How it all started:

Ever since I was a small child, I had a sort of fascination with Cuba and Cuban culture. It seemed so mysterious and surreal to me that this tiny little country so close to home was, for all intents and purposes – off-limits (prohibido).

My grandfather spoke (with a mischievous twinkle in his eyes) of the amazing cigars, the intoxicating music, and the warm disarming potency of aged rums. He was rarely ever seen without a stogie tucked tightly between his pudgy little fingers. And when he talked about Cuba, it was if he was regaling his own personal exploits (although he never made it there in person). He was single-handedly the biggest influence on my wanderlust having traveled the world in the military as a sailor, and when he spoke of his adventures it was as if he was reading straight out of a Hemingway novel. He was a most excellent human, and the finest example of a gentleman.

In college I majored in Literature, and of course soaked up every possible class that offered anything Hemingway related. Dr. Bruce Branco MacJames Stark was by far my mentor in all things Hemingway and Fitzgerald. It was during these years I knew someday I would walk the streets of Havana for myself.

How my trip to Cuba came to fruition was sort of on a lark. I was having cocktails with a friend of mine who owns a distillery and we were discussing the various tasty rums of the world. Being a distillery owner, people are extremely generous with sharing their wares (especially when looking for peer approval), and in this particular case he happened to procure a bottle of El Ron De Cuba – Havana Club 7 Year Aged rum. As we sipped the rum and enjoyed a fine Dominican cigar (ironically it was an Arturo Fuente Hemingway Short Story) I started day dreaming of what it would be like to travel to Cuba and experience it for myself. The embargos had been eased up on by the Obama Administration and travel to Cuba seemed to be something quite attainable – in fact as you read on you’ll find that my trip to Cuba was easier and more hassle-free than even traveling to Europe. *Note, from starting to plan the trip to actually arriving in Havana was less than 10 days*

So I started doing some research online, investigating possible travel arrangements. I’d heard the easiest way to arrange flights into Cuba was through another country like Canada or maybe the Dominican Republic and only if you were American. The only other way was to take a cruise, and dock in Cuba for a night (hardly seemed like enough time to even start exploring). There were all these sordid stories of people traveling to the Dominican and taking a small plane over to Cuba with even more sorted details about the Passport situation, and I started to get a little less enthused. Yes, it would be an adventure, but how many hoops did I want to jump through just to get there?

While all travel presents some uncertainty and the unknown, I was certain I was going to have one pitfall after another. But after a little more intense web browsing I found that making my arrangements for Cuba were easy breezy. In fact, I thought a little “too easy”…

I booked a straight flight from Milwaukee, WI to Havana, Cuba with a single layover in Atlanta, GA. I couldn’t believe I got a round trip ticket for $320.00 (US) with only one stop. It was less expensive to fly to Cuba than it was to Florida… I left Milwaukee at 7am and landed in Havana at noon…

When you get to the international gate for Cuba in Atlanta, all you have to do is show them your Passport and they’ll print up a Cuban Visa for you right there on the spot ($50). If you were foolish enough to buy one of the Cuban Visas online from a third party vendor for $100 (which is what I did) the ticket agent would just look at you and shake their head. (Rookie move I guess, but hey – I’m headed to Havana so who really cares what the ticket agent thinks…) I’ve never attempted to travel via another airport to Cuba, so I highly recommend going through Atlanta because clearly, they have the routine down pat…

I thought it was funny that my Visa showed up completely blank and all I needed to do was write in my information. Name, Date of Birth, Passport number and Country of Origin – that’s all you need to get into Cuba! LOL.

So here I am in the research / planning phase, and I quickly discovered that Air BNB is a magical place! Not only was I able to browse all of the rentals in Havana, but they had amazing bios on the owners, and incredibly helpful tips on how to travel to Cuba.

I secured a top floor 2 bedroom apartment for 8 days for the total sum of $210.00 (US). This was a total shocker to me, and even more impressive was that immediately I started getting emails from the owner. Enma was absolutely amazing. She said she could help me make arrangements for drivers / cars, restaurant reservations, and even exchange my money at a better rate than I would be able to get. You see, Americans get charged a premium exchange rate for the US Dollar, but a Cuban national gets a citizen rate which is much less than what American’s pay. So she exchanged my US Dollars for a very low rate. Cuban nationals are charged only 8 points for exchanging US Dollars, whereas Americans are charged 18 points. She was very gracious and only charged me 11 points (total deal). American credit cards are not accepted anywhere in the country, so you really need to bring plenty of cash with you if you want to do and see all the things.

PRO TIP #1: If you have a credit card with international banking and you’re an American, you can call you bank and request all of your charges during your trip (you have to give exact dates) are processed through a European outlet. In my case, I called my bank and they processed all of my transactions through a branch in Germany. Because it was being processed through a European bank and not an American bank, all of my credit card charges in Cuba processed without any problems. (To test this theory, I tried charging one of my meals on a different credit card and I got the fastest decline ever seen…)

PRO TIP #2: When I was shopping on Air BNB they have a section for EVENTS and other things to do. So while I was making my lodging arrangements, I started looking at local things to do. I booked a rum tour, a tour of Havana (new and old), arranged a car to Finca Vigia, booked a cigar tasting, and arranged for a walking tour of Old Havana. The beauty is that I paid for everything through Air BNB on my US debit card before I even went to Cuba and didn’t need to spend my much cherished stash of cash.

Now on to Havana!!!

During my flight over I brought a copy of The Old Man and The Sea – perhaps a cliché but it was the perfect read in anticipation for my arrival in Cuba – and simply devoured it on the flights to Havana. I was done reading it well before I landed, and now I was even more charged up to see Cuba, and especially Finca Vigia (that’s where Hemingway’s Wheeler is now stored). I also brought along my Lonely Planet Pocket Havana guide book with all of my destinations already mapped out in black marker on the map of the city. All of the restaurants I had reservations for, all of the scenic touristy spots, ALL of the bars and nightclubs, and of course my home on the top floor overlooking the malecón (Havana’s Rivera). I had dinner reservations every night at 9pm at a different “underground” restaurant. (I’ll be posting later about dining in Havana)

When I arrived at the airport, there was a definite energy in the air. Things seemed completely chaotic, but I soon found out that it was just another normal day in Havana. Everyone was line hopping, and darting in and out, and all the while they were being funneled through the same set of customs agents everyone else was going to see. It just made things congested and more problematic then it needed to be, but hey – I’m in Havana…

After I cleared customs, I went into this huge room where everyone’s luggage was being dumped, and I had to sift through a few layers of bags, luggage, luggage-like things, and a few live animals in order to find my bag. Once I did, I headed outside to get my first taste of Cuban air.

The air was thick, humid, warm and tropical. It had a familiar smell (similar to the air in Mexico) – salty and faintly sour. People were bustling about hailing cabs. Yelling could be heard when family members saw each other in the crowd and reunited. Horns were blaring in the distance as traffic into Havana was starting to form a line into the city from the airport. And the mid-day sun came out from behind the clouds and lit up the landscape right on queue.

Enma had arranged for a driver to pick me up at the airport. And when I walked out of the airport I met a man named Luis who who had a sign with my name on it. I quickly waved to him and he greeted me with a resolute respect, tipped his head slightly, and welcomed me to Havana. He reached down and picked up my backpack and asked me to follow him to his car.

When we got to his car, it was exactly as I’d seen in so many movies and pictures – a classic 1956 Chevy BelAir – in mint condition.

Here’s where I’ll stop for the moment…

Keep your eyes peeled for my next installments of daily life in Havana. Day 1 picks up from where this post leaves off…

Stay safe – stay healthy – vote for Biden!

Cheers! ~CK