The Journey Before the Journey – Rounds 1-4

By Melissa

I’ve always wanted to live in a foreign country, not just visit, but live and feel the experience of being a local in a place I initially felt anything but. I know that I get this from my parents who met in Naples and had me in the Phillipines.  Ironically, we traveled little throughout my childhood but they spoke of the world with tremendous joy and made it clear that the world was there to be lived in and explored.

David’s parents also loved to travel and passed it on to him but, initially, he was less keen on actually living in a foreign country. I think this was partially, if not entirely, driven by how half-baked my ideas were: “Let’s buy a farm in Normandy” or “let’s run a bed and breakfast in Tuscany” were greeted with “we don’t know how to farm” and “you always complain when you have to get up early”.

Despite not being on the same page about our future plans, we did agree that traveling was one of our favorite things.  We’ve chipped away at the world, or well, Europe, traveling around France, Italy, Spain and parts of Greece.  It was at the end of our trip to Greece, lamenting our need to return back home and to our normal lives when David finally said, “OK, I guess I could do it.  I could live in Paris for a year and use it as a base camp.”  Now, I should make something clear.  We weren’t imminently moving to Paris.  These were retirement plans and we aren’t anywhere near retirement age.

  1. Paris is expensive.
  2. We don’t know it well enough to know where our perfect home base would be.
  3. As an American, it is difficult if not impossible (at least it was for me) to find anyone willing to sign a year lease. Most of the leases are month to month.

It’s that last little factoid (or at least the first and the last) that made us rethink our strategy.  If we have to rent month to month anyway, does it really make sense to create a base camp, which will sit empty much of the time, in one of the most expensive places in the world?  Perhaps not. Thus, a new strategy emerged. Why don’t we rent in Paris for a few months and also rent in other places which may be even more affordable for a few months as well?  We both liked this plan way better. The question was… What other places?

We were visiting my family and staying at my sister’s house when the new scheme was concocted and spent the next several days in a kind of terrets-like world tour shouting random cities at each other.  There are a lot of options.  Eventually it became clear to us that all these great ideas we were generating made it impossible to limit this adventure to a year, we needed two.  Now, working with two years, we could give ourselves twice the options.  Looking at maps, we started to chart out paths bouncing us all over Europe and a little beyond.  Then we found the trains…

I’d seen or read something on the Trans-Siberian Railway and I googled it on the iPad and handed it over to David to peruse.  That kicked the trip into a whole other gear.  The idea of traveling that far by train through such an exotic place excited both of us and opened up our minds to travel, not just to Europe, but all over the world.  We also realized that the idea of getting places in ways other than by plane seemed pretty fun.  I should note here that this is an almost totally untested theory.  My most adventurous train trips to date have been short hops in France and Italy and the commuter train from Acton, MA to Boston (that last one can actually be pretty exciting). At this point the trip was really starting to gain steam.  We flew home from my sister’s house and immediately drove to a bookstore to buy a map.

We then got to work on the real planning.  With pins and strings we wove a path around the globe that would take us to six continents (no Antarctica in the plans yet) and more than 50 countries.  Now doing such a trek over the course of two years is possible, I suppose, but would mean constant movement.   We’ve learned from our travels together thus far that we like to find a place and stay put a bit.  We like to get to know a town without rush.  We prefer to spend hours exploring or wine sipping or people watching.  We could not travel at a slow speed to all these places in such a short time.  There was only one option.  We needed to go for longer.  At this point, we were happily up to five years and felt pretty good about the plan.  We gleefully stared at the map, dotted with more than a hundred pins of five different colors, each representing a different year of the journey.

We could only identify one problem.  We wanted to go immediately.  What was supposed to be a retirement plan was turning into a current obsession, but we were not on the eve of retirement.  I’d just turned 42.  David was the cradle robbing elder at 47.  We had a ways to go.  Now neither of us ever had designs on working into our senior years, but we’d never had the conversation of when we thought we might want to retire and how much money would we need to save to do so.  We were too young for that.

This all changed.  We’ve both worked very hard since we graduated from college and both achieved professional success.  We don’t have children.  Why work for so many years and leave so few for exploring?  I’d just lost my mother and David lost both parents in the previous decade, so we carried a heightened awareness that life is short.  If you’re lucky and live a long life it’s still short, but not everyone is lucky.  We decided to change our plan.  We would stop working and take our trip as soon as we could responsibly afford to do so.  What we wanted to know was could we, of not substantial means, actually afford to do this without going completely broke.  Our financial advisor would help us determine what we could spend and still have something left for retirement, but how do you possibly budget for a trip like this?  Where do you even start?

I think it’s important to stress at this point that I am a planner.  I love researching cities to which we’re going to go.   I’m obsessed with finding the coolest hotels within our budget and knowing where the good restaurants are close to our hotels.   I decided the only way to tackle this was to create the budget like we were leaving tomorrow.  I would create a giant spreadsheet of where we would stay and for how long.  I’d create a food and entertainment budget and figure out how much it would cost to get from point A to point B.  After that simple task was finished, we would have a savings target, assuming we’d still do a little work as consultants here and there when we were home and we’d find ways to offset expenses through airline miles, taking advantage of monthly discounts on AirBnB (which can be substantial), etc. and maybe publishing (and ideally getting paid for it) about our travels, and be able to project how many years it would take before we could really pull it off.

The first thing I did was hit the travel blogs, hard.  We couldn’t be the first people trying to do this.  How did others with similar dreams pull it off?  I always look for travel blogs when I’m researching countries in my travels because they are authentic and practical.  I feel like I can get the real scoop from real people in a way I can’t get from travel magazines, sites or guides.  It was a great place to start.  Bloggers advised us on how they worked from all over the world, the unique ways they generated income (anywhere from house sitting to teaching English), how they found accommodations and even practical things like what to pack for such a long journey.

Our goal wasn’t to work remotely across the world but we got a lot of useful information from these sites.  The two biggest takeaways were:

  • A blog is an excellent way to communicate your journey with your family and friends and, if well done, may even generate a little income.
  • AirBnb has changed the way people travel and makes it possible to really live in the places you visit. The vast number of choices accommodate many budgets and make it easy to splurge in one place and pinch in another.

I can’t even provide an estimate of how many hours I combed through AirBnb creating our first budget.  As a diligent planner, it wasn’t good enough for me to log in, pull up a city and write down the average rent.  That would be a crazy way to budget for a vacation and it was not going to work here either.  No, if I wanted a real budget, I would need to research every single destination like I was embarking imminently.  I would need to actually find that perfect place to stay in each location and I would set the lodging budget based on what I actually selected.  This was super fun.  As is the case in many of our current travels, I would narrow the selection down to three of four choices and ask David to pick his top choice.  Again, the number of hours we spent doing this would probably horrify any reader so I’m not going to even speculate.  I will just be honest.  It was a lot.

After we had the lodging budget all sewn up, I embarked on the task of estimating the travel costs. How much would our airfare, buses, boats, cars and trains cost?  Should we budget for organized tours?  If so, what tours, where, for how long?  I found a fantastic website called “Rome2Rio” and got to work.  This is when the trouble started.


Rome2Rio is a website that allows you to put in the cities you’re traveling from and to, and it provides all the ways you can get there (plane, car, train, etc.), how long each mode of transport would take, and an estimated cost of each.  It is a fantastic site.  I knew I’d hit solid gold and was starting to smugly think this little exercise was going get whipped out in just a few hours when I plugged in the third city on our trip and was told by Rome2Rio that it was not possible to get there from our departure city.  This was not a fluke and was not a flaw in the website.  Much of our itinerary may have seemed logical on a map but made no sense otherwise.  The train tracks, roads and ferries did not always follow the most direct routes.  Parts of our trip were just impossible, others possible but completely impractical.  It doesn’t make a ton of sense to spend 38 hours on a train trying to get from X to Y when going from A to B to C is efficient, cheaper and more interesting.  We felt stupid not considering this earlier.  Randomly picking countries on a map is fun, but we should have been able to deduce that understanding transportation systems is critical in creating an itinerary, especially if you’re trying to avoid planes when possible.

We started again.  We pulled all the pins from the map and replotted, this time with Rome2Rio on the laptop.  We added some spots and removed some spots, and, when we finished, we knew we had a logical travel plan and a budget.  Luckily much of the work I’d done earlier could be used and I find nothing to be more fun than finding apartments on AirBnb so I went back and researched all the new locations.  We high-fived.  Dumb mistake but lesson learned. We had a great new plan and a solid budget.  There were some details still to be ironed out.  I wanted to be sure we built in things like Visa fees and other additional costs.  This seemed pretty minor and easy.  The trip had now grown to six years but we were close to completing the plan.

David was in Vermont at a work conference when I called him and told him all was hopeless. Yes, that dramatically.  Earlier that day, I had innocently added a column to my spreadsheet and thought I’d poke away at educating myself about visa requirements by country.  I was thinking I would do a couple countries a day and plug the $100 or $200 Visa fee in the spreadsheet.  I was once again smug thinking of how impressed our financial advisor would be when she reviewed the plan.  “Wow, she’s really thought of everything,” she’d think.

Just like the Rome2Rio realization, as I scanned the requirements of traveling in a newly learned about “Schengen Area”, I came to the conclusion that we’d planned our trip in the wrong order. You need to be able to get from one place to another and, once you get there, they actually need to let you in.  I have an admission to make.  As an American, I thought I could travel to anywhere in the world (well just about, I knew we couldn’t go from the US to Cuba, for example or that Iran may not be a place to hang in today’s geopolitical environment) and stay for as long as I fancied.  I figured there would be some fees, maybe a little paperwork, but that was it.  Tops.  That is wrong.  Every country in the world has a set of requirements that you must meet to enter and a restriction on how long you can stay.  In fact, being an American (and not a European) traveling in the aforementioned Schengen Area was going to be extremely difficult and actually impossible at the pace we originally planned.  I had never heard of this cryptic area before and neither had anyone else I spoke to on the subject.  However, when I referred back to the trusty travel blogs they spoke of Schengen rules prolifically.  I read all their travel trails with an increasing sense of doom.  There was no loophole.  We were screwed.

The Schengen Zone is a coalition of 26 European countries. It is almost entirely EU nations but there are countries that are part of the EU like Switzerland and the UK that are not in the Schengen Zone and countries like Iceland and Norway that are not part of the EU but are part of Schengen.  So what is it?  It’s a pact between these nations that allows open borders for traveling between them.  It makes tourist travel much easier and makes it less costly and more efficient for these countries to transport goods across borders because they won’t be bogged down by border patrols.  In addition, it’s a cost savings for all those nations because they don’t need to maintain manned border crossing with any adjacent Schengen country.  Sounds great and it is for a lot of people.  Here’s the rub:  As a non-resident of a Schengen country, if you travel for 90 days within any country in the Schengen Zone, you must leave the entire Schengen Zone for 90 days.  So, in a 180 day period, you can only reside in the Schengen Area for 90 of it.  This area encompasses essentially all of Europe.  To travel out of it for 90 days every 90 days was not the plan.  I tried to come up with a way to rework it, but suddenly we were spending inordinate amounts of time in Bulgaria and Romania and winters in the UK.  I doubted David would love that angle.  Reworking was not going to be possible.  We needed to scrap the plan and start again.

So, on a gorgeous late August afternoon, we locked ourselves in our study. On one laptop we Rome2Rio’ed every option, on the other we checked the option against Visa requirements.  All the pins came out of the map and got replotted.  As dusk approached, we looked at each other and smiled.  No longer smug enough to high five, we now had a new, third (or maybe fourth) version of the plan.  This new plan navigates the travel from point to point and takes into account Visa requirements at every stop.  Some countries were removed and new ones added, but the core of the trip stay intact.

Our map

Here’s how we did it: We want to spend a lot of time in Europe. We love the cultures and the people and feel like we’ve only explored the tip of the iceberg.  In order to comply with Schengen requirements and still spend the amount of time we want to in all those areas, we are going to need to apply for residency at different times, in three different countries.  To apply for residency in a county, you need to personally appear at your designated consulate (ours is L.A.) and show records that you can afford to live there without working and proof that you’ve secured residency there, i.e. a signed lease.  Our new plan stretches out the trip to eight-ten years (and over 80 countries) because applying for these Visas is time consuming and, not only do you need to apply in person, you must also retrieve the visa in person, so we need to wait out the processing in the states.  We were planning on spending significant time in these countries anyway (Spain, Italy and France) so we reworked the trip to allow for travel back and forth to the U.S. and consolidated our travel in each of these countries into the years we plan to apply for the visas.  We may not get them.  I’m still unclear how much evidence we need to produce of proof of secured lodging.  I’m hoping if we purchase AirBnb apartments in many different cities in a country and produce those receipts that will work.  We’ll keep you posted on our progress…


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