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Old 10-11-2014, 10:51   #1
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Sailing from Key West to Cuba

Hi all,

Just arrived in this forum mostly because I just bought a boat, a Pearson 23 made in 1985.
All the information on the boat can be found here: PEARSON 23 sailboat specifications and details on sailboatdata.com

So I'm living from the last 6 months in Florida and have hard time finding someone with experience about sailing from Key West to La Havana... more generally crossing the gulf stream.

I'm planning in doing such navigation maybe in two years but before planning that, I want to be sure of how hard is it?

Do I have to be a highly experienced sailor? I sailed quite a lot but never in extreme situation and usually just for few days.
I welcome any feedback from somebody who already made this trip.
If I go it'll be during summer time and will check the weather every day and wait for the most clement situation to start my trip.

Thank you for your help!
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Old 16-11-2014, 17:23   #2
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Re: Sailing from Key West to Cuba

Hello
Have made the crossing form the Keys to Cuba many times. Have seen a few boats in Cuba of your size. It is doable in this size particularly in the milder summer season. However with the slower boat speed it could take 24 hours or more.
Everything you need to know is covered in the newest guide.
Cuising Guide to Cuba ,writen by Cheryl Barr and published by Yachtpilot
At Cruising in Cuba .com
Don
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Old 16-11-2014, 17:38   #3
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Re: Sailing from Key West to Cuba

It is 90 miles across open ocean. Some offshore sailing experience would be good. Most important is to check the weather. In good weather it can be a very easy trip. Try to cross in the middle of a norther and be ready to get you butt kicked.

You don't mention but if you are a US citizen I would not recommend sailing from Cuba back to Key West. You will not receive a warm welcome. In fact, even non US citizens report problems checking in to Key West from Cuba.
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Old 16-11-2014, 18:46   #4
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Re: Sailing from Key West to Cuba

Not a bad sail in the right conditions, but you will be crossing the Gulf Stream so can get rough and you will need to account for current.

Ideal just after cold front passage while wind is NW.

Lots of ship traffic in the FL Straits. VHF at the helm and AIS would be very good ideas.

Entrance into Marina Hemmingway is relatively narrow, so be sure you get it right.
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Old 17-11-2014, 12:50   #5
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Re: Sailing from Key West to Cuba

Thank you for your comments!!!

Oh yes, for sure I'll check the weather before I leave Key West and will do that only in perfect-good conditions.

I have about 1 year and a half to prepare this trip so I'll know my boat and have some offshore experiences by this time.

That's really great to heard your advises guys! For the future readers, please feel free to post any experiences/advises that you would have on this topic!

Also I have a French passport so I hope there will be no political issues... But of course we never know.
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Old 17-11-2014, 13:26   #6
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Re: Sailing from Key West to Cuba

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Originally Posted by kaguouille View Post
Thank you for your comments!!!

Oh yes, for sure I'll check the weather before I leave Key West and will do that only in perfect-good conditions.

I have about 1 year and a half to prepare this trip so I'll know my boat and have some offshore experiences by this time.

That's really great to heard your advises guys! For the future readers, please feel free to post any experiences/advises that you would have on this topic!

Also I have a French passport so I hope there will be no political issues... But of course we never know.
In good weather it will be a very easy sail and a fun trip. As Belizesailor mentions, don't forget to allow for the current that will set you to the east, typically 1.5-2 kts.

With a French passport you should be legal to go and return from Key West but I have heard complaints from other European sailors that US Customs for yachts in south Florida is not always the friendliest in any situation and sailing from Cuba seems to be something that annoys them even more.

Might be a good idea to check that situation before you leave. But in the next couple of years the situation may be totally different. Maybe by that time I can go too.
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Old 17-11-2014, 16:46   #7
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Re: Sailing from Key West to Cuba

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In good weather it will be a very easy sail and a fun trip. As Belizesailor mentions, don't forget to allow for the current that will set you to the east, typically 1.5-2 kts.

With a French passport you should be legal to go and return from Key West but I have heard complaints from other European sailors that US Customs for yachts in south Florida is not always the friendliest in any situation and sailing from Cuba seems to be something that annoys them even more.

Might be a good idea to check that situation before you leave. But in the next couple of years the situation may be totally different. Maybe by that time I can go too.
I've also had non-USA friends get a lot of grief clearing in, or even just in transit thru by plane, the USA. Some have been threatened w 6 month ban on USA travel if they visited Cuba (I don't know current official policy on this, just what friends have told me)

Do you JUST have a French passport or USA too?

If you are in the USA on any kind of visa, I suspect that a known trip to Cuba could cause you some visa issues.

Boat is USA flagged?
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Old 17-11-2014, 16:50   #8
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Re: Sailing from Key West to Cuba

Also a trip to the Dry Tortugas might be a good shake down cruise for you and your boat. A bit shorter, but no legal issues to deal with.
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Old 19-11-2014, 10:23   #9
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Re: Sailing from Key West to Cuba

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With a French passport you should be legal to go and return from Key West but I have heard complaints from other European sailors that US Customs for yachts in south Florida is not always the friendliest in any situation and sailing from Cuba seems to be something that annoys them even more.

Might be a good idea to check that situation before you leave. But in the next couple of years the situation may be totally different. Maybe by that time I can go too.
If your vessel is U.S. flagged, it doesn't matter what passport you hold. If you enter Cuba on a foreign yacht or passport, you are prohibited from re-entering the U.S. for 6 months. But your right, in a year and a half, things can change. Well maybe not, that would mean Congress will have to take some kind of action, or the President could do an executive order. This is not posted to begin a political discussion again on this subject. Just facts for the posting. Chuck
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Old 19-11-2014, 10:42   #10
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Re: Sailing from Key West to Cuba

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If your vessel is U.S. flagged, it doesn't matter what passport you hold. If you enter Cuba on a foreign yacht or passport, you are prohibited from re-entering the U.S. for 6 months.
When you say "you", you mean the boat, right? Not the passengers. There's no way to look at a passport and tell someone has been to Cuba, from what I hear.
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Old 19-11-2014, 10:43   #11
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Re: Sailing from Key West to Cuba

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If your vessel is U.S. flagged, it doesn't matter what passport you hold. If you enter Cuba on a foreign yacht or passport, you are prohibited from re-entering the U.S. for 6 months. But your right, in a year and a half, things can change. Well maybe not, that would mean Congress will have to take some kind of action, or the President could do an executive order. This is not posted to begin a political discussion again on this subject. Just facts for the posting. Chuck
Same here. Not trying to start a political discussion but based on past performance for the next couple of years (or longer?) I'm not too optimistic about anything productive coming from either side of the fence in Washington.
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Old 19-11-2014, 13:57   #12
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Re: Sailing from Key West to Cuba

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When you say "you", you mean the boat, right? Not the passengers. There's no way to look at a passport and tell someone has been to Cuba, from what I hear.

They don't issue passports to boats, only individuals. If you enter the U.S. from outside the country, you had better be able to explain and prove where you came from. Otherwise a trip to Cuba could once again be in your future, only at the U.S. Governments expense. Chuck
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Old 19-11-2014, 14:09   #13
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Re: Sailing from Key West to Cuba

I know of a sport fishing boat out of Orange Beach, Florida, that went to Cuba several years ago, thinking no one would ever find out.

When they got back, the owner was called into the local FBI office and asked if he had spent any money there. He said, 'no' and was then shown a satellite photo of himself standing by the diesel pump in Havana, watching diesel being put into his boat. The fine was $15,000.00.

Cuba is pretty much under constant surveillance by the NRO, as incredible as that may seem (that whole missile crisis thing I guess).
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Old 19-11-2014, 14:22   #14
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Re: Sailing from Key West to Cuba

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They don't issue passports to boats, only individuals. If you enter the U.S. from outside the country, you had better be able to explain and prove where you came from. Otherwise a trip to Cuba could once again be in your future, only at the U.S. Governments expense. Chuck


US citizens go to Cuba and the Cubans are very nice to offer you a stamped paper instead of putting the stamp in your passport. BUT! Anyone that thinks they can go to Cuba without some US bureaucrat somewhere having a list with their name on it is seriously fooling themselves. You may not be actively pursued over it but you better believe that they've got your number.

Would love to go, can't wait to go but don't feel like risking a fine or my boat over it. Sure lots of people go and nothing happens but with my luck I would be the one picked to make an example of. Probably end up on the 6 o'clock news right next to Charles Manson.
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