Throwing Caution to the Wind When Traveling to Cuba

I like to think I take trip planning very seriously.  I have my pre-trip blog reading, my Pinterest boards, my Google Maps, and more.  I know from traveling with my girl, Rachelle, to Thailand and going with my family to Scandinavia, that my planning can get a little OCD at times.  When I was planning my trip to Cuba, it all seemed to always be falling apart.

The initial plan was to go with my mom and daughter in either February or May.  That fell through, but my cousin Kathy had some free vacation days at the end of January, so we decided to go.  Timing wasn’t the best as I was just coming back from a pretty difficult trip to Chicago, I had friends moving away that I’d like to spend time with, and I had a daughter in school that I would have to have coverage for the daily pickups and drop-offs.

There’s also many reasons why pushing a trip up can be really difficult on the budget.  I had an idea in mind of what to save by a certain time, but wouldn’t have all that time anymore. Obviously, ticket prices aren’t where I would have wanted it to be at either.  Buying tickets don’t always need to be a well in advance though, so I used Skyscanner and Momondo to find some deals (albeit still a bit more than what I wished for). Traveling is an expensive hobby, I understand that not everyone can do it, it’s not easy for me either but I try to make it work where I can.

My cousin, Kathy, is also a planner.  We both had these visions of creating a mutually beneficial itinerary, but it soon became clear that we don’t really travel the same way.  Being out of your comfort zone can be difficult, and we both had very different things that made us comfortable in our travels.

featured image and this one from José Martí International Airport in Havana

Cuba is still a developing country and since America had only just recently opened up travel restrictions, there are a lot of things that will make going there a little difficult.  What the restrictions still include, the difficulties of outside communication, having language barriers, even how bringing cash and not being able to use your bank cards make for a little uneasiness in travel.  I will be making a separate post regarding all of that.

I wasn’t ready to go, I did do some planning, but not enough to feel comfortable.  My Spanish was pretty broken, in fact I ended up using a lot of “Tag-anish” where all the sudden I found myself speaking Filipino Tagalog in places where I didn’t know how to say something in Spanish.

My cousin almost canceled at the last minute.  The homestay in Havana told us they double booked and we had to find a new place while waiting to board our outbound plane.  There were lots of times that I though for a second that maybe this was a bad idea or maybe I wasn’t prepared enough, letting the fear get the best of me.

In the end I just went, made decisions on the fly, and just rolling with the proverbial punches.

The idea of a comfort zone was thrown out of the window as we left for what was nervously called “adventures”.  We didn’t know what was in store, but we were going to do it anyway.  There’s a thin line between fearlessness and recklessness that we found ourselves balancing on.  As I am making my way through Cuba, and learning as I go, it has really tested a lot of things I didn’t really know about myself… but in the chaos of it all has brought clarity to other aspects of my life.

Have faith in your abilities, have courage in your risks, and run with your fears.  It’s only when we push ourselves into unknown territory that we can truly understand the makeup of our character and know what the next goal should be.

“Sometimes you are just not ready to go… things are uncertain, unplanned, and unprepared… and you still go anyway, just because you aren’t the one to sit on the side either.” From my Instagram.



Leave a Reply

Your email address will not be published. Required fields are marked *