We (ourselves and our friends Kevin, Dena and their son Connor on s/v Sabbaticals) left Luperon  at 5:00 am after having a difficult time with the Dominican officials.  They didn’t want to give us our despacio the night before and said we had to leave by 8pm the previous night or wait until the comendicia came to work in the morning –supposedly at 5am which would mean we would not leave until at least 7am.  We tried to explain to them that we needed to leave no later than 5am to get into Cuba during reasonable daylight hours and to give us a cushion if the wind wasn’t favorable.  Finally they gave us our despacio with their understanding we were going to leave late that night and our understanding we were going to leave even later that night, i.e. early morning but before they got to work! 
Hauling butt to Cuba
As it turned out, we didn’t need to worry as we have 18-23 knots of wind on the stern quarter and 5-7 foot following seas.  We averaged around 6.5 knots and sometimes hit 8.5 as we surfed down some of the bigger waves.  That’s pretty fast for our 37 ton girl!  We passed through the Canal de Torture in Haiti at night, which is a 4 mile wide passage between mainland Haiti and the Island of Torture.  We kept a keen lookout for  any potential fishing boats that got a little close for comfort, but I think we were freaking ourselves out more than anything.
We passed Guantanamo around 11pm and gave it a wide berth.  The chart showed a restricted area about 3 miles around it but we decided to go out 4-5 miles.  The wind died around 11pm so we had to kick on the motor, but we had to keep her at around 4 knots so that we would get into Santiago during daylight hours. 
Finally after 50 hours we were approaching Santiago.  We called “Morro Santiago” and the Santiago Marina came back to us.  We gave them our boat name, nationality, number of persons on board and nationality of persons on board.  They then gave us permission to enter the harbor and instructed us to anchor just off the marina.  They told us the officials would be out to see us around 8:30 -9 am.  Well, about noon they started showing up! 
Beautiful sunset at sea
First came the “bug man” and the doctor.  We offered them cold soda which they both accepted.   The bug man was a jolly little fellow with a wide grin and very animated.  He looked around for bugs, mosquitos and any standing fresh water.  The doctor was great – she was dressed in a stylin’ and sexy purple dress with a white lab coat over it!   She just asked if we were sick and asked to see our medical kit.  This only took about 25 minutes – it would have been shorter but with my horrible Spanish and their broken English, a lot of it was hand gestures and lots of smiles and laughter.
The next to come was the agriculture lady and the vet for our animals.  As soon as they got on board, the woman gave us two big kisses on the cheek and welcomed us to Santiago.   We shared a cerveza with the vet and juice for the agriculture lady.  We did many cheers and toasts to our arrival in Cuba!  The woman just asked to see our fruits and vegetables and told us to keep them on board.  She also asked to see our frozen meat, rice and pasta to check for bugs. The vet just wanted to see the animals – not to inspect them, but just to verify they were on board and checked their rabies and other vaccination paperwork.  For the vet, we had to pay $21 USD or 15 euros.  He gave us a receipt and told us we would not have to pay the other vets further down when they come on board to inspect us at other ports of entry. 
The next to come was the customs guys, or Aduana.  First on the boat were two huge black labs that were scared to death!  Evidently, the other dog was a cocker spainel but he didn’t really do his job well so he was fired.  They had brought these two dogs from the airport and obviously hadn’t trained them on a boat!  The dogs did okay though – one was looking for guns and ammunition and the other for drugs.  We had to pull out our flare guns for them to smell and the dogs went through the rest of the boat pretty thoroughly. 
The Morro at the entrance of Santiago
After the dogs had done their job, 4 other customs officials searched through our boat.  Now, searched should be in quotation marks, as they just looked around and asked us to open arbitrary things such as a box full of junk, a sea chest full of tools, another sea chest full of clothes and a drawer full of odds and ends.  I had read other blogs that said this part of the search took 2-3 hours but ours only took 20-30 minutes.  Maybe it is because we have so much crap on this boat they had no idea where to start!
Next they asked us for all of our portable GPS and VHFs.  They took pictures of them and then placed them in a plastic grocery shopping bag that we gave them and taped it shut.  They did the same with our flares.
They then ask me if I had any morphine on board, which we don’t, but we do have some other pain medicine.  I gave it to them and they tried to figure  out what the ingredients were.  I told them I didn’t know, but that the effects were similar to morphine.  They apologetically told me they would have to seal it in a bag as well until we left Santiago. 
They told us to keep all the sealed bags and we would have to show them to the officials when we left.
After all this was completed, we went to the customs’ office in the marina to do the rest of the paperwork.  Boy oh boy, do they love paperwork.  They do not have copiers but rather use old carbon sheets (you know the ones – they go in between two pieces of paper to make copies).  We were told sometimes they don’t have the carbon sheets and have to copy over all the information. The Bug  man and doctor had already taken our passports to give to immigration to start the paper work nightmare,   I’m glad they did, as the immigration officer had gone through all of our passports and written down by year, beginning in 2008, of every country we had gone to.  They did not stamp our passports, even Maria’s who has a Canada passport, but just stamped the Cuban Visa paper that they put inside the passport.  Next we went to Customs who just asked us the usual questions. 
Then they asked us if we had Health Insurance.  They assumed Maria did because she is Canadian, but they told me and Josh that even if we had insurance from the States, they do not consider it insurance because we are Americans in Cuba and it would not be honored here.  Therefore, they wanted $2.50 per day from each of us to pay for Cuba Health Insurance.  I have an international travel plan and have to talk to them today further about this cost – will let you know how it turns out.
We had to pay 10 CUC (Cuba currency) for the boat and 15 CUC per person to enter Cuba.  We also will have to pay 15 CUC for a cruising permit to sail in Cuba, but they will issue that to us when we leave Santiago.  Since me and Josh are American citizens, we cannot spend any money in Cuba.  That means, lucky Maria, being the sole Canadian, has to pay for us for everything.  I’m going to love Cuba!
Finally after 4 hours, we were cleared into Cuba!
A few notes and recommendations for anyone planning on visiting:
On our computer, we put together a spread sheet that had three columns – the first had the info title in English (such as Boat Name), the second had the info title in Spanish (Nombre del barco) and the third had our boat’s info (Joana 1).  We did this for all the usual information they ask (Name, Flag, Registration number, etc.).  On the same piece of paper, we included the crew list with passport information.  We printed out 6 copies and handed it to each group that came on board and was very helpful.
We heard about some bribes in Cuba and we didn’t really experience it.  The closest we came was someone on board asked if we had a spare can of meat for their child and we gave them an old can of corned beef.  We also gave away some old fishing line and a lure.
We were asked if we had any memory sticks for the computers.  We didn’t, but if we had known, we would have bought them some place cheap and brought them to trade or sell.  Evidently, the government offices only have one or two computers for everyone to use, so they have to put their information on these USB memory sticks when going from computer to computer. 
The Cuban officials are some of the nicest and most respectful that we have come across.  Everyone welcomed us to Cuba with big smiles, hugs and kisses on the cheek. 
Nigel Calder’s cruising guide to Cuba is very good and pretty much spot on.  His depths are conservative and we got into places with our 7 foot draft where his charts, at mean low water, said we couldn’t.   Some of the places where he says we could go to shore, we were not allowed.  But this only happened to us twice, at Cabo Cruz and Los Arroyos.  We had the latest guide book, which is from 1999, so obviously some things have changed, but not much!  Even the prices he gives are still pretty accurate.