Six Month Sabbatical Travel – Part Two – Decision Making

What would you do if you had six months where you could work from anywhere in the world?

This is Part Two of a three-part introductory series about the process of planning a six-month sabbatical.

Part One: The Planning Process
Part Two: Decision Making
Part Three: Miles and Money

On September 15^th, 2017, I made my first flight reservation. I found a great deal on JetBlue to use points to fly to Costa Rica, my first destination. However, unlike most trips where I have a few glasses of wine and spontaneously book a flight, I found myself hesitating. Was I really ready to just pick up and leave my house… my home? Is this really how I want to spend six months of my life?

I stepped away from my computer for a few hours and started reflecting. Although this was just a single reservation, it felt like a bigger commitment to my overall journey. I had argued with my dad previously about how to spend this time and I began to reconsider whether this was the right thing for me professionally and personally. So I did what any normal person would do and asked Google how others had spent their sabbatical. Now I don’t necessarily think that other people’s experiences or opinions are always right for me, but I do find that you can typically pick up on themes from a collection of people. And the overwhelming theme that I came across was to do something that makes you feel uncomfortable. Being away from home for that long certainly would make me uncomfortable but it’s such a unique opportunity, I knew I’d regret it if I didn’t take advantage of it. So I went back online and booked my first trip… and it’s funny, as soon as the first one was booked, I had most of the rest of the six-month trip booked within the next month. I felt great conviction about my decision and excitement for my sabbatical experience which I think was reinforced through the initial JetBlue booking.

“the overwhelming theme that I came across was to do something that makes you feel uncomfortable”

Anyway, here’s what I came up with based on my criteria from Part One of this series.

January 17 – February 15 – Costa Rica

I actually spent two weeks in Costa Rica in January of 2017 and I absolutely loved it. I spent most of my time on the beautiful north and west side of the country but I left feeling like there was so much more to see. I spent a few days in the rainforests but would love to see more of that. I never got to go down to Manuel Antonio National Park nor did I see any of the Eastern side of the country. Plus the Pura Vida lifestyle really resonated with me. People were kind, relaxed, and had a wonderfully positive outlook on life… and who can blame them living in such a beautiful place.

So excited to be going back to Costa Rica! Such a beautiful place!

So I’ll spend a month in Costa Rica, head home to Philly for a few days, and then it’s off to…

March 3 – April 4 – Cape Town

I’ve always wanted to go and was supposed to go a few years ago but got trapped at JFK in a snowstorm and had to cancel the trip. Ultimately, this was a no-brainer for me, especially since the university calendar usually makes it difficult to travel this far during the peak times in Cape Town. Where Cape Town really shines is in the diversity of things to experience. There’s rich and interesting culture, stunning natural beauty, wildlife, a world-class wine region, and much more. I can’t wait!!

April 5 – April 10 – Vienna

I found a great award ticket from Cape Town to Vienna and booked it even though my ultimate destination is Budapest… but I figured if I’m in Vienna, I might as well spend a few days there.

April 10 – May 7 – Budapest

Budapest is a place I know very little about but has always piqued my curiosity. I can’t really even articulate why I’m drawn to it. I’ve really enjoyed my experiences in Zagreb and Ljubljana over the past few years and maybe I imagine Budapest will offer a similar experience… but really I have no idea. Weather is a bit hit or miss this time of year but winter will be over so I’ll take my chances. Plus, most of the rest of Europe fails the “Reasonably Affordable” criteria.

May 7 – May 18 – Prague

Another more reasonably priced European city with lots to offer. I’ve seen a lot of Europe already but somehow always missed this tourist favorite.

May 18 – May 23 – Paris

The original plan was to stay in Prague a bit longer but my parents will be spending May in Paris so I’m excited to get over to see them. Plus, Paris in Spring sounds pretty spectacular!!

May 23 – May 30 – Amsterdam

All of my extended family still lives in Holland and Belgium so I’ll spend some time here visiting with them as well. Plus, Amsterdam has long been one of my favorite cities (clearly biased here… but it really is awesome).

May 31 – June 6 – Singapore

Again, I found a great award ticket and booked this flight from Amsterdam to Singapore even though my ultimate destination is…

June 6 – July 15 – Bali (pending volcanic activity)

The period from May 7^th to June 6^th violates one of the criteria I set forth in Part One of this series which was that I didn’t want to bounce around from place to place and that I’d rather immerse myself somewhere for a longer period of time. However, the opportunity to spend some time with my family meant that I had to break up some of my time in Europe. So, by this time, I imagine I’ll be fairly worn from all the travel so I want to do something comfortable and maybe a little more relaxing. Bali is one of my all-time favorite destinations but the on-going volcanic activity at least puts that idea on hold so I haven’t actually booked this yet.

If Bali doesn’t work, I’m unsure about the alternatives.  Europe is out because it’s just unaffordable, especially during the peak months. Southeast Asia is tough because it’s rainy season in several countries and winter is beginning in countries lower in the Southern Hemisphere. I’ve got some time and I’d ultimately love to go and support the Balinese people who are perhaps the most kind and generous people I’ve met. I guess we’ll see…

So what would be your top destination(s) with a six month window for travel? Leave your ideas in the comments below…