The 6 Months To Go Checklist

Only 6 months to go! Time has been flying as I have been super busy with work and not had much time to do a whole lot of planning. However, we’ve been able to hit some of the big important items that I talked about in my 12 months to go post. What we’ve already done:

  1. We’ve been saving diligently. When we originally started discussing this trip we had intended to leave for a full year and our savings plan revolved around that time frame. What I just realized recently was that when we knocked the year long trip down to 6 months, our savings plan was never adjusted. Meaning – we’ve already met our savings goals and have enough cash to support the trip.
  2. We’ve started the immunization process. The best news on the vaccinations so far is that it’s only cost me $100 out of pocket for yellow fever. All other vaccinations have been covered through insurance. We’ll have to go back in a few months to get the second round of Hep A and also let them know how much coverage we need on Malaria pills.
  3. We’ve told people. While I had been sharing plans of the trip with friends and family for awhile now, I’ve also had to fit this into work arrangements as I searched for new projects. I got really lucky and found something to lock me in until the 3rd week of August and the partner had no issue with no options for extension past that date. That gives me about 3 weeks of prep time before we leave. Kristin also sorted through the work details and locked down an end date in late August.

So what’s next on the to do list?

Route Planning

Of course where we’re going and what we’re doing is the first question that people ask when they hear about the trip. Unfortunately, not a lot of it is figured out and we’re more focused on very high-level planning: what clusters of countries we want to see, where we should fly in and out of, and how long we should spend in each major destination. The good news is that we have made a few decisions on this and I’ll talk about this below.

Locking Down a Departure Date

Picking a departure can seem like such an obscure decision in the grand scheme of things. What it really came down to for us money and what we would do for work. We happen to have a wedding to head to in San Diego in the fall so why not just leave from there? That’s what we’ll be doing. We’ll hop a flight from Chicago to southern California, spend a long weekend with friends, and then hop a flight to London.

Choosing a Rail Pass


When I backpacked Europe while in college we had a 2-week travel plan around Europe and another 2 weeks stationed in Leipzig, Germany. This meant that our itinerary was pretty strict and we had a blow by blow plan for how we would be moving around the countryside. The Eurail pass also offers a steep discount to the young college type (e.g. $802 1 month continuous under the age of 26 vs. $1231 over 26 – that’s nearly a 35% discount!). But now that we’ve grown older and don’t have much of plan, it’s difficult to determine if we’ll get our money’s worth on a pass like this vs. paying point to point.

Quite a few bloggers out their have written about the topic and the moral of the story is this: Sometimes the passes are a good value and sometimes they aren’t; the only way to figure this out is to cost out point to point tickets and compare it to the pass + supplements. We’re nowhere near ready to do that kind of analysis, so for now I think we’ll just wait and see how the route planning turns out.

More Information on Eurail Passes:

Booking Key Flights

Our flight strategy will involve booking major cross continental flights in advance and leaving the details of how we get between these departure cities up for debate. I spent a lot of time looking through what major routes work best and here’s where we landed:

  1. Los Angeles to London
  2. Istanbul to Dar es Salaam
  3. Johannesburg to Bangkok
  4. Kuala Lumpur to Sydney
  5. Auckland to Chicago

For some a round the world ticket might be a good option. Booking as you go might be a more flexible option as well. For us, adding in some general boundaries and time frames around major destinations makes it a whole lot easier to plan out the details. We’ll be booking these major flights over the next few months.


For US citizens, the visa situation really isn’t too bad. There are a handful of countries that require advanced applications, and a handful more that can be issued on arrival. Do your research! What we know is that we’ll need apply for visas in Vietnam and Australia well in advance and the rest should take care of itself. I did find a Wikipedia entry on the topic that has a wealth of information.

The Exit Strategy


We’re both in an interesting situation here regarding our jobs.

For me (as an independent consultant), I can either keep paying myself or put myself on a leave of absence. I’ll keep my medical insurance current so will not need to worry about travel insurance. It all just comes down to the paperwork. I’ll be having a conversation with my accountant to figure out the pros and cons of continuing to pay myself or not.

For Kris, she’s got a great employer that’s letting her take the trip with a guaranteed job when she returns.

For you, this may be a sticky situation. If you hope to return to your current career when you return, I highly recommend trying to negotiate a leave of absence or a sabbatical with your employer. It may seem crazy, but if you are a valued employee you may very well reach a mutually beneficial agreement. For some companies, there might even be a formal sabbatical program. My formal employer (a Big 4) required you to be with the firm for 2 years at which point you could apply for a 1-month, 6-month, or 12-month sabbatical. 1-month was unpaid, 6-month was paid at 40% (plus benefits), and 12-month was paid at 60%. You then were guaranteed work when you returned home and only had to stay with the company for an additional year to avoid returning any pay you may have received during your break. You may have had to written a paper documenting your experience on your return, but that’s the easy part. Really a great benefit if you can take advantage of it.


I got my passport about 7 years ago and Kris got her’s 2 years ago. Many countries will not let you enter if you have less than 6 months left on your passport. So – if this 6 month trip turns into 2.5 years, I may need to return back to the states to get this reissued. We’ll deal with that when the time comes.

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