How to Travel While Achieving Financial Independence

In February and early March, following our usual habit, my wife Ruth and I spent five weeks in a warm climate to escape the last stretch of Canada’s winter. After we returned from Malta, regular guest blogger Devin Partida published a timely piece titled “Can you pursue financial independence without giving up Travel?” that ran on my site in mid-March.

Devin’s post prompted me to reach out to contributors at Featured.com and LinkedIn to collect opinions from financial experts and business owners on the same question. Devin’s conclusion was clear: “maintaining financial independence while traveling is entirely possible with a proper strategy.”

From my own experience, regular travel fits well with at least semi-retirement. You’ll even see a couple of photos of Ruth and me in Devin’s blog taken in Malta and Italy—small examples of blending work and leisure.

Featured travel credit cards

Few would argue that a traditional full retirement is incompatible with extensive travel; that lifestyle remains a common dream for people still working full time. Increasingly, however, members of the FIRE (Financial Independence, Retire Early) movement and those in semi-retirement or early retirement are combining travel with part-time work—often performing some or all of that work while on the road.

That’s where the term “digital nomads” comes in: people whose second careers allow them to travel and work from anywhere with a laptop and an internet connection. Running a finance website like mine and writing occasional columns can be done from almost any location.

Our family’s habit of spending six weeks abroad each winter evolved after a similar trip to Malaga, Spain, in late 2022. We followed that with a trip to the Bahamas last year and to Malta this year. In each case, we stay at least a month in one place, usually at an Airbnb where monthly rates are lower. We look for elevator access and basic conveniences—a dishwasher, microwave, washer and dryer—and a functional kitchen with a toaster and coffee maker.

People sometimes ask why we spend long stretches in one small place. Our routine mirrors life at home: we walk daily near water (at home it’s Lake Ontario), and we prepare most meals ourselves. We typically find a nearby farmer’s market or small grocery store within walking distance of our temporary home.

Because we cook a lot, our monthly food costs aren’t much higher than at home, though we do allow ourselves slightly more restaurant outings while traveling.

Internet facilitates digital nomads

The internet is central to the digital nomad lifestyle. Beyond Airbnb, we use streaming services like Netflix and YouTube—YouTube is especially helpful for local travel tips from semi-professional bloggers, plus music and light news. We typically rely on public transit—buses and trains—but when needed, navigation apps such as Waze or Google Maps make getting around easy.

By the deadline for the Featured article, I had received 84 submissions from financial professionals, travel specialists and business owners—too many to summarize here. In the longer version on my website I included about 25 responses. Most contributors agreed with Devin: travel is compatible with financial independence. As Rex Freiberger of Kibble Facts put it, “Framing travel as a threat to financial independence is mostly a myth based on the most expensive forms of travel.”

Travel doesn’t have to mean luxury spending, agrees Joshua Wahls of Insurance by Heroes: “Business-class flights, five-star hotels and $40 cocktails are optional. A $500 round-trip fare and a $60-per-night Airbnb in a place where your dollar stretches three times as far still counts as travel.”

Suggestions from contributors included renting recreational vehicles (RVs) for extended trips and making your home a low-maintenance base in a travel-friendly community to facilitate a “lock-and-leave” approach.

I also encountered a term I hadn’t noticed before: bleisure—combining business travel with leisure. Wikipedia defines bleisure as extending a business trip to include personal time. Jay Ellenby of Safe Harbours says the idea is to let your career cover transit: “We often help clients fold vacation days into business trips so they don’t incur additional airfare or lodging costs.”

Geoarbitrage

Several contributors raised geoarbitrage—the strategy of living where the cost of living is lower. Devin Partida wrote about this in a previous guest post. Living in lower-cost locations while earning in stronger currencies can let you grow your investment portfolio while enjoying a higher quality of life, a point Jay Samit explores in The Second Act Advantage.

James Tech of TripFrog explains the shift from vacationing to geoarbitrage: “A strategic traveler focused on financial independence chooses medium-term stays in places where living expenses are lower than at home. Spending months in hubs like Portugal, Mexico or Southeast Asia can often deliver a comparable lifestyle for 40% less than in major Western cities. In that way, travel can speed your path to financial independence by reducing your monthly burn rate.”

One practical tip offered was to treat travel as a regular, planned expense—set aside money for it each month rather than treating it as discretionary spending left over after other bills. This echoes the classic advice from David Chilton’s The Wealthy Barber to “pay yourself first” by allocating fixed percentages of income to savings.

Achieving financial independence doesn’t require extreme austerity, says Scott Brown of MintWit. “Move away from expensive, impulsive trips and toward planned travel that supports your FI goals. Embrace slow travel, house-sitting, credit-card point strategies and off-season destinations instead of cutting travel out entirely.”

When done well, travel can even cost less than staying home, argues Konrad Warszecha of House Sitters Guide. FIRE pioneers Akaisha and Billy Kaderli have shared practical tips on maximizing housesitting in a previous post.

Building income streams that travel with you

The core question, Runbo Li of Magic Hour AI argues, is not “Can I afford to travel?” but “Can I build income streams that travel with me?” The old model—save aggressively, cut expenses, reach a magic number, then travel—is backward, he says.

“The new approach is to develop skills and income sources that don’t require being in one place. Then travel becomes a small incremental cost on top of the life you already earn from. Skills like prompt engineering, content creation or freelance AI work can generate genuine income from a laptop in Lisbon or a coffee shop in Chiang Mai.”

Modern technology enables remote work for many professionals. A 2024 McKinsey report found that nearly 58% of professionals have the option to work remotely at least part-time, allowing them to keep earning without geographic constraints, notes Arvind Rongala of Edstellar. Financially, the shift is toward viewing retirement as a phased, flexible milestone rather than an abrupt end. Travel can be part of an intentional lifestyle supported by diversified income, disciplined saving and strategic cost-of-living choices.

To close, Sovic Chakrabarti, Director of Icy Tales, offers a succinct perspective: “Travel doesn’t have to undermine net worth; it can motivate building a more resilient and flexible financial life.” The essential shift, he adds, is to move from tourist thinking to mindful travel—treat travel as a lifestyle choice you can plan and optimize just like any other household expense.