Join Date: Aug 2009
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Unfortunately this discussion has rambled somewhat, so here is back to the nautical aspect.
Having sailed to and around Cuba for several winters since 2008, I find there are two ways to go.
If you have money and own a 60ft or bigger crewed motor yacht, go to Hemingway. There were three of them there Christmas-New Years 2009-10, one registered Fort Lauderdale, one from Newport and one from Delaware plus a large motor sailer from New Orleans (he had a Cuban wife).
If you don't have financial clout, go through the Raggeds (Duncantown) in the Bahamas to Baia la Vita in Holguin cruise Cuba for two months, one month visa renewed once (stay far off Guantanamo, the CG comes out even if you are 5 miles off and if they do, say you are going to Jamaica), do the south shore islands to Cayo Largo and head back to the Bahamas through Baia La Vita. The snorkling is fantastic and the beaches are paradise (but you have to find them, most islands are mangrove). Your paperwork will show only that you have been in the Bahamas. We have never had problems on returning to Florida. (I hope no one in homeland security monitors this).
For a short two week cruise, go from Baia La Vita to Baracoa and back. Rent scooters to visit the countryside or hire a driver.
The crossing from the Bahamas to Cuba is by far the most comfortable, with the Bahama current, no wind against current. The only really rough part is the return along the southern shore from Cabo Cruz to Punto Maisi with strong headwinds. It is not called the Windward passage for nothing. There are few anchorages along this shore, but there are harbors every 60 miles or so. We always motor sail back, port tack out in the morning and starboard tack back inshore in the afternoon as the wind shifts from northwest to southwest during the day.
As for charts, admittedly they are hard to obtain, but with GPS chips for the off shore work (they are based on old US surveys and are not accurate for inshore) you can keep track of your general position. I use Nigel Calder's guide, it has excellent and detailed inshore charts and if you take their coordinates for way points, they are dead on. Simon Charles' guide is more enterntaining than useful.
Yes, now they charge $ 3 per day for medical insurance. Don't bother with US bank or credit cards, because of the embargo they don't (or wont) work. Cash, US $, Can $ or Euros are no problem for exchange at the CADECA. Public internet, limited to the larger towns and hotels, is slow and expensive ($ 6 per hour). So bring your pretyped texts on a USB.
Don't sweat officialdom, they are awfully friendly and considerate (they even put on socks to cover their boots when they come on board). I have never seen US officials do the same. And the cocker spaniels for drug inspections are cute. Just have the paperwork ready and they do the rest. Unlike Bermuda, it is one stop shopping.
As for repair work, Cubans are very ingenious and industrious. Once when out rudder jumped the gudgeon and the rudder stock was bent in a fierce northerly (unexpected), they took it out and repaired it. The only difficulty as finding stainless steel (we took a collection amongst the foreign boats there and they re manufactured the fitting).
AH, don't forget, you won't get good marine weather forecasts in Cuba. So subscribe to a short wave service before.
Finally, US insurance firms do not cover claims in Cuba, get coverage from a UK firm.