The Holy Grail of Travel

holy grail
Photo credit: Artyominc

When it comes to time, money and travel, people fall into one of four categories:

  • Backpackers – Lots of time, but a finite amount of money
  • Vacationers – Enough money, but not much time
  • Broke People – No money for travel and very little time
  • Financially Independent Travelers – All the time and money needed to travel comfortably

In my twenties, I fell into the first category, Backpacker. I had plenty of time, but a decreasing amount of money and a nagging reality in the back of my mind reminding me that some day my traveling would end and I’d need to start working again.

holy grailToday, my family is firmly in the second category, Vacationers. We’re more of a SITCOM family now (see image to the left). While I have a job with four weeks of vacation, a two-week getaway is about the maximum realistic break I can take. Without a drastic change in our housing and lifestyle, long-term travel is out of the picture for the time being.

During my 14-month trip to Asia and South America in my twenties, I stayed in sub $5/night hotels and hostels. When I retire for good by age 55, my wife and I want to be able to travel for long periods of time, stay in nice places, take comfortable tours, and maybe even fly first class on long flights.

But comfortable travel is expensive, especially over the course of a few months on the road. So we’ll need to have plenty of investments providing income when we retire to support our lifestyle.

Ultimately, my wife and I are aiming to be Financially Independent Travelers with the ability to travel wherever, whenever, for as long as we want, and at the comfort level and pace of our choice. That is the Holy Grail we seek.

Here’s a visual representation of what I’m talking about:


Backpackers come to mind when considering the first quadrant, but this category can also include people in a cheap RV or camper, adventurers (like Appalachian Trail hikers), or even some stationary expats. Free time is the most important factor when it comes to extended travel because otherwise you’re stuck with work or family commitments that cut short an excursion. Serious backpackers leave home and come back when the money runs out, or even more extreme, don’t have a home. Depending on level of comfort, backpackers can travel for very little money for long periods of time. Economies of scale kick in the longer they are away (cost per day decreases).

The Holy Grail of TravelThe major downside for almost all backpackers is that some day it will come to an end, a heavy mental weight at the bottom of the rucksack. At some point, they’ll need to get a job, start or resume a career, and switch lifestyles and become a vacationer.


For the second category, think of your average American worker. Or anyone who is tied down by a busy schedule, career, self-owned business, or family commitments, and is not financially independent. Got a job with 2-4 weeks of vacation, a family and a mortgage? This is probably you. Every year you take a week off here and a week off there, and that’s the extent of your annual travel time. A lot can be accomplished during a week-long vacation, but it’s only a week, and it serves mostly as a way to recharge your internal batteries so that work is bearable when you return.

Broke People

Maybe you’re broke, living paycheck to paycheck, or working a dead-end job with little or no paid vacation. You’re in debt, you’re struggling to get your career in gear, and you can’t afford a plane ticket to anywhere without a credit card. You’re in category three. If this is you, the truth is you shouldn’t be vacationing too much and you need to get your shit together first so you can become a backpacker or vacationer.

Or maybe you are from a place that hinders your ability to build enough wealth to travel. It’s much more difficult for citizens of less wealthy countries to travel, like the bicycle owner I met in Myanmar on my trip. He needed to save for five to ten years to get out of his country. There’s a reason there aren’t a billion Chinese and Indian tourists in Washington D.C. every year, most don’t have enough time and money. If this is you, you need to work and save much harder than those in countries with stronger economies to make extended travel a reality.

The Holy Grail of Travel

Lastly, there’s the Financially Independent Travelers. Financial independence allows for travel for any period of time without the pressure to return and start or resume a career. An individual or retired couple in this category can stay in decent hotels, utilize airline and hotel points, and book comfortable tours around the world, with the occasional splurge on a five-star hotel.

Much like backpacking, economies of scale apply for the financially independent, because the longer the trip, the lower the costs. It makes more sense from a cost perspective to fly to another part of the world and stay for two months than to take a week-long cruise, or a ten-day whirlwind tour of Hawaii.

My wife and I often envision what our retirement will look like, and it’s the Holy Grail of travel that we crave. But it’s a long road ahead, and not an easy achievement. Not only do we have to save and invest in preparation for this lifestyle, we’re raising a family which is always our priority. Our kids’ health and education is most important, and you can’t exactly travel the world and guarantee the kids will have the best health and education everywhere you go. Perhaps it could be done through “home” schooling while on the road, or at international schools. But the right decision for us and the vast majority of parents is to raise kids in a stable home.

Our goal may not be for everyone. Some people don’t even like to travel, and some financially independent people choose to do other things with their time. The point here this – think back to your most recent vacation or the best vacation you ever took. On the last day, were you ready to leave? Would you have stayed longer if time and money permitted?

For us, the grand strategy continues to be to save and invest while our kids are growing into educated adults. When they are no longer 100% dependent on us, our time will come to freely travel the world again. Until then, we’ll have to make the best of our one-week trips to the beach every summer. I can live with that.

What category do you fit into? Are you comfortable there? What is your take on the relationship between financial independence and travel? What’s your Holy Grail?

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  1. We’re firmly in the second camp for now, but are aiming to be (one day) in the last camp, where we can travel where and when we like 🙂 one day!

    1. Nicola,
      It’s a long way off, but it’s possible to get there. We’re certainly not alone in this category!

  2. Great way to look at travel options for most people. Personally, I value time the most and think the “backpacker” mode of travel is the most relaxing, fun and interesting. In the backpacker mode you can meet far more interesting people and experience every country you visit more like locals do. Since I value time as the ultimate premium being a backpacker affords you the ability to see/experience a lot on the most frugal of budgets.

    1. DivHut,
      I’ve always thought of travel this way. When I was backpacking, there was always that thought in the back of my mind that this couldn’t last forever and eventually I’d need to get a job again. It is the most relaxing way to go, especially if you don’t have an end date. Plus it fits a budget for an early retiree. Thanks for the comments.

  3. I would love to live in a nice lil camper van and travel across north america one day when i retire. Just travel place to place for a year or two would be kool. I hope America lets me back in one day! lol

    1. AG,
      I took one road trip of about 8000 miles in the US and up to Ottawa. I ran into a lot of RV campers and older people just cruising. Seemed like an adventurous lifestyle for them. I’d like to road trip up in Canada one of these days, obviously in the summer not the winter. Grind on!

  4. RBD,

    Amazing article and really “quantifies” what area of the square you fit in. I’m in the second one – I would say with my savings rates from my wages – I have plenty of money to travel but also have 4 weeks of vacation, with an optional 5 with a rollover. In the industry I work – it’s actually hard/difficult to use all of your paid time off, which ultimately is my fault. With that being said – I save usually between 40-70% of my wage based income (depending on the month) and invest into dividend paying stocks at the moment. Always trying to pump up passages of income to hopefully one day have all the time and funds to travel comfortably as you’ve stated. Nice post!


    1. Thanks Lanny. Even with four weeks of vacation its tough to take full weeks off. There’s always the holidays and 3-4 day weekends and doctors appointments that eat up vacation. Most of us are in that vacation square, and most never get out of it, but that’s not a priority for everyone. It is for me!

  5. RBD, Great article. However, you are most definitely missing a category, one I fall into myself. I think you’ll like this category of travelers, because I think it fits with your mindset – and it can save you an unbelievable amount of money

    It’s quite easy to fly anywhere in the world (in a bed) and stay in nice or even luxury hotels for free or at a vastly reduced amount. We’re the mile and point collectors. Between repeatedly getting massive credit card sign-up bonuses and something called “manufacturing spend” you rack up so many miles/points so easily, you can go anywhere you want – in style. Literally anywhere you want in a bed for pennies on the dollar.

    Is it easy to learn? No. But you start slow and figure it out and add-on. Anyone can do it if you have good credit and are financially responsible.

    For instance,this weekend I flew to Panama at the last moment in first-class and stayed at the Radisson in the city. That would have cost me about $2,500. In reality, I spent 60,000 United miles. I can go buy gift cards at an office supply store using my Ink card and effectively buy those 60,000 miles for about $400. That’s just one trick in my arsenal. And we just repeat it over and over like robots while we rack up miles to use. And the Radisson paid me to stay there because they gave me free breakfast and a $20 food/drink credit per night. That was much more than the cost of the points I used to book the hotel.

    And anyone who wants to comment that miles are virtually impossible to use, just doesn’t know how to find the seats.

  6. How about another exception: FI backpackers.

    My husband and I prefer lower level accommodations or staying with friends (& returning the favour, of course). We get to stay where locals stay and we find travelling light is more fun/free (and we miss fewer connections). We’ve done “luxury” and prefer a different style of travel now, though it’s nice to know we can always upgrade when we want to ;). Not big on extended travel yet though. Too much fun stuff going on at home to pull anchor for extended periods…

    1. FTP,
      Thanks for commenting. FI backpacker falls on the grid between FI and backpacker. Maybe you are more in the middle toward vacationer? The four categories are broad, and obviously there will be some people that fall between quadrants.

      Another type of person that came to mind was the super rich. A guy like Larry Ellison(CEO or Oracle) has so much money he can do whatever he wants. But he keeps very busy, so he probably doesn’t take many extended vacations, and is certainly financially independent. Call him lots of money, but no a lot of time. So he’s sort of a vacationer despite being a mega-billionaire.

      1. Fair enough. In the end, doing whatever we want, at whatever level we think satisfactory, is what it’s all about.

  7. Nice post! I’m squarely in the Vacationer category! For me personally, vacation and travel aren’t huge priorities. I have everything I want and need right here at home!

    How about the goal of becoming FI stay-cationers! I think I’m on to something now…

  8. I think I fall into a different category. I’m self-employed and location independent, so I’m able to travel and vacation a lot. On the other hand, I still need to work. I hope to be a financially independent traveler one day!!!

    1. Ah yes, I was hoping to hear from someone like you. You live a lifestyle that a lot of people admire, but yes, you are still working. Kind of a backpacking vacationer, with enough money to travel and traveling often, who is still at work and not yet financially independent. I guess you would fit almost directly in the middle of the box, or outside the box somewhere. Thanks for chiming in!

  9. Some of the happiest travels was when I was a broke student sleeping with no AC on a wooden plank!

    I traveled for 10 weeks in 2012 and 2013 and felt it was a little too much. 6 weeks in 2009-2011 was a little too little so I think 8 weeks is just right!

    I’m a 3 start hotel travel 🙂

    1. I’ve aged since my last long trip, so I don’t think I’ll last more than two months traveling in retirement. But it’s nice to have the option to go longer. I like the idea of just hanging out in a cool city for a month at a time too. That way you can have the comfort of not having to unpack frequently, but still be in a new place worth exploring.