An Update from Matanzas

@DanPierson
5 min readJun 1, 2019

Friends:

This email has three sections:

1. The boring stuff

2. An update on my walk

3. A link to photos from my walk

4. A brief report on travel in Cuba (US media is wrong on many fronts)

The boring stuff:

1. If you would rather not receive future emails, no worries! Reply with “unsubscribe” and I will remove you immediately, with my apologies for the inbox invasion!

2. Please do not forward this email to anyone without my permission (feel free to ask me, I will be thrilled you took the time and interest!). Also do not share this content on social media.

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An update on my walk:

I just applied for a visa extension; one month has passed quickly here in Cuba. After a few days of rain, the sun is shining in Matanzas, a small city of 60,000 people about 90 miles south of Miami, and I am in good spirits. I am a little less than 100 miles into my walk across the island.

This update details my last two weeks in Havana, and my first week of walking.

I quickly fell into a routine in Havana:

I helped vendors sell secondhand books in La Plaza de Armas, underneath a statue of Jose Marti. Born in 1853, Marti was the founding father of Cuban independence from Spain. Loosely, he could be called a contemporary of George Washington, 100 years down the line. My new friends handled the Spanish, Italian, and French tourists, while I “sold” to folks from the UK, Canada, and the US. This might be my favorite “work” in the world. Of course, I didn’t transact any money — just helping to put the deals together.

I spent hours writing in the Plaza de San Francisco (photo attached). People from all over the world (including the U.S.) are visiting Cuba, especially Havana.

I toured galleries with my friend Adrian (the aforementioned artist) and his girlfriend Eva. Art is everywhere here; in the street, in mixed drinks, in museums, in the way custodians push their brooms. Most Cubans take tremendous pride in their work regardless of the type, and it shows in the quality of what they produce.

I dealt with street vendors. Like any tourist Mecca (see: Bourbon St., Times Sq, Las Ramblas, Picadilly Circus), many people want to sell things, such as taxi rides, cigars, places to sleep. As you know, I am extremely sociable and love making friends. Thus walking through parts of Havana and dealing with so many people felt like death by w thousand paper cuts. But like anywhere, almost everyone (including these vendors) are good people. I dropped my iPhone 6 on the street and an old man chased me down to return it. I later bought a small chair from his furniture factory.

I had issues with my back. I went to the doctor. He took an x-ray, gave me ibuprofen and shared proper technique for bending down and picking up objects.

I drank and danced nights away in bars, clubs, and homes of friends. Whether I like it or not, I am an oddity here: a 28 year old from the United States who speaks good Spanish and does not have any Latin American familial roots. Everyone wants to know me.

To this last point, leaving Havana 8 days ago came as a relief. I was ready to start my trek.

I took a ferry across the bay, climbed up a hill past Che Guevarra’s home, and started walking east towards Santiago de Cuba, 700 miles away.

I should pause to explain: Cuba is, much like the United States, a nation of immigrants. The Spanish killed almost all of the indigenous population, and in the ~500 years since, men and women from all over the world have landed on her shores. Dark Africans and pale Europeans have mixed to create every shade in between, the product being a stunning beautiful people: Cubans. Everyone here is gorgeous and looks significantly younger than their age (in relation to the U.S.) Good genes.

Very suddenly, as I started my walk, I realized people were walking straight past me, without a second glance. When I spoke Spanish in Havana, foreigners thought I was Cuban. Now, even with my U.S. clothing, backpack, and pale white skin, Cubans thought I was one of their own. It was truly a relief to start my walk as an invisible man.

After a week, there are many stories to tell from the road, but I’d prefer to keep these emails short (and more frequent!).

A few notes on the walk thus far:

I am walking on the highway, back roads, and along the beach. I have slept in hotels, Casas particulares (individually owned b & b’s), truck stop bathrooms and in the brush off the main road. I am living fully and intensely while also taking ample time to reflect and find peace within myself.

Some (brief) highlights include buying lunch for an 85 year old Cuban friend of Ernest Hemingway, invitations into houses alongside the road for lunch and a cold beer, two nights at a “campismo” (think summer camp for the whole family, with a DJ and a whole lot of rum).

One of the more difficult parts of my journey is dealing with the incredulity of the Cubans I encounter while trekking. They are always super friendly, but just cannot understand why I am walking instead of taking a luxury bus, flying, etc. Cuba has every culture imaginable, apart from adventure travel, and it is super tiring to explain dozens of times per day that I am walking by choice, rather than need. Surprisingly, a lot of Cubans (like many U.S. citizens) really just don’t like to walk more than a few minutes.

The upside to these conversations (and all conversations) is that my Spanish has improved rapidly. I am absolutely shocked that, after 15 minutes of conversation, most Cubans think I am from Spain. I am proud that almost all of my Spanish is “de la calle” (from the street), and i continue to learn new words, conjugations, etc daily.

The main danger here is the sun. I am being extremely careful to apply sunscreen several times per day, am drinking a tremendous amount of water, and just purchased a large sombrero for shade. I’m taking very good care of myself!

With that, you’re updated. I’ll try to send out the next one in a little less than two weeks.

Con paz y respeto,

Dan

(these letters were written in 2015 during my walk across Cuba). continue with part iii/iv)

If you’re interested in what I’m up to now, and how I’m applying my lessons from my personal travels to professional endeavors — check out my company Bolt Travel.

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@DanPierson

Adventurer. Founder, @bolt_travel (www.joinbolt.com) unlocking impossible experiences around the world. Formerly growth / biz dev @Lyft, @Getable, @subwaysets