Sailing: Cayman to Cuba to Florida to Charleston – May 2019

Watch our sailing video and read captain and crew logs below from our 11 day adventure sailing the Caribbean Sea, Gulf of Mexico, and Atlantic Ocean.  We left Cayman April 22, 2019, sailing north to Cuba,  then sailed around the west end of Cuba and on up to Key West for clearance,  then continued along Florida coastline and straight up Gulf Stream to Bohicket Marina, just south of Charleston, SC.

Sailing: Cayman to Cuba to Florida to Charleston – May 2019

Captain’s Daily Log

Sailing Preparations

FRIDAY, April 19, 2019

We waited all day at the Charlotte airport for our 1:00 flight, and due to storms, they finally cancel and send us home at 7 pm with a new flight scheduled for 7 AM Saturday.  We endured torturous delay announcements 1 hour at a time.


Flight delayed by an hour, but we finally had wheels up, to the cheers of the passengers.  3 hours later, we made it to Cayman, rented our car, grabbed lunch, groceries and headed to the Pilar.  Dinner seafood was Corvina, a rare treat.

SUNDAY, Easter 2019

Trip preparations begin.  We pick up Grace at the airport and head to lunch, then we head to customs authority at the port office and begin our clear out process.  Clearing out the vessel was a bit of a challenge.  We had left the vessel there more than 30 days, which requires special permission.  Although, I had called, emailed and physically mailed our request letter, we never heard back from anyone, so it took some extra effort to clear the vessel.  In the end, the customs agent was very understanding and made sure we knew that next time we would need to get proper permission.  Clearing out ourselves was no problem. We headed back to the boat and began teaching Grace everything she would need to know to have a successful sailing adventure with us.  Dinner seafood was Wahoo, another rare treat.

Goodbye Cayman,  Hello Cuba

MONDAY, April 22, 2019

Fuel fill up, Groceries, then Stephen headed off to pick up Bill and turn in rental car.  Bill arrives 11:30 and had to stop at customs port to clear out (turned in his little white slip).

At the dock, we are ready to go, and leave by 1 PM.  Out the Governors Creek channel and off into the wild blue yonder.  And WILD it was with 8-10 foot seas.  Both Grace and I were feeling a little green under the gills, which made for a rocky start to the trip.  By about midnight, I was doing okay, but Grace was down for the night.

Around 5 pm, seas subsided to 6-8 ft, and we were averaging 7-8 knots.  Then around 11 pm, the doldrums hit.  5 knots wind.  So, we decided to tack to the east, so that we would be able to sail closer to beam once the winds came back up. We sailed with one motor assisting, then around 2 pm, those northeast winds popped up with a force!   20-25 knots gave us a super-fast sail.  We turned back north and rode out the night making 9-10 knots average speed the rest of the way to Cuba.


Tuesday morning, we had a beautiful sunrise and a bit calmer sea, maybe 4-6 ft, so we made excellent progress at 8 – 9 knots, as we approached Caya Largo, Cuba. Arrival 11:30 AM.  Total trip time – 22 hours.   We radioed on 16, about 1 mile out, and were directed to head to Caya Largo Marina and we cleared in.  Super friendly agent, Pine, provided us with all the information we needed to understand the process.  Clear in, then when you leave a port, you either get a cruising permit, or you clear out totally and leave Cuba waters.  With the cruising permit, you can visit any Cuban port, but you do have to re-clear in at each port, until your final port when you clear out and final inspections are made.

They boarded the boat and did an inspection, and a doctor came on board and for a health check.  They examined the provisions the most, and the rule is that they have to seal any meat or produce to prevent any possible disease contamination of their own livestock and farms.  It remains sealed until you leave their waters.    They asked if we had a drone – they do not allow them on the island, so are sealed and inspected upon departure to ensure seal has not been broken.  The process took about 2 hours.  Payments are made in Cuban pesos (Cucs), and they have a bank at the marina to exchange your currency.

Once we rinsed the salt water off our boat, we headed to anchor by the reef and snorkel.

Super clear water, and plenty of coral to see.  Then we headed to anchor by the beach for the night, and shared dinner and great conversations that only happen on anchor on a boat!


Wednesday morning, we awake to beautiful sunshine and turquoise seas.  After scrambled eggs, bacon and toast, we head out to the beach – Playa Sirena, on the eastern end of Caya Largo.  Stephen and I walked the beach, and found much to our surprise, found that we were on a nude beach – some topless and some bottomless.  But Stephen and I both agreed, we liked each others’ better.

Grace spent time by the public beach and in the water.  Bill stayed on the boat and found some projects to keep him busy.  Icemaker was not working – kept blowing the fuse.  So, Bill took it apart and diagnosed the problem, but with no way to get parts that repair will have to wait til later.

We also had been experiencing some issues with a new water pump we had put in.  it sometimes worked, and then would get super-hot, and not work until it cooled down.  So, Stephen being a pump engineer, he had suggested some possible fixes and Bill attempted to put those in place.    Rest of the trip will be the test.

After lunch, we headed to clear out.  You have two options – you can clear completely out, or you can get a cruising permit and stay within Cuban waters until your next port and clear out there.  So, we cleared completely out, knowing our next stop would be Key West FL for checking in to the US.  Pine was sad to see us leave so soon, but we told him we would be back when we can stay longer.  You can stay 30 days on your visa, then renew for another 30 days, and extra special Caya Largo ONLY allows you to stay another 30 days.  It took about 1 ½ hours to clear out.  Interesting note: all forms are carbon paper based.  No computers are used in the clearance process.

Total cost for Cuba Stop.  75 cucs per visa, 55 cucs entry fee, 14 anchorage fee per night.  Which made the total stop cost around $400 US.  Really needed to stay longer.

Leaving Cuba was tough, but we knew we had to get to the west end to catch the right winds to get us to Florida.  So, we sailed out around 4 pm, and we watched the islands dotting the horizon to our north.  We had following seas, and light 5 knot Southeast winds to start.  This continued all through the night, so we had to motor sail.  This makes the 2 aft cabins really hard to sleep in as the engines are right next to your head.  Seems like Leopard could have planned that a little better!  You end up with your head at the foot of the bed and earplugs in.  Which isn’t the best if the person on watch is yelling to get your help.

More information on Yachting in Cuba.

Cuban Waters of the Caribbean Sea


We had a slight shift to Northeast winds around 8 am, but still very light.  We motor sailed pleasantly most of the day and enjoyed time on the front deck.  Stephen caught two dolphin fish – one large enough to keep, giving us two great meals, and a barracuda that we of course let go.  That night Grace made us her special Bananas Foster for dessert!


So, we continued on until winds shifted and again were able to fly our parasail as we went downwind.  Then, around 6 pm, a storm crossed our path.  We had been tracking this storm moving in a southeast direction and were prepared.  We had just taken the parasail down and got the main up and the genoa out, when all of a sudden 35 knot winds hit us.  We quickly pulled the genoa back in, but not easily.  The wind tossed those sheets back and forth, making it sound inside like we were being hit by bricks.

With the genoa in, we headed into the wind and left the main up. However, on the main sail, the sheets were not snug on the boom, so when Bill tried to tighten them, the sheets got caught on the antennas and pulled the Sirius weather and the GPS antennas loose.  Another casualty to fix later.

Good thing it was a small storm.  Not sure what else would have happened if it was bigger than it was.  Storm quickly blew over at that point and we were met with light winds again.  In hindsight, never should have put those sails up til the storm passed.  We just didn’t think it would contain 35-40 knot winds!

Night watch, Stephen and I decided just to take the main down, as when it flops around up there,  the noise drives you crazy at night.  That was a challenge because unknown to us, the rope holding the sail bag in place at the rear of the boom had broken, and the sail bag had worked its way forward so far that the bag of the sail just flopped over the boom.  Multiple times we let it down and put it back up.

Ordinarily that would have just been annoying, but in the middle of the dark night, it was downright dangerous.  I hate it when Stephen goes on deck in the night to do something to the sail.  I just visualize him flying off the boat and me having to push MOB, throw the boat in neutral and try to retrieve him out of the water in the pitch dark.  Of course, he wears his Spinlock life vest and locks on, but still there are times were there is no place to lock on.  Scary.

Clearing In Key West


Uneventful day on Saturday, as we had slick calm seas and no wind.  Unfortunately that also meant we had to motor the rest of way to Key West.  We prepared the boat for customs clearance and used our new mobile phone app, CBP Roam to alert them to our arrival.  We expected a 2-3 hour customs search and were amazed by how easy and fast this handy app made US clearance.

Here’s how CBP Roam works.

You pre-register and are given a pre-clearance registration number that you use in the app.  Plan on a 1 month wait time for your approval and number.  Then, as soon as you have a cell signal, you alert them to your arrival, scan your passports in, answer the usual clearance questions, and submit.  We then got a call from customs and they confirmed some questions, as well as initiating a video chat right through the app.  They needed to see our faces, especially our newest crew member, Grace, since she did not have any global traveler number.  And that was it – we were cleared.  As for the vessel clearance, we had no raw meat/produce/weapons, so we did not even have to head into port.

However, we wanted to refuel, so we headed in and anchored right outside Key West city marina.  Everyone was relieved to hear from us again, as we had no cell signal for 6 days.  Our family and friends just aren’t used to that.  Key West is not one of our favorite places,  but we decided to have dinner on land and got a nice relaxing outdoor table at “Off the Hook” restaurant.  Then we enjoyed a good night’s rest on anchor.


4 am wake up call for Bill and Stephen as they navigated us out the Key West channel and started our journey east.  Headwinds blowing out of the east, however light, as well as only a 1-foot wave chop, made for a pleasant motor trip to the southeast corner of Florida.  There we were able to take advantage of that easterly wind caused by a Bermuda high and make our way up the eastern coast.

7:45 pm, the winds turned in our favor as we round the corner of Florida and we get a beam reach sail on 20 knot winds, so we were quickly sailing along at 10 knots.  Then it’s time for a crew favorite.  Spaghetti/meat sauce.

Night watch was a mixture of wind speeds as we continued around Florida.  Quite a busy night as we met with Miami boat traffic.

Florida Coast Sailing

MONDAY, April 29

Sailing up the coast of Florida on beam reach 20-25 knot east winds and gulf stream currents gave us a 12-13 knot speed, even in 3-5 ft seas, also from the east.  Not much happened today except sporty sailing.  Monday night more of the same, but with increased seas to 7 ft.  Not much sleep for us all.


Day dawns on friendlier seas, 2-3 ft, and 15 knot winds, so we continued at 10-11 knots speed.    Morning excitement was Stephen catching a dolphin fish, and fixing our sail bag, followed by Dawn catching a dolphin fish.  REALLY, I said Dawn!   Stephen said to put his lines back out and I did, and put the teaser out, and then I saw him, swimming in the water right behind the teaser.  So, I played with the teaser – pulling it away from him, and then he was right by our bait (ballyhoo), and boy did he bite!  He jumped out of the water multiple times before I was able to reel him in, Stephen gaffed him, and we threw him in the cooler.  This is our new way of saving our boat from the blood they tend to spray all over as they thrash.

Next up, more excitement as we tried to pull our main sail down and discovered that one of the screws on the cars was loose and wouldn’t get past a point in the track.  The only way to repair it was to go up the mast.  Luckily, we had only 1 ft seas, and 10 knot winds so, Stephen went up in the boson’s chair, fixed the screw and we were able to get the sail down.

All this happened before lunch.

After lunch, Bill and Grace caught another mahi, which we let go as we couldn’t eat all the bounty the seas gave us!

Rest of the sail in to Edisto Inlet to reach Bohicket was super slick calm water, so we had to motor sail, and arrived for one more anchorage on the water at Botany Bay.  We didn’t want to be back yet!

Back Home Again


Up early, we pulled anchor, eager to get to our dock at Bohicket Marina !  Pulled in for fuel around 730 am, and our favorite breakfast sandwiches at the Bohicket Marina coffee/breakfast/lunch/ice cream shop.

Trip Dinner Menu

  • Hamburgers (could barely eat these due to rough seas)
  • Salmon/ Tossed Salad
  • Pork Chops/ Butter Beans/ Cantaloupe
  • Grilled Blackened Mahi/ Bananas Foster
  • Poor Man’s Lobster Alfredo – (boiled mahi in parmesan butter sauce with pasta)
  • Dinner Out on Key West
  • Spaghetti/ Meat Sauce
  • One pot meal in rough seas – Baked Chicken, Hashbrowns and corn.
  • Pork tenderloin wrapped in bacon, beans
  • Shrimp – fresh caught from the docks on Bohicket Creek.

Broken Things

Leftover fixes were made on several items broken on last trip:

  • Bill replaced hatch handles that were not locking properly.
  • Stephen replaced the outdoor hose sprayer shower with a totally new unit.  Had to cut some fiberglass for the new one to fit.

New repairs:

  • Icemaker – grounding wire had somehow gotten wet ?   Repair needed once we are in home port.  Really need that to be 12V.  Future replacement of an internal electronic component fixed it after much diagnostic troubleshooting.
  • Newly strung trampoline corners crew came loose.  Stephen restrung and retied it.
  • Loose screws – everywhere – never can quite figure out how and why screws just come out, but we seem to find them everywhere!  Easy fixes, but needed a bit of “help” staying in.
  • Grill not officially broken, but just doesn’t heat up very hot.  Stephen and Bill changed valve and now works like a charm.
  • Main sheet fiddler block cracked – luckily, we had a spare on board and Stephen and Bill repaired it.
  • Sirius weather/radio antennae got stuck in the main sheet and pulled loose.  Stephen was able to repair.
  • Compass light not working again – after ProYacht in Cayman fixed it, we had to fix it again.
  • Newly installed water pump with VFD would sometimes decide to stop working.   We believe that it is caused by something in the VFD, because if we are running engines or generator, we are fine, but when batteries are not being charged, it overheats and stops working.  Continued discussions with Jabsco would reveal that the pump was defective in design, meaning we had to take it out and put back our 6 GPM with accumulator tank:-(
  • Sail bag – just can’t get this bag to work right.  Might mean a new one is needed.  It just seems too small and rips by the zipper every time we use it.