Travel FAQs

Where are you going?
Broadly, we’re going to South America. Specifically, to Argentina & Chile, with a possible trip into Uruguay. For specifics in those countries, see our itinerary.

Why South America? Why Argentina & Chile? How did you decide?
Why not? 🙂 Just kidding! A lot of factors drove us to choose South America: David really wanted to go to Patagonia. Buenos Aires is on Jenny’s travel list. We’ve never been to South America (new continent!). They speak Spanish there, and we speak Spanish (mas o menos). Being in the southern hemisphere, it is summer there during our winter (good bye cold snowy winter hell in Boston!). It is beautiful and somewhere we think we’d enjoy it. It is relatively inexpensive compared to traveling in the USA. It took a long time to make a decision about where to go (so many places!) but in the end, we told ourselves it didn’t matter where we went – we just needed to go and we can go somewhere else next time.

How did you decide on your itinerary within Argentina & Chile?
Our current itinerary is more like a rough guide/skeleton. We came up with it from reading guidebooks, looking at online forums, and a long breakfast date with someone who wintered in Argentina for 3 years (thanks Sarah). It’s not set in stone and we’ll make decisions as we go based on what we hear from other travelers, and what works out well (i.e. timing, costs, etc).

How long are you going for?
We don’t have return tickets yet, but since we’re booking award tickets, it’s really flexible. We’ll probably just get a ticket-holding reward flight home then decide as we’re traveling when we’re ready to come back. We’re thinking between 2-3 months, which means coming back sometime in late March to early/mid April.

What about your jobs?
Jenny quit her full-time salaried/benefitted job at the beginning of September, then did a short-term contract position. David resigned his contract position, wrapping up just before we leave. David works for himself as a freelance mobile software developer,  allowing him to be flexible in his schedule (though he won’t be working while we’re away). While it’s a little scary to both not have jobs and know when our next income will be, we are confident that we will be able to find paid work when we return. We recognize that we are incredibly blessed to have this luxury and feel very grateful for our educations, skills, and networks.

What about health insurance?
We purchase our health insurance through the state’s insurance exchange. For traveling abroad, we purchase travel insurance, which offers 24/7 support and covers medical needs, canceled travel, and emergency evacuation. We use World Nomads. Also, health care in Argentina is free!

What about your house?
The last time we traveled for months at a time, we moved about 5 times in one year, hopping between sublets and storage. To be frank, it sucked. So we decided that this time, we’re keeping our apartment in Boston. We got some friends to housesit and take care of it while we’re gone.

How can you afford to do this?
We’re not independently wealthy and we don’t have trust funds. We knew that we wanted to travel long term again, so we lived our lives accordingly.We have intentionally made choices and sacrifices in our lives that have allowed us to do this. We live simply and below our means. Could we afford to live in a nicer apartment or buy a house? Yes. Could we afford to buy a car, go out more, have more stuff, etc? Yes. But we intentionally live as simply as we can to be able to afford to do this. We also work the miles/points system through travel hacking with credit cards and other offers, learning from FlyerTalk and The Points Guy. Our flights/to from Argentina, several internal flights, and several accommodations will all be basically free because of the miles/points we’ve accrued over the last several years. We also keep it simple while traveling – we stay in hostels and modest guest houses and don’t say “it’s vacation, let’s splurge” very often (because that works for a 2 week trip, but not a 2 month trip).

What’s the exchange rate?
The currency situation is a little unclear, as Argentina’s peso has had some stability issues in recent years.  $1USD is about 16 Argentine Pesos. $1USD is about 675 Chilean Pesos. Essentially, we’re not sure how it’s going to work, but we know that the dollar is stronger and will work in our favor. We plan to use credit cards, take pesos out of ATMs, and will also bring some US dollars to exchange, which we don’t normally do but have been advised to do for this trip.

What are you going to do while you’re there?
We are going to do a mix of vacationing, traveling, and just living. The outdoor recreation opportunities are endless – so we’ll be hiking, biking, and spending a lot of time in awe at the beauty around us. There’s possibilities of fishing, rafting, climbing, boating, camping, swimming and more. We’ll take a lot of pictures and do a lot of reading (and writing on the blog!). We’ll hopefully take a cooking class, explore the culture of the cities, go to museums, and visit wine country. We’ll practice our Spanish and see gorgeous mountains, lakes, and wildlife.

How will you get to/between all these places?
For much of the time, we will fly between places. If we’re going to multiple places in one area, we’ll take buses. Sometimes, we’ll take overnight buses that have lay-flat seats. But we’re not doing any 13-hours-in-a-vomit-box bus rides.  In Buenos Aires and Santiago, they have a subway system. You can also rent a car with a driver. We don’t anticipate driving ourselves at all.

Where are you going to stay?
We’ll stay mostly in hostels, with some AirBNBs and regular B&Bs mixed in, found through Rough Guides/Lonely Planet guidebooks, TripAdvisor, and Hostel World. We have a variety of hotel points, so at some point we’ll stay in some (hopefully fancy) hotels. We generally prefer hostels/B&Bs because they usually have free internet, breakfast, and friendly people.

Is it safe? Do you need any vaccinations or anything?
It is safe. Like any major cities, there is the usual crime. It’s not any unsafer than our daily lives in Boston. We take the usual precautions such as getting the recommend Hepatitis A and Typhoid vaccinations from a travel clinic and bringing antibiotic pills. There is no malaria or Zika in the areas we are going.

How do you go about planning such a long period of traveling?
Short answer: Painfully.
Jenny is a type A, over-planner, which she has to let go of for these type of trips. We use a variety of print resources (i.e. taking every guidebook about Argentina & Chile out of the library) and online searching.  We try to read up/get as familiar with a country as we can before we go, with a vague idea of what we’d like to do and 8 nights booked. We then plan as we go so that we can decide to stay in a place longer or shorter if we like/dislike it, and go where people recommend/as we hear about things.  That’s not to say that Jenny doesn’t do research at home and bring many spreadsheets of information that she’s already vetted (i.e. we’re going to blah town, here are 3 places I’ve already checked out that we could stay). This allows more flexibility to make decisions that work, instead of having everything pre-planned, which seems nearly impossible.

How can you go with so little planned? Aren’t you scared?
You bet it’s a little scary! But travel is about pushing out of your comfort zone and trusting that in the end, it will all work out. That’s the adventure! (and, having each other sure helps!)

Why did you take a sabbatical? Why are you traveling?
Taking a sabbatical and deciding to travel did not come as an easy decision. (Will this derail my career? Can I afford it? What will my friends and family think? Am I crazy?). But, after years of burn out and following the expected path, we just knew we needed to get off the path – fearing that one day we’d wake up 30 years from now and wonder where the time had gone and what opportunities we had missed while on cruise control. We don’t want to put everything off until retirement – but take the opportunity now while we are free from most personal and financial commitments to have a life changing adventure. Traveling opens your mind, enhance you as a person, and lays out new opportunities. Lastly, yes, this was scary for us (not settled with somewhere to live, an unknown future, less than secure jobs, traveling to unknown, foreign places). This is the adventure – it’s a little scarier, less safe, and something new and exciting to explore and challenge us.


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