Where to go:

The first step in any trip is figuring out where to go. It’s obvious, of course, but when you start planning a multi-destination trip it can really get complicated and the only way to do it right is to set your own priorities.  Nobody can tell you what to do, because in the end it is your trip. Our process took about two to three years! When we first started seriously considering a trip like this, we began by listing all the places we have ever wanted to go in the world. We then plotted the “dream destinations” out on a world map. Having a visual, we decided on a “flow”, which for us was in an eastward direction.  Due to time limits, we prioritized destinations as “must” and “like” to go, and started pricing out the tickets.  Ticket pricing proved to be a big filter for the trip since smaller, more distant destinations that had unfavorable cost/time ratios were cut in favor of staying within our budget. Weather was also a consideration, mostly because we didn’t want to have to pack for a wide range of temperatures. Finally, world events (both natural and man made) changed our plans more than we would have liked. Originally, we planned on having a Middle East leg and a Japan segment. For various reasons, we decided to drop both of those segments and spend more time in the other destinations we had picked out.

After all of this, we made a “soft itinerary” to help us estimate the amount of time we would need to see the things we wanted to see at a destination. It also gave us blocks of time to play with and build a trip within our time limit. This “soft itinerary” was probably the most useful thing we did early on, since we later also used it as a guide to buy tickets, build a budget estimate, and make our actual itinerary.


After making a “soft itinerary” based on the destinations that made the first cut, we looked into what visas would be necessary for the trip. The best source for us was the international travel section. The site links to embassy websites and gives instructions on how to go about getting the visas. Visas are obtainable either on arrival or in advance.  For those that are required in advance, you can obtain them in person at a consulate or embassy, through online applications, or through visa processing services. Sometimes visa processing services are actually required if the embassy has outsourced their visa processing (India). You’ll have to look on the embassy sites for the most up to date information, fees, and requirements.

For anything that wasn’t an “e-visa”, we decided to go with a visa processing service. For $50-$60 per visa for processing, the price is much less than traveling to the embassy or consulate twice (or more) per visa, hotel nights there, tolls getting there, fuel or flights getting there, and most importantly, the cost of taking days off work. Additionally, the agents look over the application to make sure it is filled out correctly and since they’ve already established rapport with the embassies/consulates, if there is a mistake or problem they can sometimes correct it without requiring you to reapply (and pay the fees again!). As a side bonus, you’re able to pay for the whole thing with a credit card and get rewards instead of paying for the cashiers checks to apply on our own.

Most visas must be obtained within 90 days of your first possible entry into the country.  This is tricky, because it is often advisable to get flight tickets after getting visas, but visa applications require dates of entry and exit!  On the visa applications, we listed the estimated dates from the”soft itinerary”previously mentioned. Starting early like this also helped eliminate the need to pay for “rush” fees which can add up very quickly. Unfortunately, the passport must be out of your possession for as long as it takes to get all of the visas processed. The company we used was great, so, if you are wondering who to go with, we can tell you that we had a great experience with Travisa.


There are many options, and the best choice for you depends on a variety of factors, most important being how long you plan to travel, how many flights you plan on your trip, and how much money you have to spend. We originally looked into RTW tickets from airline alliances (such as OneWorld), but we quickly discovered that this was not what we wanted due to the number of conditions required and the amount of time required to complete a trip. RTW tickets from alliances often have rules about minimum stays at stops, max segments per continent, and lots and lots of fine print that can really complicate planning and budgeting. We ultimately decided to go with a travel agency that specializes in booking multi-destination plane tickets. The company is called Airtreks, and we’ve been very happy with them thus far. Their website is very easy to use and their trip planner/airfare estimate was pretty close to what we actually ended up paying. Another bonus with Airtreks is that all trips booked with them include post-departure travel insurance. Also, you have a personal agent as your point of contact in the company. If you’re considering a multi-destination trip you should definitely check out their trip planner to get some estimates. It’s actually pretty entertaining to see what other stops get added on for some destinations.

This was definitely a source of unexpected expenses in the lead up to our trip. There’s not much up front satisfaction in dropping a few hundred bucks at a time on vaccines and travel medications, but considering the alternatives, it’s definitely worth it. We investigated what was recommended for each country by going to the CDC’s Travelers’ Health website. Fortunately for us, we had gotten most of the necessary vaccines from the Miami-Dade County Health Department when we volunteered in Haiti. Among many other things, we ended up needing a couple more vaccines, anti-malarial medications, as well as prescriptions for any and every concern we could think of: sleeping pills for overnight flights, common antibiotics for travelers, Diamox for high altitude sickness, etc. Even without prescription drug coverage, most of the drugs needed were pretty inexpensive. The one exception however, can be the anti-malarial medications. Very briefly, your choices for anti-malarial medications are as follows: Chloroquine (Cheap, but many strains are resistent to it),  Doxycycline (Cheap, but side effects including bad sun sensitivity), Meflaquine (Only needs to be taken weekly, but moderately expensive and can cause severe nightmares and mood changes), or Malarone (No resistant strains, best side effect profile, but also the most $$$). We were lucky enough to get a supply of Malarone from a coworker who had recently come back from SE Asia and had a lot extra. In general though, Malarone can run about $5 a pill and for a lengthy trip this can really add up.

Ultimately, you will need to seek out professional advice for what the necessary vaccinations and medications are for you based on your health history and itinerary. For this, our general recommendation would be to seek out a local travel clinic.  If you don’t know where to start, Passport Health is a company with many locations around the US.


If you feel like there hasn’t been much budget bargaining in the planning so far, you are right. Visas, flights, vaccines, and medications are pretty much set at the same price for everyone. Sure, you can shop around, but the prices aren’t going to vary that much. Fortunately or not, you can make or break the budget by having an accommodation plan. There are many choices and budgets to choose from, but you have to be careful to stay within your budget, without risking staying somewhere you might feel dirty or uncomfortable. If resort type accommodations are your preference, a budget dorm at the “right” price will probably make for the “wrong” vacation. Conversely, if you are more of a budget minded traveler, you might end up paying a fair bit more than you’d care to if you decide to stick to hotels and resorts for a multi-month trip.

We are pretty flexible and have slept in everything from five star resorts to open tents with mosquito nets without problems. I mean, sure, we like luxury, but it isn’t a requirement.  Our only requirements are that the proprietors don’t try to scam us, we can get showers, there is some security, and we don’t get bed bugs/scabies. For the trip, we have “first choice” lodgings where we have reservations booked, and comparable “back-up” lodgings to look into in case there is a big problem with our original lodgings. In planning on where to stay, we looked at countless reviews at every destination, and shopped around for typical prices for the area.  We looked in travel blogs to see if any of them mentioned their lodgings, and on occasion we found some useful tips/pictures. So, we’ll try to update and review our lodgings in a separate page as we go along.

Ground Transport:

Ground transport is obviously gonna be a huge part of logistics if you’re planning to go anywhere besides the airport.  Looking into what type of transportation infrastructure a country or city has is necessary if you actually plan on seeing anything! Sure, you can hire a taxi just about wherever you go, but, at what cost?  Is it the most convenient, time effective, or budget conscious choice?  In a congested city like New York or Tokyo, a train will get you into the city from the airport much faster than a taxi for a fraction of the cost. However, between Boston and New York, you can pay $75-$100 for a train ticket, or $15 for a bus, which, depending on the time of day, could be quicker than the train! The bottom line is there is no set formula or rules across the board for the best ground transport. It really depends on the location.

For ground transportation planning, we used Wikitravel, Tripadvisor, local transit authority websites, and various guidebooks to see what was feasible, at what price, and how long it would take.  We wanted some overland (or water) trips, but we didn’t want a trip full of transit stops day after day. After all, this is supposed to be a vacation! Some trips will be booked on arrival, and others had to be booked ahead of time. Seat 61 is a great site describing the ins and outs of train travel anywhere in the world.


While you want to relax, it is important not to sit around watching TV or browsing the internet when you have paid good money to be on the other side of the world. Making a flexible itinerary is the best way to ensure your days are productive. We like to make a “travel book” whenever we go anywhere.  It has everything from flight information, airline rules, embassy locations, lodging addresses (and maps), and a day by day schedule of places to go and see, things to do, with small descriptions and historic facts about the different attractions, on and off the beaten path.

To make this, we get a small notebook with non perforated pages, preferably flexible, and a small pocket to hold tickets or small notes. “Moleskine” notebooks definitely fit the bill here. We collect information needed into documents, and print the information out and paste or tape it onto the pages of the book. We highly recommend this technique, as internet access isn’t always available, and when it is, printing documents you have saved online isn’t always possible. Duplicates are online, and copies are printed and left at home with family for safety/security. This also allows family to reach us or know where to find us in case of emergencies at home or for us on the trip.

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