My son and I arrived in Havana with few expectations, just a (practically built-in) sense of adventure. I had wanted to go for years, hearing it was a “step back in time,” but also that it was “dangerous,” and not a place for a carefree vacation. When my friends had asked me a couple of years prior where I wanted to go for a special birthday, I immediately said Cuba, but they quickly declined, one of them going later on her own.
When Meredith invited us to join her and her son, approximately Aidan’s age, I jumped at the chance, even though it was August and I hate to leave our beachside home in the summer, just on principle.
It was a bit of a lark to go travelling with Meredith to begin with. We hadn’t spent so much time together since being roommates in 1989 for three weeks at a camp for gifted students of public affairs. I had known her since the year prior when we met at a different academically-focused camp, and I felt about as close to her as I did anyone. But we’d only recently reconnected after several years out of each other’s orbits. Add two teenaged boys who don’t know each other into the mix, and you could have a real disaster on your hands. As I’ve learned from past forays, travelling together can really stress relationships – even make or break them. (See another column, “Travelling Together? Leave Your Baggage at Home” for a few juicy tidbits.) Anyway, I threw caution to the wind (jk) and tagged us onto her almost-already-made plans; thankfully, she is very research- and scheduling-prone when it comes to her travels, unlike me. At some point I’ll get it together and publish my first book, like she did already years ago.
The airport in Havana was tiny, sweltering, and as dead as Pere Lachaise. The moment we stepped from it, my phone began to ring. Thinking it was Meredith, I answered right away since no identifiable number came up. Bizarrely, it turned out to be another friend of mind (thanks, Lisa) using a fake voice to pretend she was someone else, as a joke. I was disoriented and thought I was being watched. And little did I know, but these calls were costing me a fortune. Every other country I’d been to offered daily add-on rates when traveling. I guess Cuba is in a class by itself. In many ways. This was a telltale start to an eye-opening visit.
A comedy of errors and a failure of communication had us missing our travel partners in the airport, but fortunately, Aidan and I didn’t have to wait too long for the hotel to pick us up in a gleaming red classic Chevy with fins and a backseat bigger than some New York apartments. I was enamored at first contact. It was the first of several old cars we enjoyed riding in during our time in Cuba. Mechanics make a good living there, but gas is expensive, especially for gas guzzlers. Most of the classics have been modernized with updated radios and air conditioning, if not power steering and other features they may not have originally been manufactured with.
The gold dome on the Capitol building, its restoration a gift from Russia in recent years, seemed wasteful in the face of such abject poverty directly under its shade. I commented as such and was met with a disaccording stare from our walking tour guide. It was an oppression-impression if ever there was one.
Our two Airbnbs in the city were lovely. Boutique hotels as opposed to private homes, their managers seemed to be on the pulse of a boom about to happen, actively renovating during our stay. The small, private pool at Gardens, Havana, was a welcome respite from the August boil. Its proximity to the town center was ideal, and eventually we wandered out and asked where to get a good meal (most places were closed as it approached 9 p.m.), happening upon a wonderful spot with live music and a friendly stray cat. Stray animals were ubiquitous, in fact. Cuba may be the Nashville of the islands, as every spot seemed to put a high priority on authenticity via a good local band. Never say you don’t like a sort of food until you’ve been to the place from which it originates. This is how I have learned I like so many things I’d never enjoyed in the United States. The grilled fish and seafood in Cuba was wonderful, and Aidan’s (expensive) steaks looked pretty good, too.
The next night we treated ourselves to a fancy dinner at La Guarida, a paladar (private restaurant) used in films and at the top of an ancient palazzo. They tried to discourage our use of the optional TropiPay, which is like Cuba’s version of Paypal, but we insisted. And thank goodness for that, or we’d have had no money to get to our next destination. The atmosphere was perfect, however overpriced the food. We enjoyed ourselves on the rooftop of the old palace, even picking out cigars to end the night with and meandering home on foot (again, we very much needed to save cash) through abandoned lots and graffitied sidewalks. The streets were well-lit. Meredith, a lightweight/cheap date/near teetotaler, was a little tipsy, but we made it back just fine.
She had not skimped on the arrangements she made. The second Airbnb, Elvira, Mi Amor, was even dreamier than the first, with palatial rooms and a 360 degree rooftop view covered in plants and beautiful tiles. The bathtub in our room sat behind a screen; Aidan jumped on the bed soon after arrival and collapsed it, but we managed to fit it back together, sort of. Meredith’s room was in a tucked-away loft full of beautiful artwork and a bird’s eye view. Our breakfast was served on the roof in a little tropical jungle by a woman we’ve kept in touch with since on Instagram.
Our last night, we explored at our leisure and managed to get seats to the dinner show at THE Buena Vista Social Club, which, in a rare fluke, accepted TropiPay. Had we been single (and not with our teenaged sons), it might have been a night of Cuban-flavored debauchery. The wonderful music had us dancing; the chicken had us hunched over toilets for days thereafter. Or it might’ve been dengue fever – we’ll never know. In any event, someone shit their pants on the first day of school, someone fainted at work, and someone had random mouth bleeding. Only the one who didn’t eat the chicken had no strange symptoms.
A side note: Do NOT go to Cuba without all the money you expect to spend in cash. They do not accept credit cards, and our debit cards do not work in their ATMs. This was one of the lessons (and nightmares) we experienced, along with being trapped at an Airbnb that wasn’t ours, being charged egregiously for phones and internet (it’s as though they don’t want you communicating with the outside world!) and having to negotiate with a gangster to get cash from TropiPay.
The Optimistic Traveller 
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