Travel FAQs

This section was written and published while Jenny & David were traveling. If you are looking for Wedding FAQs, please visit the Wedding drop down menu!

What do you do for work that you can leave the country for months at a time?
David works for himself as a freelance mobile software developer. This allows him to be flexible in his schedule and take short-term contracts that allow him to work for a while then take time off. Jenny left her full-time, salary office job to work several part time and seasonal jobs that didn’t have long-term/winter commitments that allowed her to be flexible and work when she wants. In April 2012, she took on a full-time, permanent position, but with the stipulation that a 2 month trip was already planned for the summer.

How are you affording to travel so much?
Unfortunately, we are not independently wealthy. Making long term travel a personal and financial priority has been our mindset for years. We have intentionally made choices and sacrifices in our lives that have allowed us to do this – not committing to a long-term housing contract (and unfortunately moving excessively), saving money and avoiding overspending on unneeded items. We are not blowing our life savings to travel and have set aside money over time. We intend to stretch our money as far as possible – staying at hostels and traveling to lower costing countries. Lastly, we have become crazy travel hackers to work the system, and our flights (valued at several thousand dollars) have been paid for with frequent flyer miles – earned through a variety of credit cards and other offers; some of our accommodations will also be paid for with points. We learned to travel hack through The Travel Hacking Cartel, FlyerTalk, and The Points Guy.

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.

Where are you going?
We went to California and southeast Asia (Singapore, Thailand, Cambodia, Laos) from January – March 2012 and to the Azores, Portugal, the Tuscany region of Italy, Barcelona,Valencia, and Northern Spain from July – September 2012. See the Itinerary/Timeline section for more detail.

How did you decide where to go?
We spent months and months researching and thinking about where we should go, only to go in circles and make no progress. Being open to going just about anywhere made making a choice even more difficult. Jenny had her heart on Europe or South America, David on Thailand. David made a full PowerPoint presentation (complete with notes) to convince Jenny that Thailand was where we should go, and she gave in, later coming up with the plan to hit Thailand in the New England winter, and Portugal in the summer. David has always wanted to go to Thailand (gorgeous, delicious food, and so different from the U.S.); Portugal is where Jenny’s family is from. David is Italian and Jenny’s always wanted to go, and we both have studied a lot about Spain.

What are you going to do while traveling?
We plan to take advantage of the opportunities to do activities we wouldn’t normally get to do. To name some, we hope to take cooking classes in each country, visit regular tourist attractions, meet local people, volunteer, get some local clothing and be immersed in the culture. We’d also like to learn some language, ride bikes, ride horses, rock climb, hike, and go to the beach. We hope to use this time to explore some creative opportunities – photography, water color painting, writing (and blogging), cooking, and the general making of things. Most importantly, we’re going to eat a lot of delicious food (that is what traveling, and camping, is all about).

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 had to let go of for these trips. We have used a variety of resources including How to Travel Practically Anywhere, Rough Guides, Lonely Planet, TravelFish, and information from other people. Leaving the U.S. for Asia, we only had our flight there, 4 nights in a hotel in Singapore, a flight to Chiang Mai, Thailand, and a week stay there. After that, we made our travel decisions as we went, using websites and guidebooks to decide exactly where to go and how. It will be the same when we are in Europe. This allows more flexibility to make decisions that work, instead of having everything pre-planned, which seems nearly impossible.

Was it safe? Didn’t you go to third world countries?
Southeast Asia hosts millions of tourists each year, though more commonly from Australia, New Zealand, and the UK than from the U.S. We know many people who have traveled or lived and worked in the area and have had a great, safe time. We took all of the precautions such as getting shots (Hep A, Typhoid, Tetanus) and  antibacterial and malaria medication from a travel clinic. We were cautious, using common sense, and following all of the recommendations from various guidebooks and websites. In Europe, there is more concern for thievery and we wore a money belt, but never felt threatened or concerned. Lastly, we purchased travel insurance that offers 24 hour support and includes medical coverage, emergency evacuation, etc.

Where are you going to stay?
We stayed in a mix of hostels, guesthouses, bungalows, and hotels. We used Trip Advisor, Hostel World, CouchSurfing, and our Rick Steves, Rough Guides, and Lonely Planet guidebooks for ideas of places to stay, as well as taking recommendations from friends. For our Asian adventure, Jenny was very picky and read all of the reviews and ratings on various websites to ensure that we stayed at quality locations (with many lists and spreadsheets to help in decision making). For the European adventure it was a bit more go-with-it and find places as we went (including an awkward afternoon spent in a phone booth in Pisa, calling Spain trying to book a hostel in Spanish).


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