Hace 21 Años
I hadn’t been to Cuba since 2002, when I literally had to sneak in. Cuba was off-limits to Americans when I first visited 20 years ago. It wasn’t Cuba, but The United States, who, by law prohibited “us” Americans from going there. It could be done, illegally and under the radar, but it was a major pain in the ass and involved flying in and out of Havana from a third country…in my case – and the most popular in this scenario – Mexico. I had to buy my paper airplane ticket in cash, in Mexico, as to not create any electronic evidence. And I certainly couldn’t blog about my trip to Cuba nor post anything about it on social media for many years. I’m long past the statute of limitations, which is why I can publicly talk about it now. But going to Cuba in 2002 as an American was a very rare feat and something you weren’t supposed to do…and I loved every minute of it!
Addicted
That first trip to Cuba was my first experience going “somewhere I wasn’t supposed to be” and I absolutely adored it. It was a new kind of high for me – that took control of my body and my mind. It was the kind of adventure that made my hairs stand up, before, during and after. Years later I’d continue this m.o.,with trips to places like North Korea, Libya, South Sudan, Somalia, Venezuela and a handful of other Level 5 “Do Not Travel” destinations. It was all exhilarating and it all started with that first trip to Cuba so many years ago. Right or wrong, there’s just something so satisfying about this forbidden fruit.
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Law and Order
This time – in 2023 – it was much easier and much more legal to go. The only requirement, as an American, was to select one of the following 12 categories of “authorized” travel to Cuba:
- Educational Activities (study abroad for students, teachers, and school staff) and People-to-People travel for regular Americans
- Support for the Cuban People
- Professional Research
- Public Performances, Clinics, Workshops, Athletic and other competitions, and Exhibitions
- Journalistic Activity (for electronic and print media reporters, including bloggers)
- Humanitarian Projects
- Religious Activities
- Family Visits (connecting with close relatives in Cuba)
- Activities of private foundations or research or educational institutes
- Exportation, importation, or transmission of information or information materials
- Certain authorized export transactions (for businesses and NGOs)
- Official business of the US government, foreign governments, and certain intergovernmental organizations
The easiest and most common category that American visitors to Cuba select is number two on the list above: “Support for the Cuban People.” It’s literally just a tick of a box when you check-in for your flight online; a silly formality. But what does it actually mean? The law defines it as: “Contributing to the development of Cuban civil society or advocating for the independence of the Cuban people from the government; meaningful engagement and interaction with individuals in Cuba.” In layman’s terms, it means to support and engage with local businesses and independent entrepreneurs like artists, musicians, food vendors, filmmakers, guides, etc. This includes eating at privately owned restaurants. According the law, you’re not supposed to going here for “tourism.” The rules basically say you can’t go here to just lay on the beach and sip mojitos…you have to be actively “supporting the Cuban people.” But, then again, who’s watching you? At the end of the day, it’s really the honor system.
Apparently the big no-no (under the American law) is staying at hotels – most of which, if not all, are owned by the Cuban government. Instead, you are supposed to stay at locals’ houses (casa particulares), which you can book via Airbnb. So, that being said, for the record, I am not telling you that I stayed at The Hotel Nacional, the biggest and most famous hotel in Cuba (which of course is government owned). Any photos of the property you see on this blog were taken when I “visited” the hotel to have “meaningful interactions with locals.” No where in this article am I going to tell you I booked a room there or stayed there. Capiche? Now that we’ve gotten all the legal stuff out of the way, it’s time to chronicle the trip, which was absolutely mind-blowing for so many different reasons. So settle in, and enjoy. Here we go!
Diplomatic Pickup
An actual foreign ambassador was waiting for me at the airport when I arrived. There is a very long story here, which I will only give you a small snapshot of here. Earlier in the year, I was one of the first Americans to be admitted into Syria since the pandemic. The man who helped me with my visa just happened to be the Syrian ambassador to Cuba: My paperwork was submitted to the Syrian embassy in Havana. I may or may not have sent some treats along with my application and was able to strike up some pretty decent rapport with the ambassador during the whole visa process, to the point where I would now pay a visit to him in Havana. He insisted on “sending a car” to pick me up, so I was floored when it was actually the ambassador himself waiting for me at baggage claim, especially because I’d arrived at 1AM. What a welcome!
I’d need a full dose of melatonin to get to sleep that night. Between the excitement of being in Cuba (which is a thrill in itself) and being picked up and shuttled to my lodging by the Syrian ambassador, I was surprised I could sleep at all. My mind was racing!
Dining with a Diplomat
I hadn’t gotten into bed until after 3AM, so it would not be an early morning. It wasn’t until noon when “the car” came for me and took me to the embassy. I’d spend over an hour with the ambassador, chatting away while sipping that strong Cuban coffee and enjoying pastries served on a silver tray. I learned a lot about the ambassador, including some of his career highlights – he’d served as Ambassador to Brazil, France and The US. I learned about his family. He touched on American politics. I was so worried I’d say the wrong thing, so was really cautious anytime he broached the subject of American-Syrian relations. It’s not going well. Overall, the Ambassador was just a really pleasant man and I enjoyed our time together immensely.
I almost regretted bringing up “Slowjamastan,” an 11-acre “micronation” that I just so happen to be The Sultan of. I hope he didn’t think I was a complete weirdo, but I had to set the scene before presenting him with Slowjamastan’s “Raccoon of Friendship” award, right?
I guess I didn’t weird him out too much, because he soon after invited us to lunch. We enjoyed a two-hour meal in a private room at La Ferminia – wonderful food and conversation. Was I in a dream? None of this felt real!
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You Say You Want a Revolution
After we were dropped off back at the hotel, I grabbed a cab to Plaza de la Revolution for some official Slowjamastan publicity photos while I was still in that suit. It was obscenely hot and humid, but I wanted a few more official Cuban “diplomatic” pics. I got ’em!
We were so full from the late and very large lunch, but I’d made 6:30 reservations at Paladar La Guarida and my conscience wouldn’t let me skip out on the commitment. La Guarida is an extremely popular and highly-rated traditional Cuban restaurant – Beyoncé, Jay-Z and Barack Obama have all eaten there. We each ordered a drink and I forced myself to eat a bowl of watermelon gazpacho. It was a travesty we didn’t eat a full meal there, but there’s no way we could’ve enjoyed another bite. Plus, something very special was happening back at Hotel Nacional that I just had to be a part of. I couldn’t wait to rush back.
You’re Uninvited
I would either have thee night of my life tonight or I was going to jail. There would be no in-between. (And I hope you got the Alanis Morissette reference.)
Slowjamastani intelligence had alerted me to an important function back at Hotel Nacional where all the ambassadors would be. (Okay, The Ambassador has mentioned it.) It was a party thrown by the Saudis. I knew it was the real-deal by all the shiny black sedans with fender-flags lining the driveway of the hotel. This was the closest thing I’d ever come to a full-blown UN meeting and I just had to crash it.
Less than six weeks ago I was getting escorted out of NATO headquarters in Brussels, but somehow I had a better feeling about tonight. Maybe it was my personal time with the Syrian Ambassador that gave me the courage to crash the party. Maybe it was the very strong daiquiri at La Guarida? I don’t know. But what I do know, was that within 90 seconds I had strolled right in like I belonged there, finding my way into the buffet line, chatting up the Saudi gentlemen behind me with the red and white kaiffyeh as I piled rice and beans on my plate. Ambassador function officially breached.
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That’s What Friends are For
I was already in too deep. There was no turning back. I had to go all in or leave. There was no in-between. So, with a plate of rice and pineapple in my left hand, I used my right hand to shake hands with almost every person wearing a black suit and flag lapel in sight. There were a lot of them!
First, the Lebanese Ambassador to Cuba. He returned the positive energy and I was excited to tell him about my favorite ice cream stand in Beirut. Then I exchanged greetings and took selfies with the Burmese Ambassador and his lovely wife. Next the Moroccans; they’re usually a fun bunch and tonight was no exception. Drinks in hand, we talked about both Cuba and Morocco. The Nigerians were awfully gracious and kind and I wrapped up the night shaking hands with the Qatari Ambassador. My performance would’ve been perfect execution if I hadn’t misnamed his flag. All in all, what an incredible night, hobnobbing with world leaders in Havana. This felt like one of those really ridiculous dreams. It was amazing to be able to meet so many Ambassadors whose countries I’d all been to, and now they all know about The Republic of Slowjamastan! Oh no he didn’t…Oh yes he did. I did indeed introduce myself as “The Sultan” and explained I was the leader of the world’s newest nation, asserting our independence in December 2021. I’m not sure if they bought it, but I gave it my best shot to sell it! I did not break character! This was the moment I have been training for for years.
Cuba Libre
I enjoyed the rest of the night back at Hotel Nacional (where I wasn’t necessarily staying), sipping on Cuba Libres and enjoying a fantastic quintet belt out Cuban classics. I was almost in tears when they switched to Brasilian Bossa Nova. Their cover of Jobim’s “Wave” was a ten out of ten. Not gonna lie, the flutist made my heart go pitter-patter. Some of my favorite moments of this entire trip included just relaxing on the big couches outside, sipping drinks and taking in the music. The weather was divine at night. I needed this relaxation so much – just what the doctor ordered.
Sunday Cruise
I don’t remember being able to tour Havana in a convertible classic last time I was in Cuba, but of course, that was 2002: Uber and Airbnb were yet to be invented and I’m pretty sure internet, in general, didn’t exist in Cuba then. But today, with so many travel apps, booking websites, and of course, influencers (I hate that word), it was no surprise that city tours in colorful 1950s cars are one of the most popular activities in Havana. Who wouldn’t want a guided tour through the old streets of Havana, with a local, inside one of these historic hoopties?
Marlon was our guide, along with his driver and camera man, as we rolled around the city in the 1950s red Chrysler Windsor. They refer to these classic cars as old-timers here. We visited five municipalities in Havana, beginning in Vedado, then Miramar, and then onto the iconic Malecón and over to Old Havana. The last stop was Habana del Este, where we took in some of the best views of the city.
My amigo Chuck is a great friend, but a travel partner, eh. He has extreme sensitivity to heat. So by the time we arrived back at the hotel, he was done for the day. That was okay with me! I left Chuck in the shade and luxurious AC of the hotel (that we weren’t necessarily “staying” at) and set off on foot to soak up as much of Havana as I could for my only full day here. I started with a walk down the street for ice cream. An ice cream cone, should be simple, right? Not in Cuba.
No Ice Cream for You!
The story behind Coppelia is interesting. The ice cream parlor was originally built as a project led by Fidel Castro and named after his longtime secretary’s favorite ballet. Today it is still state-run. The building itself is as interesting as the story: The flying-saucer-shaped structure represents a UFO and was influenced by the biomorphic modernism of Italian, Mexican and South American modernists like Pier Luigi Nervi, Felix Candela and Oscar Niemeyer, who saw the opportunity to leave behind the rectangular forms of the steel high rises and utilize the plasticity of reinforced concrete. Populist ideology helped shape the design and use of the public space. Source: Wikipedia.
I was really looking forward to taking photos of this very peculiar building but was stopped in my tracks by a security guard before I could even fire off the second photo. My Spanish is pretty decent unless I have to debate. I don’t speak Spanish well enough to win any arguments (this bodes well for the Latina girlfriends), so I didn’t have much choice other than to leave after being told the place was closed. I circled back after I saw people enjoying their ice cream inside – didn’t look closed to me…but upon seeing the other side of the building, I got it: There was a line the size of a queue at Disneyland…just to get into an ice cream shop! Wow. The marvels of communism. I moved on an enjoyed perusing a small flea market next door.
Not gonna lie, I was a little disappointed. I’ll need to get a cone from Coppelia next time, I may need to show up at 6AM for a place in line. I am determined.
Johnny Walker
My favorite thing to do in old cities is to simply walk: down big streets, small streets, alleyways, through markets, parks and plazas. Anywhere and everywhere. And Old Havana is one of my all-time favorite places in the world to get lost in. Every single block is its own masterpiece. The endless rows of crumbling Colonials is a “Flip This House” producer’s dream come true.
I passed by José Martí‘s house and checked on the Hostal Valencia – the place I stayed during my first trip to Havana. I was sad to see it closed. A lady across the street told me it has been shuttered since the pandemic but would reopen soon. I sure hope so – I had such wonderful memories there.
I made a pit stop the corner El Dandy bar to refuel. I enjoyed another Cuba Libre and a plate of meats and cheeses while watching street life unfold just inches away from my table.
Tony’s House
iPhone in hand, I snapped away, capturing images of some of my favorite buildings, including the one below, with the colorful tile. I was caught in the act by the house’s owner, Tony, who spotted me from his third floor window.
“Heeeeeey! Eees my house!”
Was I in trouble? Not at all. He immediately insisted I have a tour inside and drink rum with him. Well if you’re twisting my brazo, Tony!
Inside, I climbed a set of pre-Castro Italian marble stairs, met Tony’s family, was shown his small religious shrines and was taken into every single room in the house. I even got to hear Tony’s feelings on politics and living in Cuba. He showed me his food ration cards. This was a money-can’t-buy Anthony Bourdain moment and I was here for it.
Sights, Smells, Sounds…
One of my favorite things to do while exploring foreign territory is to listen. Perhaps it’s because I’m in the audio business (radio), but I often enjoy the sounds of a place as much as its sights and smells. I have a special affinity towards the vendors and street hawkers. I adored the “lone bread guy” below – watch the video. His deep and rhythmic “Aaaaaaaye, pan suavé!” bounced off of the apartments on each side of him and echoed down the street. I covertly tailed him to get some of his shouts on video. I loved this guy!
I soaked up more of that fabulous house band and a few more Cuba Libres back at The Nacional for my final evening in Havana.
Before bed – which I’m not saying was at Hotel Nacional – I headed back out onto the street to try and find some bottled water. I ended up running into a friendly hotel staffer out on the street who offered to help me get the water. Remember, this is Cuba – there aren’t just grocery stores and bodegas on every corner – it’s complicated. According to him, the local stores only take Cuban currency – which I didn’t have – but he would get change for me. What a nice young man! Surprise, surprise; he ended up disappearing with my cash. It didn’t take long for me to realize he wasn’t even a hotel employee, just a master scammer. He was good. One day I will learn. One day.
Havana Good Time
I did nothing but chill the next morning before leaving for the airport. Three nights in Cuba was just what the doctor ordered and I found myself already plotting my return before I left. This place is so special.
Here’s the part where I will twist your arm to book s trip to Cuba. I’m usually not so insistent, but as a reader of my blog, I implore you to get to Cuba soon…for the following reasons.
- First and foremost, I love Cuba because you are soooooo close to home (if you’re American), yet you feel like you are a world away. As you can tell from my photos and stories above, this place is soooooo different on so many levels. Sure, you can go to Puerto Rico, Dominican Republic, Bahamas, etc…but you’ll see many similarities from home: McDonald’s, KFC, Wal-Mart, even things you don’t think about much, like modern infrastructure and capitalism. But in Cuba??? This is the country where time just stopped, 60+ years ago. It’s a completely different world, but yet only an hour flight from Miami. It’s just mind boggling to me that things can be so vastly different, yet so close.
- Go before it changes. It’s already changing, albeit slowly. When I went in 2002, I loved that I didn’t see even one cell phone. That was great. People had phones this time. If things change politically and Cuba opens up to capitalism, it will turn into a completely different country overnight. Do not miss this opportunity to see it now.
- It’s easy and now completely legal to travel to Cuba. Even I was shocked when I realized multiple US airlines fly to Cuba every day – I was astonished. Who knew? I don’t remember any of this being announced. Maybe US laws keep the airlines from marketing this destination? (Remember, the “no tourism allowed” regulation.) But yeah, the flights are running! No need to travel through Mexico first.
- It’s safe. The government keeps their thumb down on the people there. The good part of that is that tourists are highly protected and looked after. People know not to mess with visitors. Except for the guy the took my money. Had he been caught, he would’ve received prison time or even just “disappeared.”
- Because you need to stop going to boring places. I’m careful and cognizant about not telling others how to travel, but it breaks my heart to see my friends go to the same basic beach resorts again and again and again. Why even leave the country? Here is an incredibly rich experience like nothing you can ever imagine, and close by. Cuba will change your life!
- Support of the Cuban people. It’s not just a box on your travel document. When I’m having a blast sipping daiquiris and cruising in a classic car, I try and remember most of the people here are miserable. However every dollar I spend with the locals helps them, so by simply visiting Cuba, you are bettering the lives of the people there.
Hi Randy, this blog post is fantastic. Your time spent with Dr. Obeid alone, would have made for a great story, but then crashing the Saudi party on top of that, that’s like something you only see in the movies!
Alanis Morissette’s “Uninvited” immediately took me back to the Nicholas Cage/Meg Ryan film “City of Angels”. Have you seen it? Paula Cole’s “Feelin’ Love” is another great song, that’s on that soundtrack.
Thanks for posting so many great photographs and those two great videos. The beautiful cars and architecture…that flutist!!!
Getting invited into Tony and his wife’s home for a drink, and getting to see their ration cards was just extraordinary.
I have been curious about Cuba for a while now. A few years ago, I read a somewhat raunchy novel called “Dirty Havana Trilogy” by Pedro Juan Gutiérrez. Since then, I’ve wanted to smoke cigars and drink rum on The Malécon, just like the protagonist.
Thank you as well, for the travel tips/advice for Cuba. When I get back to Florida, I’m going to start studying Spanish in earnest.
Wishing you continued great adventures,
Danny (currently on Koh Chang, Thailand)
p.s. love the straw fedora and the guayaberas. With your beard, you look like a legit Cuban “big wheel”.
Wow, thank you Danny, I appreciate your feedback so much…so very much, amigo!