This post is also available in: Italiano (Italian)

How to do without money on a trip to Cuba is the best title according to google algorithm strategies. Initially I was undecided whether to title this story The Cuba Crisis or Never Leave Without the One You Think You’re in Love With. I had also thought of a lapidary Never fall in love (or think you have), but that seemed excessive.

There will be no pictures taken, simply because I don’t have any. But have faith, it is a story that will not disappoint.

It is probably almost impossible now to run out of money while traveling; there are many more solutions. Also what happened to us probably could have happened only in Cuba. But I think it is still interesting this story.

Below are the two podcast episodes in which I verbally recount my Cuban misadventures.

The background to the trip to Cuba

In the previous months I had derived much satisfaction from my newly singlehood after 3 years as a boyfriend. I had had fun by meeting many women and had returned to meaningful experiences of travels faced in great freedom. I also concluded my art project of having a picture with the same dumb shirt in front of several Roman amphitheaters.

Set of photos of me in the same shirt standing in front of important Roman amphitheaters
This was one of my first silly travel goals

The fundamental reason for all the trouble in Cuba was that I had in my head a person who was 15 hours away by plane from where I was. Moreover, I had not yet seen her in person and for whom I had already devoted all my mental resources for a month.

This Cuba crisis lasted 2 weeks, in July 2011, I was paired with friend. Being without money on the trip was not really the only problem.

I had just declared to myself that I was going to take a month-long sabbatical without women and start preparing for the trip to the Caribbean. But one evening, somewhat by chance, on a dating site I came across her.

In those 4 weeks we could not meet because he was not in Italy. But they were super intense from a virtual point of view, and I became convinced that I was in love.

Virtual boyfriend at the departure of the trip to Cuba

She said she was worried because we would hear from each other much less and because I was going far away. She would have to get unaccustomed to the constant phone contact and video chat nights.

The afternoon before the departure that would take place at dawn on a Saturday, he cried. She also feared that I would find who knows what and how many women. So I made her a shocking proposal: I proposed that we consider ourselves already morose. I felt extremely happy and convinced about what anyone else from the outside would have called crazy. I had been getting tickets for months and could not abandon my friend; if I had met her earlier, I would not have decided to take that trip.

Paired in Cuba, competition to see who is most inadequate

Not all travel companions are suitable for every destination. In particular, for more distant countries, even those considered easy like Cuba, it is best to be very careful, even a little wary. However, one should at least inform oneself.

That time I was none of those things. The friend I went with was a lifelong dear friend and the perfect companion for a drink or a food and wine weekend. But he had never been away that long. Never to a third world country.

My ideal trip was characterized by visits, tours, discoveries. For him, however, the highlight of each day, which had to be repeated often, was stopping at a bar and ordering a beer.

I was not convinced that we were the right couple for the right vacation, and unlike usual, distractedly I did not prepare at all while he was well convinced that we would have to improvise anyway.

On my many trips I had always set out aware of what I was getting into. Both because I considered the preparatory part to be one of the pleasures of travel and because I always thought that going to a place, to which I might never return, and letting some delicacy or curiosity slip away because it was uninformed was a crime. Also, I always thought that organization serves to save time and resources.

You can tell right away that we were off to a bad start

When, during the flight, as my friend was being entertained by his 60-year-old Danish neighbor headed to Santo Domingo on a hunt for fresh meat, I noted that in Havana, contrary to my principles, we had booked to sleep in a place decidedly out of the way, and I began to think that perhaps the trip promised some trouble.

On the night of our departure we went to a party at a bathhouse where my friend drank a number tending to infinity of beers. At 3 a.m. it was not easy to load him into the car: he fell asleep instantly. On the other hand, I was thinking about my belle and was sad to find that if we had been 1500 km superdistant so far, I was another 9000 km away. So after paying for the highway and parking at the airport, I left my credit card in the dashboard of the car.

In the Amsterdam stopover at check-in, the zealous Dutch policemen would not let anyone through. My friend had forgotten, apparently for three years, to remove a switchblade from his backpack.

Before being out of money on the road

As soon as we arrived, we went to a state-owned restaurant for dinner, and immediately got our first catch, not having read that those kinds of establishments were absolutely not recommended by all guidebooks, and not surprisingly we were the only customers. The next morning we enjoyed the lush and for us unusual breakfast at the casa particular (equivalent of our bnbs).

Lots of tropical fruit that tasted unheard of compared to what we could find in Europe, chemically ripened in containers. Little did we know that those breakfasts would be repeated for a long time and that they would be our only sources of food.

The plan was to stay 2 nights in the capital and then tour the island, while we ended up spending as many as 9 days there.

Next stage Traveling in poor countries: being wallets with legs

Guide that we practically did not take advantage of on our trip to Cuba.
We had the guidebook for the trip to Cuba but without reading it we found ourselves out of money on the trip

Trips taken, travel stories divided by continent

Countries visited in my travel stories

Anecdotes, divided by type in travel narratives

newsletter strange things traveling

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Fabio Viroli
Ho sempre avuto tante passioni, ma da sempre più o meno latenti, le principali sono viaggiare e scrivere. Tra le altre cose ho una laurea in psicologia; ho fatto per più di 30 anni l’allenatore di basket; leggo tanti libri; sono stato molto appassionato di sport e di musica rock; e faccio improvvisazione teatrale. IL mio primo romanzo, che non parla di viaggi, si chiama LE TUE GAMBE SONO BELLE COME LE TAGLIATELLE