Affording Extended Travel

Travel More, Travel Longer

2014-10-19 17.08.39.jpgWhen you return from vacation, do you dread returning to work? Are you eagerly counting the days until you’ve earned an extra week of paid vacation? Are you planning your next two or three vacations while on your current vacation? Do you sigh with envy when you read about countries where workers take whole months off or companies that give (so-called) “unlimited” vacation? Do you crave the ability to travel more, to travel longer, to enjoy longer vacations, bigger holidays? How is it that all these other people are traveling all the time?

The Internet abounds with young people who’ve foregone a conventional life to travel. Right out of college, or just a year or two into their first jobs, they set out on their grand “round-the-world” adventure. They blog every step of the way, tweet something every few minutes, post thousands of pictures to Instagram, and offer all sorts of advice on how to do what they’re doing, but naturally it’s slanted to the backpacking and hosteling mindset. What if you’ve got grown children, a house and mortgage, and an established career with commitments?

What if you’ve got a life that you want travel to be a part of, not necessarily make travel your life?

This resource page and it’s companion page on earning a living while on the road aims to help put you, the “mature” (we love that term) middle-aged baby-boomer with an established life and career, in a mindset of achieving location independence. We continue on this page with how to afford extended travel. Hopefully we can help you make longer term travel a reality for you.

Adjusting Expectations

On previous vacations to Paris, you’ve probably stayed in nice hotels near all the sights, or if you’re a beach person you’ve stayed in a condo right on the water. You gladly, eagerly, spent hundreds of dollars (or pounds or euros) a night, returned home, and began saving for the next vacation. But if you were offered the chance to stay in Paris or on the beach (or wherever it is you most want to go) for 2 entire months with the only provisions being that it would be a smaller place, without all the amenities such as a front desk or a restaurant, and farther away from all the sights, wouldn’t you consider it?

Would you stay in a 1-star hotel if it meant you could stay twice as long as in the 3-star hotel? Would you consider sleeping in a stranger’s spare bedroom, assuming you had reasonable assurances it was safe and they were decent people? Would you give up sleeping in the huge, comfortable house you’ve earned for yourself to stay a few months at a time in tiny studio flats in all the locations you’ve long dreamed about? Would you accept the responsibility of yard work or caring for someone else’s pet if it meant you got to stay a few weeks somewhere interesting for free? Would you rent a place with a kitchenette so you can eat in frequently rather than dine out 3 times a day?

2014-09-28 13.20.52.jpgIn short, wouldn’t you sacrifice a few of the amenities you’re accustomed to so you could travel for a few months? If so, you’re halfway to traveling more and traveling longer. It starts with adjusting your expectations. Unless you’ve won the lottery, traveling on a vacation mindset and a vacation budget isn’t sustainable: you’ll have to adopt a long term travel mindset and live on a long term travel budget.

We don’t mean at all that you’ll have to live in dumps, just that you’ll have to pass on the glitzy hotels and conveniences of tourist-centric resorts. In most cases (not all, actually) you’ll have to give up the conveniences and comforts of the house you’ve worked (clawed, scratched) your way into. In many ways, you’ll have to live just like the locals, which you’ll probably find a more interesting, enlightening, and rewarding aspect of long term travel anyway.

But, to make it more than worth your effort, you’ll be in Paris or on the beach or in some other location you’ve previously only dreamed of spending a month or two in.


Arbitrage means to buy low and sell high. It basically means to take in more than you spend (a concept any well-run household knows about, and a concept our government should learn about). Geo-arbitrage adds a geographic component: if your revenue is in a highly valued currency like US dollars, British pounds, or euros, you can stretch them further by spending where things are cheaper. If you’re an American, if only you could make a New York City salary while living in Alabama.

The term geoarbitrage was popularized, perhaps coined, by independent lifestyle guru Tim Ferris of The 4-Hour Workweek fame. If you’ve not read his book, order it now. What geoarbitrage means to you, the wanderlust afflicted middle-aged professional seeking to travel more and travel longer, is that you can (and should!) continue to work in your well-established career earning dollars, pounds, or euros, but plan to stretch your travel by spending your income where you get the most for it. This isn’t a new concept to any traveler: it doesn’t take a lot of thought to realize you can enjoy a longer vacation almost anywhere in the world other than London or Tokyo.


The ideal situation will be for you to work remotely while you travel: applying geoarbitrage, good budgeting, and lots of research, you can travel indefinitely. This happens to be how most pre-retirement full time nomads do it, by the way. If working remotely isn’t a possibility or a desire, but traveling more is a possibility, you can still apply these techniques successfully, just not more than your work (or preferences) permit.

Whether you’re working while traveling or not, knowing where you can go for longer periods is a key to this style of travel. It’s obvious that staying in the Paris or London suburbs is going to be cheaper than the city centers. And naturally there’s a whole lot more cities to explore out there where your dollars will go even further. Fortunately for long term travelers, staying in that right place longer is even cheaper than the typical vacation or holiday stopover.

Staying Longer is Actually Cheaper

That weekly and monthly rates are much better than daily rates is not a surprise either (in fact, you’ll find that much about long term travel is common sense). This concept does reinforce, however, that you’ll be skipping the hotels and resorts that cater to the short term vacation traveler in favor of longer stay options. 

The obvious aside, start by thinking of a simple unit of measure: the daily cost of lodging. In a vacation mindset these days, $100 a night for a hotel room isn’t bad. But if you were to stay in that hotel for the entire month of August, it’s going to cost $3100 plus taxes (often high resort taxes). It’s possible that you can negotiate a better rate, and you could also figure in the value of the hotel’s rewards program (assuming it has such a program), but at best you’re looking at $2500 total, or about $80 a night.

Now consider the cost of transportation, i.e. the cost of getting to and from your destination. Compared to your lodging, transportation is going to be a relatively fixed cost. By this we mean that it will cost the about the same to get there whether you stay a couple of days or if you spend 3 months. It’s obvious, then, that the daily cost of transportation is considerably lower when you divide by 90 days than when you divide by 3 days. It can be a difference of hundreds of dollars a day in transportation costs.

If you’re comfortable with $80 a night as your lodging budget, then good for you. But with some research and a bit of negotiation, a month in the same general area could get down to $50 to $60 a night for lodging and have an even bigger impact on your per-day transportation costs. If you’ve got the flexibility to spend even longer or stay further abroad, then it might get you down to $40.


Which brings us to flexibility…

Flexibility Saves Money

If you can stay on the outskirts (of wherever), if you don’t mind a smaller place, if you can visit in off season, or if you can stay a month instead of a week, you can save money and keep your daily cost of travel down. It’s all about the flexibility, and it’s not just flexibility in lodging. The Internet is practically brimming with “airfare hacks” that tell you flying mid-week is cheaper, that winter travel to summer resorts is the best deal, etc. No matter whether you’re talking lodging, airfare, cruises, renting cars, or taking the bus, it comes down to basic economics: you’ll find the best prices when the demand is lower. But it usually takes some flexibility to take advantage of that simple fact.

Fortunately for the long term traveler, flexibility is often easier than for vacation-travelers. If you’re going to travel for a few months, whether you travel on Tuesday versus Saturday becomes less relevant. If you have command of your schedule, taking a last minute repositioning cruise across the Atlantic become possible. If you can stay three months, off-season, on the Caribbean island of Guadalupe and don’t mind staying in a small locally-owned cottage, you might be able to negotiate a $500 per month rate for the same view that otherwise you’d pay $5,000 a month for on the nearby island of St. Croix.

Just like you’ve adjusted your travel expectations, increase your flexibility to stretch your travel calendar.

Leverage the Internet

The concepts of expectation-setting, geoarbitrage, and travel economics are big picture strategy. Your tactical advantage for traveling more and traveling longer will be research. You should leverage every research tool at your disposal, including friends and colleagues and print media and travel shows, which is part of what makes travel so fun. But in the 21st century, travel research often begins and ends on the Internet. This probably doesn’t even need to be said, but what you should keep in mind is that travel research on the Internet is a constantly-changing landscape. New websites, tools, and apps come online all the time, giving you new ways to enable your research. At the same time, old industry standards get adjusted to new realities, like airlines fighting against the commissions paid to online booking websites, mergers, and new discount airlines popping up.

Everyone has their favorite travel resource tools, our favorites won’t necessarily be yours, and everyone’s favorites change over time. A few years ago we used to be big time users, but lately we favor and booking airfare directly with the airlines. Before we embarked on full time travel, we rarely booked hotels on any single site, but lately we’ve concentrated our hotel reservations (when we actually stay in hotels) on (which happens to be owned by Expedia). And then there’s the constantly changing list of wonderfully useful travel tools, like and Bottom line: use the tools you are most comfortable with, bookmark them, find and install their mobile apps, check them frequently, use their alerts, sign up for their email newsletters, and learn all about their incentive programs. 

180x_airbnblogo.jpgIt’s the big Internet travel trends that are most exciting and the most disruptive to the industry, meaning they create big opportunities for us long term travelers. And there’s not been any more disruptive travel trend than peer-to-peer travel tools. Peer-to-peer refers to the ability of anyone in the world to connect to anyone else in the world with common interests. is known as the best example of peer-to-peer lodging, but in reality sites like and have been offering similar services for years. In all of these cases, the basic concept is that a homeowner offers a personal residence for short term rent. AirBnB just extended the concept to extra bedrooms and threw in the utility of handling the money. Peer-to-peer lodging is turning the lodging industry upside down, causing big companies to rethink their offerings and catching the interest of related industries, like peer-to-peer car rentals (,

We think there’s an even bigger trend at work here that we call social travel, a blend of the capabilities of social networking and peer-to-peer interfacing. It surpasses the peer-to-peer lodging and auto rental trends above to create entirely new ways of affording travel. Like home exchanging or house swapping (,, and house (and pet) sitting or home minding (,, Social travel promises to continue to create new ways of affordable, interesting, and rewarding travel in ways that we haven’t yet imagined.

Staying on top of all these Internet trends is where travel bloggers can be especially valuable. Find a half-dozen or so of your favorites, bloggers with a diversity of content on interesting destinations and how-to’s, bloggers who report on new trends and tools, and sign up for their email newsletters.


A thread through all of the above is that you have to pay attention to what you’re spending over a period of time. This is the dreaded “b-word”: budgeting. If you’re the mature, established traveller we imagine you to be, you’ve probably learned well how to live by a budget so you’ll find adapting to a budget of long term travel relatively easy. Especially if you are seeking to go full time with your travels, some adjustments to your budget might make sense though. We advocate simplicity in your travel budget, but if you prefer to think in deeper detail, that’s great, as long as it’s manageable, usable, and effective. We recommend only 5 top-level travel budget items.

Room – lodging, hotels, rent, etc. including related taxes and resort fees. 

Board – meals, groceries, dining, etc.

Transport – airfare, car rentals, trains, buses, ferries, rental car insurance, fuel costs, parking, etc.

Entertainment – museums, attraction tickets, passes, shows, concerts, liquor, etc.

Other – travel insurance, subscriptions to social travel websites, and any other cost that doesn’t fit neatly in any of the other categories.

You’ll notice that budget items typical to at-home life, like home owner’s insurance and life insurance and utilities, aren’t accounted for above. That’s because we’re thinking of the above as strictly a travel budget, exceptional to your normal costs. They can, as in the case of full time travel, be an integral part of your entire budget (or they don’t exist at all, as when you’ve sold your house to travel). Otherwise, we assume that you’re managing a household budget separately or that they’re costs you are going to be paying whether you travel or not. The level of detail of your budget is up to you and should reflect your preferences and objectives.

The bottom line is that long term travel, with costs that can vary from month to month, country to country, continent to continent, requires diligence in managing a budget. Otherwise, like so many others, you’ll find yourself running out of money and needing to come home long before you really want to.

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