Cuba Travel

Sailing to Cuba - Article by Don Barr

Posted October 22, 2008 by publisher in Cuba Travel.

Don Barr |

Cuba…. Opening for Yachts?

We hear this statement often from our U.S. friends who aren’t aware that for Canadians and Europeans, Cuba has been open to yachting for a long time. If Cuba becomes accessible to American boaters what are the rewards it offers?

The first big advantage is that Cuba is easy to reach. From anywhere on the eastern seaboard one can sail the inland or coastal waters to Marathon or Key West and then leave the Florida Keys late in the afternoon arriving at Marina Hemingway the following morning. Yachtsmen who cross to Nassau will have twice the distance to cover. Although both routes cross the Gulf Stream, the first route usually has a longer weather window for the crossing with prevailing easterly winds and also there is less current than what can be experienced by those opting for the Bahamas route. Wintertime northerlies hit both the Bahamas and the north coast of Cuba but Cuba has many very secure anchorages with excellent holding. The longest distance between safe anchorages (on the north coast of Cuba) is 37 miles—the distance between Marina Hemingway and Bahia Honda.

Cuba is a large island. It has over 3000 nautical miles of coastline with 81 pocket bays and miles of good water inside the reefs with this much space, Cuba can easily absorb twice the number of boats that currently cruise the Bahamas each winter giving the waters that uncrowded feeling. The island’s land mass is equal to almost half the total land area of all the Caribbean islands combined with many more natural attractions than any other Caribbean island.

Cuba has some of the most historic sites in the Americas with buildings dating as far back as 1519. Anyone interested in architecture and history, music and culture would be remiss if they didn’t spend sometime traveling inland during their winter cruise as there is just so much to see and do. 

By April/May, when it is time to head north, Havana is ideally situated as a jumping off point for Florida. In the spring the trade winds shift to the southeast providing sailors with a nice breeze on the beam together with the Gulf Stream current West Palm Beach should be reached in roughly 36 hours doable for even the smallest sailboat. But for those not wanting to travel overnight, Key West can easily be made in one day.

When the time comes that you must decide on to cruise for the winter, be it the Bahamas, down island to the Caribbean or to Cuba you will soon see that Cuba is the logical choice. Cuba is close at hand with lots of secure anchorages and so much to see.

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Member Comments

On October 22, 2008, publisher wrote:

We thank Don for submitting this article to us and hope to hear from him on a regular basis.

On October 24, 2008, tern3 wrote:

What does the author consider a “safe” anchorage?  Having lived and sailed the n coast of Cuba I take issue with the statement that 37mi is the longest distance between safe anchorages.

On October 27, 2008, Don Barr wrote:

In the northern half of the Caribbean , particularly the Florida Keys, Bahamas and Cuban north coast it is critical to have safe anchorages. A safe anchorage is a situation with good anchor holding, swinging room and shelter from wind and seas during the passing of a cold front,(a norther). This has always been a serious problem in the keys and Bahamas. Every winter we hear stories of yachts in trouble and boats playing “bumper cars” in the popular anchorages in these areas. Cuba is fortunate to have an abundance of places that meet this criteria. Unfortunately Cuba closes some of these spots to visiting yachts. Each year the off-limits ports change so it has taken us many seasons to have visited them all.There will probably some problems in the southern part of the island around the Baracoa to Vita region because of the hurricanes, but we will
cruise that area this winter and report back.
Also Club Nautica at Marina Hemingway are making arrangements to hold a cruise/parade from the marina to El Morro and back then a barbecue at the club

On October 27, 2008, publisher wrote:

Very interesting. Thanks for the information. Looking forward to hearing more.

On October 28, 2008, tern3 wrote:

What are the “safe anchorages” between Havana and Matanzas that are only 37 miles apart I must have missed them in the 16 yrs. I’ve been sailing these waters.  The only anchorage in this stretch I am aware of is Puerto Escondido which is closed to all “unauthorized” boats.  And it is more than 37 miles from Havana.

On October 29, 2008, JOSE ALVAREZ wrote:


On October 29, 2008, Don Barr wrote:

We are leaving home (Nova Scotia ) tomorrow on the way to Cuba again , so will be off line until we are in Florida. Looks like a cold trip down. While we are traveling perhaps Tern3 could post on the harbors and places he likes cruising in Cuba as quite a few Canadian and some U.S. yachts are headed there this year. Also we could get together at Hemingway and compare notes
Don Barr

On October 29, 2008, tern3 wrote:

Not that I know of.  I have had my boat in Cuba for 16 yrs. and have been married to a Cuban woman for 14 yrs. and she cannot sail with me aboard my boat.  Sorry…

On November 13, 2008, Cubaking wrote:

Hey Don,

Here is a story you might enjoy. I had just returned home from Cuba and checked my messages and there was 3 messages from Bill Wirtz and 4 from his secretary, so I called and Billy jumped on the phone. He said” Get packed we are going to Cuba” I said Billy I just left and am home. He said ” Spencer we are taking the Blackhawk ( 123’ Feadship 1971).  From Lauderdale I asked, ” Nope Cat Key” (Bahamas) he said.

  Well Billy was not someone that I was going to say “no” to. After all the Blackhawk and Bulls visits to the Sonia Henne room as his guest. So within hours his stepson Hargrave and I were on a plane to Lauderdale and the puddle jumper to Cat Key. (No rest for the wicked)

    When we motored into Marina Hemingway ( I requested Tarara but Aduana said “nope”) There was about 50 officials to “meet” us. Everything went off without a hitch and Billy and his family were delighted. I ended up staying another couple of weeks flying back. The letter and stern warning and fines arrived from the OFAC a few months later for everyone on the reentry manifest…. Of course I was not on the Blackhawk for the return.

    There was something quite nice about seeing the stern when I arrived each morning ( I was stying at my place in Centro Habana). Maybe it was the colorful indianhead logo that most Cubans enjoyed but for me it was simply the name of my home town written below: CHICAGO.

    This story is one of many in “Havana: My Kind of Town” available on on or about January 20th.

On March 02, 2009, Sharon in Saskatoon wrote:

Don—very interested in your sailing info on Cuba.  We would like to circumnavigate Cuba winter of 08-09.  We plan to leave from Florida Keys.  Any ideas, suggestions, etc.  Is your boat Canadian registered?  Name??  Can you contact me any other way??  Sharon

On May 16, 2009, Patrick wrote:


Thinking of taking my 42 ft Whitby Sailboat to Cuba, but most of the blogs and guides are old.  Nigel Calder’s book is from 1999.  very old Much has happened since then.  How can I get current info?

Patrick   Delaware, USA

On May 18, 2009, manfredz wrote:

Niced when I was in theHemmingway Marina in Havana in jan, saw several boats/yachts flying Canadian flags in port.

On May 19, 2009, Patrick wrote:

Manfred Z,

Thanks for responding.  Could we talk please? I could call you.
or my phone is in Delaware, USA 302-286-7134.  I have heard several bad stories too. I am US citizen. Obama has begun to change the policies but not very much.  Better than Bush but?  I would like to spend this winter in Cuba and live aboard.    Patrick Cornelius

On June 06, 2009, Cecile wrote:

I have a friend in the Keys who wants to sail to Cuba this month on a 37 sailboat. Is anyone planning on leaving from the Keys this month>

On August 27, 2009, Serge de Blois wrote:

My sailboat is currently in Florida and we’re planning to cross over to Cuba in April 2010 and come back to Key West after.  Should I expect any problem getting a new Cruising Permit when I’ll get back to Key West, even if the boat and the crew are Canadians?
Serge de Blois

On October 02, 2009, lisa wrote:

planning a christmas trip with the family, sailing from key west to havana.  Should we expect any problems from us officials when we depart key west?  All us citizens, foreign-flagged boat.

On October 04, 2009, Don Barr wrote:

Re Serge de Blois , you will not have any problems getting a cruising permit as Canadian yachts have been doing this voyage for many years.
Re Lisa As U.S. citizens you could expect problems. The problem will not be in Key West when you depart as it is not required to clear out . You could be stopped by the U.S. Coast Guard about 20 miles off the coast of Cuba as this is the area they patrol. Your bigger problem will on your return.
We will be cruising in Cuba again this winter ,departing Fla. before Christmas
Don Barr

On October 06, 2009, Lpegden wrote:

Hi don, thanks for the response. I’m hoping that since we will be headed for the Caribbean after our Cuba visit, we should be ok. Or should I be worried about the coast guard patrol 20 miles off shore?  Also, do you have an insurer that covers you while sailing in Cuban waters?

On October 07, 2009, Don Barr wrote:

Hi Lpegden
I have been questioned by the U.S. coast guard about 20 miles off havana for the past three years. They did not board or ask to , just asked questions over the radio, crew nationality etc. The patrols will start easing off now as the “rafting season ” is ending. I have heard some yachts say they are closing with the Cuban coast to pick up the west going counter current on their way to Mexico. If heading for the lower Caribbean from Cuba be aware that you will have to make hard easting , very difficult. I have no insurance when in Cuban waters.

On October 26, 2009, Bill wrote:


We are in Trini and will be heading up the island chain and back to NS by August 2010. We plan to visit Cuba from the DR in the Feb - May timeframe but are still figuring out where to check in, visit and stay. It isn’t clear to us if Puerto Vita on the north coast is still a check in location or not or even whether to head for the south coast instead. Can you recommend any good references to help plan our trip?

Voyageur C
Halifax, NS

On October 27, 2009, Don Barr wrote:

Hi Bill
Vita is still the port of entry on that coast. Remember Baracoa is NOT.
If cruising up the north coast at that time of year it is an easy sail but be prepared for the northers. Up the south coast you are sheltered from the fronts and more interesting places to stop. We will be cruising the south coast again this winter.
Don Barr
Mahone Bay ,NS

On November 02, 2009, Bill wrote:


Hi Don:
We have a lot of other questions. Would you mind having an e mail discussion - we are .(JavaScript must be enabled to view this email address). We may be one of a group of three Canadian boats heading for Cuba from the Eastern Caribbean.
We are insured for Cuba through Commandeur NV.

For example, where do you start your Cuba cruise from? Is your boat in Florida during the summer season?


On November 10, 2009, steve wrote:

Hi Don:
My wife and I are planning a cruise to cuba from key west or dry Tortugas in a small cruiser 30’
We are from Toronto and will be trailoring our boat to florida and have never boated in or around florida before so we dont know what to expect for marine conditions.
What time of year would you suggest for calm waters for the trip across and cruising between Havana and Bahia de Cardenas.
We are planning mid April 2010 but will obviously reschedule around potentially better conditions if that is not a good time.
Also I read mention of a cruising permit (florida) in an earlier post, will i need one? and where could i acquire one?

Thanks Steve

On November 11, 2009, Don Barr wrote:

Hello Steve
Yes if you are in the USA with a Canadian flagged yacht you are required to have a cruising permit for US waters , this is available from US Customs.
Any time of year including Nov. to Apr is ok but you do need a weather window to make the crossing from Fla to Cuba. This generally means winds from the east at less than 15 kts. If you plan to be in Cardenas bay I would suggest crossing to Veredaro first than go to Havana as it can be harder going east.
Have met many yachts in Cuba 30 ft and less. By mid April the trades are starting to ease down and move more to the south east, usually, but by May it gets to be very hot in Cuba.
Don Barr

On December 04, 2009, Robert Thuell wrote:


My son and I (both British) hope to travel to Florida Jan/Feb to purchase a yacht and then sail to Curacao via north coast Cuba and Dom Rep I would appreciate any comments you have regarding time of year, routing and the availability of safe anchorages/marinas   I believe Luperon on DR is very safe but know nothing about Cuban facilities

kind regards


On December 04, 2009, sailor wrote:

Cuba is very safe and there are plenty of good anchorages. In the summer months you must be aware of hurricanes and in the winter cold fronts ,aka northers. These conditions are very manageable because of the numerous anchorages. There are very few marinas. However going east on the north coast of Cuba and the DR can be a tough slog into the prevailing easterly winds.
Check out web site

On December 09, 2009, Foxglove wrote:

so….. north or south coast then….. hop through the bahamas and start east and head west…... what do you think????

On January 19, 2010, Chris Green wrote:

re no 25
I am thinking of a similar plan, I’m also British - buy a boat in Florida, cross to Cuba then on to Belize. Could you put me in touch with Robert Thuell, maybe we could combine forces.
I also have 2 issues to resolve:
Size of boat - for passages to cuba and belize which cross the Gulf stream is a 25-30ft adequate (safe) I have read that larger boats are difficult to manoeuvre amongst reefs eg Ambergris Caye etc although I’d prefer maybe a 35-40ft. Again shoal draft would be better for shallows, not so good mid Gulf Stream? Lifting keel designs eg Catalina?
Multihull? Greater speed for crossing , very shallow draft, much less choice and probably much more cash!
Plan to use boat in Belize, not planning to return by boat, winter it in Belize (but plan changes every day at the moment

On January 20, 2010, robert wrote:

re #28


Many thanks for your comments.  Our plans have changed.  We have purchased a boat in Curacao which is the area we want to be in.  All the best for your trip