11 Months of Travel – Phase 2-B: Cuba (Part 1)

Even though we only spent eight days in Cuba, it was such a rich, complex experience that we’ve decided it deserves at least two posts. This post is a breezy overview of our trip. Joy’s follow-on post will cover political and economic observations.

Challenges of Being American in Cuba

You can’t visit Cuba without considering the complex US-Cuba political landscape and its implications.

Ever since the 1959 Castro-led revolution that ousted dictator Bautista (who deserved to be deposed), rich white Cubans who had their homes or businesses confiscated by the government have been fleeing to the US and demanding sanctions against socialist Cuba. Some sanctions eased under President Obama, but ratcheted up under Trump, who enacted 243 additional punitive measures. President Biden has eased some of these sanctions, but changes are slow in coming. (The US re-opened its embassy ten days before we got there. I’m happy to report that we were not sonically attacked as we strolled past. The only “Havana Syndrome” we experienced was mild tummy trouble.)

Visiting Cuba as an American is easier than it had been, but there are still some travel and financial restrictions. Although you can travel solo, it’s far easier to be hosted by a US-based tour company and escorted by a guide. You need an itinerary that shows you are engaging in one of 12 meaningful travel exchange themes with Cuban people. That means you can explore historical and cultural sites and tropical nature, but not allowed to lounge around on Cuba’s spectacular beaches downing mojitos all day.

Cuban customs only stamps this document, not your passport, so no passport proof we’ve visited

Many hotels are government-owned, and hence forbidden to Americans in retaliation to American sanctions against Cuba, or private hotels sanctioned by the US government for breaking its Cuba-specific business restrictions. That still leaves plenty of hotels Americans can stay in, though.

US credit and debit cards don’t work in Cuba (a result of threatened sanctions against companies doing business in Cuba). And you can’t officially use US cash in Cuba — definitely not in government-owned services. Some private vendors will take US dollars, but generally, you have to convert your dollars into pesos at the airport. Fortunately, our travel agency consulted with us about how much cash to bring and our guide handed us a big, fat envelop of Cuban pesos in trade for our dollars. 

Cuban pesos have no value outside of Cuba, so the trick is to spend ‘em all. On our way home we reached the airport with 1,550 pesos (about $11). I wanted to keep 200 pesos to cover airport peeing expenses (the standard Cuban rate is 50 pesos-a-pee), but get rid of the rest. The Havana airport doesn’t have those giant piggy banks most international airports have where you deposit your unwanted/extra currency and it goes to a charity.  Ultimately, we gifted our left-over pesos and a few US $1s to the bathroom cleaning custodians, who, after all, must have crap incomes. 

Oh, and one final hurdle: US regulations require Americans to retain records of island activities and related expenses for five years.

Private Tour/Private Guide

Cuba tourism dried up during the pandemic but began a slow rebound in 2022— only increasing to 600,000 of the typical 4 million tourists. This has been deadly for Cuba’s economy since tourism is their main industry. Everywhere we went our guide would point out shuttered historic, boutique, and brand new hotels and restaurants that the government had decided should remain closed until tourism improved. Our Havana hotel was a lovely one-year-old French-owned hotel. It had two 25-story towers. I doubt it had more than 100 guests. 

A positive result of the lack of tourists is that our tour, designed to be a ten-person group, turned into a private tour for just the two of us. Our guide was excellent, though he was almost annoyingly informative. He knew everything! As we drove through Havana he’d point to a building, tell us what famous architect designed it, the style of architecture, when it was built, which family or company owned it before the revolution, and what its current function is (a government office, an ambassador’s residence, a shuttered hotel, home to ten Cuban families, etc.). Before you could finish appreciating the building he’d point across the street and say, “Ooh, that building …”.  Lucky we didn’t get whiplash. 

He was the same with classic 1950s American cars. “Ooh, there’s a 1955 Chevrolet Bel Air Sport Coupe. There’s a 1952 Chevy Fleetline, but made into a convertible. That’s a 1952 Oldsmobile Super 88, painted a modern color…”  There are an estimated 60,000 old American cars in Cuba, many of them spruced up and “restored” for tourism.  Cubans are inventive and undeterred in keeping them running, manufacturing replacement parts, swapping in a Mercedes diesel engine, or Frankensteining a Buick fender onto a Ford, or Chrysler seats into an Olds. 

When we arrived in Cuba, our guide greeted us with four bottles of water: two to drink on our way to the hotel and two for the evening to use for brushing our teeth and night-time rehydrating. Our hotel also provided us with 3 bottles. The next morning, our guide greeted us by handing us four more bottles. Soon, we had 10 full bottles, even after using some. Between the guide and the hotel, by the start of day 3 we were up to 14 unopened bottles. Fortunately, our hotel in Viñales didn’t provide water, so by the time we headed back to Havana, we’d made a decent dent in our stash. Even so at the end of our trip we still had 8 unopened bottles of water, which we gifted to our driver and guide. 

Cuba Beyond Havana

We spent most of our time in Havana or its outskirts but also spent three days visiting Viñales Valley, a ridiculously beautiful UNESCO World Heritage site in the heart of Cuba’s celebrated tobacco-growing region. The valley is surrounded by stunning karst hill formations (irregularly shaped steep-sided hills that can rise a thousand feet, and have bases ranging from just a few hundred yards in diameter to more than a mile in width). We also dashed out to Cayo Jutía, a coastal area with astoundingly clear water and fabulously fine sandy beaches.

Rum, Food, & Cigars


Every single lunch and dinner started with a welcome mojito, Cuba’s national drink. A few times we ordered a second round, and a few afternoons we ordered them at the hotel bar. I was never a big fan of mojitos. After tasting 348 of them in a week, I’m still not a fan. There was always about a 1/3 of an inch of undiluted sugar at the bottom of your glass. On a few occasions they would bring the mojitos to the table and then put a bottle of rum down so you could add as much as you wanted. I found this torturous. I always poured less rum than I would if I were making a drink at home because who wants to be a boorish American traveler?

Cuba Libre cocktails were universally disappointing. A) they were always light on the rum (both in terms of the amount added and because it was a light rum, which is lighter tasting and, importantly, cheaper than dark rum), B) they don’t use Coke (that whole US-Cuba thing) but instead use some inferior cola soda (and I’m not talking Pepsi), C) they consistently use pre-made lime juice, and not enough of it. By the way, the name “Cuba Libre” has nothing to do with the common misconception that it’s related to Fidel Castro & revolution. And contrary to our guide telling us the origin of the name comes from prohibition-era visitors celebrating free-flowing Cuban alcohol, Wikipedia tells us that, “Its origin is associated with the heavy U.S. presence in Cuba following the Spanish–American War of 1898; the drink’s traditional name, “Cuba libre” (Free Cuba), was the slogan of the Cuban independence movement.”

Early in the trip Joy and I bought a nice bottle of Havana Club 7 rum. All rums are blends of previous years’ productions, so in this case, the “7” meant that the youngest of the blended rum was aged at least seven years. And when rum is aged more than three years, it turns dark and richer tasting. Because you can’t bring Cuban rum into the US, we had to finish the bottle before we left. We’d end each evening sitting in bed reading and sipping rum. Between the mojitos, occasional Cuba Libres, and our private bottle, we ended up drinking a shit-load of rum. 

Cuban Food

Cuba food is …. understated and repetitive. But it’s a bit unfair to experience Cuban food on the heels of twelve days in Mexico. Yucatecan food is vibrant, varied, and spicy (which is why chef Samin Nosrat chose Merida for the “acid” episode of her TV show). Plus, so many of those Mexican dishes are wrapped in fond childhood memories. While I was in Mexico, Joy was hanging out in Texas and she felt equally underwhelmed by the Cuban cuisine, so there you go. On the other hand, we did get lobster tail three times! At one point Joy asked our guide if we could visit a pharmacy so she could buy some medicine to settle her stomach. Our guide nodded his head and said, “Yes, the spiciness in Cuban food can affect your stomach.”   Turns out, Joy and I had the exact same thought: “What spiciness?”

Cuban desserts, like Mexican ones, tend to double down on sweet.  Our guide and drivers thought we were crazy for drinking the mandatory post-meal expresso without sugar. Cubans love sugar.


Click on the arrow at the bottom of image to see a video of my pathetic cigar smoking skills.

Our Viñales trip included a visit to a private small tobacco plantation that produces leaves for Cuba’s world-renowned cigars. We met the owners and got a personal demonstration of crafting hand-rolled Habano cigars. Naturally, this included tasting a cigar. This was my first ever, and never to be repeated, use of a tobacco product.

I managed to smoke about a tenth of the cigar before surreptitiously stubbing it out. I carried it around for another two days, thinking I might try again, before “accidentally” leaving it behind. When we got home I was so happy to wash the clothes that still carried the aroma of cigar smoke.

Cuban cigars are often named after famous books or characters, like “Romeo & Juliet,” “Count of Monte Christo,” or “Sancho Panza” because historically factory cigar workers were entertained by someone reading aloud to them while they rolled and prepared cigars. I’ve retroactively named my abandoned cigar “Pepe” after the Bugs Bunny cartoon skunk “Pepé Le Pew.”

The Old Hemingway and the Sea

Hemingway is popular in Cuba and an important part of tourism. We visited the small fishing village of Cojímar, where Hemingway’s good friend (and inspiration for the main character in Old Man and Sea) lived. Cuba was very dear to Hemingway, and he dedicated his Nobel Prize to the Cuban people. We visited the bars he frequented, and stopped by Hotel Ambos Mundos, where he lived for years before buying Finca Vigía, a 15 acre farm just outside of Havana. He lived at Finca Vigía for 20+ years and Cuba keeps the house exactly as he left it, books, hunting trophies, and all (i.e. it’s getting decrepit). This is a popular tourist site. Actor Ron Perlman (HellBoy, Sons of Anarchy, Don’t Look Up) showed up just as we were leaving.

A Gift to Cuba

Months ago I bought a new digital SLR camera and telephoto lens for our upcoming Kenya safari trip. I’d been holding onto my old DSLR and accompanying lenses, not sure what to do with them. Joy had the brilliant idea of gifting them to an organization in Cuba. Our tour agency helped us evaluate possible recipients and we chose Centro A+ Espacios Adolescentes, a Unicef and EU-sponsored cultural institution that “aims to achieve a greater social and participatory inclusion of adolescents and to support the development of their potential, with a focus on rights, gender and equity.” The organization offers artistic, performance & communication arts, and new technologies workshops, including photography. They were thrilled to receive our gift and we were pleased that our old camera would have a new life helping Cuban kids learn photography.

Cuba – Worth Visiting!

Even though I started this post highlighting the administrative challenges Americans face, we thought Cuba was a fabulous place to visit and hope that Cuba becomes a bigger American tourist destination in the future. If you use a travel agency that specializes in Cuba, as we did, you’ll hardly even notice all the regulations.

Everyone we met was friendly, gracious, and welcoming. Havana, like London or Paris, is one of those cities that just drips with historical and cultural experiences. You could give yourself whiplash looking at all the things there are to see. I hope our future travels bring us back to Cuba. We only saw a small portion of the island and I’d love to experience the central & eastern areas, as well as spend more time in Havana. Even though I don’t fish, I can see why Hemingway fell in love with Cuba.

Almost every Cuban we met spoke some English, some of them quite well. Our tour included several private visits at museums, art galleries, tobacco farms, snorkeling, horseback riding, etc. Sometimes, the experts at these places preferred to speak in Spanish. They’d ask, “Entienden Español?” and our guide would respond that we understood a little Spanish. This annoyed me at first, but the reality is that Cubans speak incredibly fast and cheat by dropping off the last part of most words. I’ve asked other native Spanish speakers about this and it turns out no one can understand what the hell Cubans are saying. 

Running 11 Month Travel Totals To Date:

One month+ into our eleven month trip, we have visited (though Joy missed out on Mexico):

  • Countries: 3 (US, Mexico, Cuba)
  • US States: 5 (Oregon, California, Arizona, New Mexico, Texas)
  • Different beds slept in: 13 (17 if you include same hotel but different rooms)

5 thoughts on “ 11 Months of Travel – Phase 2-B: Cuba (Part 1)

  1. Tony (and Joy)
    Fabulous. I lived for 30 years in Mismi so some of this was familiar Lots new. I’m sitting in a coffee shop with my son (both of us visiteing my daughter in Washington Missouri) and I’m doubtless irritating him by my frequent bursts of laughter.
    You are a great guide!!
    PS out of otdrr I’m going back to read your take on Mexico


  2. Thanks for the account. It took me back to January 2017 when Sharon and I visited for three weeks. From what you say, things were more open and vibrant then. Food was the same, but that’s not why you go.

    Liked by 1 person

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