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Old 29-01-2023, 16:24   #1
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Experienced Pirates

So, inexperienced as I am about the seasonal flow of cruising, I’d sure appreciate the experience of those pirates long-in-the-tooth, with regard to making a reasonable cyclic sailing plan (with alternate/ Plan B).

I now live in Maine, *the last cheap harbor, and wish to go to the Caribbeans seasonally, & then beyond. I’ve read that it takes about a month to sail from Maine to Florida. The “Plan B” idea, relates to missing the weather window when heading home, or extending past the ABC islands to… where? The “Plan-B” also includes running from weather, should some off hurricane stomp on my well made plans…

What might be good timing round trip, and where should a first Caribbean cruise take me ‘round to?

Thx in advance…
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Old 30-01-2023, 07:54   #2
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Re: Experienced Pirates

Some of the big questions are how much time do you have with out having to work and how much money do you have to support yourself.


Assuming lots of both one could make a case for an active summer sailing on the Maine coast, NB and Nova Scotia. About October sail south to the Chesapeake and then when the weather looks good head out to Bermuda. Stop in for a drink at the sailing club at St. Georges and then when you feel like it head out for St. Martin. Hard on the wind for the first few days until you get the trades and then a beam reach to the islands. Starting at St. Martin lets you spend the winter working south to Grenada. Then you make the decision to continue on to Panama and beyond or to take the long beam reach to the Virgins,on to the Bahamas and back to Maine.
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Old 25-02-2023, 08:11   #3
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Re: Experienced Pirates

Ahoy Papasail:
You say, "I’ve read that it takes about a month to sail from Maine to Florida."
Having made the passage from Halifax, NS to Florida 4 times I'd say it's more like a
2.5 - 3 month trip. (Hopping in-and-out as you go down the coast) In the fall--aka hurricane season--it's not smart to plan an offshore passage.


Going north can take the same amount of time--unless you feel comfortable/experienced enough to just go from Caribbean to Maine, with one stop in Bermuda. I did that once and the 1700 mile passage took 20 days--including 3 days in Bermuda drinking "Dark and Stormy" cocktails. (Dark rum and ginger beer.)


North OR South Passage:
If you're doing the coastal path NEVER go outside Cape Hatteras!!! (ALWAYS use the ICW) This advice was given to me by a very experienced sailor, who as a young man survived but the owner / skipper did not when a bad storm blew them ashore.
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Old 25-02-2023, 08:33   #4
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Re: Experienced Pirates

The timing of the trip south is tight. There can be very little time after the end of the hurricanes and before the first winter storms.

My own plan has been to leave Maine in early to mid September, go to the boat show">Annapolis boat show, and then jump from Norfolk or Beaufort to the Virgin Islands in mid November.

I am not a fan of leaving the Northeast and going to Bermuda, because you can really get beat up by the first cold fronts. My general rule is that the fronts are much weaker south of 30 North.

I always went around Hatteras, because my boat was too big to go the ICW route. It is not an issue IF YOU PAY ATTENTION TO THE WEATHER FORECASTS AND DO NOT LEAVE ON A GIVEN DATE!!!

As far as going up and down the island chain, it can be done quite quickly if you sail overnight, but you are cruising, so take your time.

Going north, I made the mistake of going through Bermuda and getting into Newport by Memorial day because my wife wanted to go to a wedding. It took all summer to dry the boat out. My preferred return was the Old Bahama Channel to Florida and cruising up the East Coast.

Trinidad and Bequia were my favorite islands, I did enjoy Bonaire, but it was a tough trip back east.
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