
So I’m finally doing it…on my way to Cuba! Land of mojitos, Castro, and cigars, it is hard to describe the excitement and anxiety I feel now that I am officially booked and ready to go. I think one of the reasons everyone has always been so fascinated by Cuba is because of its perceived exclusivity. The lure of the forbidden and the excitement of the unknown has intrigued all – including myself – for decades. I was now ready to take that opportunity to catch a glimpse of a country frozen in time.
Unlike any other trip I’d ever planned, this was a bit more complicated (or so I thought) given all of the rules and regulations that have tried to prevent Americans from travelling to the little island nation for decades. Contrary to what many believe, as of the writing of this diary entry, the embargo has not been lifted and it is still technically illegal for Americans to travel to Cuba for tourist reasons. As long as you fall into one of 12 approved categories (including family visits, educational activities, cultural activities, etc.), you are good to go! Given that Lesley and I didn’t qualify for any of those categories, we had to approach the trip in the old fashion way millions of Americans have been travelling there for years (i.e., sneaking in!). Thankfully, now there are websites on which you can book flights to Cuba and airlines that have non-stop, direct flights to there which now make planning the trip a lot easier than it might have been years ago. Since we were going the “old-fashioned way”, I booked two different roundtrip tickets: one from JFK to Mexico City and the other from Mexico City to Havana. While there are other gateway countries we could’ve used (e.g., Cancun, Jamaica, Nassau Bahamas, Toronto, Cayman Islands, etc.), this routing just happened to be the cheapest and offered the most suitable flight times for us.
Despite a 2-hour delay leaving JFK, we still arrived in Mexico City with enough time to get our “papers” in order. With the delay, I was duly grateful I booked a 5 hour layover in Mexico City for us. After a pretty uneventful flight [which I am always thankful for after the “Frank experience” (see Norway post for more details)], we went through immigration and customs then made our way to the Interjet departures area so that we could check-in and get our boarding passes for the next flight. The agent requested our passport, tourist card (which we didn’t have!), and immigration form so we needed to head to the “ticket sales” desk (see picture below) to buy the tourist card. It was actually pretty simple getting the card and cost only 250 pesos (less than $20 US). They never even gave our American passports a second glance!


After sitting for a quick bite to eat and assuring our family via Facetime that we made it through the “hard part”, we boarded the 2 hour flight to Havana. We pre-booked transportation through Casa Colonial Yadilis y Joel (our casa particular) so once we located the driver, we headed to the currency exchange since most (if not all) businesses in Cuba do not accept American money. Luckily, we were one of the first outside and the line was still pretty short. Five minutes later though, the line was another story.

On the 10-minute ride from the airport, we began trying to figure out the puzzle that is Cuba. Both Lesley and I were struck by what we saw as it wasn’t what you would expect based on the media. Cuba felt like an enigma: somewhat stuck in the past, but clearly making inroads toward the future. We saw classic cars but inside was the familiar tunes of American music. There were women in traditional dress with cigars in their mouths but the latest iPhone in their purse. We heard locals who could speak and understand only Spanish but familiar with the names Obama, Rihanna, and Beyonce. It was a country of stark contrasts of the highest degree but simply amazing.





Once settled into our casa and armed with a city map from my trusty Google search (printed before we arrived since we knew there would be slim to no chance of getting Internet), we wasted no time venturing out to explore the city. The casa was in a pretty central location near the Malecon as well as the city center so it was a short walk to the restaurant. We set out for Café O’Reilly, however when we arrived, it was packed (didn’t even think to make a reservation) so we headed across the street to a little restaurant called El Frente. They too had a full house but squeezed us in on the balcony. No, seriously. They literally squeezed us on to a very narrow balcony which barely fit the two chairs and tiny table. Dinner included the essential mojito (I had a passionfruit flavored one that was soooooo delicious and refreshing), with empanadas and ceviche for an appetizer, and then the grilled lobster. We were so hungry, we forgot to take pictures of the food but trust me when I say that it was delicious…especially for under $20/person for two courses for each of us and a drink.

With our sights set on Club 1830 for a bit of salsa dancing, we took a bicycle taxi to try and locate it. After negotiating down the price a bit, we were on our way. However, after several attempts, we still couldn’t find it so instead we hit the Malecon. Between the locals we met showing us pics of Obama on their phones, folks huddled in random, low-key WiFi hotspots, and people just hanging out along the boardwalk, it turned out to be an eventful (but long) stroll back to the casa where we then immediately passed out (and no, we never did find the club).


Waking up the next day, we had a delicious breakfast freshly prepared by our host Vladimir. We feasted on fresh fruit, scrambled eggs, sausages, toast, and freshly made papaya juice…all for only $5. I could seriously get used to that kind of treatment!


After stuffing our faces, it was about a 10-minute walk to Hotel Inglaterra to meet our guide for the Havana City tour. We got a good run down on the history of the city (don’t ask me to remember what she said)…but it was HOT! I must’ve drank two bottles of water in the first hour and we still had 2 hours to go on foot.




We actually passed the communications building where we could’ve purchased an Internet card but we took one look at the line and decided against it.

The next couple of hours consisted of several stops, including the Museo de la Revolucion where we learned about Cuba’s revolutionary history, visits to the historic squares Plaza de Armas and Plaza de la Catedral, and the Havana Club Rum museum.







After a jam-packed but culturally enriching morning, it was time for a pitstop at a rooftop café followed by lunch where I also had my first cup of coffee EVER (it was DISGUSTING….never again!).



After a replenishing lunch, everyone was excited because it was the moment we had all been waiting for…the classic cars! After gliding into the backseat of the crimson and cream one (we couldn’t pass up that one!), we stopped in Revolution Square to see the famous Che Guevara mural then continued cruising down the Malecon promenade. It was every bit as exhilarating and fun as we had all imagined!




After one last stop in Miramar (the more upscale area of the city with large colonial mansions, now housing various embassies), we bid adieu to the classic cars and our tour guide. We stopped at our casa for a few minutes of rest but were on our way again, as the time for our dinner reservations at Habana 61 snuck up on us! Only a short walk from our casa, it wasn’t long before we were feasting on ceviche, black beans and rice, lobster, ropa vieja, and enjoying another mojito. Soooooo good!


We had the Parisien cabaret show that night so took a taxi after dinner to the Hotel Nacional since it was too far to walk. Seeing as we still had about an hour before the show started, we purchased an Internet card ($7CUC for 1 hour) and finally texted everyone that we arrived safely (tried to FaceTime but the signal wasn’t strong enough). The show was mediocre (but considered a must-do in Cuba which is why we did it) so we left before the end as we had a full day.
Our second to last day in Cuba was designated as our beach day! We had pre-arranged for a taxi to Varadero also known as the “Cancun of Cuba” (about 2 hours from Havana). The good news: it was only $150 roundtrip and our driver was with us the entire day. The not so good news: our driver only spoke Spanish. As expected, the language barrier and unfamiliar territory was bound to make for an adventurous day. Our first stop was the Saturno Cave, a cenote in the city of Mantanzas on the way to Varadero. Let me just say that the water was EXTREMELY COLD.



After a quick dip (actually a very quick dip!) and a couple of “next top model” shots, we headed straight to the beach! The water was crystal clear and reminded me of the water in Turks & Caicos…soooo beautiful. We paid for a couple of chairs and daiquiris ($8 for everything) then did some sunbathing while talking to some locals with the conversation ranging from everything from sports to race relations…all with us knowing moderate amount of Spanish and them knowing little English. They were actually quite mesmerized by us as they mentioned not really having seen any Black Americans in Varadero before…they actually thought we were Cuban initially (but I think our poor Spanish quickly gave us away!).

After a refreshing dip in the ocean water, we were ready for our lunch at Salsa Suarez. There, we dined on ribs, fried shrimp with coconut mango sauce, ceviche with sides of mashed plantain, rice and beans (yes, it was as good as sounds!).

After stuffing our face and bellies (yet again), we made a couple of last minute stops at the rum house (where we tasted a few different rums) and then picked up a couple of souvenirs at the side of the road before heading back to Havana.

After a quick change, we walked to the famous La Guarida for dinner. Don’t even attempt to go without reservations…it is just that popular (mainly due to the movie “Fresa y Chocolate” being filmed there years ago). It is a charming old mansion subdivided into various parts so you see locals watching novelas as you climb the winding staircase to the restaurant. Of course Lesley and I (being the nosy tourists that we are), took a peek inside a couple of rooms and started watching the novelas right along too! After finally reaching the restaurant and being seated at a great table outside on the balcony, we had to make the hard decision of what to order. EVERYTHING on the menu made our mouths water. We finally decided on the lobster with creamy rice, the oxtails, with the beef carpaccio to start and a mojito (of course). All of our dishes literally melted in our mouths. Though a bit on the pricier side compared to some of the other restaurants we went to, it was worth every penny (and still relatively cheap compared to restaurants in New York!). There is also a rooftop bar above the restaurant but it was packed by the time we got up there so only spent a short time there.




We headed home and took the opportunity to walk along the Malecon again. This time we tried to join one of the “WiFi huddles” to see if we could connect to the Internet (using our leftover card from the Hotel Nacional) but to no avail. Oh well, another Internet-less day and it felt good!
After enjoying yet another yummy breakfast from our host, we set out to enjoy our last day in Cuba and meet our guide for the cigar trail tour. Our first stop was the Partagas Cigar Factory where we listened to the history of cigars, how they make different “flavors”, and then received a firsthand look at actual workers rolling cigars.



Our next stop was a couple of cigar shops to pick up a few souvenirs and put the cigar knowledge we just attained to good use (insider tip: Cohiba and Montecristo are the best ones…or so I heard since I don’t smoke).


We then grabbed a couple of mojitos at a nearby restaurant and listened to our guide talk about her life in Cuba: how her parents are retired but still have “side jobs” because what the government gives is not enough; how those with “professional jobs” (e.g., translators, doctors, lawyers, etc.) make about 60-70CUC/month; and, how nearly everyone has a side hustle because you just can’t live on that one check alone…especially when a pair of jeans can cost up to 25CUCs! It definitely made us grateful that we are afforded the types of opportunities we have living in America.
For lunch, we headed to El Rum Rum restaurant where we had ceviche, chorizo, and lobster (seriously, it was as big as my head) alongside my standard mojito. There was a live 3-man band that played while we were waiting for our food…how I ended up dancing and shaking a tambourine with them, I have no idea.



After a quick freshening up at the casa, we bid our host Vladamir good-bye and made our way to the airport. The line for Interjet as well as other airlines was incredibly long so would recommend getting to the airport at least 2 hours ahead of time. There are a couple of currency exchange kiosks before immigration but they don’t have too much of any one currency so get as much as you can there before passing through immigration because those have even less (I changed my CUCs back to Mexican pesos). Next up was immigration where the officer asked Lesley if she wanted her passport stamped but the officer I went to actually just went ahead and stamped mine without asking (which was fine for me since I wanted the stamp anyway). After a quick and uneventful flight back to Mexico City, we boarded our midnight flight back to JFK and headed straight to work! The joys of having limited vacation days but addicted to travel…until next time!

Five Random Tips From My Experience In Cuba:
- The mojitos are STRONG…I only had one with my meals and I felt tipsy from just that one!
- Make reservations at least a couple of days ahead of time for the nicer restaurants, especially La Guarida as it is VERY popular. A lot of big groups eat at the restaurants around the same time so the restaurants tend to fill up fast.
- Budget for at least $100-$150/day. While that is on the conservative side, there is nowhere that accepts US currency or credit cards and I’ve heard stories of people running out of money!
- When in the airport heading back home, change money before you go through immigration because there are only two money exchange kiosks after immigration, and the amount of currency on hand is extremely limited.
- Head there as soon as you can! Now that the restrictions are being relaxed, everyone (and their mama) are looking to go. Cuba is at the tipping point where its unique, cultural charm is still intact for the most part, but is slowly being chipped away with the increasing number of tourists coming in…and the country is simply not equipped to handle the influx. My advice? Go now…or at least before McDonalds or Starbucks gets there!