David and I traveled to Cuba for just under two weeks in the spring of 2019. We spent the first five nights in Havana before heading to Vinales for five nights. We ended with two nights back in Havana. We flew directly between Cuba and the US. Traditionally Americans have flown through Mexico or Central America to get to Cuba but during the Obama administration, things began to thaw out.

Prior to our trip, we did some research and talked with people we knew who had recently visited Cuba on getting around, what to do, and what to expect. The biggest thing heading into our trip was carrying money because nobody accepted credit or debit cards. Not just as Americans, but all tourists needed to have cash. And as counterintuitive as this sounds, we would get a better exchange rate if we had Euros instead of US currency. Even with exchanging US dollars to Euros to Cuban Peso, we still had better exchange rates than straight US to Cuban. With a no plastic policy, I was very nervous about walking around Cuba for two weeks with so much cash. We were going to be mugged! As with anywhere in the world, be mindful of your surroundings but I had some peace of mind knowing that if I were to be robbed they would be going to prison for a long time (so they had little to no incentive to give me a hard time).

We were in Miami the day before we flew to Havana and would be flying to Havana direct with American Airlines. We took this time to get our visa’s in order and not feel rushed or stressed in the morning. It was $200 for both of us that we needed to pay with a credit card. There were several forms for us to fill out us as well. One was a Visa slip for each of us, one was a health slip for each of us, and one was a general customs card. And we could NOT travel with an electronic boarding pass, we’d get a paper pass in the morning that would also need to be stamped in recognition of filling out our paper work and paying for documentation. Some of the paperwork would be given to Customs in Cuba, some paperwork we kept for when we left. Throw away nothing! Keep any and all paperwork you get from airports, customs, even all of the receipts from restaurants and shops. I’m glad we did this ahead of time, because it was chaotic and disorganized in the morning.

I had a feeling that in my lifetime I would be able to travel to Cuba, but David didn’t think he ever would. David and I both took pictures of the gate monitors as we boarded our flight. Getting through customs and collecting our baggage was not as tough as I thought it would be. The biggest headache was how long it took for our bags to come out. At one point it almost felt like they were walking one bag at a time from the plane. Our driver was waiting for us and we quickly zipped over to our AirBnB (Casa Particular). Along the way our driver pointed out where The Rolling Stones did a free concert for one million Cubans, saw a horse drawn carriage cruising through a major roundabout in the middle of traffic, and buzzed through Revolution Square before pulling in front of our building.

Our first flat was fantastic. The views of the city and harbor were amazing from the 6th floor balcony and there was so much space. While we did feel safe in Havana, it gave us extra peace of mind having to unlock three separate doors and gates to get into the flat. Ismary, the live-in caregiver, walked us through the apartment telling us about any housekeeping like how to use the internet and what time we would want breakfast. We would get a hot breakfast every morning included in the price of our stay.

We spent the rest of the day acquainting ourselves with our neighborhood with lunch, grocery and cigar shopping, and dinner at Bicky’s (our go-to neighborhood spot with a/c). Our grocery shopping was quite an experience. The closest store was barely larger than my kitchen. There were three counters: 1 for cleaning supplies, 1 for kitchen electrics, and 1 for food and beverages. David and I wanted to pick up some bottled water, food and alcohol. They had water, beer, and rum, but not exactly what we were wanting for snacks. Where’s the fresh fruit fruit and veggies? Where’s the fresh food of any kind? Bread, milk, eggs, meat? We’d later find a bakery and other market with milk and meat. We ended our first day sitting on our patio watching the sunset drinking Havana Club rum and smoking cigars. While lounging and chatting about our observations we heard somebody whistling and calling out from the street below. When we poked our heads over the balcony to see a young man pulling his cart full of what looked like bread and butter. He would show up every night in the later afternoon, early evening.

Another thing David and I did before we left was watch a documentary about the Buena Vista Social Club, an ensemble of Cuban musicians bringing music from before the Revolution that I think is like a Cuban/Latin Jazz. While many of the members from the film have now passed there is still a nightly show in Old Town Havana near the Capital building. So on our second night, we took him up on his offer. It’s like a Dinner Theater experience. There are different pricing options for what meals and drinks you want included in your experience. David had the fish, I had the chicken. Both meals came with a salad, dessert, and 6 drinks (3 for each of us). Bring on the Mojitos and Cuba Libres!

The gentleman who picked us up from the airport offered to make a reservation for us to the BVSC and give us a ride. During our drive he asked how we were getting along, what we had done and what our plans were for the rest of our time in Havana and Cuba. During our drive we discovered that he’s got a bit of a side hustle going on. Even with the concept that Communism is meant to be a system that takes care of its people regardless if you’re social status, everybody we met seemed to have a second job or side hustle. While being a taxi driver is his main state run job, he also does private driving (which explains why he has a nicer Russian car) as well as having a few Casa Particular’s that he rents out (like ours with AirBnB). He offered to drive us to Vinales and back for a reasonable price. Cue the swarthy broken english accent that as soon as they start yelling at you across the street for your business to eat at their restaurant (slapping their menus) or will take you to their 2nd cousins husbands shop across town for the best prices on illegal contraband that fell off the back of some truck. Our drivers prices for a private ride really were reasonable and within our cash budget.

Each morning we would spend time writing and reading. The rest of our days were spent exploring Havana. One day we took a cab to Revolution Square taking the long way walking back to our flat exploring parks and restaurants. The day we went to Revolution Square taking the long way home, David found a John Lennon park and that’s where we headed. Along the way we saw a statue/memorial for Julius and Ethel Rosenberg. There was a bench with a statue of John that you could sit next to. We stopped at a French restaurant across the street for music and Mojitos. We stopped into the Yellow Submarine music club before heading to the Malecon to walk home and have lunch (Cuban sandwiches with a couple of Heinekens). Two days we spent in Old Havana by the capital, exploring shops, restaurants, coffee spots, and beer of course. David scouted out two places that made their own beer.

In getting to Vinales for the second part of our stay, David and I had the battle between taking up our driver on his offer for a private ride or figuring out the public taxis and buses. Do we splurge and go for the private ride? He’ll provide door-to-door service. Where do the shared taxis and buses pick you up? Drop you off? How do we even figure out this information with our limited internet access? We don’t even know what these outfitters are called to start our search? Can they provide door-to-door service or will we be huffing it with our bags?

After working through our cash budget of what we could afford, and feeling overwhelmed trying to figure out the later option, we went with a private ride from our airport driver. This was a source of anxiety in addition moments of not feeling prepared or in control in a cash only, no phone, minimal unreliable data/internet access third world country. As easy going as I try to be I always have my purse and an exit strategy. Cuba tested that mindset in our first few days.

The drive to Vinales was a continuation of the rundown conditions of Havana. What I would consider their equivalent of an Interstate, is more like the 4 lane country highway. Lines are not existent (thank goodness there’s a median to differentiate traffic flow). We stopped along the way at a rest stop gas station where it was similar to the communist market in Havana. No luck in just grabbing a Diet Pepsi and Pringles. The bathroom included squatting over a porcelain bowl with no toilet paper, and a woman pouring water into the bowl to flush and water on your hands to wash your hands. Once we got off the main road, it was a beautiful drive through the countryside and hills. The driving was a bit questionable as we went head on playing chicken with on coming traffic on a few spots. But it was all worth the views when we dropped into valley seeing the farmland and large hills jutting up from the opposite side. Our driver said the hills look like a herd of elephants and they did!

Once finding our place,1 block from downtown, and saying good bye to our driver (see you in a few days for pickup) we settled in to unpacking before heading into town. Tres Jotas and Dary y Tuty were are 2 main places we went to eat. Dary u Tuty was great for the free WiFi. We never mooched off of it and would order a drink or something to eat while we hung out. It was still slow internet and frustrating but it was at least something to catch up on emails and communicate with our worlds on Facebook.

Prior to our departure from Havana, we booked a view experiences through AirBnB. David and I did 2 tobacco farm tours, 1 for an hour and the 2nd for 3 hours. We also scheduled a private cooking event at a families house and a learn to make a Mojito with Juanito. The first, hour long tobacco farm tour was a great introduction of plant to cigar with everything in between. Rydan, the farmer, demonstrated how to roll a cigar and gave it to David. The 2nd, longer tobacco farm tour there was another guy on our tour from Argentina who was about my age. This tour was a lot more in depth, starting our time with a walk to the farm house where we had a cup of coffee. The beans were grown and roasted right at the farm, and there was a picture of Cinderella in the corner of the barn. From there we walked a ways over to the large barn where the tobacco leaves were hung in the rafters to dry. The 60+ year old farmer who had been working there since he was 6 gave a very in-depth talk about seeds, planting, harvesting, and drying. Like the first farmer he showed how to roll a cigar with it’s multiple leaves. However, David and the Argentinian both took turns learning how to roll their own cigars. After an hour of learning all of this, we walked on to the sorting house back on the edge of town. Once the leaves were dried at the farm, they were sent to a sorting house. The leaves were deveined and sorted by size, color and aging/dryness. The piles of tobacco leaves would eventually end up at different cigar houses in Havana for cigar rolling. Great educational and person to person relationships on both tours.

That night we had the Mojito with Juanito scheduled. Juanito would show us how to make Mojitos. However, the address we had downloaded to our offline maps was nowhere near where Juanito actually was. Thankfully we had left early enough to regroup and only be a few minutes later. Juanito had the experience scheduled for his house, not a restaurant or bar. David saddled up behind the bar and took charge of our Mojitos. Once made, Juanito put our drinks in a make shift pulley that took our drinks up to his roof and he told us to go “up.” We climbed up on top of his roof to watch the sunset over the elephant hills, sip our Mojitos, and play dominos with Juanito. The 3 of us were having such a great time, that Juanito dashed downstairs and made us another round of Mojitos to keep chatting with us. Up and down the glasses went in his pulley. David and I offered to pay him for the 2nd round. We understood that he wasn’t making a lot of money and this was his side hustle. But no. As much as we humbly offered to pay him, or tip him, he would not take our money for the 2nd round. With much thanks and goodbyes, Juanito did ask us to come back the next night. We understood that everybody we were interacting with in Cuba were hoping for great reviews on AirBnB or TripAdvisor as the return business helps them, David and I believe that Juanito genuinely wanted us to return.

Cocinando With Yusi was my most favorite experience. Again the address wasn’t correct but we weren’t as far long as we were for Mojitos. When we walked up to the correct house, Yusi and her husband both gave us double kisses on the cheeks and their 6 year old daughter gave us a big hug. Yusi quickly discovered that I didn’t really speak Spanish and had me sit on the front porch which didn’t bother me much as David does more of the cooking. After awhile I did meander back in and made an attempt to speak Spanish with Yusi. She loved it and told David to go outside and smoke with her husband. The food was amazing! It was by far the best meal we had in all of Cuba. And there was so much of it. We had both been enjoying our time so far that we wanted Yusi and her family to join us but she didn’t. David and I both concluded that she undervalued her experience for us and we left money on the table. When we left we showed much gratitude for the experience and couldn’t tell her enough how delicious were meal was. Like Juanito, she invited us to come back the next night for the company and friendliness that she gave us, not for a great review. As we arrived, everybody gave us hugs and kisses when we left.

For our last two nights in Havana, we stayed at a different AirBnB in the same neighborhood. A handful of gals in their young 20s greeted us warmly and helped us with our bags as we climbed up to the apartment over a restaurant. Our last full day in Cuba we went back to the brewery on the harbor but discovered that it was closed. We didn’t realize that several businesses were closed the first Mondays of every month. We meandered around the capital, and had a margarita at Floridita. We spent the afternoon on a city tour learning the history in an old classic car that took us to Revolution Square, Hotel Nacional for a Mafia Mojito, and the Fortress on the opposite side of the harbor. David and I wish we had done this on the first day rather than the last but better late than never.

The ladies cooked us breakfast one last time before we headed to the airport. This time we were flying on United to Houston. We got to the airport well ahead of time anticipating being slowed down for customs and being able to shop at Duty Free for rum and cigars. To our surprise, we buzzed right through and spent time in the large single room terminal. For the first 20-30 minutes into our flight, we couldn’t use the in-flight entertainment on our devices and no alcohol could be served because of some arrangement with the Cuban government. Once we arrived in Houston a few hours later, I was expected to be slowed down at Customs because we were coming directly from Havana (even with our new Global Entry status). From wheels down to walking out the airport doors with our luggage it took us 20 minutes! Fantastic! It took us longer in Denver to get our bags.