It’s been almost two weeks since we were in Havana. As I write, I’m on the plane home from Key West, where we initially made our landfall back in the continental USA for the first time since November, and where we stayed for my sister’s wedding and associated festivities for the past week. I finally have time to reflect on our passage to ‘forbidden’ Cuba.

Scroll all the way to the bottom for the full gallery of photos.


Last I wrote about the passage we were becalmed along the northern coast of the island - Cuba is huge, over 600 miles from east to west - taking one last swim and shower before landfall. The guys had a shaving party in the cockpit - a bucket full of fresh water and lathered-up faces.

Signs of civilization abounded. Fish pots we had to dodge (they were lit at night, amazingly, with fluorescent green lights on each buoy (glow sticks, like divers use? we mused), usually laid out in strings of 8-10); freighters coming and going from the old port of Havana; an old military launch that looked definitively soviet. But no sign of the marine police, USCG or other authority figures. I was almost sure we’d be boarded once officially in Cuban waters, but it didn’t happen.


Havana is the second-most culturally-exotic city I’ve ever visited (the first being Istanbul). It would hold our full attention for the nearly five days we spent ashore there, never ceasing to surprise us. But it was the first impressions of that first day ashore, drunk with excitement and literally drunk with rum that we’ll remember (ironically) most clearly. ‘Lada’s’ (old Russian box-shaped cars) driving down the canal roads spewing black smoke; the crumbling concrete on the bulkhead that had me worried enough about the fenders to return to the boat, some nine miles from the city proper, on three occasions to check them; the first old American car we saw, a green 1950’s convertible Buick, parked in the lot next to the boat; the photos of Papa Hemingway fishing with Che Guevara and Fidel Castro hanging up in the Yacht Club bar; the horse-drawn carts clip-clopping down the main road outside the marina complex, followed by ’57 Chevy’s and Russian side-car motorcycles; real mojitos and the distinctive aroma of cigar smoke on every street corner, plus signs and symbols of the Revolution everywhere you look. For five full days our senses were overwhelmed by the sights, sounds, smells and craziness that is Havana. The city is everything you’ve ever read about, compounded several times over by the sheer size and complexity of it all, and the fact that you’re seeing it in Technicolor, in full-motion, in person.


Our landfall at the entrance to Marina Hemingway coincided with the dawn. We tacked back and forth outside the narrow channel waiting for it to get light enough to enter and were rewarded with an incredible morning as the blood-red sun rose over the old city to the east, lighting up the clouds building over the mountains inland. Our entrance into the channel was thankfully uneventful. We followed a British boat who we heard on the radio, and were surprised that even on a Saturday morning at 0700, a cheerful voice with a heavily Cuban-Spanish accent was on the other end to answer and guide us onto the customs dock.

Marina Hemingway is interesting in that it’s like no other ‘marina’ we’ve ever been to. The place is huge, and is laid out in four large east-west canals, nearly a kilometer each in length and about 75’ wide, with substantial land between them. Each ‘slip’ is a designated spot alongside a dilapidated concrete bulkhead, with run-down hotels and abandoned or unfinished apartments backing the waterfront. It felt like a colorful, post-apocalyptic Ft. Lauderdale.

We were directed onto the customs dock, which is to the west of this canal system and situated on a square island that’s connected by a tiny causeway onto the northernmost landmass. The crew debated whether the canals were dug out of the landmass along the coast or if the water had been there and the land created by filling it in. Probably a combination of both.

Customs was much more efficient than we’d expected (our only guidebook onboard was Nigel Calder’s from 1999), and the folks were as friendly as everyone said the Cuban people would be. Several groups of uniformed officers came by the boat to do various inspections, and each one of them was polite and respectful, even taking off their heavy, black military-style boots as they boarded Isbjorn. A comically small, fluffy dog was brought aboard to sniff for illicit cargo. I specifically requested to have my passport stamped, which got genuine smiles from the guys behind the desks, and we were ushered off the dock and directed to our ‘slip’ within an hour of our arrival.

‘Jose’ met us at our slip on the north side of the third canal. I recognized him as the same cheerful voice that guided us through the cut just after dawn. It was the end of his overnight shift (they staff the marina 24/7), and he joined the crew in Isbjorn’s traditional landfall champagne toast, despite the fact that it was only 8 in the morning. He even requested a refill! I gave him an #isbjornsailing baseball cap to thank him for his efforts.

We’d been at sea for almost seven days. There was palpable excitement in the air amongst Greg, Dennis, Fred & Rob (the crew), Mia & I, a potent combination of sleep-deprivation from being offshore for so long, excitement at just setting foot on dry land, and the realization that said dry land was actually Cuba, this forbidden place that all six of us had dreamed of visiting for so long. Two of the guys immediately set out to look for some cold beer, ice and Havana Club rum while Mia and I cleaned up the boat and greeted the seemingly never-ending line of government officials who came to inspect everything from our toilets and trash to the vegetables we still had onboard.


It had been the plan to visit Cuba on the way home from the Caribbean ever since we bought Isbjorn. We knew for a long time that my sister was getting married in Key West in late April, so we immediately planned our passage calendar around arriving in Key West by boat in time for the ceremony. But we couldn’t talk publicly about the Cuba part until we had official permission to go there.

Enter Tom Harkin, former Democratic Senator from Iowa and fellow sailor who I’d gotten to know through Matt Rutherford. Tom knew of our ambitions to go to Cuba (and at one point was even planning on joining the crew to sail there), had been there himself before (even having lunch with Castro at some point) and obviously had connections in the government that might be able to help. As luck would have it, relations really started to thaw between the US and Cuba, with each country finally opening embassies last fall. In December of 2015, Tom had lunch with the new Cuban Ambassador in DC and specifically asked about us sailing there on Isbjorn. He got a resounding ‘Yes!’ from the Ambassador, at which point he emailed me and said, ‘go ahead and advertise the trip - I’ll help you figure out details later.’

So we did. Within a week, the crew spaces were booked. But we still didn’t have ‘official’ permission, which I was adamant about since I was taking not just the boat there, but the business too. 

Fast forward to March 31, the day before our crew was to arrive in Fajardo, Puerto Rico. By then I’d gotten the necessary paperwork completed with the USCG and finally had assurances that the boat wouldn’t get seized when we returned to Key West. The crew would be visiting Cuba on the ‘people-to-people’ general OFAC license (more about this in another post), which was a self-documented thing. But we still had no confirmation from anyone in Cuba who knew we were coming.

Finally, with the help of the Ambassador’s secretary, we got an email from Commodore Escrich at Club Nautico de Hemingway (aka the ‘Hemingway International Yacht Club’) literally the day before departure, welcoming us to Cuba as his personal guests. He’d arrange a slip for us near the YC and their facilities would be entirely at our disposal. Cool!

Seven days later and ‘Jose’ had apparently gotten the memo - our slip on the north side of Canal 3 was in sight of the YC itself, less than 100 yards from the club’s deck. A few hours after our arrival, while imbibing Havana Specials (rum & pineapple juice) in the cockpit, a guy called Leander from the YC came by to invite us to the cookout they were having that night on the deck, on behalf of Commodore Escrich (in one of an endless number of stories that makes Cuba unique, the YC was having a pig roast that evening. We walked up to checkout the YC later in the afternoon and found the pig roasting on an open fire. “That’s neat,” commented Mia. “It’s actually rotating on the spit by itself. Sophisticated!” When we rounded the corner, we saw the mechanism that made this possible - a short, tanned Cuban guy wearing a blue tank top and sitting in a chair, rotating the spit by hand. He’d be there for six hours that afternoon, he explained to us in broken English!). They had a table with our boat’s name on it reserved for us and it was free drinks and food for all. A rather good start to our adventures in Cuba. 


We’d booked a big colonial house in the Mafia-built district just west of Habana Vieja (‘Old Havana) for the entire crew to stay ashore with a local family. This got us off the boat and into city life, but importantly fulfilled part of our ‘people-to-people’ obligation by living alongside the locals.

Figaro - the owner of the green Buick - arranged transportation for us from the marina. On 10am on Sunday, after our cookout at the YC, he and a friend who turned up in a red convertible 1948 De Soto, packed our bags into the trunk and we started our journey into the city, with a few pitstops for sight-seeing along the way. Mia, Greg and I were squeezed into the back seat of the De Soto while Dennis, Fred and Rob occupied the green Buick.

It’s impossible to overstate the chaos that are the streets in and around Havana. First of all, the city is HUGE, with something like 2 million people living in the greater area. And thanks to all the old cars - this is not a cliche by the way; every second or third car actually was a classic 1950’s American car or a Russian Lada or motorcycle - the air pollution in and around the city is suffocating. I went for a couple of runs around town and genuinely had a tough time breathing and even opening my eyes in the smog. It was hard to tell if the once-colorful architecture was simply faded by time and neglect or faded by lousy air.

In any case, after a circuitous tour through the surrounding areas we arrived at Isabelle’s house, our host for the next several days. Back in the 1940s and 1950s, before Castro’s revolution, the US Mafia built an extraordinary neighborhood just west of the old city called Vedado. Enormous houses stood along wide tree-lined boulevards, neatly organized into square grids. The architecture, despite some neglect (though not as much as the media would have you believe), was incredible. Our place was on the second floor and had a balcony that fronted the main street. There were five bedrooms, each with intricate tile work on the floors and 15-foot high ceilings. The rooms were connected not by an enclosed hallway, but rather by an open breezeway that looked down onto the alley below, which contained a local pizza joint that also, somehow, served breakfast. Out front, a large open area was sort of a living area for all of us, and beyond that the balcony that looked over the main street provided a place for us to chill and drink beers in the surprisingly cool evenings.

Each morning Isabelle and her husband would prepare a feast for breakfast for us - fresh papaya and bananas, hand-squeezed guava juice, cheese omelets, fresh-baked bread and pot after pot of deliciously strong Cuban coffee. All this - housing for six, breakfast included, for three nights and four days - for $300.


I regret not keeping a more accurate diary in the moment, but there was simply so much stimulus during our short time that my brain was so fried by the evening that I could barely get my contacts out of my eyes before collapsing in bed each night, so I don’t think it would have been possible anyway. But I did take a few notes on my phone, and want to tell a few of my favorite stories from our stay.

I went to Havana extremely open to opportunity and with almost no expectations. Mia and I had been so busy with the repairs to Isbjorn’s rudder and the other business stuff that we had to attend to that we hardly had time to think about Cuba let alone make plans. We left that to the crew instead, who on the other hand, had been researching the city for months.

Fred’s Lonely Planet came in extremely handy during the passage from Puerto Rico, providing endless entertainment to all of us as we sat around on the boat during dinnertime talking about what to do.

My only real missions were to find signs of Hemingway (this was exceedingly easy - they are everywhere!), buy rum and cigars for my friends back home, ride in an old car (also extremely easy; in fact, nearly impossible NOT to!), and to learn more about Che, Fidel and the Cuban revolution (which I felt horribly under-educated on, especially coming from a country that has such a crazy history with Cuba and resides only 90 miles away…).

Mia and I followed the crew, and we made a point to stick together for the most part. Each morning started with a rendezvous at the fabulous Hotel Nacional, about 2 km east of our house in Vedado. If you take the waterfront route to get there, you’ll pass the newly minted US Embassy (formerly known as the ‘Office of US Interests’). Over the years, the US has used this tallish building as a means of spreading propaganda against Castro’s Communist government, putting posters in the windows and otherwise obnoxious signs in an effort to sway the people towards Capitalism. Just beyond this building to the east you’ll pass something like 100 flagpoles, closely clustered together and exactly as tall as the US Embassy building, and each flying a Cuban flag. This was Castro’s (clever) response to hide the propaganda from the public view while giving the ‘Office of US Interests’ the figurative finger.

The Hotel Nacional itself is a masterpiece, built at the height of mafia rule in Havana. Back then it was the home of famous cabaret shows, held a large casino and was the place to be for the celebrity class. When Castro and Che finally reached Havana in 1959, it became the HQ of the revolution, and has been the most important hotel in all of Cuba ever since. The grounds overlook the Malecon and oceanfront to the north. Several huge cannons point towards America and a long series of tunnels was dug beneath the hotel at the height of the Cuban Missile Crisis. This was practically Ground Zero during those frightening days, and the hotel was as much a fortress then as it was a hotel. 

The lobby would become the crew’s meeting point each day we spent in Havana, namely because you could exchange currency there. Cash is king in Cuba - the country employs two currencies, the ‘CUC’ or ‘Convertible Peso’ that tourists use, and the ‘CUP’ or ‘Cuban Peso’ that is reserved for the locals - and besides the banks, the big hotels are the only places to get it.

Aside from a few late-night taxi rides in an old Chevy or Buick, walking was our primary means of transportation around the city, and provided an excellent way to interact with the people at street level, stop for snacks along the road, and bar-hop our way around all the districts of sprawling Havana. Rob and Fred had an app on their phones that recorded our distance covered - in four days we walked nearly 30 miles!

After exploring our neighborhood in Vedado on Day 1, we made it our mission on Day 2 to check out the Museum of the Revolution and Old Havana. The museum used to be the Presidential Palace when General Batista ruled the land. After the revolution the place was given back to the people (kind of). You can still see the bullet holes along the marble staircase on the interior from a failed assassination attempt on Batista.

We were all fascinated at the perspective offered in the museum - how the Cuban government portrays their version of events in their long history with the US. The museum was strikingly ‘amateurish’ in how it was put together - the displays had an air of a high-school history project put together by a group of enthusiastic students with scissors and construction paper - but it was incredibly insightful and a wonderful way of seeing world events in a different light. The US is still very much the ‘bad guy’ in the eyes of the Cuban government, as indicated only recently, with Fidel’s scathing letter following President Obama’s historic visit.

On the bottom floor there is a large mural on one wall depicting the ‘Ring of Cretins’ - full-body caricatures of Batista, Ronald Reagan (dressed like a Cowboy), Bush Sr. and Bush Jr. (dressed in a Nazi uniform) with plaques next to each describing how they wanted to spoil the revolution. 

Afterwards we sauntered into Habana Vieja and it’s maze of streets looking for signs of Hemingway’s hangouts. We quickly found one of his favorites, La Floridita, Hemingway’s local and legendary home of the original Daiquiri. While cool to be there, it was a bit disappointing, as the place has become one of the biggest tourist traps in the city, and is no longer a place to go for a drink and a chat, as Hemingway so often did. There is a bronze statue of Papa himself at the end of the bar that patrons take turns posing beside for selfies. That said, it doesn’t take much imagination to see the place as it was in the 30s and 40s, as all of the decor and architecture remains original and highly authentic (perhaps the most charming part of Havana in general).

Habana Vieja has some of the most incredible architecture in the city (and indeed the world, for that matter), and it’s miraculous restoration has been widely documented. But for me, it was far from the most interesting portion of Havana. In a way, architecturally at least, it’s not unlike any other major historical city in Europe - the mostly-pedestrian streets are thronged with tourists (though refreshingly non-American, at least for now), people are hawking all sorts of silly trinkets on the sidewalk, and wide squares house old churches and used book markets around each corner. There are the requisite fancy and local restaurants, and museums of all sorts. 

We did find a particularly cool rooftop bar in Habana Vieja, almost by accident. An employee of the hotel was standing outside the stylish lobby simply announcing ‘Rooftop Bar!’ to anyone who walked by, and directed us towards the staircase inside. Nobody in our group had any hesitation. We discovered upon entering that we’d stumbled upon another of Hemingway’s hangouts - this was the famous ‘Ambos Mundos’ hotel that Hemingway frequented when visiting the city (his actual home was in the countryside), and you can still see his room where he used to write, which they’ve preserved as a sort of museum.

We ascended the six flights of stairs on foot (not wanting to wait for the small, antique elevator to take us up) and onto the roof of the place. To the east the harbor opened up before us, while to the west the sun began to sink over the Old City and surrounds. It was the ‘magic hour’, as photographers call it, when the warm light of the low evening sun cast a surreal glow on the city. Several Havana Club rum drinks decidedly enhanced this glow. We stayed up there until after dark, watching the city below us and marveling at the sights and sounds of the day.

It was after 9pm until we finally made it into Chinatown and to the Tien Than restaurant that had been recommended to us by a friend who frequents Havana (and who I’m convinced is a secret agent). The food was awesome, and the local scenery was something we certainly would have missed if not for the tip. We arranged for our driver - in a 1957 Chevy Bel Air wagon, that (barely) seated all six of us - who dropped us there to pick us up 90 minutes later to take us back home to Vedado and to bed.


The last day in Havana we sort of split up - Mia and I completed our rum and cigar mission, returning yet again to the Hotel Nacional to buy the real stuff. In Cuba, cigars, rum and coffee are prized, and sold only in official government stores. You can buy it all on the streets, but it’s probably counterfeit (particularly the cigars), so we returned to the hotel for the real deal. Currently Americans are allowed $100 each of a combination of rum and cigars, and $400 total of items purchased in Cuban for personal use back home. Since a basic bottle of Havana Club rum costs roughly $7 or so, this amounted to a lot of stock our crew of six could legally bring home.

Cigars were more expensive. Price depended on whether they were hand-rolled or not (for one thing), among other factors that I have no knowledge of (and less interest - I personally am not a cigar guy, but wanted to buy some gifts for friends). On the recommendation of my secret agent friend, we bought a box of Guantanamera’s - machine-rolled - and a couple of Romeo y Julieta’s for my more discerning friends back home. And two kilos of coffee beans for Mia and myself.

We met up with the crew later on and hopped in another Chevy Bel Air for the ride back to Vedado where we had the best meal of the trip. While the restaurants in Habana Vieja were generally excellent, and reasonably priced for a tourist town ($20 entrees, for example), the French place just a block from Isabelle’s house was my favorite. A local’s restaurant, it was classy both inside and out, the food was top notch and it was dirt cheap. $10 got you a full meal, cocktail and dessert included, with fresh bread to start and table side entertainment.

Another correct stereotype in Cuba is the music, and the stories are all true. Every cafe, bar and restaurant we visited had local, live musicians providing the soundtrack to our food and drinks. Everything from seven-piece Mariachi bands to my favorite, a man-and-woman duo at the French place. The woman played an extraordinary Latin guitar while the man effortlessly kept the beat on his maracas and sang with the voice of an opera singer. They wandered over to our table about halfway through the meal. The etiquette is to tip the entertainment if you’re satisfied - they’ll often play a few songs, then walk around the establishment with a hat to drop coins into - and we kept giving money to these two for how incredible they were. Greg even got them to do a private little concert for his two young kids back home that he got on video. I recorded some audio as well, with their permission, that I’m going to use on the podcast episode we do about Cuba, so make sure to tune into that.


’90 Miles to Freedom’

“…and they were off to Cayo Hueso by the dawn’s early light.” 

I could not help but keep replaying the Buffett song ‘Everybody’s Got a Cousin in Miami’ during most of our stay in Havana, and those lyrics in particular applied to our crew on the morning of departure (though it was decidedly after the dawn).

Following one more enormous breakfast with Isabelle at the house (and lots of hugs and kisses with our hosts and newfound friends), we piled back into the old Bel Air for the ride back to Marina Hemingway and Isbjorn. The crew scrubbed the decks, which had accumulated a fine layer of dust and air pollution in our absence, while Mia and I checked out.

I had to find more cash to pay the marina, so Mia and Rob hiked down the road a piece to a tiny little bank where they exchanged the last of my American dollars we’d brought along. The government, despite the rumors to the contrary, still charges a 10% tax on exchanging American dollars (thanks to the embargo - it’s their way of penalizing us), so while the CUC is valued at 1-1 against the dollar, the best exchange rate you’ll find is .87. Dollars go quick.

All the customs and marina fees are due at checkout. Rates at Marina Hemingway just increased on April 1 to $1/foot, so we paid $48 per day for our stay. We didn’t use power, and water was charged at a minuscule rate, so added up to less than a $1. Customs fees, however, were more. They charged us a $55 cruising permit fee, and then each crew member was tagged with a $75 departure tax. Since I was footing the bill for this as part of the trip package, it added up.

Nonetheless, it all went smoothly, if not slowly, and we departed Cuba just before sunset after another precursory customs inspection to make sure we weren’t harboring any stowaways. The passage to Key West was comfortably uneventful - a warm 12-knot easterly propelled us north while the Gulf Stream gave us a nice boost in speed - we touched 10.2 knots at times - and curved our course enough to the east that we never had to tack or even sail close-hauled, despite the contrary wind direction. We arrived into Key West Bight Marina just after dawn, making the 100-mile passage in a little over 15 hours and literally sailing right up to Mallory Square before the cruise ships in port put us in too much of a wind shadow, forcing us to fire up the motor for the first time. A fitting end to what ended up being a nearly 1200-mile passage from Fajardo.

Customs at the small airport in Key West didn’t bat an eye when we said we’d returned from Cuba. Instead, they took our passports, the USCG license I’d gotten previously, disappeared for five minutes and returned all smiles, thanking us for coming and asking us to enjoy the afternoon.


Everyone agreed that it was nice to get to Cuba ‘now’, and ‘before it gets ruined by American tourism.’ I shared that feeling to an extent, but after seeing it firsthand, I have a vastly different view on Cuba than I’d had before.

First off, the city of Havana is enormous and sprawling, thick with air pollution and traffic and yet vivid with the colors of life. Internet is still banned in households (probably bad), so people interact with each other on the streets (probably good), making us feel like time travelers as much as travelers in the geographic sense.

And I don’t think the Americans will ‘ruin’ Havana. The standard tourist traps are already there in many parts of Habana Vieja. And the city is so far from any widespread infrastructural improvements that any noticeable change there will be limited to some fancy hotels and restaurants that will inevitably pop up in the trendier areas. Greater Havana has a long way to go to fix up it’s side streets and back alleys. The sheer size of it means this is going to take a lot of time.

And anyway, it’s the people that make the case for visiting Havana specifically, and Cuba in general. Cubans are almost universally recognized as some of the nicest and most welcoming people in the world, and you can only hope that this won’t change when the country opens up. By saying opening up Cuba is going to ‘ruin’ it is a direct insult to the people there that make the place what it is. Beyond all the classic cars and crumbling architecture, it’s the people that define the city and the country and what make it worth visiting.

For those of you interested in visiting on your own boat, stay tuned for another post on the logistics of how to do it legally and efficiently.


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