TMN055: Sailing to Cuba!POPULAR 

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Sailing to Cuba is definitely one of the coolest adventures I’ve had yet as The Multimedia Ninja.

Here’s the story of how we got there. FYI, you can hear it as an audio podcast or watch it as some seriously cool video above—but if you’re more the reading type, read on! I’ve got plenty of pics, live Instagram links, and all kinda stuff here…

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Building up to this…

Jacie-Sails-ICWIf you’ve been following on Facebook, Twitter, Instagram, or in real life, you’ll know I’ve been sailing the Florida Gulf Coast and the Florida Keys for the last four years, aboard Jacie Sails, a cutter-rigged sailboat.

I’ve been building up gradually, making about a dozen longer cruises and a number of day sails.

I’ve now done over 3000 nautical miles (closer to 4000, after consulting my spreadsheet). Over 2000 of those have been solo, and over 1000 were offshore.

But I had never sailed to another country.

Jacie Sails-sailing track-2013-2016

Thankfully, I’ve got a partner that enjoys sailing with me…and I haven’t killed her yet, so she still trusts me! That would be Tanya—but we call her The Admiral. 

And The Admiral, for some crazy reason, liked my idea about sailing to Cuba. In fact, we were going to go last year at New Years, but we couldn’t figure out what damn papers and permits we needed!

Sailing to Cuba

What Documents You Need To Sail To Cuba

[NOTE: The recent announcement by President Trump may may impact the legal requirements to be able to sail or otherwise travel to Cuba. Please plan accordingly!]

Just to deliver some important info for my fellow sailing Multimedia Ninjas, here’s what an American Captain needs in order to sail from the US to Cuba and back.

As a Captain:

As a Captain, you’ll need:

  • Passport Worthy of a Multimedia Ninja
  • Visa (and if you’re sailing, you get it at customs at the marina on arrival)
  • US Coast Guard Form 3300 – Permission to Enter Cuban Territorial Waters
  • “Ship’s Papers”
  • $25 DTOPS customs decal
  • eligible “Reason” for going (that is, you can’t theoretically just go for tourism)
  • (certain vaccinations are recommended but not required)

Now that’s the simple version… I’ll save some of the details for later, and you WILL want those. If you stay no more than 14 days, you can avoid some extra hoops with the US government.

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As a Crew Member:

Of course, if you’re going there just as a crew member, all you really need is:

  • passport
  • visa
  • your vaccinations (as applicable), and
  • a legit reason to be there.

I’ll tell you this: They’re much more laid back on the Cuban side, in my experience. Don’t bring any drugs or contraband, and don’t f— up, and you should be good to go.

Final plans…

So anyway, we finally figured out what we needed, thanks to Linus from the Slow Boat to Cuba podcast and Captain Cheryl Barr’s cruising guide; and Tanya booked a one-way flight to Key West.

Passports and Cruising Guide

I really wanted to go full ninja on this trip, documenting everything from a zillion angles like Matrix bullet time, (and) bringing every piece of video, photo and audio gear that I had…but as it got closer to time to depart, I finally realized that it might just be best if I focus on getting us from Point A to Point B and back in one piece.

The whole thing of getting these permits and decals and vaccinations and making sure the boat was ready to cross the Gulf Stream with minimal prep time was starting to weigh on me a little, and finally it was just time to GO. I’d take a reasonable rig, focus on sailing the boat, and get to Cuba and back with a minimum of fuss.

A Cool Tool

Since this is the Multimedia Ninja podcast, I will just mention the one piece of gear I most wish I’d brought…and that is my Edelkrone FlexTILT head. It’s great both on a tripod, and as a stand alone stand for your camera. More on that some other time, but here it is:

St. Pete and Peter Suarez

After the usual Christmas festivities, I drove from Atlanta down to St. Pete on December 26th, arriving late at night as usual, and found the boat still afloat…which is always a good thing. I found my marina neighbor Peter Suarez aboard, and we may or may not have had a beverage once I got all the gear aboard.

If you’re not familiar with Peter from some of my Happy Ninja vlog posts on the YouTube channel, he is one talented hombre. Peter has a really amazing one man show called “Chameleon” from which the below are just a few tiny hints. (Check out the hilarious “The Prisoner’s Lament,” performed by Peter and recorded by yours truly aboard Peter’s yacht Duende.)

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Don’t cut that wire!

*I had to leave on the 28th to meet The Admiral in Key West, so that left only one day to get provisioned and get money changed…which, as it turns out was largely a waste of time. I may elaborate later, but suffice to say changing US Dollars to Canadian Dollars to change to Cuban Pesos may not be necessary.

My friend Harbormaster Dennis was kind enough to lend me his pressure washer to clean off all the birds— so we’d look respectable, and on the 28th, the mad dash began.

Well, almost! It seems that a certain boatyard, when they installed tricolor running lights at the top of the mast, removed the deck level running lights from the breaker panel. I was very proud to be able to reattach the bow lights… but when I went to hook up a proper stern light, I mistakenly cut the wire from our Solar panel that charges the batteries when we’re underway. Oops!

But I got that spliced and we were finally underway by late afternoon, in time to catch the sunset off Egmont Key in the Gulf of Mexico.

38-hour Nonstop Run (Well, almost…)

I had to meet The Admiral In Key West on the 30th, so that meant about a 38-hour run from St. Pete. I motorsailed south all night along the Gulf Coast and finally lowered the main the next morning, since it wasn’t bringing much to the party. 

At Marco Island, I topped off the fuel, got some chips and junk food at Rose Marina Marco Island, and kept on going.

I was able to set the main and jib leaving Marco, and left ‘em up all night. Since we had a following wind, I didn’t realize that it was getting pretty breezy until early morning on the 30th. Fortunately, I doused the sails and had a wet run down the Key West Northwest Channel just before dawn… A 38-hour solo run of 222 nautical miles. 

New Years Eve in Key West

After I got tied up with the much-appreciated morning help of Corey at Galleon Marina, I caught a few winks before Tanya arrived.

We had planned to leave direct for Havana on New Years Eve, but the forecast wasn’t great for the Gulf Stream, so we decided to hang out in Key West for New Years, then stop at the Dry Tortugas and wait for a good window.

The Galleon Marina was full, so we spent New Years Eve at the fuel dock at Conch Harbor Marina…which was also full, so we paid the same crazy $5 per foot “special event” dock fee that we paid at Galleon.

(Below: Conch Harbor Marina fuel dock. We docked where the big sport fisher is docked in the picture.)

Still, it’s hard to beat New Years in Key West; and we knew we wouldn’t be paying any slip fees in the next few days. 

We had our champagne toast early and totally missed whatever was going on at midnight.

The Dry Tortugas

On New Years Day just after dawn, we bid goodbye to family, friends, and the internet, and sailed—excuse me, motored—west to the Dry Tortugas.

The Dry Tortugas are about sixty miles west of Key West, and the main feature is Fort Jefferson, on Garden Key. It’s a huge fort, some 47 acres, built in 1847 and made out of 16 million bricks. It has seen very little action as a fort, and is mainly known as the place where Dr. Samuel Mudd was imprisoned, for tending to the medical needs of one John Wilkes Booth, the assassin of Abraham Lincoln. 

The water in the Tortugas is as beautiful as the rest of the Keys; and since it’s a national park, there’s wildlife galore. There are lots of pelicans at the fort, and we saw showers of minnows boil out of the water as predators hunted from below. Tanya spotted a grouper under the boat so big I had to convince her it wasn’t a shark.

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There are only two ways to get to the Dry Tortugas if you don’t have a boat: either take the ferry from Key West, or come by seaplane. The seaplanes are pretty cool, taking off and landing right next to the Anchorage… or in some cases, right through it!

The Dry Tortugas are called “dry” because there is no fresh water to be found anywhere within the 101 square miles of Dry Tortugas National Park. There is no food or drink available once the ferry leaves each day, and there is no WiFi and no cellular service. Once we got a few miles from Key West, we were off the grid until we got to Cuba…and just barely on the grid once we got there.

Fortunately for our family and friends, we carry a Spot messenger so a few select folks can follow see our exact location track updated every 10 minutes, and we can also post manual position updates that show up on our Jacie Sails Facebook page.

Sink the Dink

There was one major issue we had to contend with: The dinghy hadn’t been brought out and inflated in a good year, and it turns out it had a leak, so we didn’t have a way to get ashore. Fortunately, the park rangers were very kind and let us tie up in the only remaining space behind the ferry for a couple of hours at a time. They even found us some repair materials and updated us on the forecast. Another sailboat also donated some potential patching material to try and make the dinghy buoyant again.

Unfortunately, the patch didn’t hold, and we realized that the only way we’d be getting off the boat this trip was onto a dock or into the water…but meanwhile, Tanya was able to get some quality time on Garden Key. [Oops! That’s Bush Key, next to Garden Key. The two are now attached by a sand bar. Ironically, Bush Key is where all the birds are—and “Bird Key” is now submerged.]

Time to go…

As we checked in with the rangers on the morning of January 3, we saw from that our weather window had moved back to…now. We saw that during the evening, the Florida Straits was showing white on the chart, which means the wave height was forecast to be less than half a meter. That’s about as good as it gets, so bidding a quick adieu and thanks to The Rangers, we shoved off around noon. 

We cruised by Loggerhead Key, with its lighthouse and beautiful beach, and headed south, crossing the southern boundary of the park at mid afternoon (14:28). A few minutes later, we reached the furthest point South that Jacie Sails has ever been; and by 4:30 we reached the deepest point that Jacie Sails has ever been.

Now, the continental shelf on the Gulf Coast where I usually cruise, is very shallow and extends out a good way; so the deepest point I’d been before was around 200 feet. The Florida Staits are another matter: at the deepest point, you are sailing with well over a mile of water below you.

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As it turns out, though, the crossing south was a milk run. I swear it was smoother in the Gulf Stream than at either side. Leaving the Tortugas, we had 3 to 5 foot swells—which was no big deal, though, since they were long; and I mentioned to Tanya how different they were than the short chop on the Gulf Coast. We missed seeing the legendary purple water in the Gulf Stream, since we crossed the axis in the middle of the night…but we could live with that. The Gulf Stream itself, though, was really smooth—unlike on my way back!

We motored and put up the main, with the traveller all the way to port, so we were able to just catch the SE breeze in the main as we motored SSE, and between motorsailing and the Gulf Stream, we made 8 knots for a good while. In fact, we arrived so much earlier than the predicted 18 hours that we had to tack offshore and back until dawn, throttling down to maybe three or four knots, with Tanya and I reduced by fatigue to trading 15- and 30-minute tricks at the helm.

Are we burning?

Soon after I saw the lights of Havana, I noticed was an acrid, like burning trash. I was afraid for a minute that it was the boat. But, as I found out later, apparently it was burning trash.

Near dawn, I noticed that a couple of targets which had been headed North on my AIS during the night were now headed south toward the marina channel marker, converging with us.

Oh HELL no. I pushed the throttle down a little until we were back up to 6.5 knots with no sail up. I’d be damned if we were going to be the last of three boats into customs and into a slip.

We galloped to the buoy and then eased off as we navigated the channel, which you do NOT want to stray from. As we turned to port, we met with a beautiful sight: Sunrise over palm trees, a pretty little cove…and the customs dock to port, right where it was supposed to be!

Checking In

Customs, thankfully, were fairly perfunctory. I think maybe it helped that we were the first boat of three that pulled into the customs dock in rapid succession. They did not take our flares or flare gun…although I’d read that they would. They didn’t care about our couple of ribeyes, couple dozen eggs, cheese, etc….which I’d read that they would. Strangely, there WAS one senior-looking official who walked past us as we were docked; and his sole question was whether we had a drone aboard. Which in this case, we did not.

The customs guy was nice, patient with our language barrier, and when we messed up the form by switching the month and day, in the American way, simply provided us with new ones. 

He did ask me belowdecks near the end of the process and asked if I had any “gift”, although he made sure to say it was not required. I gave him a copy of my CD Guiro!, which I hope he enjoys.

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A female doctor in a white lab coat came aboard, took our temperature with a little infrared remote sensor, asked us a few questions about our travel, then left.

I (and then Tanya, one at a time) went into the little air-conditioned customs building with two computer stations and a spare seat in front of each. There was a little camera on a pole at each station, pointed, towards the “guest” chair. I thought they were going to take our picture for some purpose; but I decided they were actually doing facial recognition to compare us to our passport photo.

A couple of minutes later, we were given visas and directed to Canal Uno, closest to the ocean…and we were in!

(Well, almost…we still had to talk to the dockmaster and the agriculture guy, but it was no big deal. There were one or two more requests for “gifts,” they got us promptly hooked up to a new power pedestal, and once again we had air conditioning and….LAND!)

Marina Hemingway

Marina Hemingway is actually a few miles west of Havana harbor, which is pretty much reserved for cruise ship and commercial traffic. The boat slips at Marina Hemingway are comprised of four canals, each about a half mile long. We were on Canal 1, nearest the water, and there were maybe fifteen boats tied up on the South side of the canal; and none on the ocean side.
The rest of the canal was empty, except for a couple of unfortunate vessels at the East end of the canal that had seen better days.

Just a couple hundred feet west of us was the 24-hour “snack bar,” which actually had coffee, rum, water, soda, bathrooms, showers and laundry. The Admiral and I went and got a couple of espressos every morning for $1 CUC each, which is somewhere around a dollar or a dollar and a quarter, if my math is right—and depending on how you change your money. I’ll have some critical info about bathrooms and money in Part Two; but for now. I’ll spare you the details.

Fish to the Vapor with Garlic

When people ask how the food was in Cuba, the first thing I have to mention is that we ate Chinese food and Pizza pretty often, followed next most often by Cuban sandwiches at the yacht club; and ham and eggs for breakfast at the little cafe on the East end of the marina. Obviously, none of these were serious local cuisine. We did eat about half a dozen times at local paladares, which are private houses turned into restaurants; and we ate lunch twice at El Templete, on the Malecon, overlooking Havana Harbor, which is pretty much a tourist area—and thusly, pretty nice. I got gin and Tanqueray at El Templete and The Admiral enjoyed the croquetas so much we had to come back. We enjoyed the paladares a lot, from fancy exclusive ones in Havana and Playa that our special contact got us into, to more regular joints in Jaimanitas, Santa Fe and Pinar Del Rio.

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I know it sounds crazy that Marina Hemingway would have a Chinese restaurant on the property, but that’s exactly where we had our first lunch. On the second floor overlooking the entrance channel, it’s a great place to catch some rays and chill out. Some of the English translations of Chinese dishes in a Spanish-speaking country were pretty interesting. 

I did not try the “Fish to the Vapor with Garlic,” but I assumed it means “steamed.”

The Land of Castro

People have been asking me, “What’s it like down there in the Land of Castro? Are the cars all really those old Chevys?” There’s so much to say, but the phrase that came to mind was: “Good Intentions.” People listlessly sweeping a weedy track at a school stadium that I never saw in use. Tennis courts at the Marina with no nets, allegedly installed for Obama’s visit. A big blank space that looked ready to be an outdoor basketball court, but simply contained a giant wooden chair.

The basic wage provided by the state isn’t enough to get by on, so everyone has to hustle. The folks running their own legit or black market businesses are friendly, ambitious and eager to please. The folks working at their state wage jobs, understandably, are less enthusiastic. We found the Cuban people to be very warm and friendly, resilient and good-spirited despite years of privation. There’s a saying, you can get almost anything done, IF you have the materials. But there’s the rub.

Yes, there are a lot of Chevys, Fords, Packards and the like, from 1940s vintage to around 1960, I guess. The crazy thing is that every single one I rode in or saw up close had been converted to diesel.

There are also Russian Ladas from the Seventies and Eighties, some newer Chinese Geelys, and a few more common species for party officials or tourist rentals.

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I’d say the amount of air pollution per car in Cuba is more than in the U.S.—both because most vehicles are diesel; and because most, whether diesel or gas, are in need of a tuneup. Of course, there are far fewer cars here, even in Havana; and unlike, say, Atlanta, there’s a nice trade wind to clean things up.

However, I was there for two weeks and had some sort of tickly-throat coughing issue almost the whole time, which is damned rare for me; and it got bad enough to keep me awake one night after Tanya left. Maybe it was coincidence, maybe it was the air, but it seemed that some of the other cruisers and even some of the locals had a bit of a chronic cough. Maybe it was just something going around, who knows? Either way, it’s not going to keep me from going back, but I thought it was worth mentioning it to my fellow Ninjas.

The climate was amazing as advertised, though. In January, the average temperatures are a high of 79° and a low of 61°. With a Northern front, it can get a little more on the chilly side, which happened during our stay; and more importantly, it gets especially breezy during the Northers, and you do not want to be out in the Gulf Stream. But it was still kind of fun to see Atlanta expecting snow while we were wearing shorts.

Stay Tuned!

We’re only getting warmed up here as well, but speaking of Ninjas, we’re about out of time for this episode. Join us next time for info on the very cool Hemingway International Yacht Club, the Hemingway House at Finca Vigia and the countryside of Pinar Del Rio; and for some critical info you need to know about…toilet paper, money…and of course, cigars!

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3 comments on “TMN055: Sailing to Cuba!POPULAR 
  1. Carey Schearer says:


3 Pings/Trackbacks for "TMN055: Sailing to Cuba!POPULAR "
  1. […] for me to believe that the little guy I built the fort for is the same fellow that grew up to go sailing to Cuba this year… But here’s the story of the fort I built for […]

  2. […] (You may recognize some certain Cuban cigars we may or may not have indulged in… See Ep. 55 on Sailing to Cuba) […]

  3. […] or so. Man, I was knocking out the Pomodoro, so I finally got that sucker out, which you can see at I highly recommend […]

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