My Solo Walk Across Cuba: Stories from the Side of the Road Part 1 Getting In


Before I begin, let me layout the backstory.  Many of you know me well and my love affair with the crocodile shaped island across the Florida Straits, but many of you don’t.

My inaugural trip to Cuba was Oct 6, 2013.  I led the first ever Abercrombie & Kent People to People trip to the island. It was a place I never thought I would see in my lifetime, something always on the list but never contemplated seriously due to the politics between our countries.

It was an eye opening experience, seeing the Caribbean as it was 50+ years ago, a step back in time for sure and I became curious.  We went on a charter flight, on a special license issued by the Office of Foreign Asset Control through the US Treasury Department with definite do’s and don’ts with major consequences for non-compliance.  There is a book simply within the confines of that first trip but that’s for another day.

I continued returning to the island, learning the nuances of place, the idiosyncrasies of people, forming and re-forming my own thoughts on everything from Fidel Castro to rum and even my own definition of friendship as I became closer and closer to people there.

I was witness to the major events of the re-engagement of our two countries.  I was in Havana on the day the second of the Cuban Five was released and returned to Cuba.  I was in Havana on Dec. 17, 2014, the historic day of the exchange of prisoners and the announcement of the re-establishment of diplomatic relations.  I was in Havana in March of 2016 when President Obama arrived.  I celebrated with the Cuban people these historic events and became ever more entangled in their hopes for a future with better opportunity and fulfillment of their dreams.

It is now November, 2016 and I have just returned from my 31st trip to Cuba.  The latest change to restrictions on Americans in Cuba helped me to be able to accomplish something unique.  Now, Americans can go to Cuba not just with a group, but on individual people to people education programs.  And I decided to embark on the most intimate of people to people experiences.  I decided I wanted to peel back yet another layer in my understanding, I wanted to learn Cuba better from the street level and the way to do this was to slow down, escape from the growing tourist areas and simply walk.

And walk I did.

Forced Planning

I planned and executed the trip within about a month’s time frame.  I made an announcement to my colleagues in September, during an Around South America trip I was running.  Ridlon was going to be gone for a month leading a trip in October and I wanted to go have an adventure myself.  So I said, “hmmm, I think I’ll walk across Cuba”, which given the company I was in at the time and given their understanding of me, everyone simply said, “cool” and had no doubt that I would follow through.

I didn’t want to have a plan or a goal (besides just walking across the island the long way) but concern for my safety being top of the list for both my husband and my friends on the island, I did end up planning a route and some contingency, emergency action type plans.  I became a bit frustrated in the planning of the plan because I simply did not want a plan…you get it right?  I just wanted to be the free spirit and go…..But before I could get my butt onto the flight, I had to satisfy my US concerns that there was an extraction plan for accident, a plan for unwanted male advances, check in procedures each day etc….Then I had to satisfy my Cuban concerns that there would be planned places to sleep (they really didn’t like my pitch a tent idea) and a route that wasn’t too desolate, and that I was properly fed and watered.

Ok, I get it and I am appreciative and grateful for all the care, concern and help.

But again, I really didn’t want a plan.



I started walking at home about two weeks before I left and had a friend ship my backpack, trail runners, single person tent and water filter down from my home in Montana.  I was walking 6-8 miles a day in the Florida heat and up and over the bridge near my house, the only hill in the area.  I was satisfied as I wasn’t planning any days more than 10 miles.  The idea was not a marathon hike but a walk with plenty of time to sit and chat, no agenda…..a plan yes, but no agenda.

I was super excited and a bit nervous on the way to the airport.  Once through security I filled all my water containers.  The ability to find clean water was one of my few concerns and even though I had a filter and chloro tablets I preferred not to use them.


Reality Check

I boarded the flight in Miami and about 10 minutes after take off had the bomb drop in my gut.  Really?  What am I doing?  Did I just commit myself to walking the first 100 miles across Cuba?  I have no idea what life along the side of road is like. And I realized my biggest fear, something I had no idea would hit me.  I loved this place that I knew from from the window of the bus, the 5 star properties, the ability to always have an English speaking guide with me and a ride when needed at the snap of a finger.  I ate in the upscale private restaurants and everyone was super friendly of course!  Now I was about to get off the bus literally and what if, WHAT IF I didn’t like what I found?  WHAT IF I DIDN”T like the Cuba I was seeking?  What if my illusions of the past three years were simply that?  Wow, I hadn’t even considered this possibility.

It was right about then that the music I was listening to stopped and I realized that my phone had shut down.  I had entered Cuban air space. No big deal right?  Except that for some reason my phone completely shut down.  I mean, I lost everything!  My google maps, my CAMERA!, my pedometer, my DICTIONARY and all my CONTACTS.  Holy crap!  I rummaged through my pack to re-assure myself that I had indeed written down, the old fashioned way, phone numbers and emails of my contacts in Cuba including the PIN number to my Cuban cell phone which would become my lifeline.  Okay, got that.

I had planned on using my iTranslate feature and dictionary on my phone for communication.  My Spanish was basic because I always relied on my Cuban guide when I couldn’t understand.  So now, I said to myself…..”self….you’re gonna wing it!”  Buena Suerte!!!! (good luck in Spanish).

I landed in the city of Holguin, the birth province of Fidel Castro and the gateway to some of Cuba’s beautiful beach areas.  There were no tourists on my plane, only Cubans who always clap when the plane lands, whether to give thanks for a safe flight or for their return to see family I’m not sure.

Holguin is about the middle point of what would be my walking route.  I would take a taxi west to the town of Las Tunas and then walk for the next 11 days from Las Tunas, through Holguin and eastward to the coastal town of Guardalavaca.




My first test was immigration.  Usually I have a print out of the itinerary for my group and I am always pulled out of line and questioned.  I am quite used to this.  So immediately when immigration spotted the “gringa” I was instructed to head to lane 3.

The first question is always, “Do you speak Spanish?”  And no matter how good or bad my Spanish ever becomes, my answer is always, just a little because if we did this in Spanish they would ask a gazillion questions.  In English it is harder for the immigration officer and so the interview is substantially shorter.  However, I really hadn’t planned what I was going to say so in the spirit of “winging it”  I decided just to be completely honest.

Here is how the conversation went:

Immigration (I) :  What is the purpose of your visit?
Anita (me):  People to People Educational visit
I: Where are you staying?
Me: In Las Tunas in a casa particular (B&B basically)
I: How long are you staying there?
M: 1 night

I: then what?
M: Um, I’m not sure I’m walking
I: What?
M: Yes, I’m walking from Las Tunas to Guardalavaca
I: What????? That’s a long way…..walking??????
M: Yes
I:  Where will you stay?
M: Um, I don’t know I hope that people along the way will help me
I: But you don’t speak Spanish
M: Right
I: and you are walking?
M: Yes
I:  So how do you plan to have people to people interactions if you don’t speak Spanish?

M: I have a dictionary (smile!) (and in this case, now I actually didn’t thanks to my phone)
I: So, let me get this straight.  You have a place to stay tonight in Las Tunas, you are then planning to walk 100 miles to Guardalavaca without speaking Spanish and hope that people will help you find places to stay?
M:  Yes, but I also have a tent
I: ????????
I:  Do you have any friends here?
M: No (technically not true but I didn’t want to put anyone in an awkward situation with immigration)
I: No friends?
M: I don’t know anyone in Las Tunas (this was true, my friends were in Holguin)
I:  I see from your passport you have been in Cuba many many times
M: Yes, I am a tourist guide for Americans but I usually am in Havana which is why I have no friends here (big smile)
I: but now it is only you walking with no friends and no place to stay and just your dictionary?
M: Yes ( this was actually becoming fun!)
I:  Do you belong to any organizations?
M: No
I: NO organizations (oh my. I was seeing Alan Gross all over again and 5 years incarceration in my future)
M: No, I really don’t (oh, she is wondering about my hidden agenda.  If she had been in on the conversations at home before I left she would realize that not only did I not have an agenda, I tried not to even have a plan!)

I kept on smiling and I think she honestly had no idea what to do with me next so she stamped my passport and wished me luck….I WAS IN!!!!

I had decided to have some set reservations for the first day so that I wasn’t worried about simply what to do when I stepped out of the airport, but my friend in Germany who books lots of people to Cuba had difficulty getting confirmation for a taxi for me to Las Tunas so in Miami before I left I emailed my non-existent friend in Holguin who gave me the name of the woman who arranges taxis at the airport and said she would be waiting for me with a ride.

Sure enough, I was easily spotted as I stepped out of the airport, the only American woman with a backpack anyone has ever seen and she immediately said,” Anita?  Ah yes, I have a taxi for you.  Ruben will drive you.  And since you have a “non-existent” friend in Holguin who told me you were coming here is the discounted price.”  All was well.

I thanked her and hopped in the van with Ruben, who spoke no English.  He immediately told me to sit in the front seat with him and his first question as we turned out of the airport on the road to Las Tunas was, “So, do you have a boyfriend?”……….

And so it began.

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