impression for hospitality and warmth. And if you need a reminder that points can support big travel goals without full-time nomad life, this story of a $27K Europe trip booked for about $4K out of pocket shows the same core principle at work.
You can keep up with Caroline on Instagram, YouTube, and her newsletter.
The beach-laptop version of nomad life misses the point. What Caroline built is far more interesting. It is a repeatable system for work, travel, status, and daily life.
Her closing idea was refreshingly simple. Try it for a month if your job allows, because that is long enough to learn what fits, what does not, and what kind of life you want to build.
